Best Cool/Hip Summer Activities for Adults on Martha’s Vineyard
Every summer, I get asked what there is to do on Martha’s Vineyard that goes beyond the typical beaches, boutiques, and bars. So I decided to pull together a list based on my personal favorites—cool, low-key, offbeat experiences that I think really capture the spirit of the island, especially for adults who want something different.
First and foremost: Off the Beaten Trails (OTBT). This is my e-bike tour company, but even if it weren’t, it would still be at the top of the list. It’s the best way I know to experience the Vineyard’s hidden trails, backwoods paths, and secret chill spots. I lead small groups—no more than 6 riders—through terrain that most tourists never see. A few stops are cannabis-friendly, depending on the group vibe. It’s relaxed, it’s adventurous, and it’s deeply local.
Another underrated gem? Take the Chappy Ferry over to Chappaquiddick and explore Mytoi Garden or East Beach. It’s a short ride but feels like stepping into a quieter, more contemplative version of the island. Bring snacks, maybe a little something extra, and take your time.
If you're looking for great local spots to refuel before or after your adventure, Morning Glory Farm is perfect for fresh produce, baked goods, and local color. Katama Kitchen has a laid-back breakfast scene with killer views. And then there’s Backyard Taco—divey in the best possible way. It’s got that great late-night vibe, flavorful eats, and a crowd that keeps things interesting without trying too hard.
When it comes to trails, don't sleep on the State Forest, Land Bank properties, and Sheriff's Meadow trails. Each offers a different flavor of the Vineyard—some wide and breezy, others narrow and winding through the woods. While the beaches draw the crowds, it’s the interior of the island that is hugely underrated and consistently surpasses expectations for its natural beauty and animal life. Many of these trails are part of my routes with OTBT, and they’re some of the best ways to truly see the island’s natural side. If you’re looking for something more authentic than a tourist-packed lobster shack, that’s your spot.
The Vineyard can be anything you want it to be. But if you’re craving something offbeat and real, I promise—it’s here.