Eight Fun Things To Do in Oak Bluffs

Last week was hot, hot like life on the proverbial tin roof, so I lit out for the open air of the ferry to Martha’s Vineyard, hoping to catch a little wind on the way, and see the sights in Oak Bluffs. I have been to the Vineyard many times before, but never explored every nook and cranny of this hip little island town, so here — after an afternoon of beating the streets — are my favorite to things to do in Oak Bluffs:

1. Hunt for a Souvenir
From Soft as a Grape to Menemsha Blues to the Black Dog, there is a t-shirt for everyone on the main strip which is called Circuit Avenue. I wandered into the Black Dog and admired their fluffy sweatshirts with the ubiquitous large retriever. Tip for shoppers: While there appears to be a Black Dog on every corner, the “outlet” store sells much of the same stuff at a discount in a small shop down by the marina called the Dockside Premium Outlet.

2. Go Upscale
Since the Vineyard was discovered by the masses in the last decade or so (much to the chagrin of the folks who have loved it for centuries), the shopping has gone upscale, especially in Edgartown and Vineyard Haven. But even rough and tumble Oak Bluffs now has a Vineyard Vines, so don’t miss this wonderful shop painted navy and hot pink at the end of Circuit Avenue.

3. Eat an Ice Cream
Do not leave OB without an ice cream cone. Mad Martha’s, Ben and Bill’s – doesn’t matter much which place you choose, you will be sure to leave with that blissed out, I-am-on-vacation-and-I-just consumed-three-days-worth-of sugar smile.

4. Visit the Gingerbread Cottages
Just behind Circuit Ave sits the neighborhood known as the “Gingerbread Cottages.” This incredible collection of brightly-painted Victorian summer cottages was originally a Methodist campgrounds but is now on the National Register of Historic Places and is a cherished spot for visitors and residents alike. Stroll back in time on the tiny pedestrian streets, their yards cluttered with day lillies and porches jammed with Kennedy rockers painted every color of the rainbow.

5. Grab an iced coffee
Plenty of choice here for the quintessential frosty coffee crammed with ice. I went with decaf and lots of milk, and the cup in my hand kept me cool for several extra blocks of exploration.

6. Ride the Flying Horses
This 100+ year old carousel is just as charming as it looks in photos. You will see it immediately as you get off the ferry in Oak Bluffs, and be sure to wait for a ride — it’s worth it!

7. Hit the Beach
Is there anything better than a beach right next to a ferry terminal? The Jersey Shore has nothing on this, with calm waters, a waterfront park, and the shops a stone’s throw from the sand. Feeling ambitious? Rent a bike and ride toward Edgartown. You will come upon the “Jaws” bridge — with kids jumping off the causeway into the tidal currents below just like they did 30+ years ago in the movie.

8. Ride the ferry to Woods Hole
Nothing better at the end of a full day of sightseeing than flopping into an ocean-view seat for the cool ferry ride home. Watch the gulls circle above the deck and feel the southwesterly breeze on your face. Well-earned relaxation at it’s very finest.

— by Megan Jensen