If you’re planning a trip to Martha’s Vineyard, Oak Bluffs is one town you’ll definitely want to spend some time exploring.
We’ve stayed in Oak Bluffs before, although these days we usually make Edgartown our home base. Oak Bluffs has a completely different feel, with a busier downtown, lots of restaurants and bars, a lively waterfront, and the colorful Gingerbread Cottages that make the town so recognizable.
Our first long weekend on Martha’s Vineyard in 2020 was actually based in Oak Bluffs. We walked onto the ferry, stayed at the motel right across from the ferry terminal, and explored the town without a car.
Even now, when we’re staying elsewhere on the island, we almost always make our way back to Oak Bluffs a few times during a trip.
Some of the best things to do in Oak Bluffs are exploring the Gingerbread Cottages, walking Circuit Avenue and the harbor, visiting Inkwell or State Beach, riding the Flying Horses Carousel, and grabbing dinner or drinks downtown. Oak Bluffs is also one of the easiest Martha’s Vineyard towns to visit without a car.
Why Visit Oak Bluffs?
Oak Bluffs feels livelier than Edgartown, especially during the summer.
There are plenty of restaurants, bars, shops, and people walking around downtown, and there’s almost always something going on near the waterfront. We personally prefer the quieter charm of Edgartown for where we stay, but Oak Bluffs is one of our favorite places to visit when we want a little more activity.
It’s also incredibly easy to spend a few hours here without much of a plan. Walk around, get a drink, grab something to eat, wander through the Gingerbread Cottages, and eventually find yourself sitting somewhere near the harbor, people-watching. That’s pretty much our ideal Oak Bluffs afternoon.
Where to Stay in Oak Bluffs
We’ve stayed at the Surfside Motel twice and really liked it for what we needed. It was charming, walkable, and right near the ferry. We did notice some dampness during our 2019 stay, so I can’t speak to what the rooms are like now.
We’ve also stayed at The Morgan Hotel and would definitely recommend it. My parents have stayed at Summercamp too. Their room was on the smaller side, so I’d just make sure you choose the right room size for your family and needs.
If you’re visiting Martha’s Vineyard without a car, staying in downtown Oak Bluffs is incredibly convenient.
Walk Circuit Avenue and Downtown Oak Bluffs
One of the easiest things to do in Oak Bluffs is simply walk around downtown, especially along Circuit Avenue. There are plenty of shops, restaurants, bars, and little places to stop along the way.
We usually don’t go into Oak Bluffs with a strict itinerary. We’ll park, start walking, and see where the afternoon or evening takes us.
It’s definitely busier than some other parts of Martha’s Vineyard, especially during peak summer weekends, but that’s also part of the fun.
Ride the Flying Horses Carousel
The Flying Horses Carousel is one of those classic Oak Bluffs stops, especially if you’re visiting with kids. It’s right downtown, so it’s easy to add while you’re walking around Circuit Avenue.
Even if you’re not planning to ride it, it’s worth popping in to see. It’s one of those places that just feels very Oak Bluffs.
Walk Through Ocean Park
Ocean Park is another easy stop while you’re exploring downtown Oak Bluffs. The big open green space and historic homes surrounding it make it one of the prettiest areas of town.
We usually walk through here rather than making it a destination on its own, but it’s definitely worth including if you’re wandering between downtown, the waterfront, and the ferry area.
Explore the Gingerbread Cottages
You really can’t visit Oak Bluffs without walking 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 details.
This is one of those places where you don’t necessarily need anything specific to do. Just give yourself some time to walk around, take pictures, and admire the houses. Even after several Martha’s Vineyard trips, it’s still fun to come back and explore.
Spend Some Time Around Oak Bluffs Harbor
The harbor is another area we always end up walking around. We love finding a bench near the boats, sitting for a while, and watching everyone come and go. There are also plenty of places nearby to grab food or drinks, which makes it an easy area to spend an afternoon or evening. It’s especially fun during the summer when the harbor is busy and there’s always something happening.
Relax at Summercamp
We also really enjoy stopping by Summercamp. One of our favorite things to do is sit out on the front porch in the rocking chairs and people-watch for a while. It’s a simple way to slow down and enjoy the energy of Oak Bluffs without needing much of a plan.
Visit Inkwell Beach
Inkwell Beach will always be a memorable spot for us because it was the first beach we visited on our first long weekend to Martha’s Vineyard in 2020. Since we walked onto the ferry and stayed right across from the Oak Bluffs terminal, it was an easy beach for us to get to without a car. It’s right near downtown, making it a great option if you want beach time without traveling far.
Visit State Beach
State Beach stretches along Beach Road between Oak Bluffs and Edgartown, so it’s an easy stop to pair with a day in Oak Bluffs. We love walking and biking along this stretch, and Chris is much more likely to be on a bike while I’m usually walking.
The beach itself is also one of our favorites. Parking is spread out along Beach Road, so it usually doesn’t feel too crowded, and you can choose between the ocean side and the calmer pond side. Just keep in mind that there are no bathrooms.
