Favorite Things to Do in Oak Bluffs, Massachusetts

By Cathryn McCann

May 24 2017


Things to do in Oak Bluffs, MA | There’s an abundance of beautiful architecture and flowers on the island of Martha’s Vineyard.

Photo Credit : Pixabay
Peaceful in the winter, bustling in the summer, Oak Bluffs is a colorful and historic town on the Massachusetts island of Martha’s Vineyard. From sandy beaches and seafood restaurants to eclectic downtown shops and historic cottages, you’ll find more than enough to do and see in Oak Bluffs while visiting the island. It’s also easily accessible, as the Woods Hole ferry docks within walking distance of downtown, lodging, and plenty of great places to eat. To get you started on your itinerary, here are some of our favorite things to do in Oak Bluffs, Massachusetts.
Things to do in Oak Bluffs, MA
One of the vibrantly colored historic cottages in Oak Bluffs.
Photo Credit : Pixabay


Inkwell Beach

If you’re coming from downtown Oak Bluffs, Inkwell Beach couldn’t be more convenient. Located right off of Seaview Avenue and near Ocean Park, Inkwell Beach is a great waterside destination with fine sand and lifeguard surveillance during peak summer hours. It’s also walking distance from the ferry dock, which is handy for those looking to relax on the beach immediately upon arrival.

Joseph Sylvia State Beach

Love going for long walks on the beach? Take a drive down Beach Road between Oak Bluffs and Edgartown, and you’ll see miles of sandy beach perfect for lengthy strolls. Popularly known as State Beach, this is also a favorite destination for swimmers because of its gradual drop-off and gentle waves. From the beach you can access “Jaws Bridge,” so named for being the filming location of the iconic 1975 movie. It’s a favorite spot from which to take a quick plunge into the water, and it’s often full of adventurous jumpers throughout the summer.
Things to do in Oak Bluffs, MA
State Beach in Oak Bluffs as dusk approaches during the off-season.
Photo Credit : Cathryn McCann

Mocha Mott’s

You’ll likely spot the iconic Mocha Mott’s emblem on bumper stickers all over the island, and that’s because this is a favorite destination among locals and visitors alike for (organic and fair-trade) coffee, espresso drinks, baked goods, and other tasty fare. Located in the heart of Oak Bluffs, on Circuit Avenue, Mott’s is a great place to order a drink and hang out with friends and family, sipping and watching the lively town in action. Or take it to go — after all, there’s a lot more to do in Oak Bluffs!

Flying Horses Carousel

One of the most historic and beloved attractions in Oak Bluffs, the Flying Horses Carousel is the fond memory of many a child. Constructed in 1876, the carousel originally operated on Coney Island before being moved to Oak Bluffs in 1884. It was acquired by the Preservation Trust in 1986; an extensive restoration maintained the original horsehair manes and tails and glass eyes. This national landmark is known as the oldest platform carousel in the U.S., making it a must-see for any history aficionado. It still operates in the summertime, and children continue to delight in the chance to grab at the lucky brass ring.
Favorite Things to Do in Oak Bluffs, Massachusetts
The Flying Horses Carousel blends history and fun in downtown Oak Bluffs.
Photo Credit : C.S. Imming Wikimedia Commons

Circuit Avenue

Visit the island in the summertime, and you’ll see there’s rarely a moment when the one-way street of Circuit Avenue isn’t bustling with people. The colorful downtown street is packed with restaurants, bars, ice cream and coffee shops, clothing stores, and little boutiques with unique tourist trinkets. Expect lively crowds, the sounds of arcade games, and the aroma of seafood. Circuit Avenue, Oak Bluffs. 

Paddleboarding and Kayaking

During the summer, a kiosk operation across the street from State Beach rents paddleboards and kayaks to take out on massive Sengekontacket Pond. Paddle around Gravel and Brush islands, along the golf course, and into Major’s Cove. For a longer trip, paddle along the curve of the road toward Edgartown near Sarson Island and Jaws Bridge. It’s a great way to explore one of the largest ponds on the island while getting some exercise, too!

