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A winter drive through West Tisbury, Chilmark and Aquinnah on Martha's Vineyard, filmed after a January snow: the 12-mile route by Alley's and Beetlebung Corner to the clay cliffs, winter driving notes, what is open up-island between November and April, the cliffs rules, and the off-season bus to Aquinnah.
The clay cliffs with snow in the folds, the end of the winter drive.
This is a winter drive through West Tisbury, Chilmark and Aquinnah, filmed in January 2024 after a light snow under clear skies: quiet roads, white fields, hardly another car out, and the clay cliffs at the end with snow in their folds. In winter the cliffs are worth the drive on their own, and with the leaves down you see water from the road that summer hides. The video runs the whole route; below it is what you pass, how the roads drive in winter, what is actually open up-island between November and April, and how to do the trip without a car.
Filmed January 2024The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked November 2026.
A wood road after a snowfall, the oaks holding their brown leaves and one set of tracks ahead.
A plowed back road after the February 2026 snow, the oaks still holding their copper leaves.
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The drive follows South Road and State Road through the three up-island towns. It starts in West Tisbury at Alley’s General Store, trading since 1858 and the island’s oldest general store, which opens early every morning of the year (the store asks you to call 508-693-0088 for current hours), with the farmland West Tisbury is known for on both sides of the road. Into Chilmark the road climbs into wooded hills between stone walls that farmers built clearing their fields; the Chilmark General Store at Beetlebung Corner, the crossroads at the town’s center, is seasonal and closed for the year after October 9, 2026, while down in Menemsha the Menemsha Store stays open through the off-season. The last stretch into Aquinnah ends at the cliffs, which look deeper red and orange against a winter sky, with the Gay Head Light above them catching the last sun well before 4:30 in December. The short-term spaces at the cliffs overlook are free in winter (the 90-minute limit is enforced in season), the paid Moshup Beach lot sits unattended, and you will likely have the viewing platform to yourself.
The plaque at Alley's: a general store since 1858, now looked after by the Vineyard Preservation Trust, and open every month of the year.
A farm field behind a stone wall and a split-rail fence. Slocum farmed in West Tisbury and, by the Gazette’s account, farmed badly.
The Chilmark General Store at Beetlebung Corner, the up-island stop for a sandwich, a newspaper and the milk you forgot.
The road up to Aquinnah Circle, the lighthouse ahead and the parking lot on the right.
Gay Head Light at sunset on a December evening, a short way up from the cliffs.
The sun going down over the sea from the Aquinnah cliffs in December.
Winter roads on the Vineyard are generally well kept, but South Road is narrow, with sharp curves and no shoulder to speak of, and deer are out, especially at dusk, so it is a road to take slowly. Most gas stations that stay open all year are in Vineyard Haven and Edgartown, with little up-island, so fill up before you head out. The real winter risk is the nor’easter: when a big one lands, as one did in February 2026, up-island can see a foot or two of snow, damaging gusts, multi-day power outages and suspended ferries, so check the forecast and the Steamship before a winter day trip. A rental car is the practical answer for a winter week that includes Menemsha or Aquinnah, and worth booking ahead, because the agencies run a small winter fleet.
A road curving through the scrub in Aquinnah at dusk, a guard rail and no traffic. The Vineyard has no traffic light and no highway; the Hamptons have Route 27 on a Friday in July.
Conroy Apothecary, the up-island pharmacy, open through the winter with wreaths up on the porch.
Not much, and that is the appeal, but enough. In West Tisbury, Alley’s, Cronig’s Up-Island (469 State Road, the only supermarket west of the airport) and Conroy Apothecary keep the town supplied all year; State Road Restaurant serves dinner Thursday to Saturday in winter, pausing for about five weeks in late winter; 7a Foods posts daily hours on its website and is worth a call in deep winter. In Chilmark the self-serve farm store at North Tabor Farm is open year-round from dawn to dusk with produce, meats and winter soup, and the Menemsha Fish Market opens on weekends. Orange Peel Bakery Closed Closed for good in September 2026 in Aquinnah, the old honor-system stop, closed for good in September 2026, and the Wampanoag-owned shops at Aquinnah Circle are seasonal, though the trails, the beaches and the overlook stay open. All six town libraries run year-round; Aquinnah’s, in the one-room Red Schoolhouse at 1 Church Street, opens Tuesday and Thursday from noon to 6 PM and Saturday from 11 AM to 4 PM. Our year-round guide keeps the full list.
The chalkboard menu at 7a Foods in West Tisbury this October: breakfast from 7 to 11, a fall veggie melt on the lunch side, and two soups, a veggie chili and a curried lentil.
