Three Days, Three Stays: How to spend a long weekend on the Cape and Islands this spring
By StoryStudio March 27, 2018 8:00 am
As the last bits of snow finally melt and the sun peeks out from behind its months-long cloud cover, we New Englanders are ready and waiting to celebrate our hard-earned spring. And there’s no better way to do so than planning the ultimate long-weekend road trip. So why not hit three easy-to-reach destinations in as many days?
There’s a lot you can cram into 72 hours when you’re island-hopping through Cape Cod, Martha’s Vineyard, and Nantucket. And mild spring weather means a whole host of outdoor activities open up for those who visit just before the summer rush. Here, we bring you the quintessential itinerary to get the most out of your trip.
Day 1: Cape Cod
Cape Cod Rail Trail
One of the best ways to get to know Cape Cod is via the 22-mile rail trail that connects the towns of Wellfleet, Dennis, Harwich, Brewster, Orleans, and Eastham. The mostly flat bike path makes for an easy-going ride through New England’s picturesque coastline and marshland, and eventually links up to the Nauset Bike Trail leading to Coast Guard Beach.
Dessert for Lunch
While the Cape is known as a gathering spot for some of the best seafood in the region, it’s also become famous for its slew of gourmet ice cream shops. Pick one of the quaint little seaside towns off the trail and settle in for a basket of fried goodness at a nearby clam shack. Then, ask a local to point you towards his or her favorite ice cream parlor for a cool, sweet finish.
Explore Historic Route 6A
Once you’ve fuelled up, hop in the car and take a cruise down historic Old King’s Highway—spanning over 60 scenic miles—to explore Cape Cod’s celebrated antique trail and some of the oldest villages in America. Quick detours off Route 6A will take you to local gems like Heritage Museums & Gardens and Scargo Tower, the Cape’s highest point of land. Near the end of the route, stop off at Coast Guard Beach and take a leisurely stroll up to the famous Nauset Lighthouse (don’t forget to snap a pic for the ʼgram!).
Dinner and a Movie
Conclude your day in Provincetown, the Cape’s furthest tip and most forward-thinking bastion for art and culture. At sunset, hop aboard Art’s Dune Tours to survey the area’s majestic sand dunes, dotted with historic “dune shacks” where writers and artists like Eugene O’Neill and Harry Kemp found inspiration. Once you’ve worked up an appetite, head to Provincetown’s bustling Commercial Street for fresh seafood before finishing the night with a movie under the stars at the famous Wellfleet Drive-In.
Fun & Games
When you get off the ferry in the town of Oak Bluff, you’re just a short walk away from Flying Horses, America’s oldest carousel. Riding along to carnival music from an ancient Wurlitzer organ, kids can try to grab the brass to win a free ride.
Tour the Island
If you’ve had enough cycling, take a three-hour tour (in a van) around the entire island from one of the local tour companies. Stops may include the bridge where Jaws was filmed, the famed Aquinnah cliffs, historic lighthouses, art galleries, and the colorful Gingerbread Cottages of Oak Bluffs.
Arts and Culture
Martha’s Vineyard has long been known for its beauty, both natural and manmade. Drink it in by strolling a farmers’ market or artisan festival for a keepsake of your trip, then check out the Aquinnah Circle Cultural District to learn about the Wampanoag people, who have inhabited the island for millennia. Head to the top of the Gay Head Lighthouse for breathtaking views, and don’t forget to stop into the Cultural Center for a deeper look at the island’s whaling and Native American history.
Seafood at Sunset
After a day of exploration, treat yourself to a fabulous dinner prepared with locally sourced island foods before capping off the evening with a spectacular sunset at Menemsha, the center of Martha’s Vineyard’s historic fishing culture. Make the night memorable by bringing along a blanket and a favorite beverage for sipping as the stars come out.
Whaling Museum
For a break from the outdoors and an in-depth look at Nantucket’s famed whaling history, check out this well-curated museum full of dynamic exhibits and countless cultural artifacts. Spot the massive sperm whale skeleton on your way up to the roof, from where a terrific view of Nantucket harbor unfolds.
Walk the Historic Cobblestones
Downtown Nantucket is prettier than a postcard, and historic to boot. Spend the late morning strolling the town’s cobblestone streets and browsing a plethora of quaint boutiques, galleries, and shops. You’ll find one-of-a-kind artwork, home décor, clothing, jewelry, and other treasures from local makers.
Take in the South Shore
There are several excellent beaches on Nantucket’s South Shore, but Madaket Beach is best known for its sunsets and rough waters. The smaller crowds here means there are fewer amenities, so if you prefer the comforts of showers and changing rooms, check out Surfside Beach a little closer to town. Neither will be too crowded at this time of year.
Great Point Light
The island’s most famous and picturesque lighthouse, originally built in the 1700s and destroyed by a storm in 1984, Great Point Light was rebuilt in 1986 and sits at the northernmost point of the island in the Coskata-Coatue Wildlife Refuge. Rent an all-terrain vehicle via one of the guided tours (the other option is to walk five miles in soft sand) to get an up-close view and catch an amazing sunset.
Downtown for Dinner
There are seemingly endless choices for fine dining in Nantucket, but that doesn’t make it any easier to get a table during the summer. Busy season requires reservations made weeks in advance, but in the spring you can get away with waiting until a day or two ahead—or maybe even walk right in! Pick your favorite and conclude your whirlwind weekend with a few cocktails and a world-class feast.
Ready to ring in the spring? Pack your bags and head for the coast! The quintessential New England seaside charms of Cape Cod, Martha’s Vineyard, and Nantucket are waiting.
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This post is funded in part by the Massachusetts Office of Travel & Tourism.
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