A Winter Drive from West Tisbury to Aquinnah Cliffs

This is a winter drive through Chilmark, Aquinnah, and West Tisbury, filmed in January 2024 after a light snow, under clear skies. We shot the whole route from the car (quiet roads, white fields, hardly another vehicle out), ending at the Aquinnah Cliffs. In winter the cliffs are worth the drive on their own, with snow on the clay and the sun low over the water. The video runs all the way to that last stop, and there are more drives and tours from around the island on our channel.

The route from West Tisbury to Aquinnah

This winter drive covers roughly 12 miles along South Road and State Road, passing through the three up-island towns. Starting in West Tisbury, you'll pass Alley's General Store, open since 1858 and the island's oldest retail business, and the farmland West Tisbury is known for.

As you enter Chilmark, the road shifts to wooded hills and stone walls built centuries ago by farmers clearing their fields. In winter, with the leaves gone, you can see ocean views that are hidden during summer months. The Chilmark General Store is seasonal and closed for 2026 after October 9; in Menemsha, the new Menemsha Store stays open through the off-season.

The final stretch into Aquinnah ends at the clay cliffs, which look deeper red and orange against a winter sky. The short-term spaces by the cliffs overlook are free (the 90-minute limit is enforced in season), the paid Moshup Beach lot sits unattended in winter, and you'll likely have the viewing platform entirely to yourself.

Driving the island in winter

Winter roads on the Vineyard are generally well kept, but South Road is narrow, with sharp curves, and deer are out, especially at dusk, so it's a road to take slowly. Most gas stations stay open year-round in Vineyard Haven and Edgartown, and options up-island are limited, so it makes sense to fill up before you head out.

Filmed January 2024The 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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