Brewster

Brewster, East Brewster, West Brewster

Paines Creek by Judith Keneman

In search of a community with a remarkable history, a one-of-a-kind topography, countless seaside activities, and fine dining to boot? Brewster is that place!

Situated along Cape Cod Bay, Brewster has always been tied to the sea, and over the years many sea captains have made their homes here. Visitors can explore many of these grand residences, including the lovely Crosby Mansion and the Captain Freeman Inn, and The Brewster Historical Society hosts a regular bus tour—A Sea Captain’s Tour of Brewster—which visits several of the homes. The Cape Cod Museum of Natural History is another great spot to appreciate local history, with a blend of nature. Museumgoers can browse wildlife exhibits, attend workshops, and enjoy a nature walk through 400 acres of conservation land.

Topographically speaking, Long Pond, which Brewster shares with Harwich, is Cape Cod’s largest freshwater pond and it’s a popular swimming hole. Along the bay, the Brewster Flats are a magnificent natural attraction, particularly at low tide. The salt flats can stretch for up to two miles off the beaches, creating endless tidal pools filled with marine treasures. Beaches including Paines Creek, Crosby Landing, and Breakwater are also known for their sunsets.

Brewster also has much to offer in terms of activities. First, the Cape Cod Rail Trail, which cuts through Brewster’s Nickerson State Park, features 22 miles of paved trails from Dennis to Wellfleet. Next SUPfari Adventures Cape Cod offers paddleboard rentals and lessons at Brewster ponds including Long, Sheep, and Upper Mill. The Cape Rep Theatre delivers performances for children in its outdoor theater in summer, and dramatic plays (for general audiences) in the indoor theater, from May through December. Additional attractions around town include Drummer Boy Park, the Brewster General Store, and the Stony Brook Grist Mill.

Getting hungry? Eat Cake 4 Breakfast—it’s a bakery!—sells homemade macaroons and other sweet creations early in the day, while the Brewster Fish House offers seafood specialties including a heartwarming fish chowder. Just down the road, fine French dining is always on the menu at the elegant Chillingsworth Restaurant on Route 6A, and The Woodshed is a comfortable spot for live music, drinks, and dancing.

Looking for a place to stay?

Enjoy comfort and luxury in a sea captain’s home

Centrally located on historic Route 6A in Brewster, the Sea Meadow Inn allows guests the opportunity to enjoy casual luxury following a day of exploring nearby beaches, restaurants, and shops. Formerly known as the Isaiah Clark House, the renovated c. 1780 sea captain’s residence offers attractive guest rooms—each named after a Clark family member—with hardwood floors and nautical accents. Outside, the inn has acres of manicured lawns and gardens.

Guests can also enjoy another bonus: the attention and care of Debbie Adams, who has managed the inn for owner Nancy Garran since 2013. Adams began innkeeping following her daughter’s college graduation in 2011. “I had asked myself, ‘What do I love?’” she recalls. “I made a list. … I Googled the things on my list and came up with innkeeping for a profession.”

Like many others, Adams followed her passion to Cape Cod. “I love making people feel welcome,” she says. “Guests tell me that they feel right at home here, and that’s my goal.”

Sea Meadow Inn

1187 Route 6A, Brewster

508-896-2223 • seameadowinn.com

Harwich

Pleasant Lake, West Harwich, East Harwich, Harwich Port, Harwich Center, North Harwich, South Harwich

Herring River by Sandy Dimke

Harwich is a community of numerous blessings. The town has seven villages, multiple swimmable ponds and lakes, three harbors, and two A-plus ice cream shops with the word “School” in their names.

The three harbors—Allen, Wychmere, and Saquatucket—each lead out to Nantucket Sound, and offer convenient inlets for boating and fishing. The scenery is fantastic too. Departing from Saquatucket Harbor, Monomoy Island Excursions leads cruises to the waters off Chatham to view lighthouses and seals.

For on-land exploration, the Cape Cod Rail Trail runs through town, en route from Dennis to Brewster, and is perfect for a walk or bike ride. One can also turn onto the Old Colony Rail Trail, which travels east to downtown Chatham. The Harwich Conservation Trust maintains multiple land parcels around town with walking trails of varying length, and the Cape Cod Lavender Farm at Weston Woods Road is an aromatic area to explore; visitors can wander the grounds and browse lavender soaps, candles, and other goods in the gift shop.

