Sites to See and Places to Be Across the Cape and Islands

Upper Cape: Bourne • Sandwich • Falmouth • Mashpee

Bourne

Bourne Village  • Bournedale • Buzzards Bay

Cataumet • Gray Gables • Monument Beach

Pocasset • Sagamore • Sagamore Beach

“Call me when you get to the bridge,”
is a common phrase many Cape Codders use to reference time of arrival for their loved ones. With all three bridges located in town, the Bourne, the Sagamore and the Cape Cod Canal Railroad Bridge, Bourne is the first town you enter when arriving on Cape Cod. And despite it being the first town you enter, it happens to be the last town on Cape Cod that was officially incorporated. Bourne was originally established as part of the town of Sandwich in 1640, but it wasn’t until 1884 that it separated and became its own town. In total, there are nine villages that make up the town of Bourne, that are easily differentiated in relation to the canal, which separates the town. Located on the “mainland” is Buzzards Bay, Sagamore Beach and Bournedale, “on” the Cape is Bourne Village, Gray Gables, Monument Beach, Pocasset, and Cataumet, while in-between sits Sagamore. 

The Cape Cod Canal is probably one of the most well known landmarks on Cape Cod. Although it wasn’t fully operational until 1940, it was in the works long before then. The artificial waterway, part of the Atlantic Intracoastal Waterway, connects Cape Cod Bay (north side) and Buzzards Bay (south side), as well as Cape Cod to the mainland. The Canal runs almost seven miles long and has many recreational activities. Weather permitted, you can find people biking, running, walking or rollerblading along the edge of the Canal and experience the most spectacular sunsets on the bay side. 

Only five miles from the Bourne Bridge in Cataumet, The Chart Room, constructed upon a converted New Jersey Central Railroad barge, welcomes visitors at the Kingman Yacht Center. In 1953, the barge was towed all the way to Red Brook Harbor, where it is currently located, and was later converted into The Chart Room in 1966. Today, The Chart Room serves as a local stomping ground, a popular spot for great food, drinks and a fun seasonal atmosphere day to night. Make sure to stop by when they re-open for the 2021 season!

Once apart of Sandwich, one of the first towns established on Cape Cod, Bourne holds many historical buildings and landmarks, most well-known being the Aptucxet Trading Post which was originally built by the Pilgrims of the Plymouth Colony in 1627. Located midway between the Dutch settlement and the Plymouth Plantation, the spot was perfect to trade with the Wampanoag Indians and Dutch travelers. 

The Aptucxet Trading Post that stands today is actually a replica, constructed in 1930 on the original foundation of what was excavated in the 1920’s by the Bourne Historical Society. Currently, the Aptucxet Trading Post serves as just one of the many historical buildings and replicas at the Museums at Aptucxet, dedicated to the preservation and education of local history. 

Sandwich

East Sandwich • Forestdale

Sandwich Village

When it comes to the town of Sandwich, most people find it amusing that Cape Cod has a town named after a food item and often find it hysterical that the town even has “sandwich” police, but where does this name actually come from? Well, the oldest town on Cape Cod (together with Yarmouth) was the first town to be settled in 1637 by a group of Quakers from Saugus, Massachusetts. The town was named for the seaport of Sandwich, Kent, England—not the delicious food item. Sandwich houses three villages, East Sandwich, Forestdale and Sandwich Village, throughout which are many historic homes, the oldest mill on Cape Cod, and the Sandwich Friends (Quaker) meeting house, the oldest in North America. 

If you’re looking for the most scenic stroll in Sandwich, you don’t want to miss the sunsets at the Sandwich boardwalk. It was originally built in 1875 and was almost completely destroyed by Hurricane Bob in 1991. It was rebuilt again for the third (and probably not the last) time in 1992, through the sale of personalized engraved planks which are still there today. The boardwalk that sits 1,350 feet long was elected by National Geographic as one of the top 10 boardwalks in the US, most likely due to the fact that as you stroll along the boardwalk you cross over vast marshland, often spotting osprey and, if you’re lucky, sometimes you’ll even spot a crane. When you meet the end of the boardwalk, you’re greeted by the beautiful views of Town Neck Beach off of Cape Cod Bay.

The Belfry Inn and Bistro is located in the heart of Sandwich and owned by Christopher Wilson. Comprised of three buildings, each have been renovated by Wilson and are accompanied by its own unique history. The Painted Lady, an ornate Victorian era style home, was purchased by Wilson as the first building of the Belfry Inn and Bistro. Wilson restored the exterior of the property to its former glory and renovated the inside to accommodate its ever-changing needs. Today, it is known as the Next Door Burger Bar. 

What is now known as the Abbey was originally a Catholic Church, specifically the third in the town of Sandwich, built in 1901 and purchased by Wilson in 1998. Wilson has transformed it into a dining and lodging experience unlike any other. Wilson added the second floor to the old church to serve as the lodging space, with a balcony overlooking the entire restaurant. As you make your way up the aisle, you’ll find the bar at the altar, spot stained glass windows, an old confessional transformed as the bar’s wine cellar, and pews that have been reconstructed among the Abbey.

