Biking the Up-Island Routes
Can you bike the Up-Island Routes?You can, but there are no designated bike paths up-Island. The roads through West Tisbury, Chilmark, and Aquinnah are narrow, winding, and hilly, so these rides suit experienced cyclists.
- Distance
- Varies by loop
- Estimated time
- Pending verification
- Difficulty
- Challenging
- Elevation
- Pending verification
- Route type
- Loop
- Surface
- Paved roads
- Path or road
- Shared road, no bike path
- Family suitability
- Not yet assessed
- Status
- Not yet field-checked
- Last reviewed
- October 2026
Times assume a relaxed pace of 8 to 10 mph. Family suitability stays "not yet assessed" until we have checked crossings and traffic in person.
This route is highlighted. Thin green lines are the island's other bike paths, and dashed orange lines are roads you share with cars.
Route overview
- Common roads include State Road, Middle Road, South Road, North Road, and Lighthouse Road. Plan your loop on the map before you set out.
What you'll see
- Farmland, stone walls, and ocean views
- Menemsha harbor and the Aquinnah cliffs
Safety notes
- You share narrow roads with cars, often with little or no shoulder.
- Ride early in the morning to avoid traffic.
- A seasonal bike ferry crosses Menemsha Pond between Chilmark and Aquinnah.
Something wrong or out of date? Report a correction.