Winter Itinerary · Vermont · 5 Days

Vermont Winter Road Trip: Route 100, Stowe and the Ski Towns in 5 Days

Woodstock to Burlington on Vermont's spine road, built for skiers and non-skiers alike, with the winter closures that trip up first-timers.

10 min read~150 miles · 5 daysUpdated September 2026

In winter, Stowe and Smugglers' Notch Resort sit about 5 miles apart as the crow flies, yet roughly an hour apart by car. Route 108 through the Notch closes to vehicles for the season, and the detour loops all the way around the mountain. That is the kind of detail a Vermont winter road trip lives or dies on, and it is exactly what this guide is for.

The route runs Woodstock → Killington → Mad River Valley → Waterbury → Stowe → Burlington, about 150 miles over 5 days including side trips, most of it on Route 100, the plowed two-lane road that ties Vermont's ski towns together. It works whether you want five days on the slopes or none at all: every stop has a strong non-ski plan, from gondola rides and snowshoe trails to cider mills and covered bridges.

When to Go and What Conditions to Expect

Vermont's winter road-trip season runs December through March. December can be thin on natural snow. January is the coldest month. February usually brings the deepest, most reliable snowpack, which makes it the best single month for a ski-focused trip.

The two weekends to plan around are Martin Luther King Jr. Day in mid-January and Presidents' Day in mid-February. They bring the biggest crowds and the highest lodging rates of the season. Shift the same itinerary to a Sunday-to-Thursday window and you will usually pay noticeably less and ride shorter lift lines.

Late March is spring skiing: softer snow, longer days, and the start of maple sugaring season, which typically runs from late February into April. What most guides miss is what comes next. Mud season, roughly April to mid-May, turns Vermont's dirt roads into ruts and closes many inns and restaurants. Don't book it.

Boston → Stowe

About 3.5 hours in clear conditions

New York City → Stowe

About 6 hours in clear conditions

The 5-Day Route 100 Itinerary

Distances below are approximate driving miles between bases. In winter, budget extra time on every leg: a 45-mile Route 100 stretch that takes an hour in July can take 90 minutes behind a plow.

Day 1: Woodstock

Arrival day

Start in the village that looks like a holiday card. Walk the oval village green, cross the Middle Covered Bridge over the Ottauquechee River, and spend the afternoon at Billings Farm & Museum (winter hours are limited, so check the schedule before you go). Dinner in town, early night.

Village greenMiddle Covered BridgeBillings Farm & Museum

Day 2: Woodstock → Killington

~20 mi

A short hop west on US-4 brings you to Killington, the “Beast of the East.” Skiers get the biggest trail network in Vermont. Non-skiers can snowshoe, or ride the K-1 Express Gondola to the 4,241-foot summit and the Peak Lodge on a scenic-ride ticket, no ski gear required.

Killington ResortK-1 Gondola scenic rideSnowshoe trails

Day 3: Killington → Mad River Valley

~45 mi

This is the Route 100 day: a plowed two-lane road north through Pittsfield, Rochester and Granville Gulf into Warren and Waitsfield. Ski Sugarbush, or make the pilgrimage to Mad River Glen, the co-op-owned, skiers-only mountain with its famous single chair.

Route 100 northGranville GulfSugarbushMad River Glen

Day 4: Mad River Valley → Waterbury → Stowe

~20 mi + ~10 mi

Follow Route 100 to Waterbury for Ben & Jerry’s (check current tour availability) and Cold Hollow Cider Mill for cider donuts. Then continue about 10 miles up Route 100 to Stowe and check in for two nights if you can.

Ben & Jerry's, WaterburyCold Hollow Cider MillStowe village

Day 5: Stowe → Burlington

~35 mi

Spend the morning cross-country skiing or snowshoeing at Trapp Family Lodge, or walk the roughly 5-mile Stowe Recreation Path. In the afternoon, drive to Burlington for Church Street and a sunset over frozen Lake Champlain.

Trapp Family LodgeStowe Recreation PathChurch Street, Burlington

Woodstock is the easiest place to start: it is about 20 minutes off I-89 and sets a slower pace before the ski towns.

Find hotels in Woodstock, Vermont

Vermont Winter Driving: Closed Gaps and Notches

Seasonal closures to check before you drive

Route 108, Smugglers' Notch: closed to vehicles in winter, typically from around mid-November until spring. Stowe to the Jeffersonville side means a long detour.
Lincoln Gap (Lincoln to Warren): closed in winter.
Appalachian Gap (Route 17): stays open, but it is steep, twisting and exposed to wind and drifting snow.

Confirm current status with VTrans and New England 511 on the morning you drive.

Vermont has no California-style chain controls, so nobody will stop you at the bottom of a pass. That puts the judgment on you. Snow tires make a real difference on Vermont's hills and many locals run them all winter, but most rental cars arrive on all-season tires. Leave a long following distance, keep mountain roads to daylight hours, and treat any gap road as optional in a storm.

Pack a proper winter car kit too: scraper, blanket, phone charger and snacks. Our road trip car kit guide has the full checklist.

