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Cuttyhunk

The Perfect Day in Cuttyhunk

Even further removed from the outside world than Cape Cod, Cuttyhunk and its famous isolated beauty is the perfect place for, to borrow a line from David Foster Wallace, “Getting away from being pretty much away from it all.”

Cuttyhunk

Morning

If Cape Cod seems far from the mainland, then Cuttyhunk Island will seem like the ends of the earth. Anchored at the southern tip of the Elizabeth Islands, just 14 miles off Woods Hole, the island is the epitome of a quiet getaway. Most of the visitors arrive on the MV Cuttyhunk from New Bedford, or pull up on their own vessel. A morning stroll on nearby Barges Beach is a great way to begin enjoying the tranquil nature of the island. Just up the road from the ferry dock, the Cuttyhunk Fishing Club (508-992-5585) has outdoor seating for breakfast overlooking Vineyard Sound.

Afternoon

Simply known as The Island Market, this tiny general store is the one-stop-shop on the island for everything from cosmetics to groceries. A small deli counter serves up over-stuffed sandwiches that are perfect for taking down to Church’s Beach for an afternoon picnic. The island is a mecca for fishing, which makes surfcasting a pleasant way to relax over lunch. Keep in mind, however, that Cuttyhunk is a dry island. So, if you’re looking for a nice summer ale to accompany lunch, you’ll have to bring it in your luggage.

Cuttyhunk

Evening

For a brief period in the evenings, between 5:30 p.m. and to 8 p.m., Soprano’s (508-992-7530) offers crispy oven-cooked pizza and fresh seafood. Just past the Corner Store (508-784-7167) and Sea Girl Gifts (508-990-9820) retail shops, visitors can buy shellfish, chowder, fish, lobsters, ice cream, and occasionally barbecued sandwiches down at the Fish Dock . Those spending the night, or at least not catching the departing ferry, should walk up Lookout Hill for unparalleled sunset views. Once the sun has gone down, viewers can see lights from Rhode Island to Martha’s Vineyard.

Annual 2013 Event

Fourth of July Golf Cart Parade
July 4, 2013
More info: www.cuttyhunk.net

Nantucket

The Perfect Day in Nantucket

An island shrouded in romance, Nantucket is like a snapshot of America’s past. Handsome whaling captains’ homes along cobblestone streets make up much of the historic downtown, which also offers sophisticated shopping and excellent dining.

Nantucket

Morning

Many of Nantucket’s most sought-after sites are in the world-famous village right off the ferry. However, on the easternmost side of the island lies the quaint village of Siasconset, or ‘Sconset to some, where the Sconset Café (508-257-4008) serves up unmatched breakfast fare. As with most things on the island, the food here is unique. Before heading back to town, check out the Sconset Bluff Walk. A short path off Front Street runs between the ocean and stately grey-shingled homes. You will see some beautiful gardens, and if you’re there at the right time of year, the scent of roses spilling over doorways and rooftops is delightful.

Afternoon

Back in the village, the soups and sandwiches at Fog Island Café (508-228-1818) just off Main Street provide all the energy you need to explore every nook and cranny of the island. There is plenty of fine shopping here as well as superb art galleries like the Gallery at Four India (508-228-8509). A short walk out of town takes you to Jetties Beach, where beautiful specimens wash ashore.

Nantucket

Evening

Off the beaten path on Bartlett Farm Road, Cisco Brewers (508-325-5929) is the best place to spend an afternoon sharing a few cold drinks. As the name suggests, American Seasons (508-227-7111) offers up an ever-changing menu filled with creative meals and cool cocktails. And if you decide to stay over night, the elegant Union Street Inn (888-517-0707) is a fine choice, as is the recently redone and charming Centerboard Inn (508-228-9696).

Annual 2013 Event

Nantucket Wine Festival
May 15–19
More info: www.nantucketwinefestival.com
Nantucket

Martha’s Vineyard

The Perfect Day in Martha's Vineyard

Comprising six unique towns—Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah—Martha’s Vineyard is an island oasis offering charming communities, rolling meadows, world-famous beaches—and art and culture galore.

