Oak Bluffs, or “OB” as the locals call it, is one of Martha's Vineyard's busiest and most bustling towns. Nestled on the northeastern shore of the island, Oak Bluffs offers something for everyone, and during the summer months, everyone wants to be there. Originally incorporated in 1880 as Cottage City (and a part of Edgartown before that), the town has been attracting residents and visitors alike for generations. In 1907 the town's name was changed from Cottage City to Oak Bluffs, in response to the growing year-round population and the expansion of the resort community, it wasn't just summer cottages anymore.
Today Oak Bluffs boasts miles of public beaches, ponds, several accessible parks, a busy seasonal waterfront and downtown district, a golf course, expansive hiking trails, rich arts and cultural offerings, and more. One could spend their entire Vineyard vacation in the town of Oak Bluffs and still not experience all it has to offer.
From May to October, the surrounding waters of Oak Bluffs see more boat and ferry traffic than any other town. During those months visitors can choose to take a number of seasonal ferries straight into Oak Bluffs harbor including:
- The Steamship Authority from Woods Hole
- Hy-Line Cruises from Hyannis and Nantucket
- The Seastreak Ferry from New Bedford, New Jersey, and New York City
- Island Queen from Falmouth
- Martha's Vineyard Fast Ferry from North Kingston / Quonset Point, Rhode Island
- Patriot Party Boat / Vineyard Shuttle
- Water Taxi from Falmouth
When visitors arrive via any of the ferries listed above they will have direct access to Oak Bluffs harbor, downtown Oak Bluffs, the historic Martha's Vineyard Camp Meeting Association, Ocean Park, public bus stops, and several public beaches.
For more information about ferry options, pricing and schedules, we've put together a helpful Ferry Guide.
Oak Bluffs is an especially walkable town so daytrippers need not be worried if they don't have a car to get around. A majority of Oak Bluffs' most popular attractions are all within a mile radius of the Oak Bluffs ferry terminals and walking around Oak Bluffs is an attraction in itself, especially the lively Oak Bluffs harbor during the summer months.
When it comes to cycling we especially recommend the ride from Oak Bluffs to Edgartown along Seaview Ave and Beach Road where you'll be treated to views of the ocean on one side and Sengekontacket Pond on the other side.
Should you want to venture beyond downtown Oak Bluffs, bike rentals and car rentals are readily available in-town, and local taxis, Ubers, and Lyfts are just a call or app request away. The Vineyard Transit Authority bus system also operates multiple daily buses in and out of Oak Bluffs, with its central Oak Bluffs bus stop just steps from the Steamship Authority ferry terminal, making for easy transfers. The bus also transports bicycles should you want to explore beyond Oak Bluffs and cycle your way back.
Oak Bluffs is home to dozens of hotels and inns along with dozens, possibly hundreds of rental properties. The largest hotel and one of the most centrally located, is the Summercamp Hotel, a whimsical and chic summer-camp inspired property with views of Oak Bluffs harbor. Other accommodations that are an easy walk from the harbor and nearby ferry terminals include the Morgan Hotel, the Oak Bluffs Inn, the Dockside Inn, the Martha's Vineyard Surfside Hotel, the Pequot Hotel, the Madison Inn, Isabelle's Beach House, and the Narragansett House.
Expect quaint accommodations with more personalized service and more rustic-inspired lodging when considering your stay in Oak Bluffs. Many of the properties are housed in Victorian cottages that give a nod to the town's history and traditional architecture.
Check out our guide on Martha's Vineyard accommodations to find the best option for you.
Like we said, Oak Bluffs has a lot going on, especially in-season. The best way to enjoy the natural beauty of the town is to take advantage of the many outdoor activities. Take a stroll along Oak Bluffs harbor to see the boats lined up and the busy bars and restaurants spilling into the sidewalk. Don't miss a chance to try a Dirty Banana frozen cocktail from Donovan's Reef, a rite of passage for those who like to indulge in quintessential summer beverages.
Continue walking north along the harbor and you'll eventually get to the Oak Bluffs fishing pier, an impressive series of boardwalks great for fishing and admiring expansive ocean views. Nearby Oak Bluffs public beaches offer major appeal, as does Ocean Park, a large grassed park perfect for a picnic, some kite flying or playing lawn games. Iconic Victorian-style Oak Bluffs home dot the perimeter of Ocean Park making for a picturesque setting any time of year.