No visit to Harwich would be complete without a tour along Route 28. The roadway features a variety of shops, restaurants, and attractions. Some of these include the Harwich Antique Center to browse relics and treasures from the past; Schoolhouse Ice Cream, which serves up generous helpings of Irish whiskey, mud pie, and other homemade creations; and Brax Landing, a restaurant known for its Sunday brunches and lobster rolls.

Other dining favorites in Harwich include Buca’s Tuscan Roadhouse, which boasts an impressive wine menu and a fresh Cape Cod take on Italian cuisine. The Wequassett Resort & Golf Club is always an impressive experience, whether you’re savoring cocktails by the pool, or fancier fare in the elegant Twenty-Eight Atlantic. Top off your meal with another cone—this time at Sundae School in Harwichport, which serves thick frappes, and sundae flavors including hot fudge, butterscotch, and fresh blueberry.

Other Harwich highlights? The Cape Cod Theatre Company performs regular family-friendly shows, and Dr. Gravity’s Kite Store & Emporium sells kites, skim boards, and other colorful creations for the beach.

Looking for a place to stay?

Relax in town, or lounge by the beach

With two distinct properties to choose from, guests of the Winstead Inn & Beach Resort can relax in quaint but elegant settings either in Harwich Center or overlooking the beach in Harwich Port.

Open year round, the Winstead Village Inn offers 15 rooms and suites with nautical names such as the Mariner’s Hideaway and the Admiral’s Suite. Guests can relax in the seasonally heated outdoor pool or stroll to nearby Brooks Free Library or Whitehouse Field, home of the Cape Cod Baseball League’s Harwich Mariners. “We have so many people return to the inn year after year,” says general manager Doug Heywood. “We have seen the next generation of our guests grow up!”

Guests can also choose to stay at The Beach House, a cozy resort in Harwich Port with a private beach overlooking Nantucket Sound. There are 14 guest rooms, and a covered deck with rocking chairs and tables is just a step from the sand. A private shuttle is available to transport Village Inn guests to the beach.

Winstead Inn & Beach Resort

116 Parallel Street, Harwich

508-432-4444 • winsteadinn.com

Chatham

Chatham, North Chatham, South Chatham, West Chatham

Lighthouse Beach by Kathryn Scott

Located at the Cape’s southeastern tip, Chatham is a classy community known for its shopping and seafood, and recreation along the water.

Great for walking, browsing, and dining, Chatham’s Main Street offers a variety of clothing stores and gift shops, cafes and restaurants. The downtown area’s collection of art galleries is impressive, and art-lovers are sure to find inspiration in the many works on display at Chatham Fine Art, Struna Galleries, and The Artful Hand. One can also sign up for a class at the Creative Arts Center on nearby Crowell Road, or enjoy art of a different medium at the Chatham Orpheum, which screens first-run films—and Jaws every summer.

The Chatham Pier Fish Market on Shore Road is known as much for its chowder and lobster rolls as it is for the visitor experience. Each afternoon, fishermen return to the pier with the day’s catch, and they are often followed by a flotilla of curious seals—it’s quite a sight. The Fisherman’s Monument at the pier is a symbol of the community’s vibrant fishing industry.

For more great seafood, order some shellfish by the dozen at The Impudent Oyster, or stop by Bluefins for custom sushi rolls like the Tiger Eye or the Cape Cod Monster. With three unique restaurants, the Chatham Bars Inn offers everything from appetizers to fine dining—and sunset clambakes on the beach. Known for its mouthwatering pizza, Del Mar is another prime option.

For sightseeing, the Chatham Lighthouse is always a popular spot, offering spectacular views overlooking Chatham Harbor and the Atlantic. The light still functions, and is operated today by the U.S. Coast Guard. Down a flight of stairs, visitors can stroll along Lighthouse Beach, which features a strong surf, soft sand, and more seal-viewing opportunities. For a gentler swim—and food trucks in summer—Hardings Beach is great option for families. To enjoy a different view of the town, Outermost Harbor Marine rents kayaks and paddleboards, hosts fishing charters, and leads birding and wildlife tours. There’s so much to do in Chatham: First get here, then get out there and explore!

