Are you looking for fun things to in Oak Bluffs on Martha’s Vineyard?
There are many fun things to do in Oak Bluffs, Massachusetts. As one of the main towns on the island of Marthas’ Vineyard, it is a favorite place for the visitors who come to the island every year.
The ease of visiting Oak Bluffs, even for a day, is made possible by the main ferries, run by the Steamship Authority, as well as smaller ferries, leaving from towns such as New Bedford and Hyannis.
Oak Bluffs is pretty much our favorite town on the island. There are tons of shops and restaurants, but also plenty of other fun things to do, like riding the Flying Horses carousel!
The guide below shares some of the best things to do in Oak Bluffs on Martha’s Vineyard, so let’s dive in!
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Where is Oak Bluffs
Located on the east chop of Martha’s Vineyard, Oak Bluffs is one of the three major towns on the island. It’s also one of the two towns where the ferries come in. If you choose to visit Martha’s Vineyard for the day, you’ll mostly come into Oak Bluffs.
Things to Know Before You Visit Oak Bluffs
- Oak Bluffs is a very popular town with limited parking. You may want to hire a ride, take the bus, or bike into town. Also, be aware of the time limits on parking spaces.
- Traffic in town can be crazy when the Steamship Authority ferry arrives. It is always good to note the ferry schedule before driving into town.
- Oak Bluffs has a (clean) public bathroom! It is located on Kennebec Avenue between Healy Way and Lake Avenue.
- If you are bringing your dog with you on vacation, keep in mind that dogs are not allowed on public beaches from May 1st- September 15th.
🎧Enjoy this audio tour about Oak Bluffs!
Things to Do in Oak Bluffs by the Water
1. Relax in Ocean Park
Ocean Park is located adjacent to the ferries and is one of the first parts of town that you will see. It is a sprawling park where kids can run around during the day. Benches are available to provide a space for a rest break, or just a place to sit and take in all the sights and sounds of the ocean.
The bandstand in the center of the park is the main feature where the occasional concert is played.
Every third Friday in August, the Oak Bluffs Fire Department puts on a fantastic fireworks display. Folks arrive early to get a good spot on the grass of Ocean Park and listen to the band play before the illuminating show!
2. Dip Your Toes in the Water at Inkwell Beach
The closest beach to the center of town, Inkwell Beach gives visitors a chance to swim in the Nantucket Sound without having to travel too far.
Access to the beach is at the end of Tuckernuck Avenue. While you’re there, sit on the sand and watch the ferries come in and out of the harbor.
3. Have Dinner with a View at the Lookout Tavern
One of our favorite restaurants in Oak Bluffs is the Lookout Tavern.
Located on Seaview Avenue, the casual restaurant offers an extensive and varied menu. Any appetite will be satiated at the Lookout!
4. Kayak or Paddleboard on Sengekontacket
Ride your bike down Seaview Avenue bike path (it will turn into Beach Road) for less than two miles and you’ll find a perfect spot for kayaking and paddle boarding.
Island Spirit Kayak, located on the Sengekontacket side of Beach Road next to the “Little Bridge”, offers several watercraft rental options, as well as kid adventure tour camps. It’s one of our favorite things to do on Martha’s Vineyard!
Activities Your Kids Will Love To Do in Oak Bluffs
5. Ride The Flying Horses Carousel
When you visit Oak Bluffs, riding on the oldest operating carousel in the nation is a must! Built in the late 1800s, the Flying Horses Carousel was moved to Oak Bluffs from Coney Island in 1884 and has been in its prime location ever since.
Kids of all ages ride the horses while grabbing rings as they pass by the dispenser. If you get the brass ring, you win a free ride!
Don’t worry, little kids get their opportunity to win as well. The inside row of horses are smaller and have their own ring dispenser.
6. Play at the Arcade on Circuit Avenue
The Oak Bluffs Game Room on Circuit Ave. is a fun way to spend some time while in Oak Bluffs.
The doors to the arcade open wide facing the street, allowing those who pass by to hear the chimes and beeps of the game playing.
Old favorites like skeeball and newer games are available to play. Don’t forget to turn in your tickets for a fun prize!
7. Go Bowling
All of the fun things to do in Oak Bluffs isn’t on Circuit Avenue! Just off Circuit on Uncas Avenue is the Barn & Bowl Bistro, where you can go bowling and eat a delicious dinner during the game.
