Driving is the point here
Vermont has 251 towns, about 9,600 miles of highway and almost no public transit outside Burlington, which means the car is not a compromise — it is the way the state is designed to be seen. The roads follow rivers and thread mountain notches because that is where the land allowed them, and the result is that the drive between two places is frequently better than either.
Five routes matter most: Route 100 down the spine of the state, the Route 108 notch road at Smugglers' Notch, the toll road up Mount Equinox, the Granville Gulf pass, and Route 7A through the historic southwest. Each is short enough to do in a day, and each rewards going slowly.
Route 100: the whole spine
Route 100 runs 216 miles from the Massachusetts line to the Canadian border, and it is widely considered one of North America’s premier scenic drives. It never quite leaves the Green Mountains, connecting farming villages, ski towns, cider mills and roadside waterfalls in a single continuous ribbon.
Driven north to south from Stowe, the sequence is close to perfect: Stowe beneath Mount Mansfield, then Waterbury for Cold Hollow Cider Mill and the Ben & Jerry’s factory, then the Mad River Valley through Waitsfield and Warren, then Granville Gulf and its roadside Moss Glen Falls, then Rochester, Killington and Ludlow, and finally down through Weston and Jamaica to the Massachusetts line.
Do not try the whole thing in a day if you want to enjoy it. Three days with nights in Stowe or Waterbury, Waitsfield or Warren, and Ludlow or Weston turns it from a drive into a trip. Half the pleasure is stopping — general stores, honour-system farm stands and swimming holes are the actual content of the route.
Length — 216 miles end to end; 5 hours without stops, 3 days done properly.
Best stops north — Cold Hollow Cider Mill, the Warren Store, Warren Falls, Moss Glen Falls in Granville Gulf.
Best stops south — the Vermont Country Store in Weston, Jamaica State Park, the Weston Playhouse.
Season — peak foliage late September to mid-October; this is the most photographed road in Vermont and traffic reflects it.
Route 108: Smugglers' Notch
Ten miles of Route 108 between Stowe and Jeffersonville climb through Smugglers' Notch, and it is the most dramatic short drive in New England. Thousand-foot cliffs squeeze the road down to a single lane between boulders the size of houses that fell from the walls above.
The notch got its name from the trade that ran through it during Jefferson’s 1807 embargo, and later from Prohibition-era liquor moving south from Canada. Caves and clefts in the rock are still named for it.
Two hard practical facts. The road is closed to through traffic in winter, roughly November to April, and it is legally prohibited to trucks, buses and trailers year-round — the switchback at the top is too tight, and vehicles get wedged there every season. Drive it in daylight, slowly, with the windows down.
At the top, the notch parking area is also the trailhead for Sterling Pond and the Long Trail, and Bingham Falls is five minutes down the Stowe side.
Length — 10 miles, 30 minutes without stops.
Closed — to through traffic in winter; permanently prohibited to trucks, buses and trailers.
Stops — Sterling Pond trailhead, Bingham Falls, the Barnes Camp visitor centre.
Pair with — Route 15 west to Jeffersonville and Boyden Valley Winery, or south into Stowe for The Alchemist.
The Mount Equinox Skyline Drive
The highest paved toll road in Vermont climbs 5.2 miles from Route 7A in Manchester to the 3,848-foot summit of Mount Equinox, the tallest peak in the Taconic range. Hairpins and grades up to 12 per cent lead past overlooks onto the Battenkill valley and the Green Mountains.
At the top, the Saint Bruno Viewing Center explains the mountain’s unusual ownership: Carthusian monks of the Charterhouse of the Transfiguration, a silent contemplative order whose monastery occupies one flank, own most of the mountain and keep it in conservation. On a clear day the view takes in the Green Mountains, the Adirondacks, the Berkshires and the White Mountains.
The road runs roughly May to October. It is a toll road, so bring a card, and give yourself an hour and a half round trip with time at the summit.
