📆 Itinerary and Things to Do in Oak Bluffs for Martha's Vineyard Visitors (2024)
what to do, where to eat, and how to get to and from Oak Bluffs and Inkwell for a day trip on MV
MVacay’s Guide to Oak Bluffs
Who this Guide is For: Here's a guide for spending a single day on Martha’s Vineyard, perfect for two adults who are new to the island and want to experience its highlights during the peak season.
More Itineraries Here - including toddler-friendly, romantic weekend, Jaws Tour, bachelorette/girls trip, and more.
How to Get Here: We highly recommend arriving via the Island Queen Ferry into Oak Bluffs for those visiting in season. For more information on traveling from Cape Cod to Martha’s Vineyard, refer to to the Travel Section:
Just the Beginning: This guide is curated from our personal experiences and is not meant to cover everything but rather to showcase our top spots for first-timers. Given the time of year we recommend checking if these locations are open if you are visiting outside of Summer time.
Some Background on Oak Bluffs
Oak Bluffs, MA, originated as a prominent camp meeting site in the 19th century and is known for its Gingerbread Cottages and lively Circuit Avenue. It holds historical significance for the African American community as a retreat for Black elites and civil rights advocacy. The town features a variety of dining options along the harbor, enhancing its appeal as a tourist destination. Key attractions include the historic Flying Horses Carousel and Ocean Park, making it a popular spot for diverse visitors.
MV in One Day Bucket List
⛲ 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 - is only a 45 min walk from the harbor with awesome views along the way
Inkwell Beach - walk towards Joseph Sylvia State Beach (30 min walk)
Circuit Avenue is a main street - common shops/attractions here are Vineyard Vines and The Black Dog (now successful national chains, both established on Martha’s Vineyard)
🦞 Eat some Local Food
Pawnee House - a fantastic brunch option featuring inclusive veg-forward options in the heart of Oak Bluffs
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.
Tigerhawk Sandwich Co. - an awesome poke bowl or sandwich spot that you can grab and go for a picnic at Ocean park
🌊 Beach!
If you’re 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 you’re into history, there’s a few quick spots of note you can check out
Trinity Park Tabernacle - walk over to the largest covered outdoor performance space on the Island, has been a center for cultural, religious, and social activities on the Island for more than a 100 years
Flying Horses Carousel - take a ride on the oldest operating platform carousel in America. It’s tradition to try to catch the brass ring to win a free ride!
African American Heritage Trail - explore on your own some of the 30 sites dedicated to the formerly unrecognized contributions made by people of African descent to the history of the island. Info here
🍦🍹 Get a treat or drink
Cocktail - we love a coktail from The Alley, a bar tucked away downtown
Coffee - we love the specialty lattes from Aalia’s Coffee
Ice Cream - we love Ben+Bills for ice cream (lobster or black raspberry, please!)
Itinerary:
Now that you know the main players - here’s how this could realistically look for under $150 per person, leaving travel time on either side of the trip.
10:00 - Arrive, Park + Purchase round-trip ticket at Island Queen
10:30 - Depart Falmouth
11:05 - Arrive in Oak Bluffs, walk along harbor and explore the MV Camp Meeting Association + Tabernacle
12:15 - Eat a Poke Bowl from Tigerhawk Sandwich Co.
1:30 - Go for a walk to East Chop Lighthouse
2:00 - Walk up and down Circuit Avenue shops
3:00 - Grab an iced coffee from Aalia’s and walk over to Ocean Park. If you’re good on time, go sit on Inkwell Beach in the sand.
4:15 - Walk back and board the 4:30pm Island Queen Ferry home
Hours are subject to change depending on the time of year. Before your travel dates be sure to check out our Weekend Updates that share special local events and markets.