Why OTBT is the Perfect Vineyard Activity for Couples, Friends, or Solo Explorers

Martha’s Vineyard has no shortage of things to do—but if you’re looking for something that feels like it was designed just for you and your people, Off the Beaten Trails (OTBT) might be exactly what you’re after.

I started OTBT for people like me—those who want to explore and really get to know the island, that want something deeper than the usual beach day or harbor stroll. Something real. Something you’ll remember.

Our tours are intentionally small—never more than 6 riders. Whether you’re a couple looking for a mellow ride through the woods, a solo traveler wanting to connect with nature, or a group of friends planning a chill outdoor experience, this was made for you.

We’ll ride through some of the Vineyard’s most underrated landscapes. Forget the paved bike paths—this is the hidden island: forest trails, off-road climbs, secluded lookouts, and maybe even a labyrinth or two. Every ride is a little different based on the group and the day. That’s part of the magic.

We also get a lot of couples on our rides—and for good reason. It’s just the right mix of adventure and downtime. You ride side by side. You stop in places that feel secret. You connect over the kind of beauty that doesn’t ask for a filter. No loud groups. No tourist crush. Just you, the bikes, and the Vineyard.

And if you’re coming with friends, we’ll tailor the route and pace to the group. Want a 420-friendly stop along the way? Just let us know ahead of time—we’ll make it part of the journey.

No two OTBT rides are the same. But every one of them is rooted in the same idea: showing you the Vineyard most people never see, in a way that feels personal and relaxed.

If you’re looking for something truly memorable, you’re in the right place.