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ChilmarkMartha’s Vineyard
A bicycle ride through the wooded hills around Menemsha on video, with what it does not show: the Trustees' Menemsha Hills Reservation bans bikes on its trails, so this page covers the hike to Prospect Hill, the up-island roads where you can ride (North Road, Middle Road, the State Forest), safety on narrow roads, and the bus.
This ride winds through the wooded hills around Menemsha on Martha’s Vineyard, with twists, turns and enough climbing to make you work for it, and shade most of the way. One thing to know before you pack the bike: the Trustees’ Menemsha Hills Reservation itself does not allow bicycles on its trails at any time of year, so the reservation is a hike, and the riding is on the roads around it. The video below gives you a fair feel for the up-island terrain; the rest of this page covers the hike, the roads where riding is allowed, and how to get up here with or without a car. For the town around it, see our Chilmark and Menemsha guide.
Filmed June 2023The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked November 2026.
Golden hour on a boulder beach, the sun dropping over the water. Below Menemsha Hills the trail down from the bluff is steep and the tide can cover the beach, so the walk back takes a little planning.
Up-island in one signpost: West Tisbury and Edgartown one way, Vineyard Haven via Menemsha the other. It helps to know your turn before the map stops loading.
A sand road down to the water, scrub and wind-bent trees on both sides. Quiet roads and open shore are the part the two islands share.
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The Trustees of Reservations manage 211 acres here, with about 3 miles of marked trails on two connected loops. The Harris Loop, about a mile, climbs to Prospect Hill, at 308 feet the second-highest point on Martha’s Vineyard, with views across Vineyard Sound to the Elizabeth Islands, Aquinnah and Menemsha Harbor; the trail carries on down to a boulder-strewn north shore beach, past the 19th-century ruins of a brickworks with a 45-foot chimney. Count on 383 feet of climbing and 90 minutes or more for the whole thing. The trailhead is on North Road, about a mile east of Menemsha, with parking for 20 cars; it is free, open year-round from sunrise to sunset, the ground is rocky and uneven, dogs stay on a leash, and tick spray is a good idea in every month but the coldest. It is one of the classic winter walks on the island, and our hiking guide has the trail notes.
The boulder beach under the sand bluffs at Menemsha Hills. The trail down from Prospect Hill passes the 19th-century brickworks chimney on the way.
A stony shore below a sandy bluff, with wooden stairs coming down and calm water alongside.
A pond on a calm summer day, one skiff on a mooring and a low strip of beach along the far side.
The roads are the ride. North Road from West Tisbury to Menemsha, about 6 to 7 miles, is one of the prettiest rides on the island and one of the hardest: hilly, no bike lane, north-shore views and farm ponds between the trees, so it suits confident cyclists, and an e-bike helps a lot. A good plan is bus up and bike back, since the ride east is mostly downhill and the VTA racks take up to three bikes. Middle Road, which islanders call the least improved of the main roads, passes Keith Farm, where cows graze with the Atlantic behind them, and hosts the Chilmark Road Race, a 5K on the second Saturday in August that finishes at Beetlebung Corner, the crossroads where State Road, South Road, Middle Road and Menemsha Crossroad meet. South Road has an old stone animal pound from the sheep-farming days. For legal off-road riding with real climbs, the Correllus State Forest in the middle of the island has paved loops and mountain-bike trails; our mountain biking guide and island cycling guide cover them.
A stone wall, a green field and an old tractor in West Tisbury, the up-island picture most people come for.
So much of the island is conservation land that camping stays tightly limited.
The Chilmark General Store at Beetlebung Corner, flag out and the porch benches waiting.
Up-island roads are narrow, winding and shaded, with blind bends and summer traffic, and nothing here has a separated path. Ride single file, wear a helmet, use lights even by day under the trees, and keep to a pace that lets you stop for a deer or a delivery truck around the next corner. Early morning has the lightest traffic all year. Massachusetts law since 2023 asks drivers to give cyclists four feet when passing, and the signs are up on the island roads. If the roads put you off, the State Forest and the paved paths down-island are the easy days.
Menemsha’s working docks, pilings and shingled fish houses, where the up-island day ends.
A VTA bus at a West Tisbury stop in summer, a bike on the front rack and riders getting on.
Chilmark is about 25 minutes by car from Vineyard Haven. By bus, VTA Route 4 runs along North Road straight to Menemsha and Route 5 along South Road to Aquinnah, both connecting through West Tisbury Town Hall; off-season the up-island buses come every two hours, and the last bus out of Menemsha leaves at 5:01 PM, so check the last bus back before you stay for the sunset. Rides are fare-free through June 30, 2027. For lunch, the Menemsha Galley Temporarily closed Closed for the season; back in spring 2027, per its own site and Larsen’s Temporarily closed Closed for the season until May 2027, per its own site have closed for 2026 and plan to reopen in spring and May 2027; the Chilmark General Store at Beetlebung Corner closed for the season on October 9.
No. The Trustees do not allow bicycles on the trails at any time of year. Lock the bike at the North Road trailhead and walk.
About 3 miles with 383 feet of climbing on rocky ground, 90 minutes or more; the Harris Loop to Prospect Hill is the short version at about a mile.
North Road from West Tisbury is the classic, 6 to 7 miles and hilly with no bike lane; the bus up and the ride back down is the easy way to do it.
How we checked: the video is ours, filmed on the roads around Menemsha. Reservation facts (acreage, trails, the bike ban, parking) are from the Trustees of Reservations, road and race details from our Chilmark town guide and hiking guide, bus times from the VTA’s off-season timetable, and the restaurant closures from the businesses’ own notices as recorded in our Menemsha guide. Last checked November 1, 2026.
Exploring the town? Start with our complete Chilmark guide for food, beaches and parking.
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. From MV Vacation, written on Martha’s Vineyard · https://mvvacation.com/blog/exploring-menemsha-hills-bicycle-ride · printed . Hours, prices and schedules change; the page online is the current one.
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.
Four bike rides and a run around Vineyard Haven, Martha's Vineyard, filmed from the handlebars: a loop around town, Franklin and Main Street, the path to Edgartown both ways, Beach Road to Oak Bluffs, and the run to West Chop, with rentals, a map and how to get there.
Menemsha fishing village guide: the sunset crowd, Larsen's lobster, Dutcher Dock, Jaws spots, and tips for parking and dining.
Island tip of the day Timing No. 78 of 79 New tip at midnight, island time
Owen Park Beach in Vineyard Haven is almost never crowded: most visitors go straight from the ferry to bigger beaches. Calm, shallow, perfect for a last-morning swim.
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