Quintessential Martha’s Vineyard Trip in Oak Bluffs

Quintessential Martha’s Vineyard Trip in Oak Bluffs
Places to Stay, Eat, Drink, See, Relax, Play, and More

By Vic Gerami

Oak Bluffs is liveliest of  the Vineyard’s towns – more high-spirited than haute.  From the colorful gingerbread cottages to the Flying Horses carousel, from Ocean park to harbor bars, Oak Bluffs delivers on fun.

The Town of Oak Bluffs is a residential, resort community located on the northeast shore of the island of Martha’s Vineyard. Originally incorporated in 1880 as Cottage City, in 1907 the town’s name was changed because of the growth in the year-round population and the changing face of the resort required an acknowledgment the Town was not just “Cottage City” anymore.

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, MA.

Martha’s Vineyard is a 100 square mile island located three miles off the coast of Cape Cod. Formed by the southernmost advance, or terminal moraine, of the North American ice sheet during the last ice age over 10,000 years ago. Today, year-round residents, seasonal residents and hundreds of thousands of short-term visitors live on or come to the island, attracted by the unique natural, ecological, historical, cultural and scientific values that define the beauty and character of Martha’s Vineyard.

Approximately three quarters of the island’s population is concentrated in the three “Down-Island” towns of Tisbury, Oak Bluff’s, and Edgartown, each with their own unique commercial town centers. Vineyard Haven in Tisbury serves as the islands main port and is supplemented by a port in Oak Bluffs in the summertime. The three “Up-Island” towns of West Tisbury, Chilmark, and Aquinnah are more rural in character.

Covering approximately 7.37 square miles, Oak Bluffs is in the County of Dukes County. The Town is bordered by the Town of Edgartown on the south, the Town of Tisbury on the west and Nantucket Sound on the north and east. Today, Oak Bluffs is home to the largest marina on Martha’s Vineyard, a bustling seasonal waterfront and downtown, and the historic gingerbread campgrounds. Oak Bluff’s hosts several beautiful beaches and public parks; a teeming shore of wildlife, fish and shellfish; a golf course and a number of civic amenities that make the community a great place to live, work and play.


The Jetty Beach

Jetty Beach is a public beach located next to the East Chop Beach Club in Oak Bluffs. The beach, which is on Nantucket Sound, is accessed via a trail from the beach club. There is limited parking.

Set on the warm waters of the Vineyard Sound, the north-facing Jetty Beach has very low surf and is ideal for young children. The beach is located on East Chop, across the entrance of the Oak Bluffs Harbor from the Island Queen ferry landing. Enjoy views across the Sound to Cape Cod and pleasure boats, fishing vessels, and ferries in between. 75 East Chop Drive, Oak Bluffs, 02557

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. 83 Seaview Ave, Oak Bluffs, 02557

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. Edgartown, 02539

Click here for beaches of Martha’s  Vineyard


The Sweet Life

The Sweet Life is a New American restaurant inspired by classic culinary traditions and innovative, modern day approaches. We are equal parts the neighborhood hangout and the breezy outdoor café. We are good food, innovative drinks and easy hospitality. The cocktail list is meant to reflect the flavors and mood of each season and the wine list is sourced from small vineyards the world over where you can find something familiar or surprising, depending on the occasion. We work closely with island farmers and fishermen meaning our menu changes frequently based on what’s good and what’s available but it’s always a reflection of the very best of what the island has to offer. 63 Circuit Avenue, Oak Bluffs, 02557

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 to do in Oak Bluffs! 10 Circuit Avenue, Oak Bluffs, 02557

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. 1-11 Kennebec Ave, Oak Bluffs, 02557


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. 15 Oak Bluffs Ave, Oak Bluffs, 02557

Barn, Bowl & Bistro

Far from being a run-of-the-mill bowling alley, this classy, vibrant, and modern establishment, Barn, Bowl & Bistro 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. 13 Uncas Avenue, Oak Bluffs, 02557

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, 02557


Trinity Park Tabernacle

Right in the heart of the gingerbread cottages is this beautiful outdoor event complex, Trinity Park Tabernacle. 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. 80 Trinity Park, Oak Bluffs, 02557

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. Oak Bluffs Ave, Oak Bluffs, 02557


You’ll find one of the Vineyard’s three Soft As A Grape locations along Circuit Avenue, Oak Bluffs’ main commercial drag. Selling lines of men’s, women’s and children’s clothing, the Cambridge-born chain’s most well-known collection is made from a super-plush, ring-spun combed cotton.

