Our fall road trip through Vermont will take you from Montgomery, Vermont, north to the Canadian border, and then south along the Green Mountain National Forest to the New York-Massachusetts borders. The journey will provide numerous leaf-peeping opportunities and a variety of fascinating stops.
Videos by TravelAwaits
The prime time for this road trip is from the third week of September till the middle of October. The leaves change in the north first. Thus, we start our journey north and head south.
This 250-mile trip (expect more mileage for side excursions) could be done in a day or two if you shorten your visits, or expanded for extended stays at the most appealing stops.
Most of Vermont’s fall foliage color is provided by red and sugar maples. The red maples turn scarlet, while the warm orange-colored leaves are from the sugar maples. The patches of bright yellow leaves are from the aspen and birches, and the bronze and gold leaves are from the oak and beech trees.
Montgomery
This tiny town in northern Vermont is home to some of the most beautiful fall foliage spots in the region. Famous for its many scenic covered bridges, my favorites are the Comstock Covered Bridge and the West Hill Covered Bridge.
If you are into hiking, there are 15 miles of trails preserved by the Hazen’s Notch Association.
After a day on the road, you might enjoy relaxing at the Vermont Salt Cave Spa and Halotherapy Center. Massage and other services are available.
On the second day, you will travel an hour north on VT 100 to Jay Peak. You may not see another car as you wind through the backcountry hills, but there is a high likelihood of seeing a moose. We guarantee you will see some gorgeous fall foliage.
To get to the peak, you can take the Jay Peak Aerial Tramway and see the foliage from above. If you want an excellent hiking workout, hike to the top. The trail is well marked and moderate in difficulty. The view from the summit is phenomenal.
The Jay Peak Resort has a waterpark with a lazy river, a swim-up bar, and hot tubs.
You could either stay at Phineas Swann Inn and Spa in Montgomery or the Jay Peak Resort. Both are great options.
They have great food at Jay Peak and a local restaurant to try is The Belfry. After a good night’s rest, you will head to Jeffersonville.
Jeffersonville
Travel south via VT 118 for 26 miles to the tiny town of Jeffersonville. There you will have time for a quick stop at the Vermont Maple Outlet.
Then it’s off toward Stowe for a scenic drive on VT 108. Along the way, we will stop at Smugglers’ Notch Distillery for a half-hour visit. They have a small tasting room and spirits to purchase by the bottle.
Smugglers’ Notch State Park
The next stop is Smugglers’ Notch State Park. As the name implies, the area was once part of illegal trade routes into and out of Canada. The 1,000-foot cliffs were an excellent hiding place for the goods being transported.
This area is absolutely gorgeous in the fall, and as you pass through, be sure you take in the beauty of the scarlet and orange leaves reflecting in Sterling Pond, and don’t miss Bingham Falls. The park also has hiking trails with varying degrees of difficulty. Limited free parking is available on-site. Plan to spend two hours to a half a day enjoying the park.
Stowe
Talk about a scenic setting; you will know you are in Stowe by the iconic white steeple of Stowe Community Church rising above the sugar maples’ orange leaves. Depending on when you arrive, you might want to head out to the Stowe Recreation Path.
The path weaves five and a half miles between Stowe Village and the Topnotch Resort. It is a nice flat, easy walk or bike ride. You will see an abundance of colorful foliage as you walk this picturesque path. Be aware there are no water fountains or restrooms available. Plan at least two hours for this walk.
There are various farms and shops nearby, so plan to purchase some items to take home.
We will spend the night in Stowe in the Trapp Family Lodge. Yes, as in the Trapp family from the movie The Sound of Music. Have more time? These are the best things to do in Stowe, including our best Stowe restaurant recommendations.
Green Mountain Byway
In the morning, you will head out for a short scenic drive on the Green Mountain Byway to Waterbury on Vermont 100. You will have stunning views of foliage all along the highway.