Jump Off Jaws Bridge
If you’re looking for one of those classic Martha’s Vineyard experiences, Jaws Bridge is definitely one of them. Jumping off the bridge is one of those fun island traditions, but only if conditions are safe and you’re comfortable in the water.
It’s also along Beach Road between Oak Bluffs and Edgartown, so it’s easy to pair with State Beach or a bike ride between the two towns.
Kayak With Island Spirit Kayak
One of our favorite ways to get out on the water is kayaking with Island Spirit Kayak. It’s such a fun way to see a different side of Martha’s Vineyard and adds something active to a trip that might otherwise be filled with beaches, restaurants, and walking around town.
Where to Eat and Drink in Oak Bluffs
We have a handful of Oak Bluffs restaurants we return to again and again.
Offshore Ale Company
Offshore Ale is one of our most reliable Oak Bluffs stops. We usually go once or twice during a trip because the menu has something for everyone. We’ve had everything from burgers and salads to pizza, and the food is consistently good. It’s one of those places we know we can count on for an easy, casual meal.
Lookout Tavern
Lookout Tavern is one we try to visit 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.
Jimmy Seas Pan Pasta
Jimmy Seas is another Oak Bluffs favorite, especially when we’re in the mood for pasta. Their pan pasta is hearty, comforting, and exactly the kind of meal that hits the spot after a long beach day or a lot of walking around town.
Martha’s Vineyard Chowder Company
Martha’s Vineyard Chowder Company is another Oak Bluffs restaurant we’ve enjoyed over the years. We probably make it here every couple of years rather than every trip, but we’ve always had really good meals. They moved into a new location in Oak Bluffs in 2026, so we’re excited to check out the new space on a future visit.
Nancy’s
Nancy’s is one of our favorite places to stop for a drink when we’re near the harbor. For us, the location is a big part of the appeal. We love grabbing a drink, hanging out near the water, and people-watching before continuing around town.
Back Door Donuts
Back Door Donuts is such a fun place to stop for a treat. Whether you grab a donut during the day or make it part of an evening in Oak Bluffs, it’s one of those classic island stops that’s worth trying at least once.
Get Ice Cream
There are also plenty of ice cream shops around Oak Bluffs, which makes it very easy to end the night with something sweet. We love grabbing ice cream and walking around downtown or the harbor on a warm summer evening.
Play Trivia at The Ritz
If we’re on Martha’s Vineyard on a Tuesday night, there’s a good chance you’ll find us at The Ritz playing trivia. This has become one of our favorite Oak Bluffs traditions.
I’m generally our go-to person for the pop culture questions, although every once in a while I somehow pull the answer to something completely random out of nowhere. Trivia gets busy, so make sure you arrive early if you want a seat.
Oak Bluffs During the Day vs. at Night
Oak Bluffs can feel very different depending on when you visit.
During the day, we love walking around the harbor, exploring the Gingerbread Cottages, shopping, heading to the beach, and grabbing lunch or a drink.
At night, downtown gets livelier. There are more people out, restaurants and bars are busy, and the town has much more of a nightlife feel than some other parts of the island.
If you enjoy having plenty going on around you, that might be exactly what you’re looking for.
We personally tend to enjoy Oak Bluffs during the afternoon and early evening before heading back toward Edgartown, unless, of course, it’s Tuesday trivia night.
Can You Visit Oak Bluffs Without a Car?
Absolutely.
In fact, our first long weekend on Martha’s Vineyard in 2020 was completely car-free. We walked onto the ferry, stayed right across from the Oak Bluffs terminal, and explored the town on foot.
That trip really showed us how easy Oak Bluffs can be without a car, especially if you’re staying downtown and want to spend your time walking, eating, shopping, or heading to Inkwell Beach.
The Vineyard Transit Authority also connects Oak Bluffs with other towns around the island, so you can explore beyond downtown without bringing your own vehicle.
Edgartown or Oak Bluffs?
We’ve stayed in both, and our personal preference is Edgartown.
Edgartown has more of the quiet, classic Martha’s Vineyard feel that we love, while Oak Bluffs is livelier and has more going on, particularly at night.
But that doesn’t mean we skip Oak Bluffs. Far from it.
Some of our favorite island traditions are here, from trivia at The Ritz and meals at Offshore Ale to wandering through the Gingerbread Cottages and sitting near the harbor with a drink.
If you’re staying on Martha’s Vineyard for several days, I definitely recommend making time for both towns.
Final Thoughts on Oak Bluffs
Oak Bluffs brings something completely different to a Martha’s Vineyard vacation.
You can spend the morning kayaking or relaxing at Inkwell Beach, walk through the Gingerbread Cottages, grab lunch at Offshore Ale, spend the afternoon around the harbor, and end the night with trivia or a donut.
We might not choose Oak Bluffs as our home base anymore, but it remains one of those places we return to on almost every trip.
And that’s one of my favorite things about Martha’s Vineyard. Each town has its own personality, and Oak Bluffs is definitely the place we go when we’re looking for a little more energy and fun.
More From Martha’s Vineyard
Leave a Reply