Distinct homes, scenic beaches and a history of diversity makes Oak Bluffs one of the most iconic summer destinations in New England. Here’s what to do when you get there.
What was once “Cottage City,” a seasonal retreat — often for African-American tourists – is today a year-round place of leisure and unique island landscapes.
It’s not the stuffy Martha’s Vineyard vibe you’d expect if you’ve never been; instead, there’s a welcoming sense of inclusivity that dates back to the town’s heyday.
It helps that Oak Bluffs is home to the island’s largest marina, where a spring break-like energy flows on summer weekends, and throngs of visitors and locals alike head to popular waterside bars and restaurants.
Once you’ve landed on the Vineyard — checkout The Steamship Authority, Hy-Line Cruises and Seastreak Ferries to get there — here are 12 of the best things to do in Oak Bluffs to make the most of your island visit.
1. Martha’s Vineyard Camp Meeting Association
Back in the 1820s, a religious summer camp thing hit the U.S., starting in the south and eventually working its way up to folks in New England. In 1835, a Methodist preacher opened the first summer camp on Martha’s Vineyard, today known as the Martha’s Vineyard Camp Meeting Association.
That’s the formal name, but most people here know it as The Campground or the Gingerbread cottages, the peaceful community of small, intricately decorated homes centered around the Tabernacle, an old-school meeting place built in 1879.
This is one of the most peaceful spots in New England, where narrow tree-lined streets wind through grassy areas and rows of colorful cottages dating back to the 1860s. The cottages are privately owned — some available to rent — though you can take pics from the main pathways.
July and August are the best months to visit for the most history: you can take a walking tour through the area, visit the museum and say hello to residents and renters hanging out on front porches. The 34-acre neighborhood is just a few minutes from downtown Oak Bluffs, so it’s an easy walk from the ferry drop-off — here’s a map for directions.
2. Flying Horses Carousel
Built in 1876, the Flying Horses Carousel called Coney Island home before landing in Oak Bluffs in 1884, and today it’s the oldest platform carousel still in operation. It’s one of the first sights to see off the ferry, and if you’re traveling with kids it’s a good way to kick off your island trip.
The ride’s carved wood horses with glass eyes and horsehair manes make this one of the more interesting carousels around, and a brass ring game gives kids something to do during the ride. The building gets hot and crowded in the summer, so don’t expect a comfortable stay in line, but it’s worth it to ride a piece of Americana history.
3. Ocean Park
You can catch Ocean Park’s iconic bandstand and serene grassy area from the ferry, and up-close it’s even more peaceful. Benches and walking paths make the park an excellent place to unwind between shopping and eating, and the ocean views over the beach make the park a must-stop in Oak Bluffs.
To the south, restored Victorian-style homes — like the Corbin Norton House — line Ocean Park, making it easy to imagine why this was such a popular summer spot back in the 1800s. Some things never change.
4. Oak Bluffs Beaches
Hitting the beach in Oak Bluffs is easy: you can see the town beach from the Steamship Authority terminal, and it’s a quick walk to the shore as soon as you land.
This beach in front of Ocean Park is the easiest to visit, but there’s also Inkwell Beach between two rock jetties just south of the town beach. Inkwell’s an interesting, historically black beach that was a small haven for the Vineyard’s early African-American tourists, and was included in Green Book travel guides.
Finally, on the west side of Oak Bluffs is Eastville Point Beach, a small, rocky beach that’s perfect for watching sunsets, local fisherman and boats moving in and out of Vineyard Haven Harbor.
5. Downtown Shops
The main stretch down Circuit Avenue is home to tons of shops — some well known, like The Black Dog and Vineyard Vines, and others more under-the-radar. There’s The Corner Store for just about everything, and high-end souvenirs and apparel from shops like Island Outfitters and C’est La Vie.
Summer’s best for shopping: some stores close up in the off-season, though summer weekends can get hot and crowded. Still, if you go to Oak Bluffs, you probably need to come home with something.