Martha's Vineyard

Aquinnah • Chilmark • Edgartown • Oak Bluffs • West Tisbury • Vineyard Haven

Morning

Most day-trippers arrive on Martha’s Vineyard via ferries that dock in Vineyard Haven, Edgartown, or Oak Bluffs. If you take the ferry to Vineyard Haven, the Black Dog Tavern (508-693-9223) is just a block away and has some great breakfasts on the menu, including 27 different egg dishes, half a dozen bakery items, and homemade granola pancakes. You may want to walk off your breakfast on Main Street with dozens of retail shops offering unique finds from jewelry to fashion and coastal treasures. From there, hop on a Vineyard Transit Authority (VTA) shuttle to Edgartown and stop at the Felix Neck Wildlife Sanctuary (508-627-4850) stop. Six miles of trails run through woodlands, meadows, beaches, and salt marshes.

Afternoon

After exploring Felix Neck, get back on the VTA and head for Edgartown and the upper deck of the Seafood Shanty (508-627-8622), which offers great views of the harbor, delicious Bloody Marys, and quintessential fresh seafood fare. There are also tasty sushi choices here. Sharky’s Cantina (508-627-6565) boasts a massive menu chock full of great Mexican food at unbeatable prices. Catch another bus from Church Street to South (Katama) Beach, one of the most beautiful public beaches on the island.

Martha's Vineyard

Evening

Before catching a ferry home make your way to Oak Bluffs for dinner at Nancy’s (508-693-0006). Nancy’s Snack Bar on the first floor is a family favorite with great views of the harbor and a casual, affordable menu, while the second-floor Nancy’s Restaurant offers finer dining, a full bar, and outdoor patio. Families traveling with children can’t miss a ride on Oak Bluffs’ vintage Flying Horses Carousel (508-693-9481). Adults can enjoy a romantic, delicious dinner at The Sweet Life (508-696-0200), which also has an impressive wine list. After dinner, take in a live performance from one of many national music acts at Dreamland (508-560-1932).

Annual 2013 Event

WMVY Big Chili Contest
January 26, 2013
More info: www.mvyradio.com
Martha's Vineyard

Provincetown

The Perfect Day in Provincetown

On the very tip of Cape Cod, artists of all kinds, fishermen, refugees from the city, and a large alternative lifestyle community come together in Provincetown to create a marvelous, multi-cultural coastal community that is open to all.

Provincetown

Morning

Waterfront dining is always a good way to start the day. Bayside Betsy’s (508-487-6566) has all the usual breakfast finds, including eggs, pancakes, cereal, granola, even stuffed potato skins or steak and eggs. The first—and indeed only––building comprising the Provincetown skyline is the Pilgrim Monument (508-487-1310), and the 252-foot climb is well worth the view. The accompanying museum commemorates the people and events that have turned P’town into a world-famous destination.

Afternoon

Bubala’s By the Bay (508-487-0773) has a cheerful look and feel all its own. There are plenty of seafood options on the menu along with items like Jamaican jerk chicken sandwiches and barbecued spareribs. Stop in at any of the town’s great art galleries, or visit the Provincetown Art Association and Museum (508-487-1750). Take in the dramatic whitecaps at Race Point Beach, or enjoy more natural wonders by visiting the Provincetown Center for Coastal Studies (508-487-3622) or going on a whale watch with the Dolphin Fleet (508-240-3636).

Provincetown

Evening

Head out for the night in a fun P’town pedicab. For great eats, the Lobster Pot (508-487-0842) is a town landmark known for its seafood. The exterior is lit up with a landmark neon sign, a subject of many Cape paintings. For theatre, live music, restaurants, shops, and some of the best people watching around, Commercial Street has it all. Many hot spots on this lively main drag through town stay open past midnight during the summer, a rare pleasure on Cape Cod.

