Explore the most popular trails near Oak Bluffs with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Oak Bluffs, Massachusetts Map

This is a nicely groomed, flat trail but it's not very scenic and not well-marked. Without the All Trails app, I would've gotten off track several times. A lot of it is along a road and an elementary school too. There are nice, quiet, wooded areas and open meadows too though so it wasn't a total loss. If I was a local, I could see this as a go-to dog walking trail but if you're a tourist looking for scenery, look elsewhere.

These trails are short but very beautiful!
Started with the Farm Pond trail and got connected to the Trade Wind Fields trail. The Farm Pond trail goes through beautiful woods - mixture of pine and oak. The Trade Wind Fields trail goes around an all grass airfield that is surrounded by pine forest. This was a mountain biking outing. Trails are well maintained and some what marked. I was not sure what exact trail i was on, but arrow pointing the way were there. The trails were busy for December - hikers and dog walkers. Be advised that people have their dogs running all over the place and pretty much ignore the posted signs about not wandering around on the landing strip.
For the Summer goers - parking is going to be an issue. There is a 2-3 car parking spot by the airfield trail head. Or you can park alone the Sea View Ave close to the Farm Pond and proceed to the Farm Pond trail head through the neighborhood.
Watch out for ticks in Summer time!