Which of the 6 Martha’s Vineyard Towns is Best for You? A Guide.

Unspoiled seaside settings, rolling hills, and a relaxed pace have long attracted visitors to the shores of Martha’s Vineyard. This is, after all, a small island; a wonderfully rural place to enjoy drives on country roads. Its 87 square miles is an oasis of old-world charm and natural beauty in equal measure, with both a summer season and year-round population.

Located about four miles off the southeast coast of Cape Cod, Massachusetts, quaint towns and fresh ocean breezes bring hordes of visitors every year. The two famously photogenic towns of Martha’s Vineyard include Oak Bluffs, with its colorful Victorian gingerbread houses, and Edgartown, with its stately brick homes.

The island of Martha’s Vineyard is divided into two main sections: the more populated “down-island” towns of Vineyard Haven, Oak Bluffs, and Edgartown, and the more rural “up-island” towns of West Tisbury, Chilmark, and Aquinnah. Home year-round fishermen and farmers, creatives and entrepreneurs, tradesmen and teachers — and a LOT of lawyers and surgeons in the summer — a strong sense of community and unique character is the draw for many to make a home here. 

Martha’s Vineyard is a great place to partake in the simple pleasures of walking, biking, fishing, boating, crabbing, beachcombing, grilling, or simply reading a book under a tree. 

And here’s something to know: despite its name, Martha’s Vineyard does not actually contain any vineyards, much to the chagrin of wine enthusiasts (and my husband in particular). But fear not, there is plenty of wine to drink, and hundreds of other things to do in these six wonderful Martha’s Vineyard towns.

Best Towns on Martha’s Vineyard

Oak Bluffs

The down-island town of Oak Bluffs is one of Martha’s Vineyard’s most famous (and most photographed!) spots. Well-known for its charming gingerbread cottages, historical sites, and wonderful beach roads, this town offers fun attractions for visitors of all ages.

Several Steamship Authority ferries from Woods Hole dock here in Oak Bluffs, as well as the passenger-only ferry with direct service from Hyannis. You can view the ferry schedule here.

Definitely take time out to visit the iconic gingerbread houses, an essential stop for every visitor! These charming cottages painted in vibrant hues make an impressive sight that never fails to delight.

Circuit Avenue is the main street, full of delightful spots to shop and eat. Ocean Park offers an inviting seven acres of green space where visitors can walk, play Frisbee or enjoy a picnic lunch. Plus, live music and fireworks take place here every August! 

Inkwell Beach is a small but popular beach, with turquoise waters and a long history of being a haven for Black American residents and tourists. The gentle bay-side waves make this a great choice for kids.

And perhaps the best kids’ activity in Martha’s Vineyard is here in Oak Bluffs: the Flying Horses Carousel, one of the longest running continuously operating carousels in America! Children of all ages love riding its horses. And for people of all ages, here you can shop in boutiques, enjoy bars and coffeeshops, and soak up plenty of local island businesses.

Edgartown

Located on Martha’s Vineyard’s eastern end, Edgartown boasts some of the island’s most elegant and historic homes, many dating back to when whaling was at its peak in the 19th century. These houses have been beautifully restored, making Edgartown a beautiful place for a stroll.

Edgartown offers plenty of charming shops on Main Street, with everything from women’s apparel and art galleries to candy stores lining its downtown district. Explore the diverse array of dining options, with restaurants such as The Seafood Shanty, with breathtaking ocean views and some of the island’s best clam chowder, and The Wharf, with an inviting bar and delicious classic diner dishes.

Just a 10-minute walk from the town center is one of the most special lighthouses on the island, Edgartown Lighthouse, also known as Harbor Light. Built in 1828, it was actually once on a man-made island just a quarter-mile off-shore, but a new beach formed in 1939, connecting the lighthouse to the mainland.

Beachgoers will appreciate Katama Beach (also known as South Beach), located in the Katama area of Edgartown facing the Atlantic. It’s a barrier beach, with an extensive stretch of white sand that extends for more than three miles, perfect for shell fishing or just strolling with family and friends. Keep in mind that the sand gets narrow at high tide.

At nearby Katama Bay, Signature Oyster Farms allows you to take a tour of its local oyster farms. You’ll have an opportunity to walk on oyster beds and witness how these delicious bivalves are harvested before enjoying an idyllic, farm-to-table lunch.

North of town, Joseph Sylvia State Beach, known as State Beach to locals, is a fabulous place for swimming. This sandy beach was used as the setting for the 1975 movie Jaws and boasts miles of sandy shoreline for visitors to enjoy. You can jump off the Jaws Bridge, too!

