What to do in Oak Bluffs, MA

Activities, attractions and tours

colorful gingerbread houses, cottages in Oak Bluffs center, Martha's Vineyard island in Massachusetts USA on a sunny summer day
Carpenters Cottages called gingerbread houses on Lake Avenue, Oak Bluffs on Martha's Vineyard, Massachusetts, USA
Pre-dawn colors from the beach near Oak Bluffs in martha's Vineyard
Martha's Vineyard, Massachusetts. East Chop (Telegraph Hill) Light, a lighthouse near the town of Oak Bluffs in the island of Martha's Vineyard
Oak Bluffs Pier, Martha's Vineyard

Oak Bluffs Attractions

Let Expedia help you experience the best that Oak Bluffs has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Oak Bluffs is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Oak Bluffs to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Oak Bluffs Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Oak Bluffs.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Oak Bluffs attractions ensure that you’ll have a successful trip, whatever the season.

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Recommended things to do in Oak Bluffs

Number of things to do
19
Cheapest thing to do on Expedia
Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour: CA $14
Top 5 things to do
Half-day tours
With kids

What to do in Oak Bluffs

Discover the most popular places to visit in Oak Bluffs

Inkwell beach in oak bluffs on martha's vineyard

Inkwell Beach

If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.

Inkwell Beach
Oak Bluffs Harbor

Oak Bluffs Harbor

Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Harbor. Wander the area's beautiful beaches or simply enjoy one of its wineries.

Oak Bluffs Harbor
Oak Bluffs Town Beach

Oak Bluffs Town Beach

If a restful vacation is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area.

Oak Bluffs Town Beach
Oak Bluffs skyline, well-preserved landmark houses, and dramatic winter sunset cloudscape over the Ocean Park on the island of Martha's Vineyard in Dukes County, Massachusetts, United States

Ocean Park

Ocean Park is just one of the places to see in Oak Bluffs, so why not enjoy the other things to explore during your travels? Wander the area's waterfront or simply enjoy one of its wineries.

Ocean Park
Carousel in Boston Massachusetts

Flying Horses Carousel

Enjoy an outing to Flying Horses Carousel during your stay in Oak Bluffs. Wander the beautiful beaches and waterfront in the area.

Flying Horses Carousel
Martha's Vineyard, Massachusetts. East Chop

East Chop Light

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's waterfront, or simply savor its wineries.

East Chop Light

Circuit Avenue

During your trip to Oak Bluffs, you can search for that perfect souvenir at Circuit Avenue. Wander the beaches and waterfront in this relaxing area.

Circuit Avenue

Oak Bluffs Fishing Pier

After visiting Oak Bluffs Fishing Pier, make a plan to see the other sights and activities in Oak Bluffs. Stroll along the beaches or visit the shops in this relaxing area.

Oak Bluffs Fishing Pier

Oak Bluffs Public Library

After visiting Oak Bluffs Public Library, make a plan to see the other sights and activities in Oak Bluffs. Wander the beautiful beaches and waterfront in the area.

Oak Bluffs Public Library

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Oak Bluffs

Edgartown Harbor Lighthouse

Vineyard Haven

West Tisbury

West Tisbury

Aerial panorama East Chop, Marthas Vineyard, Summer 2024

East Chop

Frequently asked questions

Is Oak Bluffs worth visiting?
Oak Bluffs has a unique blend of culture, local charm and attractions. Whether you're into history, nature or traditional food, there's plenty to enjoy here.
How do I spend a day in Oak Bluffs?
Kick your day off with a visit to Inkwell Beach and Falmouth Heights Beach. Then, tour different areas of Oak Bluffs for tasty eats and some shopping.
What is the top tourist attraction in Oak Bluffs?
The top tourist attraction in Oak Bluffs is Inkwell Beach, so make sure to add it to your itinerary.
Is three days enough to stay in Oak Bluffs?
Three days in Oak Bluffs is plenty of time to enjoy the city's key attractions. Many guests book for three days on average. Inkwell Beach, Edgartown Beach and Lighthouse Beach are among the top-rated sights. Like to see more? Hang around a little longer to check off nearby hotspots such as Hyannis.
Is Oak Bluffs a walkable city?
With vibrant neighbourhoods and major attractions within walking distance of the city centre, Oak Bluffs is a great place to discover on foot. Wander between Inkwell Beach and Edgartown Beach. Then take a stroll through Lagoon Heights, located 2 kilometres from downtown, and East Chop, which is roughly 2 kilometres away.
What are some activities to do in Oak Bluffs with kids?
Planning what to do in Oak Bluffs with kids has never been easier. Whether you're travelling with teenagers or toddlers, there's no shortage of family-friendly sights to keep everyone entertained here.

What to do in Oak Bluffs for adults?
Whether you're a culture enthusiast, food connoisseur or fan of nature, there are plenty of things to do in Oak Bluffs for adults including Main Street and Chappaquiddick Graveyard.
Are there free things to do in Oak Bluffs?
One of the easiest ways to discover free things to do in Oak Bluffs is to chat to a local tour guide. You'll get insider tips on cool neighbourhoods, parks and other top attractions you can enjoy without getting your cash out. Inkwell Beach is one place that doesn't charge an admission fee.