The third property of the Belfry is the Village House, which was built in 1827, originally the home of Naaman Dillingham. It went on to become a boarding house and then offices for the company who built the Cape Cod Canal. Eventually it was renovated in 1985 to become a B&B. Purchased in 2003 by Wilson, the restored Village House currently has seven guest rooms, a beautiful veranda and gardens. 

The Sandwich Glass Museum serves as a window into Sandwich’s past, which is deeply rooted in American glass production. The original Boston & Sandwich Glass Company was founded in 1825 by Deming Jarves, who chose Sandwich for its proximity to the possibilities the Canal would bring and brought onboard several master glassblowers. Later, he founded Cape Cod Glass Works with his son John and ran it until his death in 1869. Over the years, the glass trade in Sandwich went on to evolve until it died down with the end of the Boston & Sandwich Glass Company in 1888, causing an economic depression among the town. Many tried to restore the trade, but by the 1920s there was almost nothing left of what was a prosperous industry, until The Sandwich Historical Society held its first glass exhibit in 1925. Today, the Sandwich Glass Museum serves as a reminder of the past, with exhibits and demonstrations that bring this once lost trade back to the town.

Falmouth

East Falmouth • Falmouth Village

North Falmouth • Teaticket 

West Falmouth • Woods Hole

The classic coastal town of Falmouth is the second largest town on Cape Cod after Barnstable. Falmouth was first settled by proprietors from the Hyannis settlement in 1661 and was officially incorporated in 1686, named after Falmouth, Cornwall, England. The town is comprised of six main villages: East Falmouth, Falmouth Village, North Falmouth, Teaticket, West Falmouth and Woods Hole—which is best known for its proximity to Martha’s Vineyard and the Woods Hole Oceanographic Institute. 

The Knob is quite possibly one of the most popular destinations for a scenic stroll on Cape Cod with views of New Bedford, the Canal, the Elizabeth Islands and breathtaking sunsets. Located in Woods Hole, the Knob was once property of the Carey family in the late 1870’s. The land was preserved by the family and then later repaired by Cornelia Carey, who added to the large boulders that protect the neck of the Knob. With her passing in 1973, she bestowed the land to the Salt Pond Areas Bird Sanctuaries, Inc., who now preserve and maintain the Knob to this day with the help of Quissett Harbor Preservation, Quissett Harbor House Land Trust and the local community. 

Located on Falmouth Main Street, The Quarterdeck Restaurant has been a popular local spot for over 40 years. What was once known as The Little New Yorker changed hands in 1967 becoming The Quarterdeck. The nautical themed interior comes from repurposed materials of MacDougall’s Boatyard in Falmouth Harbor; downstairs, artist Joe Downs created the charmed feeling of being below the deck of an old sailing vessel, establishing a dining atmosphere unlike any other. The Quarterdeck is currently open for lunch and dinner daily, offering call-ahead and walk-in service. 

In 1829, the first Nobska Lighthouse was built on Nobska Point by the U.S Government as a way to guide and warn ships at sea. The first lighthouse was originally built with wood, including the Keeper’s quarters, and in 1875 it was replaced with a 40-foot-tall cast iron lighthouse and a separate house for the lightkeeper; over the years, the lighthouse and property continued to be modified. The lighthouse was operated by the U.S. Lighthouse Service for 111 years, until 1937 when it was merged with the U.S. Coast Guard. In 2013, the last Commander moved out of Nobska and the town of Falmouth became the licensee of the property. In March of 2016, the town gave the Friends of Nobska Light the responsibility of restoration, maintenance, and operations as a museum. Since 2016, the Friends of Nobska Light have restored the lighthouse tower thanks to their many supporters and are currently working on the Keepers’ House. The Friends are also planning to create the Noska Light Maritime Museum in the hopes of the continuous education of the Cape’s rich maritime history. 

Mashpee

The town of Mashpee is most commonly known for its long history as a Wampanoag settlement. Today, Mashpee is the site of the tribal headquarters and home to most members of the Mashpee Wampanoag Tribe, who were recognized by the Federal Government as an official tribe in 2007 and maintain one of the largest concentrations of land ownership in Massachusetts. The town itself wasn’t officially incorporated until 1870 and is currently comprised of many summer homes, shopping centers and an abundance of restaurants, making Mashpee a hub for tourism, with a population that swells to almost 36,000 during the summer months. 

South Cape Beach State Park is a popular recreational spot in the town of Mashpee that sits between Waquoit Bay and Vineyard Sound. You’ll encounter 460 acres of picturesque sandy dunes and trails with one mile of white sandy beach. A popular spot for family activities, such as swimming, boating and fishing, the beach tends to get a lot of visitors who keep coming back each season and even locals who dare to walk the trails in the brisk winter months. 

Trevi Café and Wine Bar is a little Mediterranean restaurant at what feels like the heart of Mashpee Commons, with a Roman fountain replica demanding attention and a penny for a wish, among park benches surrounded by small welcoming storefronts. Trevi is a quaint, classy restaurant, perfect for a quick lunch while taking a break from shopping or for a relaxed night out with friends. Their wine menu is vast, perfect for pairing with each market inspired dish or, if you’re in the mood for a cocktail, they have quite a few specialties, like their Trevi Tini. 

