The Ultimate Vermont Route 100 Road Trip: A 5-Day Itinerary

Route 100 runs almost the full length of Vermont, about 200 miles through the Green Mountains, earning it the nickname “Vermont’s Main Street.” It strings together ski towns, covered bridges, waterfalls, farm stands, and more creemee stands than any one trip really needs, running south to north from the Massachusetts border almost to the Canadian line. A Vermont Route 100 road trip is the best way to explore this incredible state.

This itinerary breaks the drive into five days, running south to north, with a stretch through the Granville Gulf and White River Valley that most Route 100 guides skip entirely, plus two state parks most people never hear about.

Want to explore more amazing destinations in Vermont? I’ve got more ideas over on my Chasing ADVNTR website or check out my complete guide to exploring New England.

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Quick Trip Facts

• Distance: ~200 miles end to end
• Time needed: 3–7 days depending on pace; this itinerary is built for 5 days but you can easily adjust it and pick what is most interesting!
• Best time to go: Fall for foliage (also the busiest: book lodging early); summer for swimming holes and full access to the resorts
• A car is required: there’s no way to do this trip without one.

Day 1: Southern Vermont

Manchester (optional detour)

A short detour off Route 30 if you’re starting from NYC or Connecticut. Worth it for the outlet shops, Northshire Bookstore, and the Hildene estate.

Wilmington

Route 100 officially starts here. Walkable downtown with independent shops and galleries — good spot for coffee before heading north. If you’re visiting between May and October, the Wilmington Antique & Flea Market runs weekends and has been going since 1983.

Mount Snow

🚗 ~15 min (8.5 mi) from Wilmington

The first big resort on the route. Ride the scenic chairlift for the views, or come for kayaking, SUP, golf, and mountain biking in the warmer months.

Jamaica State Park

🚗 ~35 min (20 mi) from Mount Snow

Set on a bend of the West River — good swimming and easy riverside trails along the old railroad bed. The longer hike to Hamilton Falls is worth the effort; at ~125 feet it’s one of the tallest [LINK: waterfalls in Vermont roundup]. Stay back from the potholes at the top — swimming there isn’t allowed and it’s genuinely dangerous. There’s a campground on-site if you want to stay over.

Overnight: Southern Vermont / Ludlow area

Day 2: Weston to Killington

Weston

The original Vermont Country Store is the draw — penny candy, local cheese, maple syrup, fudge. Give it real browsing time. Also worth a look: Weston Priory (Benedictine monastery known for its music) and the historic Weston Playhouse.

Ludlow

🚗 ~20 min (12 mi) from Weston

Small, walkable downtown built around Okemo Mountain Resort — good lunch stop. Buttermilk Falls, just outside town, has a popular swimming hole.

Plymouth

🚗 ~20 min (12 mi) from Ludlow

Home to the Calvin Coolidge State Historic Site — the preserved birthplace of the 30th president, with the whole village kept as it was. Stop at Plymouth Artisan Cheese, making cheese here since 1890.

Woodstock (detour)

One of Vermont’s prettiest towns, with a famous covered bridge. Pair it with nearby Quechee Gorge if you have the time.

Killington

🚗 ~20 min (12 mi) from Plymouth

“The Beast of the East” — one of the biggest ski resorts on the East Coast. In warmer months: ride the gondola for panoramic views, hike the boardwalk trail to Thundering Brook Falls [LINK: CA trail guide], or walk a stretch of the Appalachian Trail, which passes right through. Also a serious mountain biking destination with its own bike park.

Overnight: Killington

Day 3: Granville Gulf and the Mad River Valley

This is the stretch most Route 100 guides skip: the quiet middle of the drive between Killington and the Mad River Valley.

Rochester & Hancock

Small White River Valley villages worth slowing down for — this section of Route 100 sees a fraction of the traffic the resort towns do.

Granville Gulf State Reservation

🚗 ~50 min (35 mi) from Killington, covering this stretch

A dramatic, wooded mountain notch. Texas Falls is a short, signed detour just off the road and easy to miss if you’re not watching for it.

