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. The cliffs in winter are worth the trip on their own: snow dusting the clay, low sun, and nobody else around. Stick with the video to the final stop, and subscribe if you want more drives and tours from around the island.

Route Highlights: 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, one of the oldest operating general stores in Massachusetts, and the rolling farmland that defines this agricultural community.

As you enter Chilmark, the landscape 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 worth a quick stop for hot coffee if it's open.

The final stretch into Aquinnah rewards you with the dramatic clay cliffs, which take on deeper red and orange tones against a winter sky. The overlook lot at the cliffs allows free 30-minute parking, the paid Moshup Beach lot sits unattended in winter, and you'll likely have the viewing platform entirely to yourself.

Tips for Winter Driving on Martha's Vineyard

Winter roads on the Vineyard are generally well-maintained, but South Road can be narrow with sharp curves. Drive slowly and watch for deer, especially at dusk. Most gas stations stay open year-round in Vineyard Haven and Edgartown, so fill up before heading up-island where options are limited.

Filmed January 2024The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked September 2026.