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Route 100 is the most famous road in Vermont and an absolute must do during the fall. If you are planning a trip to Vermont and want to discover all the best parts, this itinerary is for you!
Route 100 is often called “Vermont’s Main Street” because it takes you to most of the highlights. It runs almost the whole length of Vermont, about 200 miles through the Green Mountains.
Along the way you’ll pass villages, ski resorts, covered bridges, waterfalls, farm stands and plenty of creemee and apple cider donut stops.
Here’s my recommended Route 100 road trip, running south to north (which is ideal if you are driving from NYC, Connecticut or Boston).
🚗 Good to know: You’ll need between 3 and 7 days to complete this road trip. A car is essential, and fall is the best (but busiest) time to drive it. If you don’t have a car, I recommend using Discover Cars to find the best deals on rentals.
🍂 1. Wilmington
Route 100 starts in Wilmington, a small town in South Vermont.
It has a walkable downtown with independent shops, galleries and places to eat, so grab a coffee and something to eat before heading north.
If you are visiting between May and October, the Wilmington Antique & Flea Market is worth a look. It has been running since 1983 and is open on Saturdays and Sundays.
⛷️ 2. Mount Snow
🚗 Driving time: 15 min (8.5 mi)
Your next stop will be Mount Snow, which is the first big resort you’ll pass on Route 100.
In winter, it’s the ideal place to go skiing, snowboarding or snowmobiling.
But there is also plenty that you can do in summer and in the fall.
Kayaking and SUP are very popular activities but you can also ride the scenic chairlift to the top of Mount Snow (the views are amazing!).
You can also play golf, hike or do some mountain biking.
It’s a great spot for outdoor lovers and depending on how much time you have you can either just make it a quick stop or even spend a couple of days here.
🏊 3. Jamaica State Park
🚗 Driving time: 35 min (20 mi)
Next, carry on to Jamaica State Park, set on a lovely bend of the West River.
On a hot day, it’s a great place for a swim, and there are easy riverside trails to walk along the old railroad bed.
If you’re up for a longer hike, the trail to Hamilton Falls is well worth it. It’s one of the tallest waterfalls in Vermont, dropping around 125 feet. Just be careful, as the potholes at the top are dangerous and swimming there is not allowed. Admire it from a safe distance.
There’s also a campground here if you fancy staying overnight by the river.
⛪ 4. Weston
🚗 Driving time: 30 min (18 mi)
Continue north to Weston.
The highlight here is the original Vermont Country Store.
It’s a wonderfully old-fashioned shop packed with penny candy, local cheese, maple syrup, fudge and all sorts of hard-to-find bits, so leave time for a proper browse.
While you’re in the village, look out for the Weston Priory, a Benedictine monastery known for its music, and the historic Weston Playhouse, which puts on shows in summer.
⛰️ 5. Ludlow
🚗 Driving time: 20 min (12 mi)
Next up is Ludlow, a town built around Okemo Mountain Resort.
It has a small, walkable downtown with independent shops, cafes and restaurants, so it’s a nice place to stop for lunch or a coffee.
On a warm day, make sure to head just outside town to Buttermilk Falls. It’s a lovely cascade with a popular swimming hole, so it’s the perfect place to cool off.
You can also take a short detour to the Mountain Resort if you want to. There are loads of outdoor activities here.
🧀 6. Plymouth
🚗 Driving time: 20 min (12 mi)
Take a short but worthwhile detour to Plymouth.
This is where you’ll find the President Calvin Coolidge State Historic Site, the beautifully preserved birthplace of America’s 30th president. The whole little village has been kept as it was, so it’s a lovely step back in time.
Also, make sure to stop at Plymouth Artisan Cheese. It has been making cheese in the village since 1890 and it’s one of the best food stops in Vermont.
🚡 7. Killington
🚗 Driving time: 20 min (12 mi)
Back on Route 100, Killington is home to one of the biggest ski resorts on the East Coast, which is why it’s nicknamed “The Beast of the East”.
In winter it’s all about skiing, but there’s just as much to do in the warmer months.
You can ride the gondola up for panoramic views, hike to the lovely Thundering Brook Falls on an easy boardwalk trail, or walk a stretch of the famous Appalachian Trail, which passes right through.
It’s also a big mountain biking destination, with a proper bike park, so there’s plenty to get you out of the car for a while.
💧 8. Moss Glen Falls (Granville)
🚗 Driving time: 50 min (35 mi)
Keep heading north on Route 100 and watch out for Moss Glen Falls near Granville.
This is a waterfall that is very easy to reach which is why most people love it.
A short boardwalk leads from the roadside pull-off straight to a viewing area, so you barely have to walk.
It’s a quick and effortless stop.
🌉 9. Warren
🚗 Driving time: 20 min (12 mi)
Next, you’ll reach Warren, a lovely village in the Mad River Valley.
First, head to the historic Warren Covered Bridge.
You’ll also find another interesting general store here: the Warren Store. It has been going since 1839 and has a great deli and bakery (perfect for picking up lunch).
If you’re visiting on a warm day, head to Warren Falls.
It’s a natural swimming hole just off the road with rock slides and pools, making it a local favorite in summer.
🍦 10. Waitsfield
🚗 Driving time: 10 min (5 mi)
Next up is Waitsfield which is considered to be the heart of the Mad River Valley.
