Menemsha Hills Bicycle Ride, Martha's Vineyard
Bike ride through Menemsha Hills on Martha's Vineyard. Pedal through the woods in Chilmark on one of the island's best off-road routes.
Martha's Vineyard is one of the best places in New England to ride a bike, with more than 32 miles of dedicated, paved bike paths connecting its three down-island towns and threading through the island's central state forest. The terrain splits cleanly: the eastern "down-island" half is flat and laced with separated bike paths perfect for families, while the western "up-island" half rolls through farm country with no cycling infrastructure: just narrow, scenic roads shared with cars.
No bike lane up-island, just narrow tar, stone walls and 25 mph: ride single file and own your line.
Filmed August 2024The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked September 2026.
The island stretches roughly 20 miles long by 9 miles wide, and a bike is the best way to see it, especially down-island, where the dedicated path network means you can ride from beach to gingerbread cottage to harbor without sharing asphalt with a single car. E-bikes have opened up-island to riders who would never have tackled those hills, so the whole island is rideable for almost anyone willing to pedal.
Electric bikes parked among orange daylilies in Vineyard Haven.
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The Dedicated Bike Path Network
Martha's Vineyard's paved, separated bike paths are concentrated in the eastern half of the island, forming a network that links Edgartown, Oak Bluffs, and Vineyard Haven.
Edgartown–Oak Bluffs Path (6 Miles)
The island's best-known ride, and probably its prettiest. Running approximately 6 miles along Beach Road beside Joseph Sylvia State Beach, the paved path sits on a narrow barrier beach with Nantucket Sound on one side and the calm waters of Sengekontacket Pond on the other. The terrain is entirely flat. At roughly the midpoint, you'll cross the American Legion Memorial Bridge, better known as "Jaws Bridge" from the 1975 film. The path is separated from traffic by guardrails for most of its length.
Edgartown–Vineyard Haven Path (7 Miles)
This path covers approximately 7 miles through the island's interior, running parallel to the Edgartown–Vineyard Haven Road. Less scenic than the Beach Road route (you're riding alongside a road through scrub oak and pine forest), but it is the link between the two towns. The terrain is moderately hilly. At approximately the 3-mile mark from Vineyard Haven, you'll reach the Barnes Road traffic circle, where the paved path into the Correllus State Forest loops begins.
The Oak Bluffs–Vineyard Haven Gap
The network's most significant weakness: there is no dedicated bike path connecting these two towns directly. The roughly 3-mile road route follows Beach Road and is heavily trafficked in summer. The Martha's Vineyard Commission recommends detouring via East Chop Drive, which adds about a mile but trades the traffic for water views. A shared-use path between Oak Bluffs and Vineyard Haven has been studied for years, but an earlier Beach Road project was scrapped and nothing is under construction; for now this gap remains an on-road ride.
Edgartown–South Beach Path (3 Miles)
A straight 3-mile ride south from Edgartown center along Katama Road to South Beach, the island's main surf beach. Flat, paved, and dead simple to follow, the island's best family ride. For a longer loop, return via Herring Creek Road (which also has a path) and Atlantic Drive, forming a roughly 8-mile triangle through farm fields.
Manuel F. Correllus State Forest (14 Miles of Paths)
The state forest occupies the island's center and contains a network of paved bike paths plus unpaved fire roads and singletrack. The main paved loop covers roughly 10 miles through shaded pitch pine and scrub oak barrens, a globally rare habitat. A smaller 3-mile paved loop winds through the forest's northeast corner. No cars, plenty of shade, and nothing to hear but birds and your tires. Some path surfaces are significantly cracked, so stay alert. The Barnes Road paved path runs from the Edgartown–Vineyard Haven Road south into the forest as the primary access point.
Cycling through Manuel F. Correllus State Forest.
Adding it all up (Beach Road (~6 mi), Edgartown–VH (~7 mi), Katama (~3 mi), Herring Creek (~3 mi), State Forest loops (~14 mi), plus connecting segments), the total reaches approximately 32–35 miles of dedicated off-road bike paths.
Up-Island Roads: The Vineyard's Best Scenery
West of the state forest, the island's character shifts from flat coastal towns to rolling glacial hills, farmland, and fishing villages. There is zero protected cycling infrastructure up-island: no bike lanes, no paths, no shoulders in most places. All riding is on narrow, winding roads shared with cars. And it is still the best riding on the island.
Cycling on Martha's Vineyard bike path.
Three parallel roads run the spine of up-island:
- South Road. The top recommendation from most cycling guides: stone walls rolling over moors, wildflower meadows, old Vineyard farmhouses, and views of tide pools and marshes. You'll climb Abel's Hill, passing the Chilmark Cemetery where John Belushi is buried, then coast past Allen Farm's photogenic sheep pastures.
- North Road. Considered the widest and safest of the three by local cyclists, with big old trees and rolling fields.
