I’ve been visiting Martha’s Vineyard since 2019, from day trips and long weekends to week-long summer vacations
Over the years, we’ve found plenty of places we return to again and again. Here are our favorite things to do, beaches to visit, restaurants to eat at, and places to explore on Martha’s Vineyard.
Edgartown: Our Favorite Place to Stay
We’ve stayed in both Oak Bluffs and Edgartown, but our favorite, hands down, is Edgartown. It’s the part of the island we always seem to come back to. We love being able to walk to restaurants, shops, the harbor, and the lighthouse without needing to get in the car. Oak Bluffs is definitely livelier, but I’m an Edgartown and Katama person.
There are two houses we typically rent for a week-long vacation, but we have also stayed at The Richard Hotel for a long weekend and LOVED it. They provide homemade breakfast and afternoon snacks every day, and I am still thinking about their chia pudding.
Our Favorite Things to Do on Martha’s Vineyard
Walk Around Downtown Edgartown
One of our favorite things to do is simply spend a few hours walking around downtown Edgartown. On a week-long trip, we’ll usually have at least one or two days where we don’t plan much and just explore.
It’s just as fun during the day as it is after dinner. We love wandering the side streets, looking at the beautiful homes and flowers, browsing the shops, and stopping for ice cream.
In the evening, one of our favorite things to do is grab a bench and people-watch for a while.
There are also plenty of boutiques and souvenir shops, so it’s an easy place to spend a slow afternoon without really having an agenda.
Visit Edgartown Lighthouse
While you’re downtown, walk over to Edgartown Lighthouse. The lighthouse and surrounding beach make such a pretty backdrop, especially if you’re looking for a spot to take family pictures while you’re on the island.
It’s an easy walk from the center of town and one of our favorite spots for photos. From The Harborview Hotel, you can cross the street and walk along the sandy path to the lighthouse and beach.
Catch a Sunset in Edgartown
One of our favorite ways to end the day is by heading down to the waterfront in downtown Edgartown around sunset. We love finding a spot near the docks, watching the boats in the harbor, and just taking in the view as the sky changes.
It’s especially nice after dinner when you’re already downtown and don’t really have anywhere else you need to be.
Walk Around Oak Bluffs
We also love spending time walking around Oak Bluffs. The harbor is always fun to explore, with plenty of restaurants and places to stop for a drink. Nancy’s is one of our favorite spots to grab a drink and people-watch near the water.
“And make time to wander through the Gingerbread Cottages. We love wandering through the neighborhood, getting a little lost on the streets, and taking in all the colorful cottages and unique architecture.
Bike or Walk Along the Island Paths
Walking and biking are two of our favorite ways to enjoy the island. Chris usually brings his bike, while I’m much more likely to be out walking.
It’s such a nice way to start the morning or wind down in the evening, especially when you don’t really have anywhere you need to be.
Visit Alley’s General Store
Alley’s General Store in West Tisbury is such a fun little stop. They have food, souvenirs, gifts, and all kinds of random things to browse.
We’ve also heard plenty of stories about celebrities stopping in over the years. We’ve never spotted one ourselves, but every time we go, we’re secretly wondering if this will finally be the day we run into Larry David.
Trivia at The Ritz
If we are on the island on a Tuesday night, then you will find us playing trivia at The Ritz in Oak Bluffs. I’m generally our go-to person for the pop culture questions, although every once in a while, I somehow pull an answer from a completely random category out of nowhere.
Make sure to get there early, because seats fill up very quickly!
Visit the Aquinnah Cliffs
The Aquinnah Cliffs are one of those places we still stop at even after multiple trips to the island. The view of the Aquinnah Cliffs from the beach is soooo pretty and one of the reasons we come back every summer.
There are also a few small shops nearby, plus Gay Head Lighthouse, so it’s worth spending a little time walking around and exploring the area.
Visit Edgartown Books
We usually stop into Edgartown Books at least a couple of times during a trip. Sometimes we’re checking out the new releases, and other times being on vacation just puts us in the mood to pick up a new book.
It’s a small, cozy local bookstore and one of those places we almost always find ourselves wandering into when we’re downtown.
Walk to Great Rock Bight
Great Rock Bight is a great option for a non-beach day. We usually make time for it every few years when we want something a little quieter and more outdoorsy.
We love walking the trail down to the beach and then spending some time walking along the shoreline. It’s a peaceful spot and a nice change of pace from a full beach day or walking around town.
