Oak Bluffs, a perfect daytrip

Your trip to Falmouth MA is not complete without a visit to Oak Bluffs on Martha’s Vineyard. With the oldest operating carousel in the nation, a collection of twee Victorian houses that will astound you as well as several blocks worth of restaurants, candy shops, gift stores and more, Oak Bluffs makes an ideal day trip. Check out our favorite resources, insider tips and more.

Getting There

Take a ferry from Falmouth to the seasonal port of Oak Bluffs for the day.  For Woods Hole, Sippewissett and West Falmouth people, we recommend the ferry terminal in Woods Hole. Take the free shuttle bus from the Palmer Ave lot (which is a pay parking lot at 286 Palmer Ave in Falmouth) which is operated by the Steamship Authority. OR, you can ride the “Island Queen” from Falmouth Harbor (with parking offered by Island Queen company in nearby lots).

Oak Bluffs Daytrip

Gingerbread Cottages

Your first stop is the Gingerbread Cottages, also known as the Martha’s Vineyard Camp Meeting Association. This amazing collection of diminutive Victorian cottages build around a tabernacle open air gathering place is started with humble roots as a summer camp for practicing Methodists. Often referred to as “Cottage City” there are over 300 brightly painted miniature residences all painted wonderful colors. You will enjoy spying on lucky residents enjoying a cool summer day from their porch.

Oak Bluffs Daytrip

Inkwell Beach

At the ferry landing, enjoy the large park plus a stretch of sand called Inkwell Beach which is a great place for a swim (bring your towel). Early mornings, you will see a dedicated group called the Inkwell Polar Bears gathered to exercise in the cool waters of Nantucket Sound. Welcoming to newcomers, join them if you are game. You can read all about this wonderful tradition in the New Yorker Magazine.

Ride The Carousel

Check out the nation’s oldest platform carousel operating since 1884 called the “Flying Horses.” Endless fun for kids, be sure to reach for the brass ring to win a free ride.

Settle in for Lunch

It would take a lifetime of day trips to try all the lunch options in Oak Bluffs. The Vineyard, known for fine local farms and excellent chefs, has a deep tradition of innovative cuisine which is on display here in OB. We recommend MV Chowder Company for their award winning quahog chowder, Lobsterville Bar and Grill for harborviews and lobster rolls, or Lookout Tavern for ocean views, great salads and sushi.

Oak Bluffs Daytrip

Do Not Skip Dessert!

Do not leave the island without sampling a few of the delightful sweet shops, and take some candy treats home for the family. Check out Murdick’s Fudge, and Back Door Donuts to make your visit to Oak Bluffs a perfect day.

Oak Bluffs daytrip

Now for Some Shopping

Circuit Avenue is crammed with t-shirt shops, gift stores and more, but the must visit places include Soft as A Grape, Menemsha Blues, Black Dog and Vineyard Vines. Each has iconic Vineyard themed logos and street wear that you will sport back home to remember this special visit.

Take a Quiet Walk

The hustle bustle of the main streets of Oak Bluffs can get a bit overwhelming, so find a little tranquility with a walk towards Waban Park and Farm Pond in the quiet residential neighborhood behind Seaview Avenue. More Victorian themed homes and porches dominate here, but this time with yards and ocean views. You will start dreaming of the day you can return for a week or two to rent one of these beauties with time to kick back, sip your iced tea and count the tourists walking by.

Daytrip Oak Bluffs

Seasonal Note

Oak Bluffs is quite seasonal, and ferry service to this harbor starts in May and ends in October. In the off season, there are still businesses open (although by no means all of them) and to visit you will take the Steamship Authority ferry from Woods Hole to Vineyard Haven, then ride the bus (or a taxi) ten minutes to Oak Bluffs. The Gingerbread Cottages are equally delightful in any season, and if you are looking to avoid the crowds, this is a great option.

Oak Bluffs daytrip

Directions to the Woods Hole Ferry

Falmouth Eats

Click here to learn about Falmouth's many fine eateries and bars. 

Falmouth Restaurants