6. Backdoor Donuts
Back Door Donuts isn’t about hyperbole: they literally sling donuts from the back door, and it gets the people going. During the day, the bakery out front sells delicious baked goods as expected, but when nights hit — 7pm in the summer — Back Door Donuts starts selling their signature late-night treats.
All the donuts here are good, but the apple fritter is in its own stratosphere. “Hard to say there’s a better apple fritter anywhere in the country,” said one Google review.
Their hours are seasonal, so check Instagram for current hours and latest updates.
7. Ice Cream
If you can’t wait ‘til evening to grab Back Door Donuts, consider ice cream to tide you over in the meantime. There’s no shortage of ice cream options in Oak Bluffs — the hard part is figuring out which place to hit up.
Classic ice cream joints here include Mad Martha’s Homemade Ice Cream, Ben & Bill’s Chocolate Emporium, and Nauti Cow. There’s frozen yogurt at Rosie’s and more treats at Big Dipper, as well as Vineyard’s Best Ice Cream and Coffee Co. You really can’t go wrong with any of them, but check out their menus online if you’re looking for something specific.
8. Bicycle Oak Bluffs
Like ice cream, bicycling is something of a pastime in Martha’s Vineyard, and there are plenty of spots in Oak Bluffs to rent a bike or moped for the day. Check out All Star Martha’s Vineyard Bike Rentals or Anderson’s Bike Rentals, or a handful of other rental shops nearby.
Once you’re in the saddle, there are a few loops and roads you can take in the Oak Bluffs area, as well as a longer trip down to Edgartown via Beach Road, where you’ll pass by Jaws Bridge and Joseph Sylvia State Beach. If you have the time and energy, this is a great way to see more of the island.
9. Visit Island Spirit Kayak
Island Spirit Kayak offers a number of kayak and stand up paddle board tours that focus on enjoying the island environment while also learning about it.
“The guide taught us how to safely catch baby horseshoe crabs, recognize endangered birds, and distinguish different species of clams,” said one Google review.
They offer traditional day-time tours in Sengekontacket Pond, and come night-time, Island Spirit hosts “glow tours” on glass-bottom kayaks and paddle boards that bring the pond’s biology to life at night. And if you want to do your own thing, they offer rentals from three hours to three months and deliver the goods anywhere on the island.
10. East Chop Lighthouse
To get into Vineyard Haven Harbor, boats have to pass somewhere between West Chop and East Chop. A lighthouse was built on the west side in the early 19th century, but it wasn’t until 1869 that someone finally built an East Chop light to signal that side of the harbor.
The original wooden lighthouse was destroyed in a fire, but the iron house built in 1878 still stands today. It’s a cool place to hang out north of town — follow Chop Drive up to Telegraph Hill to get there. Normally, the light is open to visitors on Sundays in summer, though the 2022 season is closed down for lead abatement.
11. Pirate Adventures Martha’s Vineyard
If you’re bringing kids to the Vineyard, spice things up for ‘em with Pirate Adventures, a 90-minute sailing experience that includes swashbuckling mayhem worthy of Jack Sparrow himself.
It’s one of the highest-rated tours on the island for a reason, and the crew’s 40-foot Sea Gypsy X is more than capable of handling even the rowdiest of pirate children. In summers they sail up to three times a day, four days a week, and also offer private charters, sunset cruises and birthday parties.
If your kids are anything like ours, pirate ships are up there with excavators, Amazon vans and monster trucks on the cool vehicle scale, making Pirate Adventures one of the coolest kid-friendly things to do in Oak Bluffs.
12. The Skipper of Oak Bluffs
If you can’t be a pirate, the next best thing is a fisherman or fisherwoman, which you can be on the Skipper of Oak Bluffs. For more than 30 years, the Skipper’s hosted fishing charters around Martha’s Vineyard in search of sea bass, fluke and other local fish.
A typical fishing charter is 4 hours, offered twice a day in summer and once a day in spring and fall. The Skipper also offers private charters, sunset trips and marine life trips along with the Felix Neck Wildlife Sanctuary.
No matter what your itinerary, you’re in for a good time.
“The captain and mate aboard the skipper made our trip one of the best days I’ve had on the water by far,” said one Google review.