The 6 Towns On Martha’s Vineyard: Where to stay on your Vacation

Trying to decide where to stay on your Vineyard vacation? You’re in the right place to learn more about the 6 towns on Martha’s Vineyard and how to choose which one to stay in.

In the 25 years I’ve been visiting the Vineyard, I have come to love how the six towns – Aquinnah, Chilmark, West Tisbury, Edgartown, Oak Bluffs and Vineyard Haven – each offer something unique to visitors.

In this guide, I’ll highlight which towns are best for all kinds of traveler, including families looking for kid-friendly activities, couples seeking a romantic getaway and adventurers ready to explore somewhere new.

From the stunning natural beauty of the Aquinnah coastline, to the busy beach-town atmosphere of Oak Bluffs and the relaxed elegance of Edgartown, here’s everything you need to know about the best vacation spots on Martha’s Vineyard.

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Best Towns On Martha’s Vineyard

I am often asked, What are the best towns in Martha’s Vineyard for lobster, sunset, families etc and while this is really down to your personal preference, I have listed my favorites below, based on my own experience

Best Town On Martha’s Vineyard For Breakfast

Vineyard Haven is the best town for breakfast because of the number of consistently high quality restaurants with a broad choice of items at a range of budgets to suit everyone.

The Black Dog Tavern (open year round), Scottish Bakehouse, The Waterside Market, S&S Kitchenette and the crown jewel of the Vineyard Haven breakfast scene – The Artcliff Diner.

Between them, these restaurants offer all the classic staples like pancakes, french toast, breakfast sandwiches, omelettes, granola, baked goods, fruit, coffee and anything else you can think of!

Best Town On Martha’s Vineyard For A Day

If you only have one day to spend on Martha’s Vineyard, spend it in Oak Bluffs. You’ll be able to maximise your time here by getting a ferry right into town so you won’t have to drive to another location when you arrive.

The main attractions here are all within walking distance of each other. Your list should include: the Flying Horses Carousel, the colorful gingerbread cottages of the Campground, the cottage museum, shopping on Circuit Ave and a visit to Inkwell or State beach.

A little further out of town you could visit East Chop Lighthouse or jump off the famous Jaws Bridge on Beach road. Another way to see a lot in a short time is to take a tour.

There are short, self-guided tours of the town available year-round. Seasonally, you can take an African American Heritage trail tour of Oak Bluffs. This will take you to sites highlighting the contributions of people of African descent to the history of Martha’s Vineyard.

Best Town On Martha’s Vineyard For Lobster

Chilmark is the best of the towns on Martha’s Vineyard for lobster. Fishermen from all around the island (and even some towns on the Cape) land their catches in the Chilmark village of Menemsha.

You will find lobster served in nearly every restaurant in the west of the island and sold in stores like Larsen’s fish market and Menemsha fish market. Try the Homeport restaurant or Menemsha Galley for lobster rolls or fresh steamed lobster

Jay Lagerman sculpture, “The Family” in Oak Bluffs

Best Town On Martha’s Vineyard For Families

If you have a baby or very young children, you have less requirements for constant entertainment and restaurants with children’s menus so I would recommend staying in Edgartown.

It’s walkable, quieter than Oak Bluffs, there are small, baby-friendly beaches with calm waters in town and playgrounds for little kids nearby.

Oak Bluffs is the best part of Martha’s Vineyard for families with older children as there are a huge variety of family-friendly restaurants to choose from.

You also have attractions like the Flying Horses Carousel, the amusement arcade, bowling and basketball courts in town as well as nearby tennis and sailing summer camps.

Oak Bluffs is a safe and easy town for older children to navigate by themselves and there is more for them to do here than in Edgartown.

Best Town In Martha’s Vineyard For A Bachelorette Party

Oak Bluffs is the best town for a Bacherlorette party because you have endless dining and accommodation choices as well as a lively bar, live music and nightlife scene.

During the day, you have the beach right in town, private boat trips leaving from the marina, a wide range of shopping options and outdoor activities like paddleboarding, kayaking or biking.

