Secret Trails & Hidden Beaches on MV You Won’t Find on Google Maps

I’ve lived on the Vineyard long enough to know that the best parts of the island aren’t in the guidebooks. You won’t find them with a Google search or by asking the concierge at your hotel. But I’ve made it my mission—literally—to help people discover them.

With Off the Beaten Trails, I take riders through landscapes that most visitors to Martha’s Vineyard never experience. Think dense woodlands, winding sand trails, ocean bluffs, and stone labyrinths tucked deep in the forest. Some of the spots we visit don’t even have official trailheads. You just have to know where to turn.

There’s something powerful about riding to a beach that’s completely empty, especially during peak summer. No umbrellas, no snack shacks—just wind, water, and maybe a cold drink pulled from a backpack. You get a moment to breathe, disconnect, and feel like this place is yours.

People come to the island to relax, but the kind of peace you find out there on the trails? That’s something else. And it’s exactly why I started OTBT in the first place.