Menemsha Hills Bicycle Ride, Martha's Vineyard

Menemsha Hills Bicycle Ride, Martha's Vineyard

Bike ride through Menemsha Hills on Martha's Vineyard. Pedal through lush woodland trails in Chilmark on one of the island's best off-road routes.

This ride follows the trails through the Menemsha Hills on Martha's Vineyard. The paths wind through the woods with plenty of twists, turns, and climbs — enough to make you work for it — and the trees are tall enough that you're riding in shade most of the way. It's a good ride if you want something more demanding than the island's flat paved paths. Watch the video below to scout the route, then bring your bike and try it yourself. 

Continue Exploring Martha's Vineyard

⚠️ Safety Notice: Martha's Vineyard roads — especially up-island — can be narrow and heavily trafficked during summer months. We strongly recommend sticking to the island's dedicated bike paths rather than riding on roads shared with motor vehicles. If you must ride on roads, wear a helmet, use lights, and exercise extreme caution. Cycling conditions change seasonally; always check current trail and road conditions before your ride.

📱 Island Tip of the Day — Tech

The SSA eFerry system lets you buy walk-on tickets from your phone — no standing in line. Tickets use NFC tap-to-board at the gate. Set it up before arriving.

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Disclaimer: The information in this article is provided for general guidance only and was accurate at the time of writing. Beach conditions, hours, prices, lifeguard schedules, ferry fares, and business operations change frequently and without notice. Ocean swimming carries inherent risks including rip currents, undertow, and cold water shock. Always verify current conditions with official local sources before your visit. MV Vacation assumes no responsibility for any loss, injury, or inconvenience resulting from the use of this information. Swim only where lifeguards are on duty, supervise children at all times near water, and follow all posted safety signs.
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