Best Town On Martha’s Vineyard For Sunset

Aquinnah wins the prize for best sunsets on Martha’s Vineyard. With unobstructed western views over the ocean, you can see the very moment the sun drops below the horizon and into the sea.

The Aquinnah cliffs are the most popular location for visitors to catch a sunset due to the high vantage point. If you are a true sunset lover, you can’t beat renting a vacation home in Aquinnah and enjoying a private sunset view at the close of every day.

Best Town to stay in Martha’s Vineyard for a Romantic Getaway

Edgartown is the best town for a romantic getaway. It’s classic and charming, with beautiful historic homes and lovely beaches. Walking through the quaint streets feels like stepping back in time, which adds a romantic touch.

There’s great dining and shopping, too, especially if you’re on the hunt for a unique piece of jewelery for a special occasion. Check out CB Stark’s Vineyard-inspired collections of charms, necklaces and rings. 

Visit in May or September for a romantic getaway. Fewer crowds and kids still in school means you’ll have more privacy, space for intimate dinners and the beaches all to yourself.

December is the time to come for the magical, 4-day, Christmas in Edgartown event. Stroll through decorated streets, take pictures with Santa, watch the holiday parade and enjoy Edgartown Lighthouse adorned with festive, twinkling lights.

Towns on Martha’s Vineyard

Martha’s Vineyard’s six towns are divided into two areas. Up-Island Martha’s Vineyard refers to the northern and western part and the island towns of West Tisbury, Aquinnah and Chilmark.

Heading west,  you’ll drive by the rolling hills, woodlands, meadows and ponds of West Tisbury before arriving at the ruggedly beautiful coastline of Aquinnah.

The up-island towns make up the quieter part of the island with fewer hotels and restaurants and private homes on larger parcels of land. If you are looking for peace, solitude and proximity to nature, this is the best part of Martha’s Vineyard to stay.

Down-Island Martha’s Vineyard describes the south and east of the island. This area contains the largest population centers on the island, including Edgartown, Oak Bluffs and the town of Vineyard Haven.

If you are looking for an active, busy vacation with lots to do, right on your doorstep, this is the best area to stay in Martha’s Vineyard. Most of the island’s hotels and restaurants are here, as well as shopping districts, galleries and most of the island’s traffic during the summer!

Gay Head Cliffs and Lighthouse

1. Aquinnah

Formerly known as Gay Head, the town of Aquinnah is the westernmost town on the island. It is renowned for its stunning natural beauty, impressive cliffs and lighthouse.

The most noteworthy site in Aquinnah is undoubtedly the Cliffs. These colorful clay formations are visible from both land and sea.

You will still hear both town names being used so if you see references to the Gay Head Cliffs or Gay Head Lighthouse and the Aquinnah Cliffs or Aquinnah Lighthouse, they are actually the same place.

Follow a boardwalk down to Moshup Beach, a public swimming beach located at the base of the cliffs if you want to see them up close.

If you are looking for one of the island’s best sunsets, Aquinnah is a great choice. Sunset at the cliffs is truly spectacular although be warned, you will be experiencing this spiritual moment with hundreds of other visitors if you go during the peak summer months.

If you’re celebrating a special occasion or looking for a romantic location for a meal, you cannot beat the Outermost Inn for incredible food in an incredible location. My expert tip: this is the spot for a front-row, no-crowds, Martha’s Vineyard sunset you’ll never forget.

Aside from its natural beauty, Aquinnah is also known for its rich Wampanoag history and culture. You’ll find locally owned shops selling Wampum jewellery and other crafts in the cultural district. The Aquinnah Cultural Center is the place to learn about the earliest inhabitants of this region.

The town of Aquinnah is private and quiet in the off-season, but come summertime, local eateries, shops and hotels re-open and welcome visitors.

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Menemsha Harbor

2. Chilmark

The last dry town on Martha’s Vineyard, Chilmark is located next to Aquinnah in the west of the island. It’s one of the more rural towns, sparsely populated but home to stunning sunsets and the most expensive real estate on Martha’s Vineyard.