Gingerbread Cottages

The gingerbread cottages at the Oak Bluffs Campground are an iconic, can’t-miss attraction. (The area is the original location of Methodist camp meetings — hence the name “Campground.”) The 19th-century cottages, with their delicate trim, picket fences, and wee size, have the look of storybook gingerbread houses, earning their name now widely known among visitors. Make sure to visit this National Historic Landmark, or take it a step further and rent one for your visit to the island. SEE MORE: Gingerbread Cottages at Oak Bluffs Campground
Things to do in Oak Bluffs, MA
One of Oak Bluffs’ intricately constructed gingerbread cottages.
Photo Credit : Cathryn McCann

Trinity Park Tabernacle

Right in the heart of the gingerbread cottages is this beautiful outdoor event complex. In the summer it offers shade for weekly outdoor church services and hosts cultural and entertainment events in the evenings. The structure was built in 1879 with an octagonal cupola, large arches, and colored glass windows, and the integrity of that original structure has been maintained with some upgraded amenities. It’s worthwhile to attend an event here or just take some time to view a unique structure that’s earned a spot on the National Register of Historic Places.

Coastal Drive (East Chop Lighthouse)

There’s nothing quite like rolling down your windows and going for a lovely coastal drive. East Chop Drive in Oak Bluffs follows a long, seaside curve with beautiful water views on one side and architecturally beautiful homes on the other. Along the curve in the road you will find the East Chop Lighthouse, where you can sit on a bench and watch the Oak Bluffs ferry go by. Heading further down the road will take you past Oak Bluffs Harbor, where lovely boats and yachts dock, and then back into town via Lake Avenue. SEE MORE: Cape Cod, Nantucket & Martha’s Vineyard Lighthouses | Photos
Favorite Things to Do in Oak Bluffs, Massachusetts
The East Chop Lighthouse in Oak Bluffs.
Photo Credit : Marc Belanger Wikimedia Commons

Barn, Bowl & Bistro

Far from being a run-of-the-mill bowling alley, this classy, vibrant, and modern establishment is a great destination for adults and kids alike. The alley has 10 lanes with couch seating, coffee tables with a pull-out ice bucket shelf for beer and wine, HD televisions, and full service for some tasty sustenance while bowling. Lunch and dinner are served daily at the bistro, which is acoustically separated but overlooks the alley. The bar has a wide selection of craft beers and custom drinks.

Back Door Donuts

If you follow a delicious bakery aroma to a long line of people on a warm summer night in Oak Bluffs, you’ll likely find yourself at Back Door Donuts. Martha’s Vineyard Gourmet Café and Bakery is open regular hours from mid-April to mid-October, but its “back door” opens from 7 p.m. to 1 a.m. The pastries are made fresh in the bakery twice daily, with classic options as well as some more adventurous flavors (e.g., maple bacon or butternut crunch). The apple fritters are also a popular treat.

Ocean Park

It’s hard to visit Oak Bluffs and not spend some time in Ocean Park, with its inviting greenery, graceful gazebo, and ornate, Victorian-style houses. It’s an ideal place to go for a walk, toss a Frisbee, or enjoy a picnic lunch. The grounds are expertly groomed year-round, with bright potted flowers in the summer and a large setup of Christmas lights in the winter. Every last bit of grass in the park is covered with chairs and blankets for the Ocean Park fireworks in August, when people gather to watch the spectacular show. 2 Seaview Ave., Oak Bluffs. 
Things to do in Oak Bluffs, MA
The wide-open landscape and beautiful gazebo of Ocean Park.
Photo Credit : Cathryn McCann

Sharks Game

Attending a Sharks baseball game is a favorite pastime for both visitors and island residents. Every summer, players representing the best college baseball talent from around New England and beyond are housed by families on the island while they take on other teams in the Future Collegiate Baseball League of New England. Feel the island spirit on a beautiful summer night while sitting in the bleachers at the “Shark Tank” (Martha’s Vineyard High School athletic complex) and cheering on the players in purple and white.

Strand Theater

If you’re tired after a day at the beach or simply looking to get away from the crowds, the Strand Theater in downtown Oak Bluffs is a great place to catch a movie. The historic 1915 single-screen movie theater reopened in 2015 after extensive renovations; now it looks similar to its original form but with a new marquee, lobby, and stage, plus significant modern improvements and comforts.

Farm Neck Golf Club

For those who like to get in some golf while on vacation, Farm Neck Golf Club in Oak Bluffs is considered by many to be a premier place to tee off. Golfers can enjoy their favorite sport amid woods, meadows, marshes, and beautiful views. The club also offers lessons, clinics, junior golf, and tournaments. For those not interested in golf, the club has six outdoor tennis courts open to the public. And, of course, you can fuel up with some lunch at Farm Neck Café. What are your favorite things to do in Oak Bluffs, Massachusetts?

SEE MORE: 10 Prettiest Coastal Towns in New England Martha’s Vineyard Winter Weekend Retreat Coastal Weekend Getaways in New England | Your Perfect Weekend