Annual 2013 Event

Lighting of the Monument
November 26, 2013
More info: www.ptownchamber.com
Provincetown

Truro

The Perfect Day in Truro

Truro undergoes one of the biggest summer swells on Cape Cod. This tranquil seaside town of 2,000 during the off-season expands tenfold to accommodate happy visitors looking for rest and relaxation along quiet wooded lanes and on the sands of stunning beaches.

Truro

Truro • North Truro • South Truro

Morning

Breathe in fresh ocean air on the outdoor patio at the Top Mast Café (508-487-2099) over a hearty, home-cooked breakfast. Located just steps from the sea, the café dishes out super breakfasts. Further down Route 6A, Pond Village Beach is a sleepy little beach perfect for soaking up some morning sun without the hustle and bustle of large crowds. Anglers can often be seen surfcasting, hoping for their next big catch.

Afternoon

Wine aficionados and amateurs alike are in for a pleasant afternoon at Truro Vineyards (508-487-6200). Tastings are held every half hour in the outdoor pavilion where visitors can sample several different wines. Two complimentary tours of the vineyard are held daily from Memorial Day to Columbus Day weekend. Keep the Mediterranean flare going at Montano’s (508-487-2026), where you can find delicious Italian cuisine—the pasta and home-baked bread here are scrumptious. For a fine picnic spot, head to the Pamet River.

Truro

Evening

High atop the Truro dunes sits the Highland Museum and Lighthouse (508-487-3397). The perch at the top rewards climbers with views of both the Atlantic Ocean and Cape Cod Bay, while the museum tells the story of the town’s earliest residents. For great seafood, stop in to Moby Dick’s (508-349-9795). Truly delicious pizza can be hard to come by outside of major cities, but the brick oven pizzas at Sweet Escapes & Savory Pizza Grill (508-487-2225) never disappoint. Leave room for the homemade ice cream.

Annual 2013 Event

Agricultural Fair
September 1, 2013
More info: www.truroagfair.com
Truro

Wellfleet

The Perfect Day in Wellfleet

Art and nature go hand in hand in Wellfleet. Main Street and Commercial Street are dotted with fine art galleries, often containing works inspired by the town’s National Seashore and Wellfleet Bay Audubon Wildlife Sanctuary attractions.

Wellfleet

Morning

Route 6A is the main vein running through Wellfleet. Once you spot Van Rensselaer’s (508-349-2127), look no further for a great meal. The breakfast menu includes eggs any way you can imagine, waffles, pancakes, French toast, sandwiches, and more. For a preview of Wellfeet’s abundant natural glories, stop into the Wellfleet Bay Wildlife Sanctuary (508-349-2615), one of the liveliest places on Cape Cod to see the local fauna. Listen to songbirds along the five miles of trails and check out the nature center’s two 700-gallon aquariums for a closer look at the sanctuary’s marine life.

Afternoon

The rolling seas, sweeping dunes, and soft sands of Newcomb Hollow Beach compose the quintessential Cape Cod landscape. Catch up on summer reading, watch for bobbing seals, walk miles of pristine coastline, or relax and do nothing at all – whatever you choose, you’ll be satisfied with a day spent here. If you need a break from the sun and surf, walk up the dune to the famous Beachcomber (508-349-6055). Many of the seafood options make a short trip from surrounding waters before appearing on your plate, and the grill options are plentiful.

Wellfleet

Evening

Dine in a historic captain’s home at Winslow’s Tavern (508-349-6450). Spacious patio seating and elegant indoor dining rooms are the perfect venues for enjoying classic seafood fare prepared with unique twists. The broad wine list is enough to make any sommelier jealous. Take the time to enjoy a disappearing American pastime at the retro Wellfleet Drive-In Theatre (508-349-7176). Double features are shown all summer long and make for an unforgettable family evening.

