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Things To Do In Oak Bluffs

Where To Stay In Oak Bluffs

The Rise of Tourism on Martha’s Vineyard – Oak Bluffs, July 2020

The last two times my family and I have used VRBO to book our house. Weve booked the same house both times and we absolutely love it. Its on the main road that leads into town and is easily accessible to other areas. Id probably recommend staying in a house over a hotel as you can stay in and cook on nights when you dont want to go out and its just a much more comfortable lodging experience. However, if thats not your thing then you can certainly stay in a hotel!


Summercamp is located right in the heart of Oak Bluffs and we pass it every single day! Its got an amazing location thats right on the water and directly across one of the most popular restaurants, Nancys. The rooms are all very nice and lovely, and its actually situated right by the historical Gingerbread House Campsite . Ive also heard great things from guests who have stayed there.

  • Editors Note: Theres definitely more lodging options, but these I feel the most comfortable/knowledgeable about sharing.

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Some of the information about the attractions and locations below may have changed due to new safety regulations. Please contact the location for the most up-to-date information.

Things To Do With Kids In Oak Bluffs Ma

  • TripBuzz found 194 things to do with kids in or near Oak Bluffs, Massachusetts, including 171 fun activities for kids in nearby cities within 25 miles like Edgartown, Hyannis, Barnstable and Sandwich.
  • From Oak Bluffs Campground to Joseph Sylvia State Beach, the Oak Bluffs area offers 103 different types of family activities, including: Beaches, Fishing, Farms & Ranches and Bike Rentals.
  • Located on the scenic island of Martha’s Vineyard is the charming resort town of Oak Bluffs. Picturesque cottages, known to the locals as the ‘Gingerbread cottages’, line the streets that are adorned with stately shady trees. The city operates the largest marina on the island is a popular area for boating and fishing.

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Have Coffee At Mocha Motts

Mocha Motts is all of the locals favorite place to grab a tasty coffee in Oak Bluffs! They also have a location in Vineyard Haven. The interior of the coffee shop is super bright and cozy. Theres always fun decor on the yellow walls and it has a very comfortable feel to it.

On the menu are tons of different coffee types. They have lattes, cappuccinos, espressos, mochas, drip coffee, cold brew, and more. They also have snacks and meals in case youre hungry during your visit, like bagels, sandwiches, soup, and even chocolate-covered espresso beans, which are a specialty.

Mad Marthas Ice Cream

THE 15 BEST Things to Do in Oak Bluffs

When you want a sweet treat, make your way over to Mad Marthas. 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 Pigs Delight, a 12-scoop sundae with tons of toppings, whipped cream, and a cherry on top!

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Joseph Sylvia State Beach

Love going for long walks on the beach? Take a drive down Beach Road between Oak Bluffs and Edgartown, and youll 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. Its a favorite spot from which to take a quick plunge into the water, and its often full of adventurous jumpers throughout the summer.

State Beach in Oak Bluffs as dusk approaches during the off-season. | Things to Do in Oak Bluffs, MA

Cathryn McCann

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 wont 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!

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Browse The Featherstone Center For The Arts

It also has a vibrant arts community that you will find at the Featherstone Center for the Arts at Featherstone Lane in Oak Bluffs.

This incredible arts center caters to the local arts community through its year-round educational program for all ages.

In addition, it has a fixed exhibit and galleries that you can visit.

Suppose you have a lot of time during your vacation to Oak Bluffs.

In that case, join one of its summer art camps and other educational programs to enhance your artistic talents.

If you’re interested in local arts, don’t forget to drop by the Featherstone Center for the Arts.

Take A Closer Look At The Jaws Bridge

Top 12 Best Tourist Attractions in Oak Bluffs, Massachusetts

The American Legion Memorial Bridge in Edgartown became popular because of its appearance in the monster flick “Jaws” in the 1970s.

It was where the infamous shark swims and attacks someone in the movie.

Today, it’s a famous tourist attraction where many people visit and jump on the waters below.

Locals consider jumping off the Jaws Bridge as a rite of passage.

It eventually became famous with tourists as well.

However, local authorities have made jumping off the bridge illegal, warning everyone of its safety risks.

Nonetheless, everyone can still stop by and take photos of this iconic bridge.