- Middle Road. Hay bales and stone walls, but narrow and winding. Best ridden early morning on a weekday.
The distance from Vineyard Haven to Aquinnah is approximately 20 miles one-way. From West Tisbury to Aquinnah via South Road and State Road, it's about 12 miles. The island's highest point is Peaked Hill in Chilmark at 311 feet, modest by mainland standards, but the constant climbs and descents accumulate.
Key stops along the route include Alley's General Store in West Tisbury (a good place to stop), the Chilmark General Store (celebrity-watching from its famous porch), the Quitsa Pond Lookout (the view over Menemsha and Nashaquitsa ponds), the Aquinnah Spring just past the town line (ice-cold water from a roadside pipe; refill your bottles here), and the Gay Head Cliffs observation deck and lighthouse at the terminus.
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Five Routes Every Visiting Cyclist Should Know
A sandy trail through the pine woods in Edgartown.
1. The Down-Island Triangle (16 Miles)
Links Edgartown, Oak Bluffs, and Vineyard Haven in a roughly 16-mile loop. Two of the three legs follow dedicated bike paths; the Oak Bluffs–Vineyard Haven leg requires road cycling. Mostly flat, taking 2–3 hours at a casual pace. Highlights include State Beach, Jaws Bridge, the Oak Bluffs Gingerbread Cottages, the the Flying Horses Carousel, and the Black Dog Tavern in Vineyard Haven.
2. The Katama Beach Loop (6 Miles)
The island's easiest ride, good for families. Pedal 3 flat miles south from Edgartown center to South Beach, swim in the Atlantic surf, then return via Herring Creek Road through farm fields. The entire route is on dedicated paths or very low-traffic roads.
3. The State Forest Explorer (10 Miles)
Paved paths through the heart of Manuel F. Correllus State Forest. The main 10-mile loop is flat, shaded, and car-free, ideal for riders who want distance without traffic stress. The forest also offers unpaved fire roads and singletrack for mountain biking, maintained by the Vineyard Off Road Bicycling Association (VORBA), which hosts group rides every Sunday morning at 9 AM.
4. The Up-Island Epic to Aquinnah (40 Miles Round-Trip)
Starting from Vineyard Haven, follow State Road to West Tisbury, then take South Road through Chilmark (the best 5 miles on the island), continue on State Road to the Aquinnah town line, and finish on Moshup Trail with its long descent to the Gay Head Cliffs. One-way distance is roughly 20 miles; a round trip via a different return road totals approximately 40 miles. If you want the whole thing, a full island perimeter loop runs 60–68 miles. It is hard: significant hills, narrow roads with traffic, and no shade for long stretches.
Know your bail-out options: Vineyard Transit Authority (VTA) buses carry 2–3 bikes on front-mounted racks, first-come first-served, and the service has been fare-free through a Massachusetts Fair Share Amendment grant (fare-free again this season per our August check; funding is renewed year to year). The Menemsha Bike Ferry, a 25-foot pontoon boat operated by the Taylor family, crosses Menemsha Channel between Chilmark and Aquinnah for about $5 per crossing, saving roughly 7 miles of hilly riding around Menemsha Pond (daily in summer, weekends in spring and fall).
5. Chappaquiddick Island
Take the tiny Chappy Ferry from Edgartown harbor and ride to Mytoi Japanese Garden (about 2.5 miles from the ferry landing), Three Ponds Reservation, or further out toward Cape Poge. Roads are rough. A hybrid or mountain bike is recommended. Total on-island biking covers roughly 10–12 miles.
Where to Rent Bikes Across the Island
Several of the big shops (All Star, R.W. Cutler, Rent Bikes MV) offer free island-wide delivery to hotels, vacation rentals, and ferry terminals; ask when you book, since not every shop delivers.
Oak Bluffs
- All Star MV Bike Rentals (5 Oak Bluffs Ave, one block from the SSA ferry terminal). Over 30 years in business. Comfort/cruiser bikes $35/day, Trek FX Sport hybrids $45/day, e-bikes $85–$90/day. Weekly: comfort bike $140/week.
- Martha's Vineyard Bike Rentals / Rent Bikes MV (15 Circuit Ave Extension). E-bike specialist with a modern fleet and free island-wide delivery.
- Sun 'n' Fun Rentals (28 Lake Ave). Comfort bikes from about $40/day, e-bikes from $96/day.
- Island Hoppers Bikes and Mopeds (Circuit Ave Extension, mvmopeds.com): bikes plus the island's moped fleet, a minute from the ferry.
Island Hoppers with the fleet out front and a spare bike on the roof, next door to Big Dipper.
Note: Anderson's Bike Rentals, which rented bikes in Oak Bluffs for 52 years, has permanently closed.
