Martha's Vineyard is known throughout the upstate area as a premier vacation destination.
Still, there's more to this tiny island than meets the eye.
Oak Bluffs is one of the six towns in Martha's Vineyard situated in the northern portion of the island.
This small but charming town is a worthy travel destination you need to consider checking out.
Oak Bluffs is a mixture of a resort community and a residential area.
The town was once Cottage City back in the 1800s.
However, in 1907, the town's name changed to Oak Bluffs due to its progress and growing population.
Oak Bluffs is in Martha's Vineyard, where you'll see the natural beauty of Cape Cod, Cow Bay, and the Atlantic Ocean.
Today, Oak Bluffs is one of the famous destinations on the island for vacationers who want to explore its natural beauty, history, and heritage.
There are a plethora of activities waiting for you in Oak Bluffs.
For a broader idea of what this Martha's Vineyard town has to offer, here are the 20 best things to do in Oak Bluffs, Massachusetts:
Start Your Travel Adventure at Ocean Park
Experience Oak Bluff's genuine beach vibes right after arriving in town and head to Ocean Park along Seaview Avenue.
This beautiful community park in Oak Bluff is the best place to see the town's beauty, especially if you're taking the ferry from New England.
Ocean Park spans seven acres of green open space, while a bandstand is in the middle of the park.
Before the town converted it into a park, it was a residential area with numerous sports facilities.
The town eventually converted it into the beautiful park it is today.
Locals and visitors in Oak Bluffs love to hang out and enjoy the fresh ocean breeze while having a picnic.
In addition, Ocean Park is where most of Oak Bluff's community activities happen.
Take a Dip at Inkwell Beach
Inkwell Beach is the most accessible beach in Oak Bluffs, boasting a long stretch of white sand usually packed with people on a sunny day.
This public beach in Oak Bluffs has access off Seaview Avenue, walking distance from Ocean Park.
So, after spending some quality time with your loved ones or travel buddies at Ocean Park, head to Inkwell Beach for more fun.
Inkwell Beach is more than just Oak Bluff's top beach destination; it also holds historical significance, especially to the African Americans.
Historically, Inkwell Beach got its name from African Americans frequenting this beach in the early 19th century.
They consider this beach their favorite area to hang out in the entire Martha's Vineyard due to the racial segregation rampant back then.
Thus, its name referred to the African-Americans who spent their time there.
Oak Bluffs, in general, is also the first lodging in Martha's Vineyard that welcomed African-Americans without prejudice.
This lack of prejudice eventually attracted thousands of African-Americans to enjoy vacations in Oak Bluffs.
Today, Inkwell Beach is more than a tourist destination on the island.
It is also a testament to the struggle of the African-American people back in the day.
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.
Take a Sip at the Offshore Ale Company
For a satisfying experience while touring Oak Bluff's attractions, check out the Offshore Ale Company along Kennebec Ave.
This award-winning brewery started in 1997, serving locals with top-notch craft beer, great food, and a fantastic atmosphere.
Today, it's one of the most-recommended watering holes in Martha's Vineyard, not because it's the only one found on the island but because it lived up to everyone's expectations.
Besides their finely-brewed craft beer, they also serve delicious foods to match with beer, such as pizzas, sandwiches, seafood, etc.
In addition, their pub offers everyone a cozy and welcoming atmosphere which instantly relaxes your mind.
So, reward yourself with a mug of craft beer and some delicious food at the Offshore Ale Company after a whole day of wandering Oak Bluff's attractions.
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.
Treat Your Taste Buds at Back Door Donuts
Back Door Donuts is the most famous bakery in Martha's Vineyard.
It's pretty easy to notice why it's famous.
You'll commonly see many people queue in line at an alley at the back of their bakery to taste its delicious donuts.
Formerly known as Walmsley's Bakery, it opened in 1948 and changed its name to Old Stone Bakery in 1971.
Instead of the usual front door entrance, people queue behind the bakery along an alley to buy donut leftovers at night.
This open secret in Martha's Vineyard became popular, which paved the way for the bakery's success.
Buying its freshly-made donut is a must-try in Oak Bluffs.
At the same time, you can also grab other sweet treats and sugary pastries there.
Appreciate the Natural Beauty of the Joseph Sylvia State Beach
Compared to Inkwell's crowded beach, the Joseph Sylvia State Beach offers a quieter atmosphere amidst its beautiful stretch of white sand and shallow waters.
The Joseph Sylvia State Beach, despite its peaceful atmosphere and beachside houses, became famous in the 1970s for being the shooting location of the iconic monster flick "Jaws."
The adjacent bridge to the state beach was where the protagonist's son saw the great white shark approaching the boating pond.
However, Joseph Sylvia State Beach is the opposite of how the movie portrayed this place.
People can enjoy its relaxing atmosphere and swim safely through its calm waters.
In addition, anglers love to cast their line at this beach to catch some striped bass, the most common fish species in the area.
During windy days, kitesurfers and windsurfers flock to this beach.
Flex Your Skills at the Farm Neck Golf Club
The Farm Neck Golf Club boasts a scenic golf course offering golfers and visitors a picturesque view of Cow Bay.
This golf course is known for its well-maintained greens and fairways, making it a recommended place for vacationers in Martha's Vineyard who want to play golf.
