Head "up island" to escape the crowds but still enjoy one of America's iconic islands.
Kristen Shelton Fielder
1 of 6Photo: Brooks Kraft
Martha's Vineyard Magic
Tucked away seven miles off the coast of Cape Cod, Martha's Vineyard is an island full of unspoiled natural beauty and, during the busy season, lots of admirers. Until sometime in late August, the 100-square-mile isle's population swells with visitors and second-home owners, and it's easy to feel the crush—but you can find a quiet, uncrowded slice of the Vineyard. Just head "up island," as locals call it, to the towns of Chilmark, Aquinnah, and West Tisbury, where you'll find rolling, grassy hills, restaurants that don't need reservations, and low-key beaches blissfully free from crowds.
2 of 6Photo: Brooks Kraft
The scent of blooming hydrangeas welcomes you in Chilmark, a small community that includes both Chilmark proper and the working fishing village of Menemsha. Staying here gives you access to Chilmark's private beaches, which are tucked in coves and naturally pristine: Squibnocket offers great fishing and surfing, and Lucy Vincent (known as a bathing suit-optional beach) has clear views of the island's famous red clay cliffs.
If you're up for a walk or a bike ride, try the trail that climbs to the Quitsa Pond Lookout, where on a clear day you'll see not only Nashaquitsa and Menemsha ponds—dotted with shore-birds and sailboats—but also Vineyard Sound and the Elizabeth Islands two miles to the northeast.
Visit June through September to enjoy a little fresh-air retail therapy at the Chilmark Flea Market every Wednesday and Saturday in a grassy field on North Road. You're sure to see ceramics, artwork, jewelry, soaps, and antiques.
At the end of the day, the best spot on the island to watch the sun set over the water is the public beach at Menemsha Harbor. To complete the experience, pick up fried clams (to go) from The Back Door at the Home Port Restaurant. Or, for an iconic East Coast delicacy, head to Home Port or Larsen's Fish Market, which both sell lobster so fresh it might have been swimming earlier that morning.
The historic village of Aquinnah is at the western end of the island. Also known as Gay Head, Aquinnah is home to the Wampanoag Indians and the Aquinnah Cliffs that meet the sea in sediment layers of bright red, orange, silver, and white clay. Because of erosion, the cliffs aren't safe for climbing, but they're a photo op must.
For another dramatic sea view, the clifftop Aquinnah Shop Restaurant serves fresh seafood in a kitschy diner atmosphere, and the adjacent Gay Head Light is open seasonally for tours.
4 of 6Photo: Brooks Kraft
The beaches around the western end, such as public Moshup Beach, are as spectacularly colorful as the cliffs: Aqua water shines against yellow sand and lush green grass. Make sure you get great views of all that scenery—and plush comfort in your room, too—by staying at The Outermost Inn, but book early. The inn has only seven rooms and famous relatives (the owners are related to singer James Taylor), so you never know who might be in town.
And speaking of famous faces, you may even catch a glimpse of President Barack Obama. Every summer the Obama family rents a property up island and frequents local restaurants and businesses.
It feels like time stopped in West Tisbury. Martha's Vineyard's second-largest village continues to honor the past with historic churches and landmarks open to the public, and residents who've restored sea captains' homes. For a unique spot to stay off the beaten path, Lambert's Cove Inn, originally a farmhouse built in 1790, consists of a main house, carriage house, and guesthouse. The inn is located in a lush, wooded area, but it's a short walk to a private beach where it's just you and the occasional seal.
In town, if you're looking for a mix of pretty much anything, Alley's General Store is the place to find it. Because it's the oldest operating retailer on the Vineyard, the vintage possibilities are endless. Grange Hall hosts an impressive farmers' market on Wednesdays and Saturdays, as well as community events throughout the year.
6 of 6Photo: Brooks Kraft
Around 35 percent of the Vineyard has been set aside for conservation, so areas such as Cranberry Acres, Ripley's Field Preserve, and Tisbury Meadow offer amazing walking trails. West Tisbury is also home to lively festivals, including a weekly artisan festival where you can chat with the local artists while perusing beach house--perfect paintings, ceramics, and furniture.
At State Road Restaurant, flanked by low stone walls and flower gardens, try a delicious fried green tomato BLT or savory field greens salad for lunch. If you make it in time for breakfast, the homemade granola is a heavenly way to start the day. Either way, pick up a chocolate bar to go. Made in house with ingredients such as caramelized almonds, pistachios, and espresso, the bars are named after towns and trails on the Vineyard, and are the sweetest finish at the end of a long weekend spent winding down up island.