The town of Mashpee is a popular tourist destination; in fact, the open-air shopping center, Mashpee Commons, remains one of the top year-round destinations on Cape Cod. The center first opened under the name New Seabury Shopping Center in the 1960’s and was home to a few small shops. The outdoor shopping center changed names in 1986 to what it is known as today, Mashpee Commons. The shopping center has majorly evolved over the years and currently houses over 100 businesses and 77 residential units, with an abundance of locally owned shops, restaurants and cafés. The Commons draws in tourists each year, as many must drive by its busy bustle as they make their way down Cape on Route 28. For many locals, Mashpee Commons evokes the feeling of being in a miniature city, an escape amongst a small coastal town that you could get lost in for hours. 

Mid-Cape: Barnstable • Yarmouth • Dennis

Barnstable

Cotuit • Marston Mills • Osterville

Hyannis • Centerville

Barnstable • West Barnstable

The Town of Barnstable was established in 1639 and may be categorized as the largest town on Cape Cod due population and size. But within this town lies seven quaint villages that encompass the quintessential feel of small-town life. These villages include Cotuit, Marstons Mills, Osterville, Centerville, Hyannis, Barnstable and West Barnstable. And if you didn’t think the concept of villages was already confusing enough, Hyannis holds two more “villages” with their very own zip codes, Hyannis Port and West Hyannis Port. Each village is what makes the town of Barnstable unique and their residents will emphatically tell you that their village is the best. 

With 101 acres of land and 2.5 miles of scenic trails, Long Pasture Wildlife Sanctuary on Bone Hill Road is one of the most beautiful places in Barnstable. The sanctuary offers live animal exhibits of local species, aquatic cruises, educational programs and much more. You can find different species of colorful butterflies around their Butterfly Mosaic trail and bees buzzing around in the observation hive. As you make your way down the trails, you’re greeted with a million-dollar view of Barnstable Harbor and Sandy Neck Light at Bone Hill Beach. At low tide, you can make your way miles out onto the flats, finding all sorts of little creatures the tide uncovers. 

In a little shop tucked away in Marstons Mills, you’ll find Chef Sigmund’s Chowder Co. and quite possibly the best chowder you’ve ever tasted. What started 50 years ago with Zygmunt Karolczak and a chowder recipe has since carried on with his son Jan Karolczak, who recently opened a small food store with his partner Karen Crosby in 2019. Karolczak is selling prepared gluten-free chowder, “A recipe that hasn’t changed” says Jan, and gluten free bisque base. Along the way, Jan has created a few other specialties that pair perfectly with Chef Sigmund’s chowder, like his spicy chorizo stuffed quahogs, crab cakes and much more. Make sure to stop by this local gem open Tuesday-Sunday!

Throughout the Cape’s history, there have been many famous figures who have called the Cape home, but the most mesmerizing has to be our 35th President, John F. Kennedy. President Kennedy and his wife Jacqueline Kennedy called the Cape home and used the salty shores of the Kennedy Compound in Hyannis Port as a base for his presidential campaign, a summer White House and, most importantly, a safe haven for their family. Today, the John F. Kennedy Hyannis Museum has forever memorialized President Kennedy’s life, legacy and love for Cape Cod with changing exhibits, interactive programs and more. 

Yarmouth

Yarmouth  •  West Yarmouth

South Yarmouth • Yarmouth Port

The town of Yarmouth was officially incorporated as part of the Plymouth Colony in 1639, making it the oldest town on Cape Cod, alongside the town of Sandwich. What was once a modest farming community, was transformed at the end of the 19th century into the popular summer resort town it is today. The town is comprised of four villages: South Yarmouth, West Yarmouth, Yarmouth and Yarmouth Port, and within each you’ll find beaches, hotels, seaside summer cottages and an abundance of miniature golf courses. 

Gray’s Beach in Yarmouth sits on the bay side of Cape Cod, making it one of the many spots in town to catch the perfect cotton candy sky at sunset. As you make your way down the boardwalk at Gray’s, you’ll find it’s extended over picturesque marshland, perfect for a scenic evening stroll or bird watching. The small sandy beach is the ideal spot for kids to enjoy building sandcastles and discovering the small critters that like to live near the marsh. You’ll even find a family friendly recreational area, with a spacious picnic area and a shady pavilion. 

Located just off the busy bustle of 6A sits the Old Yarmouth Inn, which has historically been serving the Cape since it opened as a wayside inn/stage stop in 1696. The Old Yarmouth Inn kept with the tradition of housing guests until 2007 when they officially closed housing and focused on their “contemporary Cape Cod cuisine.” The Inn is comprised of three main rooms, the traditional dining room, where they often host larger parties and their famous Sunday brunch pre-pandemic, the Red Room which is the oldest room at the inn, and the Tavern which draws guests in with its wood-burning stove and large wrap around bar. Today, the Inn is only serving dinner and doing takeout and recently added outdoor dining to their resume, as the town granted them the ability to host customers on their lawn. Owner Sheila FitzGerald is currently working on improving the outdoor dining space with larger than life umbrellas to cover their guests rain or shine. Somehow, even in these unprecedented times, the Old Yarmouth Inn maintains a warm and welcoming atmosphere that draws in locals and visitors alike reminiscent of the inn’s earliest of days.