Routing around closed notches and gaps? TripsGalaxy.com builds your Vermont winter drive on open roads with scenic stops and opens it in Google Maps.

Plan it free

Best Winter Things to Do If You Don't Ski

Plenty of Vermont winter trips include someone who never clicks into a binding. These are the best things to do in Vermont in winter off the slopes, ranked.

1
Horse-drawn sleigh rides
Farms and inns around Stowe and Woodstock run sleigh rides when there is enough snow on the ground. Book a late-afternoon slot so you finish near dusk.
2
Snowshoeing at Trapp Family Lodge
Trapp’s outdoor center in Stowe has groomed cross-country trails and marked snowshoe routes, with rentals on site. It is the single best non-ski day on this route.
3
Sugarhouse visits in sugaring season
Sap usually starts running in late February or March, depending on the thaw-freeze cycle. Call ahead: many sugarhouses boil only on certain days, and some open to visitors only on weekends.
4
Covered-bridge photo stops
Woodstock’s Middle Covered Bridge is right in the village, and Stowe has its own red bridge on a back road. Fresh snow and flat morning light make the best photos.
5
Cider mills and craft breweries
Cold Hollow Cider Mill on Route 100 is the classic stop. Waterbury and Stowe also have enough craft breweries to fill an afternoon, so pick a designated driver before dark.
6
Burlington’s Church Street
A pedestrian mall with restaurants, shops and bars that stays lively all winter, which is the easiest evening on the whole trip.

Skip the base-lodge lunch.Resort cafeterias charge resort prices for reheated chili. Vermont's general stores and diners along Route 100 make better sandwiches and soups for a fraction of the cost. Skiers can drive down at lunch; non-skiers should plan their day around them.

Killington vs Stowe vs Sugarbush

All three sit on or just off Route 100, so you can ski more than one without changing your plan. The real question is which one to build your stay around.

Resort	Vibe	Best for	Nearest town
Killington	Big, busy, party on the Access Road	Mileage-hungry skiers, groups, long seasons	Killington / Woodstock
Stowe	Polished, classic, upscale village	Mixed groups of skiers and non-skiers	Stowe
Sugarbush	Low-key, local, two mountains	Advanced skiers who hate lift lines	Warren / Waitsfield

Killington is the biggest operation in Vermont and usually one of the first in the East to open. Stowe, on Mount Mansfield, Vermont's highest peak, pairs serious terrain with the best village for non-skiers. Sugarbush is the quieter choice, with two linked mountain areas and fewer crowds.

Pass products change year to year. Recently, Stowe has been on the Epic Pass while Killington and Sugarbush have been on Ikon, with Killington on limited-day tiers. Check each resort's site for the current season before you buy.

The purist's pick: Mad River Glen

Owned by a skier cooperative, snowboard-free, and famous for its single chair and the motto "Ski It If You Can." Snowmaking is limited, so it shines after a natural dump and suffers in a dry spell. It has historically accepted the Indy Pass; confirm for your season.

Find hotels in Stowe

Where to Stay: Base Towns Compared

Woodstock

Classic inns and a walkable village. The best base for non-skiers, about 20 miles from Killington.

Killington Access Road

Condos and lodges minutes from the lifts, plus the livest après scene in Vermont.

Waitsfield / Warren

Quiet valley, farmhouse B&Bs, and a short drive to both Sugarbush and Mad River Glen.

Stowe

The best all-rounder: skiing, snowshoeing, restaurants and shopping in one place.

Burlington

A small city with hotels, restaurants and often the best rates midweek.

Two bases beat five one-night stays. In winter, every check-out means scraping the car, repacking wet gear and losing a morning. Split the trip into two or three nights around Killington or Woodstock and two nights in Stowe, and treat the Mad River Valley and Waterbury as day stops.

Whichever base you choose, you will spend a lot of time walking between the car, the inn and the village on slush.

Pro Tip

Village sidewalks and trailheads stay slushy for days. Waterproof boots beat fashion boots.

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The best Vermont winter trip is not five towns in five nights. It is two good bases and one scenic road between them, with Route 100 doing the work and the closed notches left for summer. Pick your bases, check VTrans the morning you drive, and plan your Route 100 drive around daylight.

Common Questions

Is Vermont good for a winter road trip?+

Yes. Route 100 links Vermont's ski towns, covered bridges and villages, and it's plowed as a main route. Plan around seasonal closures like Route 108 through Smugglers' Notch and Lincoln Gap, and drive mountain roads in daylight.

Is Route 108 through Smugglers' Notch open in winter?+

No. Route 108 through Smugglers' Notch closes to vehicles in winter, so driving between Stowe and the Jeffersonville side means a much longer detour. Check VTrans for current status.

What can you do in Vermont in winter if you don't ski?+

Snowshoeing, sleigh rides, cross-country skiing at Trapp Family Lodge, cider mills and breweries, covered-bridge stops, and Burlington's Church Street are all good non-ski options. Sugarhouses become a draw in late-winter sugaring season.

When is the best time for a Vermont ski trip?+

February usually offers the most reliable snowpack. Avoid MLK and Presidents' Day weekends if you want lower prices and smaller crowds, and target midweek stays.

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