Okay so if you're counting, I visited the Vineyard twice this summer. The second trip was a girls trip to experience the Martha's Vineyard African American Film Festival. The first was a bike trip with hubby and you can read all about that trip on my Martha's Vineyard post.
The coolest part of the trip was the Film Festival and the fact that the Vineyard is a riding town. There is little parking and biking is just convenient. There are lots of asphalt trails all over the island.

I rent a bike at Anderson's in Oak Bluff. They pick up and deliver and a weekly rental runs about $80. Now I will say that I always go and pick out my bike. Your bike has to fit you. Bikes come in different heights and styles. (We will talk more about how to find the best bike for you in a future post). Anderson's has cruisers with baskets and a few hybrids. If you are looking for a racing bike, Anderson's might not be your spot. I usually get a hybrid which has more of a racer seat, but all of their seats are padded.
Popular rides are from Oak Bluffs to Edgartown and Oak Bluffs to Vineyard Haven. Be careful on the ride to Vineyard Haven from Oak Bluffs because once you cross the drawbridge into Vineyard Haven the bike trail runs out and you have to ride in the street. The ride from Oak Bluffs to Vineyard Haven by bike is about 3.6 miles via New York Avenue. There is the usual shopping and great places to eat in Vineyard Haven. The Art Cliff Diner is a great place to stop in Vineyard Haven. Go early or late afternoon, they do not take reservations and the wait can be up to 2 hours

I mentioned in another Martha's Vineyard Post that my favorite ride on Martha's Vineyard is the ride along East Chop. So thanks to my GoPro I was able to get a snippet of what the ride looks like. Full disclosure I am new to GoPro. I did some research (it's a thing in our house) and settled on the GoPro Hero6 Black. I hope you enjoy.
https://videopress.com/v/y5R2Y5zl?autoPlay=true
Oak Bluffs to East Chop