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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 three of Martha's Vineyard's most scenic 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 parking area at the cliffs is free in winter (summer requires paid parking), 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.
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Island Tip of the Day · Timing
The Chappy Ferry has short waits early morning and after 5 PM. Midday summer weekdays: 20–30 min wait. Peak weekends: over an hour. Only 3 cars fit per crossing.
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.