Moss Glen Falls (Granville)

Not to be confused with the other Moss Glen Falls near Stowe (Day 4). A short boardwalk leads straight from the roadside pull-off to a viewing area — one of the easiest waterfall stops on the whole route.

Warren

🚗 ~20 min (12 mi) from Moss Glen Falls (Granville)

Stop at the historic Warren Covered Bridge, then the Warren Store (running since 1839) for a deli lunch. If it’s warm, Warren Falls is a local-favorite swimming hole with rock slides just off the road.

Waitsfield

🚗 ~10 min (5 mi) from Warren

The heart of the Mad River Valley. The Historic Waitsfield Covered Bridge is one of the oldest still operating in Vermont. Grab a creemee from the Canteen Creemee Company before you settle in for the night.

Overnight: Mad River Valley / Waitsfield

Day 4: Waterbury to Stowe

Waterbury

🚗 ~30 min (20 mi) from Waitsfield

One of the best food stops on the whole trip. The Ben & Jerry’s Factory tour is $6 and worth it for the Flavor Graveyard alone. A few minutes further up Route 100, Cold Hollow Cider Mill has warm apple cider donuts and fresh cider. For coffee, Vermont Artisan Coffee & Tea has a giant coffee silo out front — hard to miss.

Little River State Park / Waterbury Reservoir

An easy add-on right off Route 100 for a paddle or swim before continuing north — most itineraries skip it entirely.

Stowe

🚗 ~20 min (12 mi) from Waterbury

One of the best small towns in Vermont . Walk Main Street, pop into Shaw’s General Store and Stowe Mercantile, and stop at the viewpoint for the Stowe Community Church against the mountains. Just outside town, visit the von Trapp Family Lodge (yes, that von Trapp family) and stop at the Bierhall for a lager. Between mid-June and mid-October, the SkyGondola runs up Mount Mansfield, Vermont’s highest peak.

Smugglers’ Notch (Route 108 detour)

One of the most scenic mountain drives in New England, and worth the backtrack even though it’s not technically on Route 100.

Moss Glen Falls (Stowe)

🚗 ~10 min (5 mi) from Stowe

The second Moss Glen Falls of the trip — reached by a short woodland hike, ending at a tall, pretty cascade.

Overnight: Stowe

Day 5: The Northeast Kingdom

Morristown & Hyde Park

🚗 ~15 min (8 mi) from Stowe

Less touristy than Stowe, which is the appeal, local shops, cafes, a couple of good breweries, and the Lamoille Valley Rail Trail if you want to walk or bike.

Elmore State Park

Home to Lake Elmore and the fire tower hike up Elmore Mountain — one of the best payoff views on the whole route, and almost never mentioned in Route 100 guides.

[IMAGE: Elmore State Park]

Eden & Lake Eden

🚗 ~20 min (13 mi) from Elmore

A quiet lake for a swim or a paddle, surrounded by mountains. The Green River Reservoir nearby is an even more remote option if you want to get off the beaten path.

Westfield

🚗 ~30 min (18 mi) from Eden

About as tucked-away as Vermont gets — mostly scenery and quiet, which is the point. Jay Peak is a short detour if you want one more mountain before the trip ends.

Newport

🚗 ~25 min (15 mi) from Westfield

The finish line, on the shores of Lake Memphremagog — a glacial lake stretching up into Canada. Walk the waterfront, wander the Gateway Center, and in warmer months take a boat cruise out onto the lake.

A Few Practical Tips

• A car is essential — budget the full 5 days if you want to actually stop and do things, not just drive through.
• Fall is the best time for the drive but also the busiest; book lodging well ahead if you’re going for foliage.
• Bring proper shoes for the waterfall hikes and swimwear for the swimming holes — several stops (Hamilton Falls, Warren Falls, Buttermilk Falls) are genuinely worth getting in the water for.
• Watch for creemee stands, farm stands, and cider mills along the way — they’re half the fun of this drive.

Is Route 100 Worth Driving?

Yes. It’s one of the most scenic drives in the country: mountains, waterfalls, covered bridges, small towns, and a steady supply of Vermont food along the way. Whether you drive one section or the whole thing over five days, it’s one of the best ways to see the state.