Length — 5.2 miles each way, about 90 minutes round trip with the summit centre.
Season — roughly May to October; closed in winter.
Pair with — Hildene, the Robert Todd Lincoln estate, and Manchester Center’s outlets and Northshire Bookstore.
Granville Gulf and the Route 7A corridor
Granville Gulf is a six-mile state reservation on Route 100 south of Warren where the highway is hemmed between steep forested cliffs and the winding White River. It is one of the few places in Vermont where the road itself feels like a canyon. Moss Glen Falls drops 80 feet immediately beside the pavement — there is a small pull-off, and you are at the base in thirty seconds. The gorge stays cool through the hottest part of summer.
In the southwest, Route 7A is the slow, beautiful alternative to Route 7 between Bennington and Manchester. Marble sidewalks, white-clapboard inns, the Equinox, and turns west into Arlington and the West Arlington covered bridge. Add the ten-minute run north on Route 30 to Dorset for the marble quarry swimming hole and the 1816 Dorset Union Store.
Two more worth the detour: the Lake Willoughby road, Route 5A, running between thousand-foot cliffs on both sides of a glacial fjord in the Northeast Kingdom; and Route 108 north from Jeffersonville into the Missisquoi valley for covered bridges and near-empty roads.
Granville Gulf — 6 miles on Route 100; Moss Glen Falls is roadside with a small pull-off.
Route 7A — Bennington to Manchester, 30 minutes slowly; add Arlington and Dorset.
Route 5A — Lake Willoughby’s east shore, cliffs on both sides, in the Northeast Kingdom.
Season — all four are best from late May through October; Route 5A is spectacular in early October.
Practical driving notes
A few things surprise first-time visitors. Vermont has thousands of miles of dirt town roads, and your navigation app will route you onto them without warning — they are usually fine in summer and genuinely impassable during April and May mud season. Do not attempt a Class-4 road in a rental car.
Fuel and food thin out fast outside the corridors. In the Northeast Kingdom and along the higher sections of Route 100, fill up when you see a station rather than when you need one, and expect general stores to close early. Cell coverage drops out entirely in the valleys and notches, so download offline maps.
Wildlife is a real hazard at dawn and dusk, particularly moose in the Northeast Kingdom and deer statewide. Slow down through wooded stretches in the first and last hour of light.
And in winter, snow tyres are not optional if you plan to drive mountain roads. Several of the best drives — the Equinox toll road, the Smugglers' Notch through-route — simply close.
Compare live prices for a night at each end of the drive in the search below, with free cancellation on most rooms.
Good to know
What is the best scenic drive in Vermont?+
Route 100, which runs 216 miles down the spine of the state past ski towns, cider mills, covered bridges and roadside waterfalls. Five hours without stops, but three days with nights in Stowe, Waitsfield and Ludlow makes it a proper trip.
Can you drive through Smugglers' Notch?+
In season, yes — Route 108 climbs ten miles between Stowe and Jeffersonville through single-lane gaps between fallen boulders. It closes to through traffic roughly November to April, and trucks, buses and trailers are prohibited year-round because the top switchback is too tight.
Is the Mount Equinox Skyline Drive worth it?+
Yes. It is 5.2 miles of paved toll road from Route 7A to the 3,848-foot summit, with grades up to 12 per cent, a summit viewing centre explaining the Carthusian monastery that owns the mountain, and views over four states. Open roughly May to October.
Where is Moss Glen Falls on Route 100?+
In the Granville Gulf State Reservation, on Route 100 south of Warren — an 80-foot fall immediately beside the road with a small pull-off, about thirty seconds' walk from the car.
Do I need to worry about Vermont’s dirt roads?+
Yes. Navigation apps route onto unpaved town roads without warning. They are generally fine in summer but impassable during April and May mud season, and Class-4 roads should never be attempted in a rental. Download offline maps — cell coverage fails in the valleys.