Biking Martha's Vineyard

First, the downside: you'll be sharing winding roads with wide trucks and tour buses cruising right by your elbow, inexperienced moped riders, and automobile drivers unfamiliar with the island roads, not to mention other cyclists of various experience levels. In addition, most roads are bordered by sand—even those that aren't near the beach. The bottom line is this: pay attention at all times. And if ever there was a place to commit to wearing a helmet, this would be it.

That being said, the Vineyard is also a cyclist's paradise, and you don't have to be an experienced rider to enjoy the paths and roads here. The highest elevation is about 300 feet above sea level, and you'll find relatively easy uphill and downhill biking with well-paved bike paths both Down-Island and Up. There are a couple of fun roller-coaster-like dips on the state-forest bike path (watch out for the occasional inline skater here). Quiet country roads wind up and down gentle hills covered by low-hanging trees that make you feel as though you're riding through a lush green tunnel. The views—across open fields to the Atlantic Ocean, alongside ponds with floating swans, or of sun-flecked meadows where handsome horses graze—will nearly knock you off your bike seat. There is another benefit: you'll be helping environmentalists who would rather see more nonpolluting bikes here than fossil fuel–guzzling vehicles.

Two of the quietest and most scenic roads without paths are North Road, from North Tisbury center all the way to Menemsha; and Middle Road, from its start at Music Street west to Beetlebung Corner, where South Road and Menemsha Cross Road intersect. This ride from Up-Island to the western tip of the island in Aquinnah is challenging—winding and sandy roads with a steep hill or two—but worth the reward of spectacular views.