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The boulder beach under the sandy bluffs at Menemsha Hills. Bikes aren't allowed on the reservation's trails, so this view is one you reach on foot.
An up-island bike ride near Menemsha Hills in Chilmark on Martha's Vineyard. Bikes aren't allowed on the reservation's trails, so lock up and walk down to the boulder beach.
This ride winds through the wooded hills near Menemsha on Martha's Vineyard, with plenty of twists, turns, and climbs (enough to make you work for it) and shade most of the way. Before you pack the bike, though: the Trustees' Menemsha Hills Reservation does not allow bicycles on its trails at any time of year, so save the reservation itself for a hike. For legal riding with real climbs, head for the quiet up-island dirt roads or the mountain-bike trails of the Correllus State Forest, and use the video below for a feel of the up-island terrain.
Filmed June 2023The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked October 2026.
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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.
Exploring the area? Start with our complete Chilmark guide: food, beaches and more.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one price range. 
Island tip of the day Timing No. 58 of 79 New tip at midnight, island time
Oak Bluffs restaurants are packed 6–8 PM. Eat at 5 PM or after 8:30 PM: same food, half the wait, easier parking.
Lobster on Martha's Vineyard from trap to paper plate: how the small Menemsha fleet fishes, the Massachusetts rules on size, egg-bearing females and whale-safe gear, where to buy lobster off the boat (Larsen's, Menemsha Fish Market, The Net Result), how to eat it on the dock with your own bottle, and how a visitor can get a permit and catch a few.
Every farm stand and visitable farm on Martha's Vineyard, checked with the farms in September 2026: Morning Glory, Beetlebung, North Tabor, Mermaid Farm's 24-hour dairy shed, Native Earth, Allen Farm, Island Alpaca, the FARM Institute and the West Tisbury Farmers Market, with hours, honor-system rules and the fall pumpkin dates.
Cycling Martha's Vineyard in 2026: about 38 miles of bike paths, 5 routes from easy family rides to the 60-mile island loop, rental prices, and e-bike rules.
Chilmark guide: Beetlebung Corner pizza, Chilmark Tavern BYOB, Allen Farm, Menemsha Hills hiking, and the flea market that has run since 1967.
A bicycle ride from Edgartown to Vineyard Haven on Martha's Vineyard: the full route between the two towns, filmed in 4K.
Bicycle ride along Franklin Street and Main Street in Vineyard Haven, Martha's Vineyard. Boutiques, galleries, and harbor views from the seat of a bike.
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