History Buffs in Oak Bluffs Take Note
Oak Bluffs is home to a number of cultural and historical attractions that give context to this beloved resort community and the significance it has held to countless generations. Families love flocking to the Flying Horses Carousel, the oldest operating platform carousel in the country where adults and kids try their luck at grabbing the coveted brass ring.
Just up the street is the Martha's Vineyard Camp Meeting Association, home to hundreds of colorful gingerbread cottages that have become an iconic symbol of the town. Once a popular Methodist campground the area eventually gave way to a sea of summer cottages and this enclave of adorable homes sees thousands of visitors a year. The Martha's Vineyard Camp Meeting Association Cottage Museum and Shop is where you can learn all about this National Historic Landmark and its rich history dating back to the early 1800s.
If you're considering a summer vacation to Oak Bluffs mark your calendars for the Grand Illumination, or Illumination Night generally held on the third Wednesday of August. Illumination Night is a time-honored tradition where all of the houses of the campground are adorned with paper lanterns and are set aglow.
Oak Bluffs' history is also immersed in African American history, as the town has long been a safe haven and summer colony for the black community. Visitors can take the African-American Heritage Trail Walking Tour which is made up of 30 sites where descriptive plaques have been placed in dedication of the formerly unrecognized contributions made by people of African descent to the history of the island.
Another long-standing and culturally significant landmark in Oak Bluffs is the East Chop Lighthouse which sits atop a large bluff in Oak Bluff on a peninsula known as East Chop. While it will be closed for the 2022 season for improvements, the East Chop Lighthouse is typically open seasonally on Sunday evenings around sunset courtesy of the Martha's Vineyard Museum.
Oak Bluffs is for Art Enthusiasts
As a historical, colorful town Oak Bluffs has long provided inspiration to artists and writers from all walks of life. Today visitors can browse the galleries of Circuit Avenue and Dukes County Avenue, as well as visit the Oak Bluffs Open Market every Sunday in the summer months to browse the work of our talented local artists and creators. Oak Bluffs is also home to the island's year-round mecca, Featherstone Center for the Arts, which offers gallery exhibits, art classes, and special events in the summer including outdoor concerts.
Oak Bluffs for the Sports and Outdoor Enthusiasts
When considering sports that keep you on land Oak Bluffs' offers Farm Neck Golf Course, one of the nicest golf courses on Martha's Vineyard and a favorite among celebrities and politicians, including President Obama and Spike Lee. Farm Neck is considered by many to be one of the premier golf experiences in the Northeast and one of the most beautiful. Players are treated to an impressive variety of surroundings–from woodlands, to open meadows, to salt marshes, to stunning overlooks revealing the open ocean.
Tennis, baseball, and basketball also attract hundreds of players each summer, to the courts and fields of Niantic Park and Viera Park. For those sports fans looking to spectate the collegiate summer baseball team of Martha's Vineyard, the Martha's Vineyard Sharks, calls Oak Bluffs home. The Sharks offers dozens of games throughout the summer at their home field, aptly named the Shark Tank, at the Martha's Vineyard Regional High School.
Walking, hiking, biking, and running are all great ways to get around and admire Oak Bluffs. Additionally, the waterfront town lends itself to a number of water activities too, including charter boat excursions from Oak Bluffs harbor; kayaking, kite surfing, stand-up paddleboarding on Sengekontacket Pond; and swimming and sunbathing along the public beaches.
Oak Bluffs has some of the most accessible beaches on Martha's Vineyard. All of Oak Bluffs' shoreline is open to the public and much of it is easily accessible on foot from the nearby ferry terminals. It's totally feasible (and worth it!) to hop the boat to spend a day on the beach in Oak Bluffs.
Oak Bluffs Town Beach
A popular spot to enjoy is Oak Bluffs Town Beach, a sandy beach with generally calm water that is a destination for families. There are staircases down to the beach along the seawall with handicap access at the end of the beach away from the ferry terminal. With access to town facilities, local restaurants, shopping, and parking along the road and throughout town, this is a great place to visit if you don't have much time on the island. If you are staying in town, this is an ideal option for a full beach day to a quick ocean dip.
The famous Inkwell Beach is also part of Oak Bluffs Town Beach. Since the 1800s Inkwell Beach has long been a popular destination and summertime sanctuary for black families and it is beloved by many. It is a small stretch of beach that has been visited generationally and is a hub of culture and activity in the summer months.