Annual 2013 Event

Wellfleet OysterFest
October 19–20, 2013
More info: www.wellfleetoysterfest.org
Wellfleet

Eastham

The Perfect Day in Eastham

Eastham is the first Cape Cod National Seashore stop. It was here, beside Coast Guard Beach, where Henry Beston wrote the American classic, The Outermost House. The quiet, breathtaking landscape of Eastham has inspired artists and nature-lovers for generations.

Eastham

Morning

Laura and Tony’s Kitchen (508-240-6096) was once described by famed foodie Rachel Ray as one of Cape Cod’s best-kept secrets. The food here is homemade, fresh, and creative—the cinnamon rolls are a breakfast favorite, and a Bloody Mary or a Mimosa is just $3. After starting off your day with such sinfully good treats (and a few extra calories), head for 22 miles of open roads along the Cape Cod Rail Trail. The paved roads are perfect for cyclists, and the wide shoulder along the side makes for great walking or horseback riding.

Afternoon

Now a Cape-wide franchise, the original Box Lunch (508-255-0799) on Briar Lane has been serving up tasty rolled-up sandwiches since 1977. With a menu whose size rivals that of any full-on restaurant, the roll-ups can satisfy diners of all palates. As the name implies, the food here is perfect for take out (the lobster roll is a good choice) and can be enjoyed at a picnic along the spectacular Cape Cod National Seashore (508-771-2144). Start off your visit with a trip to the Salt Pond Visitor Center to learn about the fascinating history and panoramic scope of this precious natural resource.

Eastham

Evening

With a raw bar, Richardson’s ice cream, and a mini-golf course on top of a sprawling seafood shack menu, award-winning Arnold’s Lobster & Clam Bar (508-255-2575) offers everything you need for a true Cape Cod meal. Once the crowds have moved on for the evening, Coast Guard Beach is the perfect place to gather around a bonfire with friends and family. Just make sure to get a permit from the National Park Service first!

Annual 2013 Event

Hands on the Arts Festival
June 15–16, 2013
More info: www.handsonthearts.com
Eastham

Orleans

The Perfect Day in Orleans

History is still very much alive in Orleans, the only town in the continental United States to come under fire during both the War of 1812 and World War I. Orleans is also home to appealing and unusual shops, first-class art galleries, and popular restaurants.

Orleans

Orleans • East Orleans • South Orleans

Morning

Approval from locals is often the sign of a good place to eat. And from traditional New England breakfasts to special dishes like the Apple Crisp French Toast, the Homeport (508-255-4069) has been getting thumbs up from Orleans residents since day one. Once the bottomless coffee has you wide awake, take a hike in the Kent’s Point Conservation Area. The mile-long loop weaves through woodlands with numerous species of local birds and offers beautiful views of the surrounding harbors.

Afternoon

Join the staff at Goose Hummock (508-255-0455) on Route 6A, for a kayak tour of the Nauset Marsh. Next, head over to Land Ho! (508-255-5165)—their burgers and seafood dishes are to die for. You can find anything from a beach chair to that perfect furnishing for your seaside cottage at Snow’s Home and Garden (508-255-0158), a marvelous department-style store with modern-day pizzazz and old-fashioned service. Nauset Lantern (800-899-2660) is a must-stop for Cape-crafted lighting, and some of the best artwork around can be found at the Addison Art Gallery (508-255-6200).

Orleans

Evening

Sir Cricket’s (508-255-4453) showcases a favorite Cape Cod dish—fish and chips. With limited seating, most patrons opt for take-out here. Boxed and ready to go, find a quiet perch along Rock Harbor. Fishing charters unloading their catch make for a scenic sight. If you’re looking for a romantic dinner with top-shelf cuisine, the Captain Linnell House (508-255-3400) offers elegantly served fare from Wellfleet oysters on the half shell and escargots, to delicious salmon, lamb, roast duckling, and pork entrées.