You’ll find one of the oldest operating covered bridges in Vermont here: the Historic Waitsfield Covered Bridge.
There are also a few independent shops, galleries and farm stands to browse.
Make sure to grab a creemee from the Canteen Creemee Company. This is another local favorite and to be honest, if you haven’t gotten a creemee yet, you really need to!
🍎 11. Waterbury
🚗 Driving time: 30 min (20 mi)
Waterbury is one of my favorite food stops on that trip as there is loads to do!
Firstly, you’ll get to the actual town. The Main Street is nice and you should stop if you want to stretch your legs and have a wander.
But after that, you’ll get to one of the highlights of any Vermont road trip: the Ben & Jerry’s Factory. Take the tour (it’s only $6) to see how the ice cream is made and taste the flavor of the day, and don’t miss the Flavor Graveyard outside.
Then keep driving a few minutes up Route 100 and you’ll get to Cold Hollow Cider Mill. It’s the perfect place to stop for a bag of warm apple cider donuts and a taste of fresh (and hot) cider.
For a coffee, stop at Vermont Artisan Coffee & Tea. It has a giant coffee silo out front so you can’t miss it.
⛪ 12. Stowe
🚗 Driving time: 20 min (12 mi)
Stowe is one of the best small towns in Vermont, so give it a proper stop (it’s one of my favorite places in the state too and you can easily spend a few days here).
Start downtown where you can walk along Main Street, pop into the old-fashioned stores like Shaw’s General Store and Stowe Mercantile, and head to the viewpoint to see the white Stowe Community Church against the mountains.
Just outside town, visit the von Trapp Family Lodge, the Sound of Music family’s Austrian-style estate. Say hi to the highland cows by the café and stop at the von Trapp Bierhall for a lager.
If you’re visiting between mid-June and mid-October, drive up to Stowe Mountain Resort and take the SkyGondola up Mount Mansfield, the highest peak in Vermont.
And don’t miss the drive through Smugglers’ Notch (Route 108), it’s one of the most scenic mountain drives in Vermont and it’s absolutely stunning in the fall!
I know it’s a detour but it’s worth it!
🥾 13. Moss Glen Falls (Stowe)
🚗 Driving time: 10 min (5 mi)
Just outside Stowe is a second Moss Glen Falls (not to be confused with the Granville one!).
This one is reached by a short woodland hike, and rewards you with a tall, pretty cascade.
It’s a lovely leg-stretch and a nice bit of nature before you carry on north into the Northeast Kingdom.
🏡 14. Morristown & Hyde Park
🚗 Driving time: 15 min (8 mi)
Continue north to the low-key towns of Morristown (Morrisville) and Hyde Park.
They’re much less touristy than Stowe, which is exactly the appeal. You’ll find local shops, cafes and a couple of good breweries, plus the Lamoille Valley Rail Trail if you fancy a walk or a bike ride.
It’s a nice glimpse of everyday Vermont life, away from the crowds.
🏞️ 15. Eden & Lake Eden
🚗 Driving time: 20 min (13 mi)
Further north, the tiny town of Eden sits on Lake Eden, a quiet spot for a swim or a paddle surrounded by mountains.
If you love the water, the nearby Green River Reservoir is also a great option for a more peaceful visit.
It’s a lovely, off-the-beaten-path stretch of the drive.
🌲 16. Westfield
🚗 Driving time: 30 min (18 mi)
Keep driving in the Northeast Kingdom until you reach the little village of Westfield which gives you a real taste of rural, tucked-away Vermont.
There isn’t a lot here beyond the scenery and the quiet, and that’s exactly why it’s worth slowing down for. You’re also not far from Jay Peak if you want to add a mountain stop.
🌊 17. Newport
🚗 Driving time: 25 min (15 mi)
Finish your journey in Newport, on the shores of Lake Memphremagog, a long glacial lake that stretches right up into Canada.
Enjoy the pretty waterfront, walk around the Gateway Center, and take in the lake views. In the warmer months, you can even take a boat cruise out onto the lake.
It’s a relaxed, scenic spot to end an epic Route 100 road trip.
➕ Detours worth adding
If you have extra time, these are all worth a detour off Route 100:
- Manchester: a southern Vermont town with designer outlets, the Northshire Bookstore and the grand Hildene estate.
- Woodstock: one of the state’s prettiest towns, with a famous covered bridge and Quechee Gorge nearby.
- Smugglers’ Notch: the dramatic mountain pass on Route 108 near Stowe, one of the best drives in New England.
🗺️ Map of this Route 100 Road Trip
💡 A few practical tips
- A car is essential, and you can do the highlights in a couple of days or take a full week.
- Fall is the best time to drive Route 100, but also the busiest, so book your accommodation well ahead.
- Bring proper shoes for the waterfall hikes and swimwear for the swimming holes.
- Keep an eye out for creemee stands, farm stands and cider mills along the way, they’re part of the fun.
❓ Is Route 100 worth driving?
Definitely. It’s one of the most scenic drives in the country, taking in mountains, waterfalls, covered bridges, charming villages and plenty of Vermont food.
Whether you drive a section or the whole thing, it’s a wonderful way to see the Green Mountain State.
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