Oak Bluffs to Menemsha Bike Route

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What is Oak Bluffs to Menemsha Bike Route like?

A scenic ~17-mile bike ride from Oak Bluffs across Martha's Vineyard to Menemsha harbor. Passes farm fields, conservation land, and coastal views of Sengekontacket Pond. Mix of paved paths and quiet roads. Ends at Menemsha fishing village on Vineyard Sound.

Plan your walk

Oak Bluffs to Menemsha Bike Route

Directions to the trailhead

When should you go?

Best time to go

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Weather and sun times from Open-Meteo for the nearest part of the Cape.

What’s the trail like?

Length: 17 mi
Difficulty: Moderate
Surface: Paved
Dogs: Allowed (leashed)
Kids: Not noted
Accessible: Not noted
Views: Not noted
Good for: Biking

What should you know before you go?

Dogs

Allowed (leashed)

Where is the trailhead?

Oak Bluffs to Menemsha Bike Route, Oak Bluffs, MA

Get directions Open in Google Maps

Where else can you walk in Oak Bluffs?

Easy · 4 mi
Edgartown to Oak Bluffs Bike Path
Paved
A scenic 4-mile paved bike path connecting Edgartown and Oak Bluffs, passing through salt marshes, open meadows, and coastal views of Vineyard Sound. One of the most popular rides on Martha's Vineyard — flat, family-friendly, and completely car-free. Bike rentals available at multiple shops in both towns.
CCC Visited · Verified 2026-09-29
See details
Easy
Sheriff's Meadow Sanctuary
Mixed · Sheriff's Meadow Foundation
The founding Sheriff's Meadow preserve — a short shaded boardwalk loop around a pond known for birds. (Local note: A leisurely shaded stroll with boardwalk and abundant birdlife (sits at the OB/Edgartown line))
Listed & Verified · Verified 2026-06-22
See details
Easy
Trade Wind Fields & Farm Pond Loop
Mixed · Martha's Vineyard Land Bank
The signature ~3.1-mile loop joining Trade Wind Fields and Farm Pond preserves near Circuit Ave. (Local note: 135+ AllTrails reviews; consistently the top-rated Oak Bluffs trail)
Listed & Verified · Verified 2026-06-22
See details
Easy · 2 mi
Trade Wind Fields & Lagoon Pond Trail
Mixed · Martha's Vineyard Land Bank
An open meadow and shoreline trail looping around Lagoon Pond at the Oak Bluffs Land Bank parcel. Mowed grass paths through wildflower fields transition to woodland edges and pond-side views. A serene, family-friendly walk accessible from central Oak Bluffs.
Listed & Verified · Verified 2026-06-25
See details

Every Oak Bluffs trail Trails across the Cape

Directions

Where else can you walk in Oak Bluffs?

Easy · 4 mi

Edgartown to Oak Bluffs Bike Path

Paved

A scenic 4-mile paved bike path connecting Edgartown and Oak Bluffs, passing through salt marshes, open meadows, and coastal views of Vineyard Sound. One of the most popular rides on Martha's Vineyard — flat, family-friendly, and completely car-free. Bike rentals available at multiple shops in both towns.

CCC Visited · Verified 2026-09-29

See details

Easy

Sheriff's Meadow Sanctuary

Mixed · Sheriff's Meadow Foundation

The founding Sheriff's Meadow preserve — a short shaded boardwalk loop around a pond known for birds. (Local note: A leisurely shaded stroll with boardwalk and abundant birdlife (sits at the OB/Edgartown line))

Listed & Verified · Verified 2026-06-22

See details

Easy

Trade Wind Fields & Farm Pond Loop

Mixed · Martha's Vineyard Land Bank

The signature ~3.1-mile loop joining Trade Wind Fields and Farm Pond preserves near Circuit Ave. (Local note: 135+ AllTrails reviews; consistently the top-rated Oak Bluffs trail)

Listed & Verified · Verified 2026-06-22

See details

Easy · 2 mi

Trade Wind Fields & Lagoon Pond Trail

Mixed · Martha's Vineyard Land Bank

An open meadow and shoreline trail looping around Lagoon Pond at the Oak Bluffs Land Bank parcel. Mowed grass paths through wildflower fields transition to woodland edges and pond-side views. A serene, family-friendly walk accessible from central Oak Bluffs.

Listed & Verified · Verified 2026-06-25

See details