Go back to Yarmouth’s roots (literally and physically), by visiting the Taylor-Bray Farm in Yarmouth Port. The Taylor-Bray Farm was once land inhabited by Native Americans, until the European Colonization and its first settlers made their way to Cape Cod. Among the first settlers were Richard and Ruth Taylor who made their home on what is today the Taylor-Bray Farm. In the late 19th century, the property took on new ownership with Willie and George Bray and passed ownership twice more. In 1987 the town of Yarmouth purchased the farm, recognizing its special history, with the goal of historic preservation and conversation. Today, the farm offers tours of the 18th century Taylor farmhouse with rotating displays of farm artifacts, friendly farm animals, and much more for the public to peek into the past.

Dennis

Dennis Port • Dennis Village • East Dennis

South Dennis • West Dennis

Originally a part of Yarmouth, which was established in 1639, and known as its East Precinct, the town of Dennis wasn’t officially incorporated until 1793. In the town’s earliest years, its settlers had to find an alternative to farming for a living due to the lack of land, so this coastal town turned to the sea. Shipbuilding became a thriving industry in Dennis, much accredited to Shiverick’s Shipyard and their clipper ships. Today the town is still drawing on its seaside charms to bring in tourists every season to its five quaint villages: Dennis Port, Dennis Village, East Dennis, South Dennis and West Dennis. 

Cold Storage Beach in East Dennis rests on the bay side of Cape Cod, making it the perfect beach to capture those quintessential Cape Cod golden hours. Sitting adjacent to the mouth of Sesuit Harbor, you’ll be able to watch the passing boats exiting the harbor; you’re likely to even spot the popular Lobster Roll boat as you stand and wave to its passengers on the jetty. You’ll often find friendly fishermen casting off the jetty, some whom have done so at that spot for years, beachgoers beachcombing in hopes of finding the perfect shell to take home as a token or children enjoying the shallow waters the large tide often brings. 

If you ever make it to Cold Storage Beach, you won’t want to miss the popular harborside seasonal restaurant on the other side of the mouth of Sesuit Harbor, Sesuit Harbor Café. With waterside outdoor dining at classic picnic tables, a raw bar, stunning sunset views and unrivaled lobster rolls that won Cape Cod Life’s Best of Lobster Rolls in 2020, this little seafood shack has locals and visitors alike coming back every season with lines out the door. 

At the top of Scargo Hill, the tallest hill on the mid-Cape, sits Scargo Tower, and an unbeatable view you don’t want to miss. The tower was originally built in 1874 using wood, then destroyed and rebuilt in 1900. It was destroyed and rebuilt for the third and final time in 1901 using the cobblestones we see today. As you ascend the spiral staircase up the 30 foot-high tower, you are greeted with a breathtaking vista. On a clear day, you can see all the way out to Provincetown in one direction and the Sagamore Bridge in the other.  

Lower Cape: Brewster • Harwich • Chatham • Orleans

Brewster

Nicknamed “The Sea Captain’s Town” for its prosperous captains in the 1800s, Brewster still emits the aura of its glory days of long ago. Its notable charm is centered around key sites: old captain’s mansions like the Crosby Mansion and The Cobb House, the Stony Brook Grist Mill, and the Windmill Village at Drummer Boy Park. Natural beauty and history unite here, with plenty of historic sites and miles of Brewster flats down the road.

In the 1800s, over 50 sea captains returned to shore, ecstatically building mansions for their families. Today, many are beautifully preserved inns for the public, like the Candleberry Inn, the Captain Freeman Inn, and Brewster by the Sea. The Stony Brook Grist Mill was once a hub of commerce, with the mill grinding corn, and the factory village creating shoes, furniture, and fabric. Such sites are beautifully preserved landmarks worthy of stopping by on your trip. In 2021, the town remains a quaint, beautiful getaway. For those looking for a New England retreat, a drive through Brewster will transport you back in time. 

The Brewster flats are the largest tidal flats in North America, covering 12,000 acres across a 10 mile stretch. Definitely check out the array of calm beaches to see the miles of shoreline unfold with the lowering tide. Crosby Landing is a fan favorite, especially for sunset. Make sure to time your visit with the tides; at its lowest point, the shore will reveal endless stretches of flats that are just waiting for their photo to be taken.

Located on Main Street in Brewster, Apt Cape Cod is a hidden gem for true food lovers. The entire menu is farm-to-table with locally sourced ingredients. Currently, it is open Friday through Sunday for dine in or takeout breakfast from 7am-1pm, as well as Friday and Saturday for takeout dinner from 4-7pm. The breakfast menu stays steady with classic favorites, while the evening chef’s tasting menu is weekly 3-course prix fixe. Apt Cape Cod has summer plans to enhance their outdoor space for a fine dining experience. “We’re trying to think outside the box and do something that’s unique. That’s why we change our tasting menus once a week—to keep it fresh,” says chef and owner Regina Felt Castellano.

For nature walks and a dive into history, The Museum of Natural History is definitely a don’t miss spot. The museum’s property has beautiful walking trails that stretch through salt marshes, to Wing Island, out to tidal pools, forests, and Stony Brook. Inside the museum, exhibits about the Cape’s natural history are informative and interactive for all ages. In the Marshview Room, enjoy the views of the marshes and watch the OspreyCam, a live view of the marsh’s osprey nest. Stop by with the family for a unique, immersive experience during your trip. 

