Oak Bluffs Travel Guide: The Best Things To Do In Oak Bluffs, Martha’s Vineyard

Oak Bluffs, Massachusetts, a small town on the Northeast shore of Martha’s Vineyard known for its fanciful gingerbread cottages, rich history, and playful charm, is the perfect vacation destination for all. Whether you desire to relax by the beach, explore the vibrant downtown area, or learn more about the cultural heritage of Oak Bluffs, there are endless things to do in the “Cottage City.” 

Oak Bluffs Restaurants

With a vast array of food and drink options, there is something for everyone to enjoy. Whether you’re craving an extravagant seafood platter or a classic cheeseburger, Oak Bluffs has got you covered. 

If you’re looking for good old-fashioned American food, try Linda Jean’s Restaurant. 

Linda Jean’s, known for its excellent breakfast, as well as its expansive menu, is sure to please the whole family. From pancakes, omelets, and home fries, to salads, sandwiches, burgers, pasta, and seafood, you’ll find something on the menu for you.

If you’re looking for mouth-watering seafood dishes, check out Martha’s Vineyard Chowder Company and Lookout Tavern.

Martha’s Vineyard Chowder Company is the go-to spot in Oak Bluffs to enjoy lobster rolls and clam chowder, and Lookout Tavern is the perfect dining choice if you love a waterfront view. Also famous for its lobster rolls, Lookout Tavern offers a fantastic raw bar, sushi, and plenty of seafood options.

If you’re looking for the perfect brewpub to savor a well-crafted beer and a few slices of pizza, make your way over to Offshore Ale Company.

Offshore Ale Company is the prime spot on Oak Bluffs for beer lovers. Serving yummy beer, wines, specialty cocktails, brick oven pizzas, burgers, sandwiches, salads, and starters such as truffle fries and wings, this is the place to go for a few drinks and some pub food.

If you’re looking for a fun, family experience, go to The Barn Bowl & Bistro.

The Barn Bowl & Bistro serves a wide selection of food options, including salads, pizza, burgers, pasta, steak, and seafood, and also offers a 10-lane bowling alley. It’s sure to keep kids entertained and the entire family happy.

If you’re looking for an eccentric, lively, and out-of-the-box atmosphere, The Red Cat Kitchen is the place for you.

Filled with funky art pieces and serving menu items with names such as “Beets for Dr. Dre,” The Red Cat Kitchen is not just a fun dinner spot but an experience that you have to try for yourself.

If you’re looking for Italian, Mexican, or Thai cuisine, don’t worry – Giordano’s Restaurant, Sharky’s Cantina, and Bangkok Thai Cuisine have you covered.

A family-style restaurant serving Italian classics like pizza and pasta, Giordano’s is the perfect restaurant for Italian lovers. Sharky’s Cantina, a bar and grill known for its Mexican food and cocktails, and Bangkok Thai Cuisine, serving authentic Thai food, are delicious options if you’re in the mood to eat different types of cuisine. 

If you’re just looking for a quick treat, Oak Bluffs is also home to many coffee shops and dessert must-haves.

Mocha Mott’s serves delicious coffee, espresso, and baked goods. Back Door Donuts is the donut shop to try in Martha’s Vineyard, and Mad Martha’s Ice Cream is a must if you’re craving some homemade ice cream.

Oak Bluffs Shopping

In addition to many fine dining options, Oak Bluffs has plenty of shops to explore. 

There are numerous gift shops to browse through, C’est La Vie being a fan favorite. With various clothing and accessory options, you will surely find something to commemorate your trip to Oak Bluffs or a gift to give to a loved one. 

The Black Dog General Store is another staple in Oak Bluffs. This shop is perfect for dog lovers, selling clothing and other accessories with a cute black dog logo for your dog and your family. 

If you want to purchase a stunning piece of jewelry, look no further than Stephanie Wolf Designs. Whether you wish to treat yourself to a new, jaw-dropping accessory or collect an item as a memento from Martha’s Vineyard, Stephanie has many vibrant designs to peruse. 

Also selling jewelry, specifically catering to those seeking inspirational gifts, Sanctuary is the shopping destination for fans of spirituality and wellness. Browse through hand-selected jewelry, candles, stones, and home decor. 

Ben and Bill’s Chocolate Emporium is the shopping destination in Oak Bluffs for those with a sweet tooth. From bark, truffles, caramels, and creams to fruit, candies, and gummies, this shop will satisfy your sweet cravings.

For those who enjoy games, The Lazy Frog is a must-visit. Selling board games, card games, puzzles, kites, outdoor games, and more, this shop has plenty of options to entertain the family.

Oak Bluffs Beaches and Parks

If you’re looking to relax in nature, there are a few destinations you must put on your list of places to go. 

Inkwell Beach, only a walking distance from the ferry dock and located centrally, is a fine beach perfect for visiting as a quick stop just after entering the town or after a day in the downtown area.

For those who savor long walks on the beach, Joseph Sylvia State Beach is the place for you. With gentle waves and long stretches of sand, it’s a great spot to take a stroll and have a nice swim.

If you want to go on a walk and enjoy the gorgeous scenery but don’t want to go to the beach, consider visiting Ocean Park. Filled with beautiful, open greenery, there is plenty of space to picnic, play games with family or friends, and walk around. 

If you prefer a joyride to a walk, go on a coastal drive across East Chop Drive. Enjoy water views, and take a pit stop at East Chop Lighthouse. Basque in the scenery, and watch as the ferry goes by!

Oak Bluffs Art

For history and architecture fans, going on a walking tour with Martha’s Vineyard Camp Meeting Association is a necessity. Serving as a National Historic Landmark, this group oversees The Campground, an eclectic, colorful gingerbread cottage collection. Filled with history and religious significance, these houses are not only fun to look at but have more profound meaning that you can learn about.

In addition to the gingerbread cottages, there is a lot of other art to explore in Oak Bluffs. The Oak Bluffs Arts District and Circuit Avenue hold several incredible art galleries. The Featherstone Center for the Arts is another great option for art lovers, especially those who want to create art. With galleries to visit and studios to actively create art, Featherstone is every creator’s dream!

Oak Bluffs Fun and Games

The oldest platform carousel in the United States, The Flying Horses Carousel is a top attraction in Oak Bluffs. This spot is a fun ride and a historic landmark, perfect for children and adults alike.

If you want to spend more time enthralled in fun and games, take your party to Ryan Family Amusements. From bowling to arcade games and party rooms, this is the place in Oak Bluffs for some classic fun.

For golfers, Farm Neck Golf Club is the ideal place to get in a few rounds during your stay, and for baseball fans, you can catch a Sharks baseball game. 

Come Stay With Us

Whether you want to spend your vacation in Oak Bluffs fine dining and shopping, immersing yourself in nature, adventure seeking, or all three, we have you covered. Here at Pink Rock Rentals, we want to provide you with the best experience possible during your time in Oak Bluffs.