Martha’s Vineyard, Massachusetts

Located off the coast of Cape Cod, Martha’s Vineyard is the quintessential image of New England’s sea-side. We’ll admit – when we first arrived, everything seemed overpriced, and many of the “must do” activities seemed over-hyped. However, after spending a couple of days on the island, it quickly became one of our favorite places. 

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Martha’s Vineyard is only accessible by ferry, and if you want to bring your car, plan to schedule your tickets several months in advance. However, you do not need your car thanks to the island’s bus system. While we had heard of the bus, we chose to bring our car in order to fully explore the island.

Where to Stay on Martha’s Vineyard

Of the three largest towns on Martha’s Vineyard, we suggest staying in Edgartown. It is the most quintessential summer east coast town (complete with white or grey houses and dark painted shutters). While it is a short drive from the two ferry terminals, it is the nicest of the towns. Additionally, the Edgartown lighthouse, only a few minutes walk from the center of town, is perfectly located for evening strolls or daytime beach games.

Our Favorite Overall Place to Stay: The Charlotte Inn

The Charlotte Inn, located in the center of Edgartown, is a quintessential East Coast hotel that values its history. This hotel is the only Relais & Chateau rated hotel on Martha’s Vineyard, and it was only recently that the hotel even offered online booking on their website. The hotel only has 18 rooms, and each is carefully and ornately decorated. Plus, guests can enjoy the hotel’s private gardens and courtyards, which are a quiet reprieve from Edgartown.

Best Options for Families

If you are visiting Martha’s Vineyard with a large group or with children, you should look into short-term house rentals. Because Martha’s Vineyard is a summer destination for families from New York City and Boston, many homeowners rent their homes to families. These homes can vary from small cottages to large gathering places. Additionally, the houses offer plenty of space, and flexibility in location. Check local listings and AirBnB for the latest rental options.

For families who would like to stay in a hotel, we suggest staying at the Harbor View Hotel. Located across from the Edgartown Lighthouse, this hotel has recently renovated many of its rooms, and also offers a select number of Captains Cottages: 1-3 bedroom cottages that are a part of the hotel’s grounds. Harbor View Hotel offers everything from a pool to lawn games, plus it boasts a large front porch and restaurant that look directly at the Edgartown Lighthouse.

Where to Eat on Martha’s Vineyard

The small villages across the island have fun little restaurants that you can explore. Here were our favorite restaurants that we enjoyed while on Martha’s Vineyard:

Restaurants in Edgartown

  1. Seafood Shanty: Located on the waterfront in the center of Edgartown, this restaurant offers panoramic views of the bay and the island of Chappaquiddick. Fresh seafood is a must here, as this restaurant is focused on its old fashioned New England roots.
  2. Among the Flowers (Breakfast): Also in the center of Edgartown, Among the Flowers is a lively breakfast restaurant, drawing tourists and islanders alike. Be prepared to wait for a table, but once seated, you will be treated to great breakfast food in a fun atmosphere.
  3. Ice Cream and Candy Bazaar: A must-visit location in Edgartown (in our opinion)! This ice cream shop, located on the water (next to the Seafood Shanty), boasts everything from basic vanilla ice cream to a decadent chocolate fudge brownie flavor. After paying, go outside and sit on the benches by the docks to look out.

Restaurants in Menemsha:

  1. Menemsha Deli (Lunch): Menemsha Deli was our pit-stop for lunch during our day-long tour of the island. It’s a simple sandwich shop, but thanks to it’s rather isolated location, variety of sandwich options, and fun picnic tables out front, we found it really enjoyable. Also, if someone in your party doesn’t love fish, this is the best food option on the west side of the island.
  2. Fish Markets in Menemsha: For those interested in seafood, Menemsha is a great destination. It is known as the docking location for many of Martha’s Vineyard’s fishermen. Fish markets along the docks offer fresh catch (both raw and cooked on-site). Grab your food and head out to the benches or docks for the best view in town.