Gay Head Light on a December evening, with the lawn and a ring of low stones in front of it.
The clay cliffs are Wampanoag tribal land: climbing the face or taking any clay is prohibited, and the Tribe enforces it. From the overlook the South Head Loop of the Aquinnah Headlands Preserve drops to Moshup Beach beneath the cliffs, free in winter, and seals are reliably seen off the cliffs and at Lobsterville Beach on calm days around mid to low tide. The Gay Head Light opens for climbing from Memorial Day weekend, so in winter it is a view from the lawn and the footpath beside the road, which is where the December photographs on this page were taken. For the full story of the cliffs and the lighthouse, see our Aquinnah guide. The short clip below is a winter sunset in Aquinnah, with the lighthouse and the road sign pointing to the cliffs.
Filmed October 2026
The Gay Head Lighthouse catching the last sun on a December afternoon in 2025.
The tribe’s sign at the cliffs in Aquinnah, with both names on it.
Gay Head Light under a pink sky on December 20, 2025, from the footpath beside the road.
On the off-season VTA timetable (October 4 to April 15) the Aquinnah bus is one bus the whole way: Route 5 leaves Vineyard Haven at 7:07 AM and every two hours until 5:07 PM, and the last bus back from the cliffs leaves at 6:05 PM. It is fare-free through June 30, 2027. That makes a winter cliffs trip possible without a car, as long as you watch the clock; the VTA schedule page has the current times.
Yes, if you like empty roads and big views: the cliffs show their color against the snow, the ocean shows through the bare trees, and the overlook is free and empty.
State Road Restaurant in West Tisbury on Thursday to Saturday nights, 7a Foods by day, the Menemsha Fish Market on weekends and the North Tabor Farm store for picnic food. Everything else waits for spring.
No. The tower opens for climbing from Memorial Day weekend; in winter the view is from the lawn.
How we checked: the video and the photographs are ours, from January 2024 and the winters since. Opening hours and closures come from the businesses’ own notices as recorded in our year-round guide and winter guides, the bus times from the VTA’s off-season timetable, the cliffs rules from the Wampanoag Tribe’s posted signs, and the lighthouse season from the Martha’s Vineyard Museum. Last checked November 1, 2026.
Exploring the town? Start with our complete Aquinnah guide for food, beaches and parking.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one price range. From MV Vacation, written on Martha’s Vineyard · https://mvvacation.com/blog/a-winter-drive-from-west-tisbury-to-aquinnah-cliffs · printed . Hours, prices and schedules change; the page online is the current one.
Where to go birdwatching on Martha's Vineyard: the top eBird hotspots (Aquinnah Cliffs, Felix Neck, Wasque, Long Point), the seasons from ospreys to sea ducks, the free Martha's Vineyard Bird Club walks with 2026 dates, the Christmas Bird Count and where this week's sightings get posted.
Stargazing on Martha's Vineyard: how dark the island really is (the town lighting bylaws, no official rating), the best moonless nights and Milky Way windows, meteor shower dates 2026–2027 with moon phases, the Chilmark library telescope loan, Felix Neck's moonrise paddle, and what works for night photography with a phone or camera.
The island's farmers markets, checked October 2026: the West Tisbury Farmers Market at the Agricultural Hall (Saturdays to October 31, 9 AM to noon), the Harvest Festival on October 24, the indoor winter market, Edgartown's summer Tuesday market, and the farm stands that stay open all year.
Where to learn to sail on Martha's Vineyard, checked October 2026: Sail Martha's Vineyard's summer classes on Lagoon Pond, private lessons for adults, Sunfish rentals in Vineyard Haven and Menemsha, schooner and catboat sails, summer races you can watch or crew, and what the wind and currents are like.
All six town libraries on Martha's Vineyard, checked October 2026: hours and addresses, how visitors get a library card, free Wi-Fi, the concerts, art shows and programs, the Libraries of Things with beach chairs and stargazing kits, museum and beach parking passes, and a short history of each building.
Where to play pickleball on Martha's Vineyard in 2026: the town courts in Oak Bluffs (Niantic Park), Vineyard Haven (Lake Street, $20 an hour) and Edgartown, the indoor option at Airport Fitness, fees, how the summer queue works, and why up-island has no public courts.
Island tip of the day Timing No. 78 of 79 New tip at midnight, island time
Owen Park Beach in Vineyard Haven is almost never crowded: most visitors go straight from the ferry to bigger beaches. Calm, shallow, perfect for a last-morning swim.
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