This golf course has operated for more than four decades, offering golfers a one-of-a-kind experience through its unique landscape and challenge.
While you play, you will pass through a charming variation of vegetation and topography—from treelines, salt marshes, and meadows to brushes on the oceanside.
Whether you're a top-notch golfer or an ordinary tourist, you will surely appreciate this golf course's beauty.
Roam the Felix Neck Wildlife Sanctuary
The Felix Neck Wildlife Sanctuary in Edgartown is a great natural area for everyone.
It is a sanctuary for local wildlife and habitat where everyone can visit and witness its natural beauty.
Enjoy hiking, wildlife photography, wildlife viewing, and educational tours in this wildlife sanctuary.
Traverse more than four miles of trails, taking you to ponds, meadows, woodlands, salt marshes, and shorelines teeming with local flora and fauna of the island.
You can enjoy kayaking at the Sengekontacket Pond or join the sanctuary staff's educational program.
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, the Manuel F. Correllus State Forest is famous for hiking, biking, skiing, hunting, disc golf, and nature viewing.
Do a Kickflip at Martha's Vineyard Skatepark
Martha's Vineyard Skatepark is an exciting place to visit whether you're a skater or an average tourist.
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.
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.
Discover the Pecoy Point Preserve
The Pecoy Point Preserve is another natural attraction worth visiting, especially for nature lovers and wildlife enthusiasts.
The preserve comprises salt marshes, grasslands, and a freshwater pond.
Many tourists visit this preserve, especially those who want to see migratory birds, local bird species, and other animals.
In addition, outdoor activities such as hiking, mountain biking, picnicking, and horseback riding are prevalent and famous here.
In addition, water activities such as boating and kayaking are also tourist favorites.
So, if you want to enjoy the outdoors without traveling far from Oak Bluffs, check out the Pecoy Point Preserve.
Take a Closer Look at the Jaws Bridge
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.
Browse the Featherstone Center for the Arts
Martha's Vineyard is not just known for its beautiful beaches, history, and natural attractions.
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.
Spend some Quiet Time at Eastville Beach
Eastville Beach is one of the more underrated spots in Oak Bluffs, a perfect place for solitude or a tranquil time with a loved one.
You can experience the beautiful waters of the Vineyard Sound here, as the beach is situated by a lagoon area near Oak Bluffs’ Beach Road.
Depending on the season you go, Eastville Beach has varying charms as it transforms each season.
During winter, it becomes clad in snow, so it’s highly recommended that you visit this beautiful spot during spring or summer instead.
Equipped with benches and some walking trails, Eastville Beach is a fantastic place to just relax and take a break.
Go for a Run at Waban Park
Just across Seaview Avenue lies Waban Park, a vast open space where you can do some light jogging before or after visiting Inkwell Beach.
Waban Park is a huge open space that doesn’t have a lot of trees, so this is a great place to do some sports activities as well, such as frisbee or kite-flying.
Plenty of locals congregate here as well, making this a fun place for community immersion.
In fact, Waban Park is a popular attraction for music festivals and other events, so go check if something is happening during your visit.
Easy to access and just a stone’s throw away from the iconic Inkwell Beach, Waban Park is a great complement to your trip in Oak Bluffs.
Take Photos of the Flower of the Winds
Flower of the Winds is one of the prime attractions in Oak Bluffs’ historic cottage district that showcases the vintage Victorian houses in the town.
Adorned with beautiful pink paint, Flower of the Winds is a perfect place to do some Instagram-worthy pictorials as it’s one of the icons of Oak Bluffs.
What’s even better is that Flower of the Winds is surrounded by other Victorian house cottages of different colors, making this a fantastic place for urban exploration.
During the winter season, this section features clumps of snow which add to the picturesque charm of the place.
If you’re not planning on doing a tour with Martha’s Vineyard Camp Meeting Association, you can visit this street section along Trinity Park Walkway.
Go Fishing at Oak Bluffs Fishing Pier
If you’re an avid angler, Oak Bluffs Fishing Pier is a no-brainer for you to try out.
Located along Seaview Avenue, Oak Bluffs Fishing Pier features a beautiful boardwalk that takes you to the rich seas surrounding Massachusetts.
The best part about this is that you don’t even need to go fishing to appreciate it, as it’s also one of the most scenic places that gives you sweeping views of the ocean.
The fishing pier is also a great place to do some boat watching, as plenty are docked by the shores of Oak Bluffs.
It’s also just a stone’s throw away from Oak Bluffs Town Beach, so jogging or walking to get here is an easy addition to your itinerary.
Watch the Sunrise at East Chop Beach
Just a few miles north of Oak Bluffs Fishing Pier lies East Chop Beach—another great location to appreciate the sea.
East Chop Beach offers something different compared to the others, as this place has a more rocky terrain.
While that may not sound good, it actually adds to the unique appeal that East Chop Beach brings; a great place for seaside photography.
It’s also convenient to get to since it’s close to the epicenter of the town.
East Chop Beach is also one of the best places to watch the sunrise, especially if you want a quieter version compared to other mainstream beaches in the town.
Oak Bluffs is why Martha's Vineyard is a special place to visit.
This small oceanside town has many exciting things to do and discover from its beaches, historic landmarks, and vibrant community.
Visiting Oak Bluffs is genuinely worth your time and effort.