Harwich

The expansive town of Harwich is bursting with things to do and sites to see. With four harbors, three of which are man made, several villages, acres of natural landscapes to explore, several cranberry bogs, and plenty of shops and restaurants, the town is full of culture and beauty. In the 1660s, Harwich thrived as a farming and fishing hub. In the 1800s, it became the first place in the world to harvest the cranberry for commercial sale. By the 20th century, three of its harbors, Wychmere, Allen, and Saquatucket were built, providing major maritime hubs. 

Today, the town’s villages are distinct areas of their own. Downtown Harwich Port continues to expand with bustling businesses and restaurants, truly coming alive in the summer with its outdoor bars and quaint shops. As a whole, Harwich’s population swells from around 12,000 year-round to 37,000 in the summer months. Its true character, beauty, and small business owners shine year-round. 

On Weston Woods Road in Harwich, the Cape Cod Lavender Farm has attracted thousands of visitors for the last 25 years. The farm is family owned and operated, with three generations currently tending to their peaceful crop. The farm is open from March through December for visitors to explore the grounds and the shop with a variety of their famous lavender products to calm your senses. Stop by between late June and mid-July for a stunning photo op at peak bloom. You will leave with beautiful photos, memories, and a true sense of ease.

Over in Harwich Center, a new year-round restaurant is creating lots of buzz. The Seal Pub & Cafe opened in February 2020 with a freshly renovated space and menu. Within a month, the pandemic hit and The Seal persevered, remaining open for breakfast takeout, and reopening the deck when permitted come June. Owners Bob Young, Josh Winston, and Mike Scott were influenced by time in California, New Orleans, and Cape Cod, which is reflected in their fresh menu. In the summer months, stop by for a bite after getting off the nearby bike path. In the cooler months, the deck is winterized with heaters for a cozy atmosphere. Their breakfast fare, the Seal’s signature, is offered starting at 6am daily, with pastries, freshly brewed coffee, and their fan-favorite breakfast sandwiches. “People discovered us this year, but it has been a year of perseverance. I’m excited for this season. We’ll have the flowers blooming again, and the deck is ready for some more good weather,” Young comments. The Seal Pub & Cafe is open daily at 6am for breakfast, lunch, and dinner.

Just past downtown Harwich Port, Bank Street Beach is tucked along Nantucket Sound, with its warmer water in the summer, perfect for swimming. One of the most popular beaches in town, Bank Street Beach is a lively destination. Watch as the many boats pass by and relax on its smooth sand. With stunning views of the Wychmere Beach Club to the left and beachfront homes tucked back behind the dunes, this spot feels like a luxury vacation. Just a short walk from the shops and restaurants downtown, Bank Street Beach is a perfectly placed, must-see destination

Chatham

In 1656, William Nickerson became the first English settler to live in Chatham. In the following years, his family grew, and more settlers followed. Though most early settlers were farmers, it became whaling and fishing that were central to developing the early economy. As the maritime industry grew, so did the population. By the late 19th century, cities were industrializing, but Chatham remained its rural, quiet self. Tourists began to buy summer homes, hotels sprung up, and by the 1930s Chatham was transforming into the tourism hub it is today. Today, the year-round population is around 6,000, growing to more than 25,000 in the summer. Dotted with stunning homes, a quaint downtown, as well as many historic sites, Chatham still attracts those looking to slow down and take in the charm of this quintessential seaside town.

Located on Bridge Street in Chatham, the Mitchell River Bridge is a scenic, historic wooden drawbridge originally constructed in 1858. The new bridge, finished in 2016, contains a piece of it’s predecessor, and is considered one of the last remaining wooden drawbridges in the country. Take a walk down from the Chatham Lighthouse to the bridge in the afternoon and witness the river and the bridge in its golden hour glory. The bridge is an unexpected historic treasure, surrounded by fishing shacks and the quiet river, and may become your new favorite scenic walk or drive. 

Pate’s Restaurant is making waves as a redefined classic Chatham restaurant. Executive Chef/Owner Anthony Silvestri translates his impressive global and local experience into his cuisine, offering an incredible menu with many locally sourced ingredients. The interior has a refined look as well, transforming into an upscale coastal environment perfect for special occasions. Since 1957, Pate’s has been a Cape Cod household name, and if you ask a longtime local, they will likely have fond memories visiting for birthdays or special outings. Today, Pate’s is continuing this legacy with a fresh twist, providing top-notch welcoming service, decadent cuisine, and a newly renovated space for an all-around incredible experience.

There is no shortage of beaches to walk along on the Cape. Harding’s Beach, however, offers a unique, peaceful experience that leads to the beautiful Stage Harbor Lighthouse. From the beach parking lot to the lighthouse is about a mile along the sand. Though not open to the public, the view of the lighthouse at the end of your walk makes it all worth it. In the evening, park at the beach at sunset for a panoramic view, whether you prefer to stay in the car or sit in the sand. One of the calmer beaches in Chatham, Harding’s is a great destination for the family.

Orleans

An artistic and charming haven, Orleans attracts a community of creative souls. Its collection of galleries, shops, and restaurants are all quaint, local treasures. Along the water, its history of maritime industry is evident. Originally a part of Eastham in 1644, Orleans was not incorporated as its own town until 1797. In its early years, the peaceful Nauset tribe taught settlers how to shellfish, which is still a large industry today. In the 1800s, salt-making was a large operation, with salt works located along the bay and used for domestic as well as fishing needs. 