A few miles further down beach road you will find Joseph Sylvia State Beach, or simply State Beach. This beach is a two-mile-long barrier beach that runs alongside Beach Road, and protects Sengekontacket pond. This beach straddles Oak Bluffs and Edgartown, while the Edgartown side is called Bend in the Road Beach.
The Jaws Bridge at State Beach
The Bridge that separates the Oak Bluffs and Edgartown sides of this beach is known to many as “Jaws Bridge,” after its memorable moment in the 1975 classic film “Jaws.” Though there are signs that warn you not to, many people take the plunge and jump from the bridge into the fast moving water flowing in or out of Sengekontacket Pond. It's a rite of passage for many and an exciting time for all that take the plunge.
Many perfect summer days in Oak Bluffs start with the beach, followed by a stroll along Circuit Avenue, shopping the main street's many retail shops. It's the go-to place for your iconic Martha's Vineyard T-shirt and basically any other souvenir you can imagine. From art galleries to clothing stores, hats, and sunglass shops you'll find more than enough ways to spend your vacation allowance here.
Circuit Avenue also offers one of the island's only independent-owned grocery stores, Reliable Market, a beloved family-owned and operated store known for its deli counter and hearty meats. A bit further away from downtown, you'll find Tony's market, a small scale grocery store and the only market in town that sells beer and wine. In fact, Oak Bluffs is one of only two towns on Martha's Vineyard that sells alcohol. While Tony's sells beer and wine you can find a large selection of wine, beer, and liquor at Jim's Package Store, Our Market, and Vineyard Wine & Cheese Shop.
After an afternoon of shopping in Oak Bluffs you'll have worked up quite the appetite and the town delivers on variety among its dining options. Restaurants in Oak Bluffs offer something for everyone from pizza, to barbeque, to casual bites and fine dining. Along Oak Bluffs harbor you'll have your pick of casual waterfront establishments with seafood-heavy menus and open-air waterfront seating at Fishbones, the Sand Bar, Lobsterville, Coop de Ville, Nancy's, and nearby Lookout Tavern.
Dining on Circuit Avenue and Kennebec Avenue
Circuit Avenue and Kennebec Avenue are also home to many more desirable dining establishments depending on your palette and preferred cuisine. For classic dishes that pack a lot of flavor check out Flavors MV. For more creative cuisine there's the Cardboard Box and the Sweet Life Cafe. Giordano's or “Gios” serves up Italian favorites in their dining room as well as popular pizza outpost and clam bar with all those quintessential New England seafood staples served hot and ready to go. If breakfast is your preferred meal to indulge in, Biscuits near the Oak Bluffs harbor serves up southern-inspired breakfast fare that never disappoints. There will likely be a wait for a table but it's always worth it.
If you want to dine where the locals dine you can't miss Offshore Ale Company, the island's only brewpub that serves up award-winning beer with a smile. This beloved bar and tavern is known for its friendly service and reliable eats. After dinner must come sweets and there's no shortage of ice cream and candy shops to satisfy your sweet treat day or night. Whether it's Ben & Bill's, Carousel Ice Cream, or Mad Martha's, ice cream just tastes better in Oak Bluffs, and so do donuts. That's right, donuts. And not just by day but by night too. Oak Bluffs is home to the famous Back Door Donuts, a bakery serving up hot and flavorful donuts until the wee hours of the night. No trip to Oak Bluffs is complete without one of their heavenly apple fritters, you can thank us later.
Looking to keep the party going while you're in Oak Bluffs? You've come to the right town. Oak Bluffs is one of only two towns that offer late-night options. Bars along the Oak Bluffs harbor and Circuit Avenue are some of the busiest places on-island during those coveted summer nights.
For live entertainment head to the Loft above the Martha's Vineyard Chowder Company, which has also partnered with the Martha's Vineyard Concert Series to host a series of live performances in the summer months. The Ritz is the local watering hole and famed dive bar that can't be missed. Generally serving up live music nightly you're likely to find a party, and a packed dance floor, at the Ritz.
Outside of the downtown area but accessible via bike and the public bus is Noman's, a lively restaurant with a sprawling lawn for playing games, as well as an oversized patio that is often home to bands and special events. Enjoy a night (or two!) on the town and make the most of your Oak Bluffs vacation.