The town of Chilmark is favored by people who want to get away from it all and it’s a popular choice for vacationing celebrities. The sprawling estates, acres of woodland and large farms makes it the perfect spot for those seeking privacy on their vacation.

The fishing village of Menemsha looks like a traditional, old-world fishing village straight out of the movies. Perhaps this is why it was chosen as a filming location for the movie, Jaws.

This village is my pick for the best fresh seafood on the island. Go to the Menemsha Galley for a lobster roll and a postcard-perfect view of the harbor.

Menemsha Beach is another hotspot for outstanding sunsets but will be crowded during the summer months. Parking is limited so get there early or take public transport.

If you are driving from the east of the island to Chilmark, take Middle Road as it’s the most picturesque drive. It reminds me so much of Ireland, with green fields, sheep and stone walls all around.

There are a few stores in Chilmark but most of the town is agricultural or residential land. This is a great part of the island if you like to buy your food from farm stands. I go to North Tabor farm for the best eggs and the Grey Barn for their award-winning cheese.

Private vacation rentals are your best choice for accommodation in this part of Martha’s Vineyard or The Beach Plum Inn if you prefer hotel-style lodgings.

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The Agricultural Hall in West Tisbury

3. West Tisbury

I’ve always found it confusing that West Tisbury is considered “up-island” as it is located right in the middle of Martha’s Vineyard. This town stretches across the island and has a north shore as well as a southern coast. Similar to Chilmark, it is an agricultural town.

The Martha’s Vineyard airport is located here in West Tisbury, Massachusetts.

One of the biggest events of the Vineyard calendar takes place in West Tisbury. The Martha’s Vineyard Agricultural Fair has been an annual tradition for over 160 years.

My kids look forward to this every year and I look forward to a delicious burger from the West Tisbury Firefighters stand. Throw a tip in the firefighter boot and they’ll ring the bell!

Long Point Wildlife Refuge in the south and Lamberts Cove in the north are two excellent West Tisbury beaches, however, Lambert’s Cove is only accessible to area home owners and renters during the summer season and a permit is required. Visit in October when permits are no longer required.

You will love West Tisbury if you enjoy outdoor pursuits like hiking and biking. Long Point beach is actually inside the 600 acre wildlife refuge and there are countless trails to choose from while exploring Martha’s Vineyard. Check out the free TrailsMV app for maps and more information

Another West Tisbury attraction is Polly Hill Arboretum. This botanical garden is a perfect spot for a peaceful stroll or a family picnic among a diverse collection of trees and plants. Visit in April to see the early blooms

One of my favorite breakfast sandwiches on Martha’s Vineyard is from 7a foods in West Tisbury (next to Alley’s General Store) but get there early – they sell out fast!

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4. Edgartown

The town of Edgartown is situated on the southeastern coast of the island. It’s regularly labelled one of the most beautiful, quaint towns in Massachusetts and is known for its spotless beaches, stunning architecture, and rich whaling history.

One of the main attractions in this classic New England village, is the picturesque harbor. I recommend strolling along the docks or standing on top of Memorial Wharf to watch the boats come in and out.

The harbor area also offers several options for dining overlooking the water such as the Seafood Shanty or Atlantic Fish & Chop House

Downtown Edgartown is a walkable hub featuring elegant stately homes, art galleries, high-quality dining, luxury hotels and upscale boutiques in the town center.

From here, you can hop on the “On Time” ferry and take a short ride to Chappaquiddick. This island offers a tranquil escape with its unspoiled natural beauty and secluded beaches.

The Katama neighborhood is attractive to visitors because of its peaceful ambience and proximity to the pristine South Beach.

This is a great location to stay if you want the convenience of Edgartown village without the hustle and bustle. It’s just a short drive (15 mins) or bike ride to the downtown area.

If you would like to know more, you will find everything you need in my in-depth guide to Edgartown which covers things to do, accommodation, dining, events and frequently asked questions about the town.

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Gingerbread Cottages, Oak Bluffs

5. Oak Bluffs

Oak Bluffs is a vibrant port town located on the northeastern coast of the island. It was originally known as Cottage City and this is where you can see the famous, colorful, gingerbread cottages.

