24 Hours in Oak Bluffs

​There’s a good chance if you’re arriving to Martha’s Vineyard during the summer months that you could be coming straight into Oak Bluffs, or “OB,” one of six Island towns and a popular seaside hub. The Steamship Authority operates seasonal ferry service from Woods Hole to Oak Bluffs, as well as the Island Queen from Falmouth, the Sea Streak from New Bedford and New York and the Martha’s Vineyard Fast Ferry from Rhode Island.
 
Oak Bluffs is a colorful town with a ton of history and a lot of action. If you’re only able to stay for a day here’s what not to miss. All of these places can be visited on foot and are walking distance from the ferry slips. 

​A stroll along Oak Bluffs harbor
When you step off the boat in Oak Bluffs harbor you’ll be immediately inundated with dining, drinking and shopping options. You’ll find the iconic Black Dog Dockside Cafe here, as well as their Dockside General Store & Premium Outlet, which offers cheaper prices than the Black Dog General Store just steps up the street. The Dockside itself is a marketplace with various other retail shops as well as ice cream and candy if you want to start or end your day on a sweet note.
For waterfront dining take your pick of Fishbones, Coop de Ville, the Sand Bar, Lobsterville or Nancy’s (one of President Obama’s favorites and home to the beloved Donovan Reef beach bar which serves up a famous Dirty Banana frozen drink), which all offer seafood and snacks in a casual atmosphere.
 
Continue up Circuit Avenue
Circuit Avenue is Oak Bluffs’ equivalent to Main Street and it’s lined with shops, restaurants and attractions. This is the place to find your Martha’s Vineyard souvenirs, and the selection will not disappoint. You’ll also find the town’s only full grocery store here, Reliable Market, which has been family owned and operated since 1947. If you’re travelling with kids you might want to pop in to the Oak Bluffs Game Room a family friendly arcade that would keep them entertained for the full twenty four hours if they had their way. For the music lovers the Ritz cafe offers lunch and dinner as well nightly music and late-night entertainment. Chocolate lovers will rejoice at the sight of Murdick’s Fudge which gives passersby a look into their fudge making process through their storefront windows. A stop inside to sample their fudge, peanut brittle and popcorn is a must.
 
The best bites and sips along the way
Oak Bluffs is also home to the famous Back Door Doughnuts, a full-service bakery under the name of Martha's Vineyard Gourmet Cafe & Bakery by day, that reopens in the back each night and enables hungry doughnut lovers until 1am. They’re known for their gigantic apple fritters, which can easily be shared by 2-3 people. You’ll often find a long line weaving across the parking lot but it’s worth the wait and the aromas pouring out of the back door are hypnotizing.
Just next door you’ll find Offshore Ale Company, a year-round pub and brewhouse adored by visitors and locals alike. They brew their own award-winning beer on location and it’s also available in cans and growlers to take home. Further down Kennebec Avenue you’ll find Giordano’s Pizza and Clam Bar. No trip to Oak Bluffs is complete without a slice of pizza from “Gio’s.” It’s available out of their take-out window and worth every penny, be sure to bring the green stuff, it’s cash only.

Explore the Campground, home to the renowned Gingerbread Cottages
Oak Bluffs is most known for the Gingerbread Cottages, a quaint cluster of colorful and adorable cottages that was originally settled as a Methodist camp site.  Beginning in 1835 annual summer camp meetings of Methodist church groups would congregate here in communal tents which eventually gave way to family tents, and then wooden cottages which line the streets today. Take a stroll through the campground and admire the uniqueness of the houses, the bright colors, and architectural detail and charm, as well as the Tabernacle, an open-air steel structure which hosts weekly concerts and events. The Campground is also the setting for the famed Grand Illumination Night, which marks the end of the summer season with a glorious show of Japanese lanterns hanging from all the nearby homes. ​

Ride the Flying Horses Carousel
Oak Bluffs is also the home of the Flying Horses Carousel, the oldest continuously operating carousel in the country. Its horses were hand carved in New York City in 1876. This historic landmark is maintained by the Martha’s Vineyard Preservation Trust and is open daily during the summer, and on weekends in the spring and fall. ​

Walk along Ocean Park
Ocean Park is a charming oceanfront park surrounded by Victorian mansions and gingerbread houses. The park features a bandstand which holds weekly band concerts during the summer and is perfect for picnics, playing Frisbee or flying kites.