Martha’s Vineyard Travel Guide: Where to Stay, Eat, and What to Do

Martha’s Vineyard has a long-standing cultural presence for Black travelers, because it was one of the first places in the history of this country where Black people could own property but also escape their daily lives for a bit of reprieve from racism. It is a very communal place where mainstays know each other and peaceful togetherness is important, which you feel as soon as you arrive.

Island life has a much slower pace, each town has its own personality, and the experience is more about settling into a gentle rhythm than constantly going and doing. If you feel compelled to move around, the island asks you to do it unhurriedly, and if you don’t feel like doing anything, the island allows you to relax into it. I did Martha’s Vineyard as a reset during a time in life where I was a bit stressed, and it was the first time that I traveled to a new destination without an itinerary. That turned out to be the right way to experience the island for me, but it’s also great for a social, good-time summer experience as well.

Edgartown Harbor/Katama Bay area

Where to Stay in Martha’s Vineyard

Each town in Martha’s Vineyard has a slightly different feel, and where you stay depends on what you want to do most and how you plan to get around. No matter where you stay, I recommend booking extremely early. The island fills up quickly and accommodations can be limited and/or expensive the closer you get to the summer. When I say early, I mean six months to a year in advance, if possible. Trust me on this.

Oak Bluffs

Oak Bluffs is probably the most popular area, especially for Black travelers. There’s a strong sense of community and it’s home to Inkwell Beach plus many great shops and restaurants on Circuit Ave. You’ll also find the famous gingerbread cottages here. It’s a great option if you want to be close to everything plus be able to walk everywhere within in town.

Martha's Vineyard Camp Meeting Association Cottage Museum also known as the Gingerbread Cottages

Edgartown

Edgartown is slightly quieter than Oak Bluffs, but similarly, there are boutiques and restaurants here as well. Edgartown is also the home of the Edgartown Lighthouse. The streets are lined with white houses with impeccable landscaping so the walk to the lighthouse from town is quite charming.

Edgartown Lighthouse

Vineyard Haven

Vineyard Haven may be the most low-key and residential, and I spent the least amount of time here, but it’s convenient for ferry access and also has shops and restaurants.

The Morgan Hotel

I stayed at the Morgan Hotel which is just across the street from Circuit Avenue and a hop, skip, and a jump to the beach. It was a comfortable stay, and it’s also dangerously close to Back Door Donuts, a late night treat shop you don’t want to miss out on.

When I traveled to Martha’s Vineyard, it was just after the summer rush in early September, so the hotel was self-entry. You can enter the building and your room using a code, and though front desk staff was not always available, your room is still cleaned daily by housekeeping and there’s access to things like water, coffee, and towels if needed. For my first time in Oak Bluffs, I loved this stay for its proximity to everything and home away from home feel.

The Morgan Hotel

Things to Do and See in Martha’s Vineyard

Starting with the beaches, Inkwell Beach is one of the most well-known and culturally significant beaches on the island and is a great place to spend a full day, but you can also explore other beaches around the island depending on where you’re staying. For example, there is a beach right at the lighthouse in Edgartown, which is nice if you want to kill two birds with one stone, or you can spend a day at Moshup Beach (Aquinnah Public Beach) whichever day you go to the Aquinnah Cliffs Overlook.

Take time to walk through Oak Bluffs, especially Circuit Ave. Conveniently, you can get to the gingerbread cottages from an entry point in the middle of Circuit Ave. The area is colorful, quiet and one of the most unique parts of the island.

In Edgartown, you can get away with just strolling through town, no plan necessary. Hang out at a book store, browse other shops, and stop for food or coffee.

Moshup Beach (Aquinnah Public Beach)

Where to Eat in Martha’s Vineyard

You have to eat everywhere you go, which naturally makes discovering new food and good restaurants a big part of the travel experience.

In Martha’s Vineyard, places like The Sweet Life Café are great for an intimate, sit-down experience with a thoughtful menu while you can hit a place like Fat Ronnies for a really good, sloppy burger.

There are plenty of other spots across the island, and one of the best ways to experience the food scene is to keep your plans flexible and try different places as you go. Though you can make a reservation at some of the restaurants, and you probably should during peak season, I didn’t have a reservation for anywhere I went on the island in September and I was able to walk in and be seated and served quickly.

If you want a full breakdown, I’ve shared everything I ate in a separate article.

Scallops at The Sweet Life Cafe

Getting Around Martha’s Vineyard

Martha’s Vineyard is small, but getting around still requires a bit of planning, because you can’t walk from town to town.

You can bring a car over on the ferry, rent a car once you arrive, or use bikes and public transportation. If you’re staying in one area like Oak Bluffs, you can walk to a lot of places, but if you want to explore multiple towns, having a car or bike makes it much easier.

Speaking of the ferry, many people have expressed concern for there being limited slots on the ferry, which makes it difficult for everyone to bring a car across. This is worth considering when deciding whether to fly directly to the island or to fly into Boston and take the ferry over. In my case, I flew Delta directly to the island, which turned out to be the best case scenario for me.

Best Time to Visit Martha’s Vineyard

The most popular time to visit is during the summer, especially from June through August. This is when the island is most active but also when it’s most crowded and expensive.

I went the first week of September, which gave me a quieter experience. The weather is still nice, but the crowds have thinned out, and I was able to relax into my time there. I do imagine, though, that I would love to visit again when there are crowds, because it must be a magical experience to be amongst so many Black people in community and on vacation together.

Inkwell Beach

Tips for Visiting Martha’s Vineyard

• Book your accommodations early, especially if you’re traveling during the summer.

• Plan ahead for restaurants, especially for dinner.

• Give yourself time to explore more than one town.

• Pack layers. It can get cooler in the evenings.

• Don’t over-schedule your days. Part of the experience is slowing down.