Home to two of the Cape’s most popular beaches, Nauset and Skaket Beach, there is no shortage of sand for long summer days in the sun. The bike trail passes right through the center of Orleans, making it a perfect town to stop for refreshments or to explore. The walkable downtown has lots to discover, like boutiques, cafes, and restaurants. The heart of the Lower Cape, Orleans is a beloved year-round and summer destination.

One of the Cape’s most famous beaches, Nauset Beach is a ten-mile stretch along the Atlantic that offers views of wild, crashing waves, and stretches of white sand. For a more adventurous beach experience, look into acquiring an Over Sand Vehicle sticker to offroad on Nauset. An experience like no other, taking your car with loved ones offers a full-day of elevated experience in the sand. 

An Orleans favorite, La Bella Vita is home to fresh Italian cuisine and a warm year round ambiance. Their expansive deck with cafe lights is a perfect space in the summer or shoulder months, and indoors is equally as delightful. The deck is currently heated and ventilated for safe and comfortable dining. Be sure to check out their daily specials that range from creative cocktails, pizzas, and pastas. Their Theme Nights are an attractive signature, with specific specials from Monday through Thursday. 

Addison Art Gallery has a high reputation for personal service, community support, and integrity. For 25 years, the gallery has represented artists from across the Americas and France. Known for its unmatched collection of artists and its welcoming atmosphere, Addison Art Gallery is fondly known as many art lovers’ favorite place on the Cape. When traveling through Orleans, definitely make Addison Art Gallery a stop on your list any time of year.

Outer Cape: Eastham • Wellfleet • Truro • Provincetown

Eastham

Interestingly enough, Eastham is the only Cape Cod town founded by the Pilgrims. In 1644, seven men from Plymouth Colony were sent to explore Eastham as a possible new town center. Though the colony decided not to relocate, the seven men decided to stay and create a new town. Its early years consisted of shell fishing in the town’s harbors and salt making. In the 1800s, agriculture expanded, and Eastham exported grain, cranberries and asparagus on the railroad. Eastham has both bayside and Atlantic beaches and untouched land to explore, with 11 percent of the town a part of the Cape Cod National Seashore. Today, its unique businesses uphold the beauty and character of this age-old town. Eastham’s rural, natural charm continues to attract those looking to slow down and enjoy a quiet seaside landscape.

One of the most picturesque spots on the Cape, Fort Hill’s expansive, elevated views make it a stunning photo opportunity. It seems fitting that the Pilgrims favored it as their highest point of natural defense in Eastham, at the time called Nauset. In the 1600s, Governor Thomas Prence and Reverend Samuel Treat owned acres of this land. The Fort Hill Trail, a mile-long loop, offers a closer look at the scenery along the way. From the top, marvel at the sweeping view of the marshes and the shifting sands and tides.

With South African recipes that go back five generations, Karoo is a beloved Cape restaurant like no other. Chef and owner Sanette Groenewald has been serving her favorite dishes from her home in South Africa to the Cape for 18 years. Karoo offers a friendly, welcoming atmosphere with a distinct, flavorful menu. Right off of Route 6 in Eastham, be sure to stop by when they reopen for the 2021 season. Sit back on the deck or in the garden and enjoy authentic cuisine and warmer days to come.

Located on Cape Cod Bay in Eastham, First Encounter Beach is a spot of major historical significance, as well as panoramic views. Its name is representative of it being the site of the first encounter between the Pilgrims and Native Americans before the Pilgrims made their way to Plymouth. 400 years later, it is a beloved Cape beach. On a clear day, you can see from Brewster to Provincetown, and look across the bay to see Plymouth, the South Shore, and sometimes even Boston. 

Wellfleet

With two-thirds of its land mass protected by the Cape Cod National Seashore, Wellfleet is a peaceful place of wonder, offering a glimpse into the natural history and landscape of Cape Cod. With kettle ponds, salt marshes, woodlands, and the roaring waves along the Atlantic coastline, there are oases around every turn here. Between the Cape Cod National Seashore Headquarters and the Massachusetts Audubon Wildlife Sanctuary, this precious landscape is well cared for, with hopes for future generations to enjoy the region like we do today.

Originally part of Eastham, settlers in the 1650s discovered the opportunity for fish in Wellfleet Harbor. In the 1700s, the whaling industry rose and fell, bringing great wealth to the town. By the 20th century, shell fishing became Wellfleet’s bread and butter. Today, farming for and dining on the famous Wellfleet oysters remains a central part of life here.

Year-round, Wellfleet has around 3,500 residents, increasing to 17,000 in the summer. With plenty of shops, restaurants, and art galleries, whether tucked into the quaint downtown of the Central Village or scattered along the rural areas, Wellfleet is home to seemingly endless spots to explore.

To immerse yourself in an enchanted-like forest, look no further than the White Cedar Swamp trail. To access the start of the trail, head to the Marconi Station Area and follow the signs for the White Cedar Swamp. Follow the mile-long boardwalk trail that winds amidst an oak and pine forest and descends through the beautiful swamp. Following the entirety of the boardwalk will reveal a stunning photo op at every turn. The trail is a tranquil, unexpected addition to your Wellfleet itinerary.