Annual 2013 Event

Orleans Historical Society Antiques Show & Sale
June 8, 2013
More info: www.orleanshistoricalsociety.org
Orleans

Chatham

The Perfect Day in Chatham

Chatham is well known for natural wonders like the Monomoy National Wildlife Refuge. Attracting devoted visitors and year-rounders to its four villages, Chatham also has splendid shopping, authentic coastal cuisine choices, and elegant art galleries.

Chatham

Chatham • North Chatham • South Chatham • West Chatham

Morning

Celestino’s (508-945-9700) in Chatham serves up fine European-style breakfast cuisine. Belgian waffles, crepes, and omelettes are all made with fresh ingredients. Chatham’s natural attractions are many, but Monomoy National Wildlife Refuge (508-945-0594) is a spectacular Cape Cod gem that feels a world away. The only way to get to this special place offering up-close views of birds and seals in a gorgeous ocean setting is via boat or ferry. Guided tours are available, but you are free to explore the island on their own as long as you respect its “Leave No Trace” policy.

Chatham

Afternoon

Drive past mansions along Shore Drive to the Chatham Fish Pier Market (508-945-3474) for fresh seafood straight off the boat. Chatham’s charming village is full of fine shops, including art galleries galore like Eastwind Silver Company (508-945-2470), Struna Galleries (508-945-5713), Odell Studios and Gallery (508-945-3239), or the Gallery Antonia (508-469-4020). Create your own touch of Cape Cod with a hand-carved house name or number sign from Chatham Sign Shop (508-945-1909).

Chatham

Evening

For fine dinnertime cuisine, visit Pate’s (508-945-9777), which serves up delicious, uncomplicated dishes. Hand-cut steaks, fresh seafood, and a lighter lounge menu are accompanied by an impressive selection of wines. Chatham’s Main Street is a wonderful spot for an evening stroll. Finish the evening at the Chatham Squire (508-945-0945), which serves up great seafood—including some of the best lobster bisque on the Cape—and remains the spot for lively nightlife with colorful local flavor all summer long.

Annual 2013 Event

Chatham First Night
December 31, 2013
More info: www.firstnightchatham.com

Harwich

The Perfect Day in Harwich

The five towns of Harwich are full of colorful cranberry bogs, pristine beaches, one-of-a-kind attractions like a famous lavender farm, fine restaurants offering a terrific buffet of culinary options, and great boating and fishing opportunities.

Harwich

East Harwich • Harwich • Harwichport • South Harwich • West Harwich

Morning

For breakfast all day long, go to the Family Diner (774-408-7580), a fun new spot with 1950s flair right on Route 28 in the former Friendly’s restaurant. For the kite of your dreams, stop into Dr. Gravity’s Kite Store (508-430-0437) and fly it on Red River Beach. You can’t leave Harwich without a visit to Cape Cod Lavender Farm (508-432-8397). Walk the rows of lavender and woodland trails or browse the gift shop and take the sweet scent of Cape Cod home with you.

Afternoon

Watch boats bob in charming Saquatucket Harbor out on the back deck at Brax Landing (508-432-5515). Whether it’s just a drink and appetizers before heading off or the massive one-and-a-half pound steamed lobster, you’re bound to enjoy a meal with a serene view. White sands await down the road at Bank Street Beach. The warm waters of the Nantucket Sound average above 70 degrees in the summer, making the beach a swimmer’s haven. Nearby, the blues and stripers off the Wychmere Harbor jetty make for great fishing.

Harwich

Evening

Eating out every meal of a vacation can get expensive, but at Land Ho! (508-430-0404) you don’t have to break the bank for great food. Just like its original location in Orleans, friendly staff serve an array of seafood and grill options, soups, sandwiches, and daily blackboard specials. The stuffed clams are big and legendary! And the fun and excitement of Fenway Park can be found right on Cape Cod at a Cape Cod Baseball League (508-432-6909) game in Harwich Center. The Harwich Mariners are one of 10 teams in the league and took home the championship in 2011.

Annual 2013 Event

Toast of Harwich
May 10, 2013
More info: www.harwichcc.com

Harwich
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