On top of enjoying a beach experience, visitors to Edgartown should also explore some of its historic landmarks, including Vincent House Museum and Old Whaling Church. Both of these historic museums provide fascinating insights into this island’s past.

Chappaquiddick Island is technically part of the town of Edgartown and takes just one minute to get to on the tiny Chappy Ferry, which can fit just a few cars. That said, I think it’s best to explore Chappaquiddick by bike — it’s small and flat, finding parking is much easier, and you won’t have to wait in the car line for the ferry.

On Chappaquiddick you can visit Cape Poge Wildlife Refuge and its eponymous lighthouse; you can also check out East Beach, visit the Mytoi Japanese Gardens, or enjoy the endless expanse of sea at Wasque Point (pronounced WAY-squee).

Vineyard Haven

Vineyard Haven is the commonly used nickname for the town of Tisbury (different from the town of West Tisbury, which we’ll mention further down). Located on the North Shore of the island, the Steamship Authority ferry stops here, but it’s absolutely worth lingering a little!

Much like Oak Bluffs and Edgartown, Vineyard Haven has a bustling atmosphere with lots of things to do. However, while the other two towns feel super tourism-oriented, Vineyard Haven feels like it’s designed for the many locals who call this town home.

Vineyard Haven is also the location of the Nobnocket Boutique Inn, where I loved staying during my time in Martha’s Vineyard! (More on Nobnocket below.)

Downtown Vineyard Haven is a lovely place to wile away the afternoon hours shopping, whose walkable downtown looks just as timeless as it did decades ago. Be sure to stop by Waterside Market for lunch to fuel up beforehand; they served a giant BLT that knocked my socks off. 

The Black Dog Tavern, an iconic and world-famous Vineyard establishment, has the best chef-crafted entrees, perfect for breakfast, lunch, or dinner. Here in Vineyard Haven you can also visit The Black Dog Store, and Black Dog Bakery (which has great cookies).

Whether or not you’re a history buff, the Martha’s Vineyard Museum will give you invaluable insight into the island. (It’s also a great rainy day activity on the Vineyard.) Discover the rich history and vibrant heritage of Martha’s Vineyard and its surroundings in this museum, located in an 1890 Victorian marine hospital. Exhibits feature lighthouses as well as those dedicated to the Indigenous Wampanoag people.

Lighthouse completionists can stop by the West Chop Lighthouse — while this one is not open to the public, it does serve as a wonderful photo opp! It’s about a 30-minute walk from.

If you have time, do try to see a production at Martha’s Vineyard Playhouse. Located on Church Street, they put on a nice variety of events throughout the year.

Read More: A Visitor’s Guide to Vineyard Haven, Martha’s Vineyard

West Tisbury

West Tisbury, one of the up-island towns on Martha’s Vineyard, is an idyllic and tranquil village. Comprised of acres of State Forest, serene beaches, and abundant farmland, its New England village charm is preserved through general stores, white churches, post offices, and family-run farms.

The relaxed and cozy vibe makes it feel like a country town and is home to an extensive range of locally produced goods. Fresh produce, homemade soaps and lotions, handcrafted wood furniture as well as some great restaurants can all be had. Refuel at Woods Restaurant at Lambert’s Cove, which serves island-inspired meals. 

Shopping at Alley’s General Store is a must. As one of the oldest continuously operating retailers on Martha’s Vineyard, you can find it behind a historic barn with a gray shingled roof. Since 1897, this stoop-to-porch establishment sells everything you may want during your visit.

This rural agricultural community offers numerous attractions that are both free and inexpensive. One such attraction is Long Point Wildlife Refuge, an old prairie remnant now home to globally rare plants and wildlife; also featuring sandy beaches, coastal ponds, and small lakes perfect for bird watching.

Polly Hill Arboretum provides a beautiful place for picnicking on Martha’s Vineyard, featuring an elegant oak tree as well as other species planted to resemble its natural environment. This was one of the quietest and most serene places I visited on the island.

Finally, Long Cove Pond provides some of the island’s most breathtaking landscapes, while also serving as an excellent location for snorkeling and fishing.

Chilmark

The south shore town of Chilmark offers both beauty and tranquility harmoniously. There is plenty to do and see with its fellow up-island neighbors of West Tisbury and Aquinnah.

One thing I love about Martha’s Vineyard is visiting local farmstands for locally made produce. One of the best is The Grey Barn and Farm in Chilmark, which makes excellent cheeses and also has plenty of fresh produce, a bakery, and a butcher shop. Need a pick-me-up? Chilmark Coffee Roaster is a popular spot for both locals and visitors. 