A one-stop destination for rare books as well as waterfront casual dining, The Bookstore & Restaurant has been attracting returning visitors since 1964. Named after the bookstore in the back, Oceans of Books, The Bookstore is a unique waterfront property overlooking the Wellfleet Harbor with classic New England seafood favorites. Originally a clam shack, the restaurant is now under third-generation family ownership and continues to serve their classic dishes. Enjoy your meal in the cozy indoor bar, or out on one of the three decks. Definitely check out Oceans of Books, too, for an impressive collection of rare, new, and used books behind the restaurant. Afterwards, a stroll along the waterfront is always refreshing. For 2021, The Bookstore & Restaurant is hoping to reopen completely by mid-February or early March.

When it comes to iconic Cape restaurants, The Beachcomber is surely at the top of the list. Sitting atop the dunes of Cahoon Hollow Beach, this seafood bar is alive from morning until night in the warm summer months. Head down to the beach in the morning and come back up for refreshing food and drink to finish off your day. Definitely check out their apparel shops, one in the bar and another down the road, for their signature clothing. Originally a U.S. Lifesaving Station, the Beachcomber holds a whole lot of history and is the only truly oceanfront restaurant on Cape overlooking the Atlantic.

Truro

Incorporated in 1709, the town of Truro’s small population made a living farming and fishing, like its surrounding Cape towns. Its isolated landscape demanded hard work for its residents. In the 1800s, Truro men travelled to Nantucket to assist in the booming whaling industry. The construction of the railroad brought summer tourists, and soon, hotels were built throughout town. In the 20th century, Route 6 brought even more tourists looking for a seaside escape. Thanks to the National Seashore, two-thirds of the town’s land is protected, allowing its beloved natural environment to be savored and preserved. Though a quieter winter town, the summer months can see a population of 15,000 flocking to the near-tip of the Cape to enjoy its fresh air and expansive beaches.

In 1797, George Washington commissioned Highland Light Station as the 20th lighthouse in the United States. Highland Light was originally constructed as a wooden tower with a keeper’s house. The light was rebuilt as a stronger brick structure in 1831 and again in 1857. Highland Light has been a favorite spot on the Cape since its construction, and has been written about by Henry David Thoreau. In 1996, the light was moved back 450 feet from the cliff after a century of erosion. Stop by to take a snapshot of this landmark deeply rooted in history.

An authentic, unmatched Italian restaurant in Truro, Montano’s has been serving fresh, homemade pasta since 1988. Owner and chef Bob Montano began Montano’s at 26 years old and is entering his 34th season, continuing to serve the community traditional Italian delights. “We make everything from scratch and we cook it all to order. I make fresh pasta every day. We use the authentic bronze die, which allows the sauce to cling to pasta, and semolina flour to give great flavor,” Montano says. From fan-favorites like chicken and veal parmesan to signature dishes like goat cheese gnocchi wild boar ragù, everything on the menu is made from scratch. Don’t forget to indulge in dessert, like their key lime pie or tiramisu. Montano’s is open year-round daily at 4:30pm.

For wine lovers, history buffs, or simply those who love to unwind in nature, Truro Vineyards is a perfect spot to visit on the Outer Cape. Open since 2007, the owners, the Roberts family, moved into this 200-year-old farm and turned it into a successful vineyard, mastering the wine making process in this region. Open on weekends from 12-5pm for outdoor seating in the off season, their quaint, historic grounds offer a scenic weekend activity complete with cozy firepits and heaters. Food trucks are often featured from local favorites like Pizza Barbone and Blackfish Restaurant’s Crush Pad Food Truck, serving savory treats to pair with your wine.

Provincetown

In 1620, those aboard the Mayflower landed at the tip of Cape Cod in what would become Provincetown and signed the Mayflower Compact before continuing onto Plymouth. Centuries later, Provincetown witnessed distinct eras. In the 1800s, it flourished as a whaling center, becoming the wealthiest town in the state. The 1900s saw the beginnings of tourism and Provincetown as a bustling art colony. Writers, artists, and actors settled here, establishing Provincetown as an artistic haven. Today, Provincetown is a lively, artistic center and LGBTQ+ destination. From the excitement on Commercial Street to the boutique inns, its iconic restaurants, art galleries, and stunning beaches, there is something for everyone here.

In 2020, the pandemic called for the adjustment of the commemoration of the 400th anniversary of the Mayflower’s arrival and the meeting of the Pilgrims and the Wampanoag. This past October, the Pilgrim Monument’s Provincetown 400 Virtual Gala was a smashing success, raising funds to support the monument’s mission to continue sharing this history in an inclusive, truthful manner.

Located at the very tip of Cape Cod, Race Point Beach offers views of the Atlantic and one of the best sunset experiences on the Cape. The dunes and sand stretch far for plenty of space to enjoy the beach. The bike trails begin off of the parking lot, making this a wonderful finish line for the end of your ride. Race Point Beach is the site of the Old Harbor Life Saving Station, now a public museum open seasonally. Built in 1872 to save those in the surrounding dangerous waters, the station was manned by brave volunteers. It was operational until 1915 and was later transformed into a museum in the 1970s. Stop by to discover more about this fascinating history.