Lanes are typically available for reservation in the evenings, so plan accordingly. The Barn & Bowl Bistro is open Monday-Saturday.
8. Explore the “Cottage City”
One of the most unique things about Oak Bluffs is the Victorian-style gingerbread cottages that line the walkways of the Martha’s Vineyard Camp Meeting Association, or the “campground.”
Cottages are painted in fun, bright color combinations, and visitors are welcome to walk around and take photographs. As enticing as the houses are, they are all privately-owned, so when touring the campground, please respect their property and privacy.
The Cottage Museum on the premises allows visitors to see what a typical cottage looks like on the inside. It also contains a small gift shop.
At the end of the summer, during the third week of August, the campground hosts the “Grand Illumination Night.” Chinese lanterns are hung from the porches of the cottages while a band plays music in the Tabernacle (see below). It is a very popular event that has been taking place since 1869.
Shop & Eat on Circuit Avenue
Once in town, head over to Circuit Avenue, the main drag in town. Stores offer souvenirs, seasonal wear, and some unique and funky styles. You won’t go hungry either! Plenty of restaurants and treat shops line the street. There are few spots you should visit before leaving the island so you can have an authentic Vineyard experience!
9. The Black Dog Store
One of the most famous logos from Martha’s Vineyard is the Black Dog. Though the namesake tavern is located in Vineyard Haven, you can buy (almost) anything you’d like in their clothing and housewares store! Sweatshirts, stickers, or socks. You name it, they have it!
10. Mad Martha’s Ice Cream
When you want a sweet treat, make your way over to Mad Martha’s. Savoring the homemade ice cream that comes in classic and fun flavors is a must-do on the Vineyard for visitors and natives alike.
If you have a large group or are feeling hungry, you can order the Pig’s Delight, a 12-scoop sundae with tons of toppings, whipped cream, and a cherry on top!
11. Back Door Donuts
In a nondescript loading area on Kennebec Avenue, behind the MV Gourmet Cafe, you will find people lined up waiting for donuts. Backdoor Donuts opens around sunset and serves freshly made delicious donuts.
Traditional flavors like Boston Creme as well as more unique combinations, like maple and bacon, are available for purchase.
It is a fun experience that feels like a well-known secret! Though you may wait up to 30 minutes before you get your hands on a warm and fresh donut, they are certainly worth the wait!
12. Offshore Ale Company
Another popular eatery on Kennebec Avenue is the Offshore Ale Company. Come hungry and thirsty, as the large portions of the delicious food and the beers offered from this microbrewery will fill you up! We recommend their thin crust pizzas!
Enjoy Some Music in Oak Bluffs
13. Sing in the Tabernacle
In the center of the “Cottage City” campground is the Tabernacle, a large circular, open building. During the summer months, visitors can attend a church sermon while seated outside, enjoying the fresh air.
Wednesday nights, also during the summer months, there is a “Sing” where families can come together and sing favorite old tunes, like ‘Home on the Range” and “I’m in the Swiss Navy.”
Other events and concerts, like the Island Community Chorus summer show, are also held in this historic building.
Built in 1879, the Tabernacle was designated a National Historic Landmark, as well as the entire campground, in 2005.
14. Listen to the Vineyard Sound
This a cappella group is a 25-year (and counting!) summer tradition on Martha’s Vineyard. Every summer, about a dozen young men live together on the island and perform nightly concerts.
Every Monday and Friday night for about 10 weeks in the summer, the college-aged group performs at the United Methodist Church in Oak Bluffs.
15. Enjoy a Concert at Featherstone Center for the Arts
Although the Featherstone Center for the Arts isn’t in “downtown” Oak Bluffs, it still is worth the drive down Barnes Road to visit.
Featherstone offers several ways to enjoy the arts on Martha’s Vineyard, including their live musical performances. In addition to concerts, they also host outdoor movie nights, And guests can also visit their several galleries and art space.
Other Ways to Enjoy Martha’s Vineyard
Martha’s Vineyard offers more to do on the island! In addition to Oak Bluffs, we love to explore and shop around Edgartown.
While in Edgartown, make sure to stop by some of the filming locations for Jaws!
Lastly, there are plenty of ways to spend your time outside of the major towns on Martha’s Vineyard.
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