Things to Do in Martha’s Vineyard

Island Tour

After spending the first couple of days of our trip in Edgartown, we headed out to explore the island. We were shocked by how each town and community on Martha’s Vineyard had a truly unique character. While Edgartown is the island’s hub for wealthy summering families, Menemsha is nearly a complete 180: a small fishing village. Plus, the famous lighthouse on the other side of the island is definitely worth your drive. Martha’s Vineyard is a rather large forested island (it takes over 30 minutes to cross from Edgartown to Gayhead Lighthouse). Below were a few of our favorite highlights during our island drive:

Gayhead Lighthouse

1. Gayhead Lighthouse

Located on the direct opposite side of Martha’s Vineyard from Edgartown, Gayhead Lighthouse is beautiful. It’s located in a rather remote area of the island, but a few tourist shops and food stalls have opened up near the parking lot. Gayhead is located atop steep cliffs that lead into the ocean, creating a dramatic photographic stop on our island tour.

Docks at Menemsha, Martha's Vineyard

2. Menemsha

Located on the northern side of the island, Menemsha is Martha’s Vineyard’s fishing village. As an active docking site, this is arguably the best place to get the freshest seafood on the island. Menemsha is also a great place to watch the sun set, and islanders and tourists gather nightly to watch together. We visited Menemsha at lunch time, and enjoyed the town’s food options. Additionally, we loved to stroll along the fish markets and docks to watch the fishermen do their work.

3. West Tisbury, Aquinnah, and Chilmark

Located around the island, each of these towns are adorable blink-and-you’ll-miss-it communities. Make sure to peak into the unique stores in each: from a packed general store, to a busy lunch spot for pizza and sandwiches. While each town is small, they are clearly the places of childhood memories and traditions, and have plenty of charm to share with newcomers too.

While some people complete their island tour by visiting the other two towns on the island (Oak Bluffs and Vineyard Haven), we preferred to see them another day, as each town is relatively big, and we wanted to have enough time to explore each on their own.

Other Things to Do on Martha’s Vineyard

Visit Katama Beach/ South Beach:

Only a 10 minute drive from Edgartown, Katama beach is located on the southern side of Martha’s Vineyard. The sandy beach is a favorite for families, and the wind-swept grasses leading to the beach are fun to see. Be wary of the waves coming off the Atlantic Ocean however (it is fine for those just enjoying the beach, but during certain times of the year, if you have younger children, consider finding a calmer beach on the North side of the island).

Visit Vineyard Haven

Vineyard Haven is one of the two ferry ports on the island. The town offers a fun central shopping street, and (while still expensive), boasts stores that have more reasonably priced shops as compared to Edgartown. We loved Vineyard Haven for its New England architecture and location just above the ocean. We also enjoyed that Vineyard Haven was much more relaxed as compared to Edgartown. Vineyard Haven also offers a small movie theater for families looking for a fun outing if there is a storm.

Oak Bluffs, Martha's Vineyard

Visit Oak Bluffs

Oak Bluffs is where the other ferry port is located. The town is way more laid back compared to Edgartown or Vineyard Haven, and offers the most amount of character of any of the three. Circuit Avenue and Kennebec Avenue are the two main shopping streets in town, offering everything from beachy clothing stores to doughnut or ice cream shops, and restaurants. The town also has a historic carousel that was originally operated on Coney Island, which kids would enjoy.

By far the most striking part of Oak Bluffs is the campground of small cottages that look more like gingerbread houses. Originally a Methodist church camp, the houses were the final iteration of housing built for the camp. Almost all of the houses are now privately owned, and are carefully cared for. Owners take pride in their unique design finishes, from brightly colored cornices to pastel trims. Winding through the walkways that connect the houses is always a fun end to your day in Oak Bluffs, as you can see the variety in each house, and appreciate the owners who live there and keep them up.

Edgartown, Martha's Vineyard

Spend Time in Edgartown

While there is a ton to explore around Martha’s Vineyard, we chose Edgartown as our home-base for a reason: the town is famously the postcard image of Martha’s Vineyard, and is home to some of the islands most classic landmarks. Wander through the streets of town, and make sure to walk around the surrounding neighborhoods as well. All of the buildings in Edgartown are covered in either white shiplap or wood shingle siding, weathered gray, and Hydrangea bushes are as ubiquitous as grass in front yards, giving the town a unified and elite feel. Shops in Edgartown vary from a general store that is overflowing with beach toys to small boutiques and even the very first Vineyard Vines store, making it fun to browse. Also make sure to walk out to the Edgartown Lighthouse and explore the beach it sits on!