Martha's Vineyard Island Towns
AQUINNAH
Home to the Wampanoag tribe, Aquinnah inhabits the relatively remote westernmost point of Martha’s Vineyard. From Lighthouse Road to Moshup Trail, Aquinnah boasts some of the island’s most expansive water views, bordered by native cranberry bogs and rare heath lands. Dogfish Bar is a favorite spot for surfcasting, especially during the Martha’s Vineyard fishing derby each fall. The Gay Head lighthouse, built in 1799, stands sentry over the clay cliffs whose dusty orange colors glow in the sunset and inspired the long-ago sailors who gave the place its former name. The rustic shops atop the Gay Head cliffs sell wampum jewelry, handmade goods, and souvenirs. The Aquinnah Cultural Center in the restored Vanderhoop homestead just south of the cliffs features changing exhibits on Wampanoag history, and nearby Moshup Beach stretches for miles around the southwest curve of the island.
DON'T MISS: Stop by the Orange Peel Bakery on State Road, where Wednesday pizza night invites the community to bring the toppings for fantastic brick-oven-baked pizza, shared family-style.
For more information, see Aquinnah Town Offices and Aquinnah properties for sale.
CHILMARK
This serene town spans the island’s narrow western neck, with frontage on the north shore overlooking Vineyard Sound and the Elizabeth Islands, and the dramatic south shore facing the Atlantic Ocean and its surf. In between are rolling pastures and farm fields interspersed with woodlands and two little villages: Chilmark center and Menemsha. The center of town is small. Blink and you’ll miss it. But if you keep an eye out, you’ll spot the Chilmark Store, renowned for its porch and its pizza, which makes great last-minute beach fare. Continue a hundred yards west to experience the delicious and decadent selection at Chilmark Chocolates. Menemsha, an old-fashioned fishing village where the boats pull up to the dock and unload their bounty directly into the fish markets, has a small family-friendly beach. Working farms dot the bucolic Chilmark landscape, and the farm stands at Beetlebung, Grey Barn, and Mermaid Farm sell fresh vegetables, milk, cheese, meats, and more. Two of the island’s most stunning beaches, Lucy Vincent and Squibnocket, are restricted to town residents and their guests – buy a house here and you’ll be popular for life.
DON'T MISS: Pick up dinner-to-go from the back door at the Homeport Restaurant, then stroll down the road to catch the sunset from Menemsha Beach.
For more information, see Chilmark Town Offices and Chilmark properties for sale.
EDGARTOWN
The village of Edgartown, a historic New England whaling port then called Great Harbour, was the first town on Martha’s Vineyard to be settled by the English in the late 1600s. It’s home to the Old Whaling Church, stately whaling captain’s houses, and fragrant roses spilling over white picket fences, with a 1939 lighthouse overlooking the outer harbor at the eastern end of it all. Edgartown boasts some of the highest-priced real estate on Martha’s Vineyard. Located on the southeastern side of the island, the town’s highly desirable water frontage includes Edgartown harbor and Katama Bay, Nantucket Sound, the Atlantic Ocean, Sengekontacket Pond, and several great ponds. South Beach in Katama is famous for its long sandy beach and rolling surf, with bike trails and shuttle bus service from town in the summer.
Edgartown wears its preppy hat proudly, with an active yacht club, traditional 4th of July parade and fireworks, and upscale restaurants, art galleries, and boutiques (hello, Lilly Pulitzer and Vineyard Vines). The Martha’s Vineyard Museum chronicles the island’s rich maritime heritage, with the original Gay Head light on display. If you’re into living local, visit the FARM Institute in Katama and the renowned Morning Glory Farm.
DON'T MISS: Venture over to the little island of Chappaquiddick (Chappy) for a walk on the wild side, especially the ocean-facing Wasque and East Beach, where the views are dramatic and surfcasting can be sublime.
For more information, see Edgartown Town Offices and Edgartown properties for sale.