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Quintessential Marthas Vineyard Trip In Oak Bluffs

Quintessential Marthas Vineyard Trip in Oak BluffsPlaces to Stay, Eat, Drink, See, Relax, Play, and More

By Vic Gerami

Oak Bluffs is liveliest of the Vineyards 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 Marthas Vineyard. Originally incorporated in 1880 as Cottage City, in 1907 the towns 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 Marthas Vineyard. From sandy beaches and seafood restaurants to eclectic downtown shops and historic cottages, youll find more than enough to do and see in Oak Bluffs while visiting the island. Its 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.


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.

Inkwell Beach


See The Gingerbread Houses

Believe it or not, but the Gingerbread Houses are a unique set of buildings that look just like gingerbread cottages! They feature pops of bright color, like, pink, purple, yellow, and orange accents on traditional New England-style buildings.

The buildings genuinely look like they were taken straight out of a storybook. Historically, they were built in the 19th century as a Methodist campground, but so many of the buildings from the campground are still standing today.

There used to be approximately 500 different cottages that were standing in the campground, but around 300 of them are still standing today. If youre lucky enough to visit in August, you can attend the Grand Illumination Night, when the cottages are all decorated and lit up.

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Explore The Martha’s Vineyard Camp Meeting Association

The Martha’s Vineyard Camp Meeting Association or MVCMA at Trinity Park in Oak Bluffs offers visitors rich history and culture dating back to 1835.

People refer to this place as “The Campground.”

The organization is known for its well-preserved cottages and other historical buildings.

The MVCMA initially started as a religious group that held camp meetings in the early 19th century until many of MVCMA’s members found their permanent home in the area.

Visiting this iconic historical attraction in Oak Bluffs offers everyone a better understanding of Martha’s Vineyard’s history.

Today, the MVCMA offers walking tours seasonally, where visitors can explore the beautifully-designed cottages.

In addition, the MVCMA also has a museum and a souvenir shop worthy of visiting as well.

Explore The Cottage City

THE 15 BEST Things to Do in Oak Bluffs

One of the most unique things about Oak Bluffs is the Victorian-style gingerbread cottages that line the walkways of the , 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.

Learn more about the history of The Cottage City from this book available on Amazon

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 . It is a very popular event that has been taking place since 1869.

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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 Im 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.

Super Fun Things To Do In Oak Bluffs Marthas Vineyard

Primarily now known for being a resort community, Oak Bluffs is a beautiful place to visit in Massachusetts. There are also so many things to do in Oak Bluffs Marthas Vineyard!

The island of is beautiful and is right off the coast of Massachusetts. Its popularly visited during the summer months but can be breathtaking year-round. With fun activities and a view of the water almost anywhere you go, you cant go wrong with visiting there.

Here are all of the best things to do in Oak Bluffs Marthas Vineyard!

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Do A Kickflip At Martha’s Vineyard Skatepark

This vast skate park caters to hundreds of local and visiting skaters from New England.

Situated at Edgartown-Vineyard Haven Rd, this skatepark is where all skaters from Martha’s Vineyard’s six towns converge for some skating sessions.

Suppose you don’t know how to skate.

In that case, watch skaters do their thing at the sideline or perhaps regularly watch local competitions.

Head to Martha’s Vineyard Skatepark if you want to take a break from exploring Oak Bluffs.

Visit The East Chop Lighthouse

Visit Oak Bluffs, Martha’s Vineyard’s Most Colorful Town

There are many great lighthouses in Massachusetts, and the East Chop Lighthouse in Oak Bluffs Marthas Vineyard is one of them. This historic lighthouse is a classic one thats white with black on top, like many other lighthouses in New England.

The lighthouse opened back in the 1800s and is one of the few lighthouses thats actually on Marthas Vineyard. Its open seasonally throughout the year, normally at sunset. Many people will stop by to see the lighthouse in the evening and then watch the colors of the sky change while theyre there.

Occasionally, there is work being done on the lighthouse to keep it in tip-top shape. If thats the case, the lighthouse may be closed to the public, but this doesnt happen often.

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From Relaxing On Sandy Beaches To Strolling Circuit Avenue And Viewing Historic Gingerbread Cottages There Are So Many Things To Do In Oak Bluffs Ma On Martha’s Vineyard

Cathryn McCann3.388

Please note that many establishments throughout New England have modified their hours and/or operations in response to COVID-19. Please check with individual businesses and organizations for the latest information before making travel plans.

