Top Cannabis-Friendly Experiences on Martha’s Vineyard

Now that cannabis is legal in Massachusetts, people are looking for ways to enjoy it responsibly—and meaningfully. That’s part of what inspired me to start Off the Beaten Trails. I wanted to create an outdoor experience that embraced the laid-back culture of the island while staying true to the law and the land.

Our e-bike tours are built for people who want more than just a ride. We go off-road, we explore secluded spaces, and yes—when appropriate and permitted, we create space for cannabis-friendly stops. The vibe is mellow, respectful, and rooted in the idea that nature and cannabis can absolutely complement one another.

There is one local dispensary on island, Island Times for those who want to pick something up. Then we head out—just a few riders, no big crowds—and take the day as it comes. Sometimes it’s a peaceful ride through a shaded forest. Other times it’s a stunning ocean overlook with the sound of waves and nothing else.

This isn’t about partying. It’s about presence. It’s about slowing down and really being in the place. That’s what OTBT is all about.

If you’re looking for a cannabis-friendly outdoor experience in Massachusetts—especially on the Vineyard—you don’t have to settle for generic. Come ride with me.