On Commercial Street, Patio American Grill serves fresh New England cuisine with a modern twist. Check it out for lunch or dinner and enjoy a delicious meal and one of their creative cocktails. Dine indoors or amidst the bustle of downtown on the outdoor patio, adorned with colorful pillows and outdoor cushions. A favorite seasonal spot, make sure to try it in the warmer months for a luxurious experience.

For an off-road adventure, look no further than Art’s Dune Tours, a classic Cape Cod experience since 1946. The business was started by Art Costa with a 1936 Ford Woody, and is today carried on by his son, Rob. From March through mid-November, Art’s Dune Tours offers one-hour daily tours, two-hour sunset tours, and “Dune and Water” tours- combining your dune tour with kayaking, sailing, charter fishing, or speed boating. With such a history and care for this landscape, Art’s Dune Tours is a one-of-a-kind experience through Provincetown’s protected dunes within the Cape Cod National Seashore. 

Martha’s Vineyard

The charming island of Martha’s Vineyard sits just seven miles off the coast of the Cape. Named by Bartholomew Gosnold in 1602, the island was originally home to the indigeneous Wampanoag who called the land Noepe, meaning, “land between the waters.” Today, the year-round population is around 17,000 with the island’s population swelling to to almost 200,000 as seasonal visitors hope to catch a glimpse of its beauty. The Vineyard is home to six towns including Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark and Aquinnah, each with their own individual charm, but most commonly known for their colorful gingerbread architecture, waterside activities and grand vistas; warranting the vineyard’s notoriety as a must visit summer destination. 

Driving down Beach Road to Edgartown, you’ll often come across the joyful screams of kids jumping from Jaws Bridge. Most commonly known for its appearance in the 1975 classic film, “Jaws,” the bridge serves as a common photo stop for those visiting the island. Although the fictional shark made its way under the bridge and out to sea, today the sea is far more benign. 

Bad Martha Farmer’s Brewery opened their doors in 2014 and has become a seasonal staple of the vineyard serving freshly crafted beer in a setting of flowers, native grasses and the island’s salty air. The barn that sits on the Donaroma’s Nursey property in Edgartown was designed by renowned architect Patrick Ahearn, and built by Rosbeck Builders with the help of three Amish men enlisted for the job. Their beer is brewed with grape leaves from the island and the brewery features a seven-barrel brewing system, but most of their beer is brewed at Mercury Brewing in Ipswich, a partnership that came back in 2013 as Bad Martha’s founders Jonathan Blum and Peter Rosbeck were making their dream come to fruition, while also doing a little bit of good, donating their first portion of profits to a local hunger relief and giving back to the community that has given so much to Bad Martha’s. 

Alpacas: not something immediately associated with Martha’s Vineyard. In fact, there is a small farm that hosts a herd of over 50 colorful Huacaya alpacas. The Island Alpaca Company in Oaks Bluffs started in 2004 with 19 acres of land and just eight alpacas. The farm has since grown and continues their care and breeding of alpacas, while producing high-quality fleece and soft alpaca products available in their gift shop. Island Alpaca Company strives to educate the community about these friendly animals through events, like Island Alpaca Yoga, Shearing Day, Alpaca-Grams and much more. In the future be sure to check their website for any upcoming events or simply plan a visit for the day, the farm encourages all to come and encounter these fluffy friends! 

Nantucket

Thirty miles out to sea, a quaint island community thrives with the legacy of its past woven into its character. From a prospering whaling community to an art colony and then a charming resort community, Nantucket has seen history unfold. In the 1800s, once the busiest whaling port in the world, whalers left their wives and children for years at a time, hoping to come back with extreme wealth. Many of the captains’ mansions around the downtown are results of their adventures. In the 1920s, artists arrived, gathering in cottages around the waterfront to live and create. Today, the island is a little oasis for visitors from around the world. A community of 11,000 year-round residents swells to more than 50,000 in the summer.

When arriving at the beginning of Main Street on Nantucket, the compass rose mural stands as a historic welcoming point, situating this small island within the rest of the world. In the 1930s, H. Marshall Gardiner, owner of Gardiner’s Corner, created the mural on the side of his store to showcase Nantucket’s whaling history and its connection to far corners of the globe where whalers once traveled. The building is now Ralph Lauren’s Nantucket location, and in recent years Ralph Lauren and the Nantucket Historical Association teamed up to restore the mural. Stop by for a photo in front of the mural, a classic landmark demonstrating the local care for the island and its captivating history.

At 1 Main Street, The Club Car is an antique railcar transformed into an innovative restaurant with an incredible ambiance. In 2020, The Club Car introduced a summer Mexican-inspired menu made with local ingredients. A fun take for an unpredictable summer, the restaurant offered a beachy atmosphere and a fresh menu while taking COVID-19 precautions seriously. Whether you were dining inside coastal space or outdoors on the beautiful patio, The Club Car offered customers a fresh beacon of light in the 2020 season.

Also on Main Street, The Lemon Press is an organic cafe serving up coffee and wholesome breakfast offerings. From their avocado toasts to refreshing smoothies, coffees, and breakfast sandwiches, everything is made to start your day off right. Seasonally, Lemon Press offers cocktails and small plates in the evening. Call ahead for their innovative catering boxes, a collection of perfectly portioned bites for a small group to take to the beach or enjoy at home.