Looking for a place to stay?

History, elegance, and service with a smile

After living on Nantucket for 34 years, Andrea and David Smith made their way across the Sound and purchased the Chatham Gables Inn in 2012. “I’ve always been immersed in the hospitality industry,” Andrea says. “We dreamed about owning an inn for 10 years, and we finally decided to take the plunge.”

The inn, which dates to 1839, features many elegant touches. The eight well-appointed guest rooms are named for Nantucket locales—such as Madaket, Surfside, and Cisco—and boast hardwood floors, antique furnishings, Turkish towels, and beds dressed in Italian linens.

The property also features calming gardens filled with hydrangeas, hollyhocks, and birds singing in 200-year-old trees. The inn is located just a short walk to the beach as well as shopping and dining on Main Street. Andrea says she and David love to meet people, and make them feel welcome and relaxed. “Our guests,” she adds, “say that time stands still here.”

Chatham Gables Inn

364 Old Harbor Road, Chatham

508-945-5859 • chathamgablesinn.com

Orleans

East Orleans, Orleans, South Orleans

With coastline along both the Atlantic and Cape Cod Bay, the town of Orleans offers spectacular natural scenery, and the community prides itself as a mecca for art and culture. Orleans also has a fascinating history that’s tied inextricably to the sea.

For visitors, a good starting point is Nauset Beach, which extends for miles along the Atlantic-facing coast. The sand is smooth, and the beach is spacious so sunbathers can spread out and walkers can amble to their heart’s content. The strong waves make Nauset great for surfing, and those interested can find gear, clothing, and lessons at Pump House Surf Shop. On the other side of town, Skaket Beach attracts many beachgoers traveling with children due to its calm waters and tide pools. It’s a great spot for weddings, and some argue Skaket Beach has the best sunsets on Cape Cod. The view from Rock Harbor is similarly stunning.

Many artists gain inspiration from Orleans’ scenic vistas, and their works are on display at Tree’s Place, Gallery 31 Fine Art, Addison, and other galleries in town. On Saturdays in summer, several galleries host extended hours so visitors can meet the artists. Looking for a laugh, or some drama? The Academy of Performing Arts Playhouse hosts at least 12 shows per year including dramas, comedies, and musicals.

History buffs flock to many sites in Orleans, including the Jonathan Young Windmill, which dates back to 1720, but occupied two other locations before arriving at its current home next to Town Cove. Tours are held on select dates in summer. Next door, one can’t miss the Orleans Waterfront Inn, an enchanting six-story hotel that reportedly has a ghost or two in residence. Finally, The French Cable Station Museum has exhibits on “Le Direct,” the underwater cable through which communications were sent between the U.S. and France from 1898 to 1959.

After these adventures, consider heading to Mahoney’s Atlantic Bar & Grill for tasty dishes like blackened tuna sashimi or Portuguese bouillabaisse. Another popular spot is the Old Jailhouse Tavern; the building itself has an arresting history, and the tavern is known for its Cape Cod Reuben and other pub fare.

Looking for a place to stay?

This inn has its own love story

What many might not know about the Ship’s Knees Inn is that the property is where one local romance began. In 1970, William Butcher purchased the inn, and soon after, his teenage son Peter met Denise Carlson, a young summer resident who was staying in a seasonal dormitory on site. “That was when the love story began for my wife and I,” Peter Butcher recalls. Today, Peter and Denise run the inn together.

A landmark in East Orleans, the inn was built c. 1820 as a home for Captain Freeman Snow. Today, the main house and barn, both completely restored, offer 16 rooms, a suite, and an apartment with an ocean view. Popular summertime activities include lounging by the pool and relaxing on the patio and by the fire pit. Open from April 1 to January 2, the inn also has Adirondack chairs and hammocks, and is

just minutes from Nauset Beach.

An accomplished cook, Denise is always finding new ways to prepare familiar breakfast favorites including savory soufflés and creative wraps. “Guests swoon over Denise’s breakfasts,” Peter says.

Ship’s Knees Inn

186 Beach Road, East Orleans

508-255-1312 • shipskneesinn.com

~Marina Davalos, Ashley Owen