Vineyard Haven
- Martha's Bike (4 Lagoon Pond Road). Walking distance from the SSA ferry terminal, renting bikes since 1989. Hybrids, mountain bikes, cruisers, kids' bikes, trailers, and e-bikes with free delivery.
- Cycle Works (351 State Road). Primarily a full-service bike shop with rentals secondary. Great for repairs.
Edgartown
- R.W. Cutler Bike Shop (1 Main Street). Operating since 1947, the oldest bike rental on the island. Mountain/hybrid bikes $35/day, road bikes $60/day, Class 1 e-bikes $80/day. Kids' bikes $25/day. Substantial multi-day discounts.
- Wheel Happy (8 South Water Street). In its 33rd year, voted Best Bicycle Shop on Martha's Vineyard eleven of the last sixteen years.
- Edgartown Bicycles (212 Upper Main Street). Premium shop carrying Trek, Specialized, and Pinarello brands.
Across all shops, helmets, locks, and trail maps are universally included with rentals. Advance reservations are strongly recommended during July and August, especially for e-bikes.
E-Bikes Changed Island Cycling
Exploring Martha's Vineyard by bicycle.
Routes that once demanded serious fitness, particularly the 20-mile ride to Aquinnah, are now accessible to casual riders, older visitors, and families. Daily rental rates typically range from $70 to $96.
Massachusetts law recognizes Class 1 e-bikes (pedal-assist only, motor cuts out at 20 mph) and Class 2 e-bikes (throttle-equipped, motor cuts out at 20 mph). Both classes are legally treated as bicycles: no license, registration, or insurance required. Both Class 1 and Class 2 e-bikes are allowed on paved bike paths throughout Massachusetts. No Martha's Vineyard town has enacted a restriction as of 2026.
On natural-surface trails, including unpaved paths within the Correllus State Forest, e-bikes are generally prohibited unless the land manager expressly permits them. Stick to the paved loops in the state forest with your e-bike.
The routes that benefit most from e-assist: the up-island roads to Aquinnah (eliminating the Chilmark hill challenge), the full island loop (making 60+ miles realistic), and even the Edgartown–Vineyard Haven path (the moderate hills disappear). The Vineyard Sound headwind stops mattering with motor assist.
Getting Your Bike to the Island
Bringing your own bike on the ferry is straightforward and affordable:
| Ferry Service | Route | Bike Fee (Each Way) |
|---|---|---|
| Steamship Authority | Woods Hole to MV | $5.25 |
| Island Queen | Falmouth to Oak Bluffs | $4.00 |
| Hy-Line Cruises | Hyannis to Oak Bluffs | $8.50 |
| Seastreak | New Bedford to MV | $9.00 |
No reservation is needed for bikes; just arrive 30 minutes before sailing. E-bikes need more care: Seastreak charges them $18 each way, and the Steamship Authority proposed new e-bike rules in August 2026 (commercially manufactured bikes only, and crews can refuse them), so check your line's current policy before sailing.
Safety and Practical Tips
Massachusetts requires helmets for all riders age 16 and younger on public roads and bike paths. A 2025 MV Commission traffic study found that Martha's Vineyard has a higher crash rate than the state average, with Five Corners in Vineyard Haven rated the island's most dangerous intersection.
Roads requiring extra caution:
- State Road in Vineyard Haven (site of a fatal cyclist accident)
- Beach Road between Vineyard Haven and Oak Bluffs (heavy traffic, sand accumulation)
- All up-island roads during peak summer hours
For families cycling with children: the down-island paths are ideal. The flat Katama Road path, the Beach Road path to Oak Bluffs, and the small State Forest loop are all suitable for kids who can ride 3–5 miles. Multiple shops rent child-size bikes, Burley trailers, baby seats, and tag-alongs. Avoid up-island roads with children. If the family wants to visit Menemsha or the Aquinnah Cliffs, the VTA bus is the right call.
The Martha's Vineyard Commission publishes an official bike map available as a free PDF at mvcommission.org, covering all eight named routes with descriptions and safety tips. The TrailsMV app (free, iOS and Android) maps over 220 miles of public trails and works offline with GPS, crucial given the island's spotty cell coverage.
The best months for cycling are May, June, September, and October. The annual Bike MS: Ride the Vineyard charity event, running each spring since the late 1980s, offers 25, 45, and 60-mile route options. Peak summer (July–August) brings the most congested roads and hardest-to-book rentals. If you must ride in peak summer, start before 9 AM when the roads are quiet and the light is still low over the water.
Single-use plastic water bottles are banned on the island, so bring a reusable bottle you can refill. The Aquinnah Spring on the road out to the cliffs has ice-cold water flowing from a roadside pipe.
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.
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Island tip of the dayTimingNo. 82 of 86New tip at midnight, island time
Edgartown Lighthouse is climbable daily in summer, roughly 10 AM–4 PM, with the shortest waits right at opening. Small admission ($5 at last check). Staff may close the door a few minutes early.
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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.