The history of these homes is fascinating and I highly recommend a visit to the Cottage Museum to find out more.

One of the most popular attractions in the town of Oak Bluffs is the Flying Horses Carousel, which is the oldest continuously operating platform carousel in America.

Put this on your “must-see” list – you can’t leave the Vineyard without taking a ride on one of the beautifully crafted, carefully restored horses.

Ocean Park is a nice place to take a walk in Oak Bluffs as it offers stunning views of the ocean and provides plenty of space for picnics and relaxation. The park also hosts events throughout the summer and is a favorite spot to sit and watch the fireworks in August. Get there early!

Oak Bluffs offers plenty of opportunities for indoor, rainy day activities as well as outdoor activities such as fishing, kayaking and sailing excursions. The town beach is a short walk from the main street, Circuit Ave and the popular Inkwell beach is also close by.

Most of the island’s bus tours depart from Oak Bluffs, opposite the Steamship Authority ferry terminal.

There are plenty of summer camps and activities for kids available in Oak Bluffs. It’s one of the best towns on the island of Martha’s Vineyard for families.

There’s also a huge range of dining options in this town, especially for casual meals out with kids. I like the row of restaurants and bars at the dockside marina for the great views of the harbor. This is always a buzzing, lively area. 

For those who love to shop, Circuit Avenue is the place to be! You’ll find everything from unique souvenirs and beachwear to handmade jewelry, local art, and specialty foods. It’s the perfect spot to pick up island-themed gifts too!

Nancy’s restaurant is a popular spot here for cocktails and fresh seafood.

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View from the Blackdog Tavern

6. Vineyard Haven

Vineyard Haven is actually the name for the village/harbor area within the town of Tisbury. Although Tisbury is the official town name, you will rarely hear it being used. The town is most often referred to as Vineyard Haven by visitors and locals, alike.

This bustling port town has year-round ferry services and is the main port of entry for visitors to the island, especially in the winter when the Oak Bluffs ferry terminal is closed. See if you can spot the iconic West Chop Lighthouse as you cross Vineyard Sound and approach the harbor.

If you enjoy spending time on the water, this is a great spot to pick up a private sailboat charter. The dock at Owen Park is an easy place to depart from and you can take a short sail to the nearby town of Oak Bluffs, or a longer one over to the mainland or the Elizabeth Islands.

Vineyard Haven is less of a resort town and more year-round residential community so if you are looking to visit off-season, the village of Vineyard Haven would be a great place to stay.

Vineyard Haven is somewhat of a cultural and creative hub with the Vineyard Playhouse Theatre, The Field Gallery, the MV Film Center and the Martha’s Vineyard Museum all located here.

The Museum is well worth a visit, my favorite things to see here are the original lamp from the Gay Head Light House and the Jaws exhibit documenting the making of the film on Martha’s Vineyard.

The variety and quality of restaurants in Vineyard Haven has improved each year and the easing of restrictive town liquor laws has helped with this. I think it’s the best town on Martha’s Vineyard for foodies because of all the new, excellent quality restaurants that have opened recently.

For a great view while you eat, it’s hard to beat Garde East, El Barco or The Black Dog Tavern. The windows frame a perfect postcard of the beach, ocean and the Steamship Authority ferry as it approaches the dock.

My top tip: go on a cold day off-season and order an overflowing mug of their excellent chowder to warm you right up.

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Final words about the towns on Martha’s Vineyard

Each of the towns on Martha’s Vineyard has its own unique character, history and attractions, making it easy to find one that suits your interests and preferences.

From the picturesque streets of Edgartown to the energy of Oak Bluffs and the peaceful beaches of Aquinnah, there is something for everyone on this idyllic, small island.

Whether you are looking for a quiet getaway, an active outdoor vacation or an unmatched culinary experience, there is a town on Martha’s Vineyard for you!

As you explore these towns, you’ll discover a sense of community, warmth, and a slower pace of life that is both refreshing and rejuvenating. Join our Martha’s Vineyard Travel Tips group for more information on the island and enjoy your trip!