OAK BLUFFS
On Martha’s Vineyard, it’s hard to beat Oak Bluffs for nightlife. The harbor is chock full of boats all summer, Circuit Avenue has restaurants galore and a lively music scene, and the locally famous Back Door Donuts is great for a late-night snack. The town’s rich cultural heritage includes an active African-American summer community that goes back generations, and 19th century Methodist camp meetings that became today’s community of quirky, colorful gingerbread houses, a National Historic Landmark. Amble among the Victorian cottages, especially when August offers up its magical Illumination Night, and during the evening sing-a-longs at the Tabernacle.
The Flying Horses Carousel, another historic landmark, is the country’s oldest platform carousel and a perennial family favorite. Also family-friendly are the long beaches with calm waters fronting Nantucket Sound along the Inkwell and State Beach. The East Chop lighthouse is atop Telegraph Hill, north of town heading toward Vineyard Haven. Oak Bluffs has dramatic water frontage overlooking its harbor, Vineyard Haven’s outer harbor, Eastville Beach, and Nantucket Sound. Quiet waterfront can be found in the wooded areas along Sengekontacket Pond, near the Farm Neck golf course, and Lagoon Pond.
DON'T MISS: Bring a blanket and a picnic supper to Ocean Park for the legendary fireworks over Nantucket Sound in late August.
For more information, see Oak Bluffs Town Offices and Oak Bluffs properties for sale.
VINEYARD HAVEN
First, a clarification: Most people call it Vineyard Haven, but the official town name is Tisbury, and you’ll hear it both ways when people refer to the island’s only year-round ferry port. Charm defines this town (which used to be called Holmes Hole), from the William Street historic district to the illustrious Bunch of Grapes bookstore to the Black Dog Bakery overlooking the active working harbor. Known for its wooden boat-building heritage, the town’s waterfront includes the harbor, Nantucket Sound to the east and Vineyard Sound to the north, Lagoon Pond, and Lake Tashmoo. West Chop is its northernmost point, with a historic lighthouse, views of Cape Cod across the water, and stunning sunsets from the West Chop flagpole. Nearby is Mink Meadows Golf Course.
Downtown culture includes the Vineyard Playhouse, which draws top actors, directors, and plays throughout the year, and the vintage movie experience of the Capawock Theater. Last-minute dinner is a cinch with a bounty of fresh fish, take-out, and sushi at The Net Result, and several Vineyard Haven restaurants offer take-out, too.
DON'T MISS: When it comes to fresh, plain-and-simple lobster rolls with a side of chips and iced tea, the line down the block at the Grace Church on Friday afternoon says it all.
For more information, see Vineyard Haven / Tisbury Town Offices and Vineyard Haven properties for sale.
WEST TISBURY
The island’s agricultural heart, West Tisbury’s landscape is peaceful and pastoral. Its meadows, farm fields, oak woodlands, and state forest are a soothing respite on an up-island drive. Stop at the Polly Hill Arboretum for a stroll or a class, or shop among the businesses in North Tisbury on the way to or from Vineyard Haven.
The center of town is lively, with Alley’s General Store, the Field Gallery’s sculpture gardens, and the ever-popular West Tisbury library. Nearby is the historic Grange Hall, home of the West Tisbury Farmer’s Market and the Artisans Festival. The Agricultural Hall just north of town hosts events throughout the year, most notably the sprawling and wonderful Ag Fair every August.
The town’s waterfront includes the north shore bluffs overlooking Vineyard Sound, the Atlantic Ocean, and Tisbury Great Pond. Town residents and their guests can enjoy Lambert’s Cove Beach, which is open to the public off-season. Long Point Wildlife Refuge on the south shore is popular for its surf on the ocean side and its tranquil pond inland. There’s also safe swimming along the shore of Uncle Seth’s Pond on Lambert’s Cove Road.
DON'T MISS: One of the island’s most beloved nature preserves is Cedar Tree Neck Sanctuary, which includes meandering trails through woodlands and wetlands down to the north shore.
For more information, see West Tisbury Town Offices and West Tisbury properties for sale.
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