A Winter Drive from West Tisbury to Aquinnah Cliffs

A Winter Drive from West Tisbury to Aquinnah Cliffs

A scenic winter drive through West Tisbury, Chilmark, and Aquinnah on Martha's Vineyard. Rolling farmland, stone walls, and dramatic cliffs in snow.

Join us on a tranquil winter drive through the picturesque towns of Martha’s Vineyard. Experience the serene beauty of Chilmark, Aquinnah, and West Tisbury in January 2024, adorned with a delicate dusting of snow, set against a backdrop of sunny, crisp skies. We glide through charming streets, capturing the essence of the Vineyard’s winter landscape, leading up to the breathtaking view of the Aquinnah Cliffs. Witness the contrast of the stark winter beauty against the vibrant sunny horizon. Don’t miss the serene moments of our final stop at the famous cliffs, a sight to behold in the off-season chill. Subscribe for more peaceful drives and scenic tours!

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.

 

Continue Exploring Martha's Vineyard

🍽️ Island Tip of the Day — Food

Net Result (79 Beach Rd, Vineyard Haven) has some of the best lobster rolls on the island. Great for grabbing takeout sandwiches before your ferry departure.

Planning a trip to Martha's Vineyard?

Get insider tips, seasonal updates, and beach reports — straight to your inbox.

No spam. Unsubscribe anytime.

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.
MV Vacation

MV Vacation

Your insider guide to Martha's Vineyard — beaches, dining, events, and island living. We share local knowledge to help you plan the perfect Vineyard getaway.

Island prices, hours & details change often — please verify with businesses before you go. Full disclaimer

We use a few cookies to keep trip planning smooth — never to sell your data. Cookie policy