Also on Circuit Avenue is another Massachusetts chain, Black Dog General Store , the first of which opened in Vineyard Haven in 1992. The Martha’s Vineyard original is filled with sailing attire, rain jackets, water bottles, tote bags and a vast array of other products bearing the image of a Lab-boxer mix named after Black Dog, the character from Robert Lewis Stevenson’s “Treasure Island.”

Craftworks (42 Circuit Ave.), a contemporary sales gallery, sells whimsical pieces fashioned by both local and national artisans (think garden ornaments, handmade jewelry and decorative wood sculptures). For more unique keepsakes, walk to the Oak Bluffs Arts District (just west of Circuit Avenue at Dukes County and Vineyard avenues), home to Alison Shaw Gallery (88 Dukes County Ave.), Lucinda Enamels (11 Vineyard Ave.) and other artsy independent businesses.

Along the Circuit Avenue Extension, the Dockside Marketplace & Marina on Oak Bluffs Harbor features several restaurants and bars as well as another Black Dog General Store, the Black Dog Premium Outlet, The Christmas Cottage, Dockside Jewelers and Martha’s Gifts.



The Oak Bluffs Inn

Come be a kid again at our whimsically renovated Oak Bluffs hotel. Formerly the Wesley Hotel, this new incarnation is designed as a nod to Oak Bluffs’ history as a summer “camp” destination for the Methodist Church. Summer camp also reflects the rustic, retro and nostalgic touches that any former camper (or former child) can embrace! Gaze at the harbor from your deck chair, grab a snack from the Camp Canteen, or play ping pong or Twister in the game room.

Located across from the harbor in historic Oak Bluffs, our reimagined Martha’s Vineyard boutique hotel is a nod to the past with an eye to the future. Offering Martha’s Vineyard hotel accommodations for every lifestyle and budget, Summer camp is your place for fun and relaxation of this magical island. 70 Lake Ave, Oak Bluffs, 02557

Cozy Bluffs

Built in 2013 and nestled in a quaint Oak Bluffs residential neighborhood, Cozy Bluffs is a one-bedroom, one and one-half bath home is located only .5 miles from Circuit Avenue and the Oak Bluffs ferry terminal. Extensive renovations include a new handmade platform bed with new Saatva Cal King mattress, new backyard deck area with outdoor shower, BBQ grill, outdoor dining set and seating areas.

The first floor features an open living space with kitchen, living area, dining table and chairs and a half bath. Washer and dryer are in the basement. A/C & heat wall mounted splitters located on first floor and in master bedroom. Parking space area for one car in front of house. Backyard deck with outdoor seating/dining area and gas grill.

Master bedroom with new Saatva California King mattress and en suite bathroom with rain shower on second floor. Sliding doors open to a small balcony off the bedroom. The home has a work space loft with desk, office chair and comfy couch in reading nook on the second floor.

If you are looking to spend your vacation in a quaint, luxurious, and comfortable house near the beach, then Cozy Bluffs is your answer. It personifies the quintessential Martha’s Vineyard experience.


Whether you love beachcombing, wine tasting, bike riding, sailing, or hiking you won’t be bored on your vacation at Oak Bluffs. Adventurous spirits can spend the day zipping through the water on a jet ski or rambling through the countryside in a jeep. After a full day of exploring, watch the sunset while sipping a cocktail at one of the eclectic bars and reflect on the amazing memories you have just made.