Peaceful in the winter, bustling in the summer, Oak Bluffs is a colorful and historic town on the Massachusetts island of Marthas Vineyard. From sandy beaches and seafood restaurants to eclectic downtown shops and historic cottages, youll find more than enough to do and see in Oak Bluffs while visiting the island. Its 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.

One of the vibrantly colored historic cottages in Oak Bluffs.


Have A Blast At The Ryan Family Amusements

The Ryan Family Amusements along Circuit Avenue in Oak Bluffs is the top entertainment hub for locals and visitors in town.

It’s best known for its plethora of video games, prize games, and arcade games for your travel buddies or family.

In addition, it features a ten-pin and candlepin bowling alleys and party rooms for private affairs.

There are numerous locations of Ryan Family Amusements found in New England, and Oak Bluffs is lucky to have one.

So, when you’re planning to have fun and spend time, especially with your kids, take them to this amusement center and discover dozens of video and arcade games.

Overall, it’s a must-visit place, especially in a small town like Oak Bluffs, where everything is within your reach.

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Go Golfing On A Public Course

If you love to golf, then take advantage of some of the gorgeous golf courses in Marthas Vineyard. There are three golf courses open to the public that would be most convenient for anyone visiting for the weekend. These courses are Mink Meadows Golf Club Farm Neck Golf Club and Royal and Ancient Chappaquiddick Links. Each course has something special to offer and clubs can be rented if you did not pack yours on your trip.

Mv In One Day Bucket List

THE 15 BEST Things to Do in Oak Bluffs

Walk Around Downtown Oak Bluffs

Here are some of the more scenic walk suggestions of places you can route to in your phone while you walk around town

  • MV Camp Meeting Association – see the Gingerbread Houses

  • Ocean Park – large open area with a gazebo that overlooks the water

  • East Chop Lighthouse

  • Inkwell Beach towards Joseph Sylvia State Beach

  • Circuit Avenue is a main street – common shops/attractions here are Vineyard Vines and The Black Dog

Eat some Seafood with a View

Some personal favorites:

  • The Lookout Tavern – our favorite lobster roll on island, and if you want to do it like a local, get it hot! We also love the popcorn shrimp.

  • Nancys – we love the lobster mac + cheese here!

  • Giordanos – Take Out Window – Get some fish + chips or fried scallops to go, and eat them on the picnic tables in Ocean Park!


  • If youre into laying on a beach, you can go to the beach to Oak Bluffs town beach the left of the ferry, or Inkwell to the right. It is walkable within minutes of getting off the ferry, and close to town.

Do something tourist-y

Whether or not youre into history, theres a few quick spots of note you can check out

Get a treat or drink

  • Cocktail – we love a Dirty Banana from Donovans Reef at Nancys

  • Ice Cream – we love Ben+Bills for ice cream

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Kayak Or Paddleboard On Sengekontacket

Ride your bike down Seaview Avenue bike path for less than two miles and youll 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. Its one of our favorite things to do on Marthas Vineyard!

Celebrate Unique Artworks At The Louisa Gould Gallery

Louisa Gould is an artist from Vineyard Haven who became famous for her unique and stunning abstract art and contemporary photography.

Her gallery in Vineyard Haven near Oak Bluffs has operated for 18 years.

Many tourists and locals love to visit the gallery to witness her new creations and masterpieces.

Her pieces interpret and express the natural beauty of Martha’s Vineyard.

Art lovers will love this fascinating gallery in Martha’s Vineyard.

In addition, the gallery also holds exhibits from emerging, local, and regional artists featuring different mediums.

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Explore The Manuel F Correllus State Forest

With more than 5,300 acres of forest and natural area, the Manuel F. Correllus State Forest is Martha’s Vineyard’s most extensive natural attraction.

The Heath Hen used to live in this state forest.

This bird was a species of grouse that went extinct in 1932.

To honor the extinct animal, the park officials built a statue of the Heath Hen in the middle of the park.

Suppose you’re up for more outdoor activities.

In that case, theManuel F. Correllus State Forest is famous for hiking, biking, skiing, hunting, disc golf, and nature viewing.

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