While hiking and admiring nature’s splendor are rewarding experiences, kayaking or sailing at Nashaquitsa and Stonewall Ponds is another fantastic option.

Many island visitors flock to watch the sunset at Menemsha Beach at Menemsha Village — its waters become painted in hues that rival some of New England’s most stunning and romantic sunsets! Surrounded by large rocks, this beach offers beautiful and peaceful surroundings. Rent a bike, or just come down with some beach chairs to join everyone else as the sun dips down.

Menemsha Hills Nature Reserve should be included on any itinerary to the island. Just outside Chilmark, this protected 211-acre reserve boasts diverse mini-environments such as woodland groves, coastal plains, and low wetlands, as well as breathtaking views of Vineyard Sound and Elizabeth Islands from 308-foot Prospect Hill!

Aquinnah

Aquinnah is the westernmost town on the island, and was formerly known as Gay Head. It is the cultural home of the Aquinnah Wampanoag nation and features so much natural beauty, including stunning over-water sunsets at Moshup Beach (my personal favorite beach on Martha’s Vineyard!).

If you’re looking for things to do in Aquinnah, most people come to visit the Aquinnah Cliffs, a protected, multi-color natural wonder. Both the cliffs and the beach are off-limits due to their delicate nature, but you can view them from the Aquinnah Cliffs Overlook. I recommend visiting at golden hour, just before sunset, when they light up in bright colors (this was when the photo above was taken).

A visit to the Aquinnah Cultural Center is a must — and offers a wonderful history of the Indigenous peoples of Martha’s Vineyard. This museum is worth a visit and walking distance from the cliffs lookout and Moshup Beach.

Looking for an incredible view over the Atlantic Ocean? Climb to the top of Gay Head Light, one of the Martha’s Vineyard lighthouses you can visit.

Long Point Wildlife Refuge is an idyllic natural area, which once formed part of an island prairie ecosystem, now boasts an extraordinary collection of plants and animals — plus several beaches and a two-mile hiking trail for your enjoyment.

Where to Stay on Martha’s Vineyard

For a quintessential Martha’s Vineyard stay, Nobnocket Boutique Inn will take care of you. I absolutely loved my stay here.

Located on a quiet street in Vineyard Haven, owners Simon and Annabelle Hunton provide outstanding service from the moment you step into the property. Chic, modern furnishings accentuated with elegant artwork make you feel like pampered royalty without the pomp and circumstance. 

The guest rooms exude a quiet elegance with comfort firmly in mind. The Nobnocket achieves that delicate balance of a modern, stylish aesthetic while keeping the atmosphere cozy. Thoughtful design touches can be found throughout, from the plush bed linens to the inviting wainscoting in the bathrooms. 

Most boutique inns offer complimentary coffee, tea, and even board games in the lobby, but the Nobnocket ups the ante by offering a bit of port, whiskey, or brandy, along with light snacks, just in case you fancy an evening nightcap. When you want to stretch your legs, an expansive backyard provides the ideal spot to relax, dine outside, or walk the beautiful grounds.  

But the Inn’s breakfast is the wow factor here! Every morning is different, usually beginning with a creative fruit parfait before moving to the main event. This can include waffles with a delectable topping such as mango and sherbet, avocado toast with egg and pancetta, or creamy bread pudding topped with fresh berries. All are paired with Chilmark Coffee’s locally roasted beans, tea, and juice. 

There’s even a turndown service with cookies! No better way to drift off to dreamland.

More on Martha’s Vineyard:

• A Guide to Oak Bluffs, MA — Home of the Gingerbread Houses
• A Guide to Edgartown, MA — Prettiest Martha’s Vineyard Town
• A Guide to Vineyard Haven, MA — Authentic Town on Martha’s Vineyard
• Visiting Chappaquiddick Island – Things To Do & More

More on Cape Cod:

• Which of the Towns of Cape Cod is Best for You?
• 24 Fab Things to Do in Cape Cod
• 22 Fabulous Things to Do in Provincetown, MA

More on Massachusetts: 

• Where to Stay in Boston: Hotels, Neighborhoods & More!
• 40+ Fun Things To Do In Boston At Night
• Best Time to Visit Boston
• What NOT to Do in Boston
• The Best Museums in Boston
• 25 Historic, Spooky Things To Do in Salem, MA
• 27 Fun Things to Do in Rockport, MA
• 24 Cool Things To Do in Cambridge, MA
• 33 Best Things to Do in the Berkshires, MA
• Best Towns in the Berkshires, MA
• 24 Cool Things to Do in Lenox, MA
• 12 Fun Things to Do in Stockbridge, MA

Have you been to Martha’s Vineyard? Where’s your favorite town? Share away!