There are numerous places to stop along the way, including three state parks, the Waterbury Reservoir, and Mount Mansfield, the most prominent natural feature in the area and the highest peak in Vermont.
There are numerous opportunities for leaf-peeping, hiking, nature walks, and other recreation if you desire to stop.
Waterbury
Stop for the Ben and Jerry’s Ice Cream Factory Tour and some ice cream samples. Cheese lovers will want to stop at Cabot Farmers’ Store for some Vermont Cheese. In Waterbury, you will find a walkable town center.
Enjoy lunch at Cold Hollow Cider Mill and Restaurant, where you can watch as cider is pressed.
Plan to spend a half a day here. After lunch, continue south on Vermont 100 for 12 miles to the Mad River Valley.
The Old Stagecoach Inn is a fun place to stay if you desire to spend more time in this quaint town.
Mad River Valley
Mad River Valley has several places where you could stop to enjoy activities, and fall foliage is plentiful in the area. You can enjoy the colorful masterpiece Mother Nature creates from leaves by car, bike, foot, kayak, horseback, glider, or chairlift. Plan to spend the afternoon.
If you decide to spend the night, I recommend the Mad River Inn.
Lincoln Gap
Mad River Valley to Lincoln Gap is a 20-minute drive. You follow Vermont 100 for six miles and then turn onto Lincoln Gap Road, which you take for just under five miles.
Lincoln Gap is the highest mountain pass in Vermont accessible by vehicle.
Beautiful views of picturesque fall foliage surround you, and you can see it all from the comfort of your car. Lincoln Gap is part of a loop that includes Granville Gulf, Moss Glen Falls, and Middlebury. There is a large waterfall in the town of Middlebury.
Middlebury might be the best place to stop for lunch. Take a step back in time and enjoy a meal at the Fire and Ice Restaurant.
Next, you will go through Middlebury Gap, the Appalachian gap, and then past Texas Falls before ending up back on Vermont 100.
Be sure to stop and enjoy the views along the way! This could take the better part of the day depending on where and how often you stop.
After we are back on Vermont 100, we will head south through the White River Valley for 28 miles to Killington.
Killington
The best views of the area and the colors of fall are from the top of Mount Killington. If you are feeling energetic, you can hike to the top, or you can enjoy the Killington Mountain Scenic Gondola, which takes you to the summit.
After several days of traveling, you might want to indulge in a relaxing massage at Killington’s Grand Spa. End the day with a stay at the Killington Grand Hotel, which boasts an 18-hole championship golf course, a heated outdoor pool, and a fire pit for roasting marshmallows.
Weston
Head off on a 45-minute drive as we continue south on Vermont 100 for a stop in Weston.
Two places you might want to visit while in Weston are the Mill Museum and the Vermont Country Store. They still offer penny candy and toys you played with as a child.
Then we are off to Bennington, first on Vermont 100, then west via VT 09. As you drive, enjoy the vibrant leaf colors.
Bennington
Bennington sits near the border of New York and Massachusetts and is our final destination.
Visit the 306-foot-tall Bennington Battle Monument. Guests can see for miles and into three different states from the tower observation deck.
Other things to see and do in the area include the Bennington Museum, covered bridges, and The Old First Church of Bennington.
Lake Shaftsbury State Park, Robert Frost’s grave, and the Robert Frost Stone House Museum are nearby.
Two unique places to eat in Bennington are The Publyk House and Jensen’s Family Restaurant. Spend your final nights at the Four Chimney’s Inn.
Travel Tips
- Foliage season is a popular time to visit Vermont, so if you want to stay in a particular place, call in advance to make sure rooms are available.
- Because you will be viewing fall foliage from different elevations, the weather may go from nippy to downright cold in a day. Pack and dress appropriately.
- If you are planning to hike anywhere along the way, be sure to wear sturdy footwear, not sandals.
- Most of the parks and scenic areas are open April through mid-October. If it snows, some roads may close.
- For detailed driving directions, see our Perfect Vermont Fall Foliage Google map.