Our Favorite Martha’s Vineyard Beaches
State Beach
My favorite thing about State Beach is that it doesn’t usually feel too crowded, thanks in part to the parking being spread out along Beach Road. You can sit on the ocean side or the pond side, so if it’s especially windy or you’d rather have calmer water, the pond side is a great option. On a windy day, you can even catch windsurfers on the pond side, making for great entertainment.
The only con? There’s no bathroom.
South Beach
South Beach in Katama/Edgartown is one of my favorite beaches to visit. There’s plenty of parking, plenty of space on the beach, and bathrooms.
One thing to keep in mind is that the surf can be rough. There can be a noticeable drop-off when you enter the water, along with strong waves and currents, so this is definitely a beach where we pay attention to the conditions.
East Beach on Chappaquiddick
East Beach on Chappaquiddick is one of our favorite beaches on Martha’s Vineyard. You do have to pay to take the Chappy Ferry over from Edgartown, but for us, that’s all part of the experience.
Once you’re on Chappaquiddick, you’ll drive a few minutes before parking near Dike Bridge, the site connected to the infamous 1969 Chappaquiddick incident.
From there, it’s free to access the beach. You’ll walk past The Trustees stand, where there are a few bathrooms, and continue along the path to the sand.
There are no lifeguards, so definitely pay attention to the conditions, but we’ve found East Beach to be a beautiful, peaceful spot with calm water that’s great for swimming.
Moshup Beach
We love Moshup Beach and make a point to visit at least once every summer. Located in Aquinnah, it’s one of our non-negotiable beach days. The view of the Aquinnah Cliffs from the beach is absolutely breathtaking and one of the reasons this spot feels so special.
Non-residents do have to pay to park, usually around $30 to $35, but we think it’s worth it. We typically drop one person off with all the beach gear, then the driver parks and walks back down.
The beach usually doesn’t feel too crowded, and while the waves can get choppy, we’ve had plenty of great swimming days here. Just pay attention to the conditions.
One thing to know is that there is a clothing-optional section farther down the beach beyond the rocks, so keep that in mind if you’re visiting with kids or exploring the shoreline.
Our Favorite Martha’s Vineyard Restaurants
We typically eat dinner out every night when we’re on vacation. The houses we rent have kitchens, but our mindset is pretty simple: we only get access to these island restaurants so often, and we have the rest of the year to cook at home.
We have a handful of favorites we try to visit each summer, while still leaving room to try at least one new restaurant on each trip.
Seafood Shanty
Located in downtown Edgartown, Seafood Shanty has become more of a drinks spot for us than a dinner destination. They have frozen drinks, beer, cocktails, and a rooftop deck that’s such a fun place to sit on a nice day.
The food has been a little hit-or-miss for us, especially since Chris doesn’t eat seafood, but I always enjoy the sushi. If we’re looking for a drink and a great atmosphere in Edgartown, this is one of our go-to spots.
Lookout Tavern
Lookout Tavern in Oak Bluffs is one we try to get to every year, although realistically, it’s probably closer to every other year.
We usually grab seats at the bar, but they also have outdoor picnic tables. The menu has plenty of options, including sandwiches, salads, and sushi, and we always seem to leave happy with both our food and drinks.
Martha’s Vineyard Chowder Company
Another Oak Bluffs favorite is Martha’s Vineyard Chowder Company. We probably make it here every couple of years, but we’ve always had really good meals.
They moved to a new location on Kennebec Avenue in 2026, so we’re excited to check out the new space on a future trip.
Behind the Bookstore Cafe
Behind the Bookstore Cafe in Edgartown is one of our favorite spots to stop for coffee, tea, or breakfast.
It can definitely be on the expensive side, and you may not always see prices listed, so we tend to go more for the atmosphere and experience. It’s tucked away right in downtown Edgartown and feels like a little escape from the busier streets.
Among the Flowers Cafe
Among the Flowers Cafe might be one of my favorite breakfast spots in downtown Edgartown. It’s such a cute little place and is open for breakfast and lunch.
Their breakfast is SO good. I love the açaí bowl, and they also have yogurt and granola bowls, breakfast sandwiches, and plenty of other options. It’s a 10 out of 10 for us and one we try to visit every year.
The Newes from America
The Newes from America is another Edgartown dinner spot we’ve returned to over the years. Its menu can be a little hit-or-miss for us and has felt more limited on some visits, but we still really enjoy stopping by.
Our favorite part is sitting outside with a drink. It’s great for people-watching, and depending on the night, you may even catch live music nearby.
After so many trips to Martha’s Vineyard, these are still the places we find ourselves coming back to. And knowing us, this list will probably keep growing every summer.
And I’m sure this list will keep growing with every trip!
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