What to do and see in Oak Bluffs, Massachusetts (MA): The Best Budget-friendly Things to do

August 2, 2021 Terina Blouin

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. The population was 4,527 at the 2010 United States Census. It is one of the island's principal points of arrival for summer tourists, and is noted for its "gingerbread cottages" and other well-preserved mid- to late-nineteenth-century buildings.
Restaurants in Oak Bluffs

1. Oak Bluffs Public Library

56R School St., Oak Bluffs, Martha's Vineyard, MA 02557 +1 508-693-9433 http://www.oakbluffslibrary.org
Excellent
86%
Good
11%
Satisfactory
3%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 37 reviews

Oak Bluffs Public Library

2. Anderson's Bike Rentals

23 Circuit Ave Ext, Oak Bluffs, Martha's Vineyard, MA 02557 +1 508-693-9346 http://www.andersonsbikerentals.com/
Excellent
87%
Good
11%
Satisfactory
1%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 90 reviews

Anderson's Bike Rentals

Reviewed By jnonn12 - Baltimore, United States

Easy walk from the ferry. They have plenty of different bikes to rent. The people who work there were so friendly - he told the time to go over the map with the various bike trail options and gave recommendations along the way. He set us up with 2 bikes, a basket, a bike lock, and bungee to hold our big bag down all for $25 a day per person. I recommend the trail to Edgartown and stopping at beach / Jaws bridge along the way! It was the perfect day that started at Anderson’s!

3. Sun 'n' Fun Rentals

26 Lake Ave, Oak Bluffs, Martha's Vineyard, MA 02557 +1 508-693-5457 http://www.sunnfunrentals.com
Excellent
88%
Good
11%
Satisfactory
0%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 123 reviews

Sun 'n' Fun Rentals

Reviewed By 493carmenb - Wakefield, United States

The guys working there were so helpful. We rented a jeep and they helped us the next day to put the top down. Gave us a map of the island and told us all the places to see! We will definitely rent from them again!! Super friendly staff!

4. My Brother Charters

Slip 72, Oak Bluffs Harbor, Oak Bluffs, Martha's Vineyard, MA 02557 +1 774-836-7465 [email protected] http://www.mybrothercharters.com
Excellent
96%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
4%
Overall Ratings

5.0 based on 23 reviews

My Brother Charters

Private fishing charters for Family or groups of 6 people or less. Great for kids of all ages. We are hands on ensuring that all aboard will catch fish!

5. Pirate Adventures: Martha's Vineyard

Excellent
96%
Good
3%
Satisfactory
0%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 822 reviews

Pirate Adventures: Martha's Vineyard

Ahoy mateys! Join us as we set sail on a pirate's treasure hunt along the shores of beautiful and historic Oak Bluffs on the legendary island of Martha's Vineyard. On our custom pirate ship your kids will dress and talk like a pirate, assemble a treasure map, battle rival pirates with water cannons and hoist sunken treasure from the ocean floor! Once aboard the Sea Gypsy, we must work together to build a treasure map and determine our course. Along the way, we find a message in a bottle and discover that Stinky Pete, the Island’s smelliest pirate, has stolen the keys! We must raise the battle flag, fight off our enemy with water cannons, and steal back the keys to claim our treasure! The voyage culminates as we discover where "X" marks the spot...we must work as a team (heave-ho!) to raise the treasure chest from the ocean as it's heavy with sea water and sparkling booty. Every one of the crew will be rewarded for their efforts and take home their fair share of the loot. There’s singin’, dancin’, and drinkin’ of pirate grog as we sail back to port victorious in our spoils. You’ll be amazed how quickly the Pirate Adventures crew taps into the wonder of your child’s imagination. This wholesome, family-oriented cruise is perfect thing to do on a day trip, vacation, weekend or really just about anytime your are seeking a child-friendly and action-packed bunch of fun while on MV. There is a reason why Pirate Adventures is ranked high on a family’s vacation highlights. This isn’t a performance by actors - this is a highly interactive pirate experience where each of our trained crew makes sure your child is involved and engaged throughout the whole journey. It's a fun, unique, memory-making adventure cruise designed for families by a family (a pirate family of course).

6. Inkwell Beach

Seaview Ave, Oak Bluffs, Martha's Vineyard, MA
Excellent
54%
Good
31%
Satisfactory
12%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 121 reviews

Inkwell Beach

This Oak Bluffs beach and surrounding area of colorful gingerbread Victorian houses have strong links to African-American heritage on Martha's Vineyard, dating back to the Revolutionary War. The beach was the setting for a teenage romance movie called "The Inkwell."

Reviewed By Hgtravl - Marlton, United States

I had no clue just how beautiful the beaches where at Marthas Vineyard until I arrived. As soon as we left the ferry, we noticed the aqua crystal clear beaches! I cannot get over how "tropical" colored the water was- felt like we where in Flordia! The beach was spotless clean. Not a single piece of trash- even for peak tourist times. Beautiful beach with crystal clear waters... Loved the beautiful tumbled rocks by the jettys- found a few keepers!

7. Joseph Sylvia State Beach

btwn Oak Bluffs and Edgartown off Beach Rd, Oak Bluffs, Martha's Vineyard, MA 02539 http://www.dukescounty.org/pages/dukescountyma_naturalresources/sylvia
Excellent
61%
Good
33%
Satisfactory
5%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 109 reviews

Joseph Sylvia State Beach

Small waves, low dunes and lots of seashells make this narrow, two-mile stretch of public beach popular with families. The beach runs between Oak Bluffs and Edgartown, and is called "Bend-in-the-Road Beach" on the Edgartown side.

Reviewed By ebrraiin - Jersey City, United States

Great beach, east to get to via bike or car. The water is clear and warm. The waves were quiet. Looking forward to going back.

8. Ocean Park

Seaview Ave., Oak Bluffs, Martha's Vineyard, MA 02557 +1 508-693-2303
Excellent
71%
Good
24%
Satisfactory
4%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 231 reviews

Ocean Park

Victorian mansions surround this charming Oak Bluffs park.

Reviewed By HollsinSavannah - Fryeburg, United States

Wonderful park to listen to bands in summer. Also great place to walk to with a coffee and a back door donuts donut and sit

9. Oak Bluffs Land and Wharf Co. Tours

Excellent
81%
Good
5%
Satisfactory
4%
Poor
1%
Terrible
9%
Overall Ratings

4.5 based on 118 reviews

Oak Bluffs Land and Wharf Co. Tours

Join us for a 2.5 hour narrated tour of all six towns, including a mid-tour comfort stop at the beautiful and famous Gay Head cliffs and lighthouse. Along the way you will see beautiful and enchanting island vistas, historic homes, scenes from Jaws, and the Gingerbread cottages of Oak Bluffs. Tour price includes admission to the Martha's Vineyard Museum and the Gay Head lighthouse ($17 value.)

10. Circuit Avenue

Circuit Avenue, Oak Bluffs, Martha's Vineyard, MA +1 508-693-6181
Excellent
50%
Good
35%
Satisfactory
12%
Poor
3%
Terrible
0%
Overall Ratings

4.5 based on 308 reviews

Circuit Avenue

Off-beat and quirky shopping enclave in Oak Bluffs.

Reviewed By py236 - Albany, United States

Circuit Avenue is in the heart of Oak Bluffs once upon a time where African Americans went on vacation because they weren't allowed to be anywhere else. Restaurants, tourist shops and ice cream stores line the street. Every night, people walk up and down the block, gather to talk or sit outside. It's just down the block from the pier, which has a wide range of food and activity offerings. Truly the heart of the town and walking distanxe to the beach and town square.

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