Vermont Fall Foliage Road Trip: A 2-Day Itinerary

Hannah Truman
Oct 26, 2021
4 min read

Updated: Oct 14

Chasing Autumn Colors: The Perfect Vermont Fall 2-Day Foliage Road Trip

I had been eager to embark on a fall foliage road trip for a considerable time, and I finally fulfilled that wish this year. We filled two entire days with scenic views and stayed overnight in Burlington. Explore a few of the memorable moments from our journey to admire the changing leaves across Vermont.

Additionally, I've put together an itinerary you can use for your own fall road trip in Vermont, complete with stunning spots for leaf peeping, hiking trails, and picturesque farms where you can purchase local treats.

Itinerary in Brief:

Day 1:

Quechee Gorge Bridge
Sugarbush Farm, Woodstock (driving time: 12 mins from the gorge)
Sleepy Hollow Farm, Pomfret (driving time: 12 mins from Sugarbush)
Deer Leap Overlook Trail, Killington (driving time: 34 mins from Sleepy Hollow Farm)
Drive from Killington to Burlington (driving time: 1 hr 40 mins)
Check in hotel in Burlington
Dinner at Church Street Marketplace

Day 2:

Old Red Mill, Jericho
Mills Riverside Park, Jericho
Smugglers' Notch
Sterling Pond Trail
Bingham Falls Trail, Stowe, VT
See Stowe's Downtown, Main Street

Quechee Gorge

Our Vermont road trip kicked off with a stop at Quechee Gorge, which is akin to Vermont’s Little Grand Canyon. This stunning natural landmark is one of the state’s most photographed spots (and for good reason).

The Ottauquechee River cuts through the gorge, creating a dramatic 165-foot drop surrounded by dense forest. In the fall, the views are especially breathtaking, with the cliffs and colorful trees.

We parked near the Quechee Gorge Bridge, which offers the best panoramic view, and then followed the short trail down to the riverbed below. The path winds through peaceful woods before opening up to the rocky banks, where you can look up and see the bridge towering above. It’s a great place to stretch your legs, snap some photos, or simply take in the crisp mountain air before continuing deeper into Vermont.

Vermont Farms

Our stop at Sugarbush Farm in Woodstock, VT was a highlight of the trip. This family-owned farm offers a variety of Vermont-made goods, including pure maple syrup, jam, and mustard. After visiting the farm store, we took a self-guided tour to learn how the syrup is made. Before hitting the road again, I couldn’t resist trying their old-fashioned lemonade, freshly made by the farm. It was the perfect treat!

The drive out to the farm was just as beautiful as the stop itself, with stunning views of the rolling hills covered in vibrant fall foliage.

Next, we drove to the Instagram-famous farm, Sleepy Hollow Farm, in Pomfret for the iconic photo. The scenery in this area was gorgeous, with its rolling green meadows and vibrant foliage among the quaint farmhouses.

To my surprise, this place wasn't a secret at all; there were lots of people gathered, all aiming to capture that 'gram-worthy shot!

Killington

During our visit to Killington, we embarked on the Deer Leap Overlook Trail, a 2.2-mile out-and-back path offering a fantastic vantage point of Killington Mountain and the vibrant fall foliage. Our timing couldn't have been better for enjoying the leaves in all their glory.

If you're considering a hike, I strongly suggest trying out this trail. It strikes a perfect balance – not overly long or challenging, yet it rewards you with a truly spectacular view.

Burlington

Burlington was part of the trip I was most excited to see! We stayed at the Hilton Garden Inn, right in the heart of the city, just a short walk from both the waterfront and Church Street Marketplace.

Church Street is a lively pedestrian only street lined with shops and restaurants, making it the perfect place to spend part of your day. It’s the heart of Burlington’s vibrant downtown, small in size but full of character and charm. Whether you're shopping, people watching, or grabbing a bite, Church Street is a must see for any visitor.

For more on what to do in Burlington, check out my Summer Weekend in Burlington post!

Jerricho

On the way to Smugglers' Notch, we stopped at the Old Red Mill and the Mills Riverside Park in Jerricho. I wouldn't recommend going out your way to visit these spots, but if you are going through the area they were worth a quick stop.

Smugglers' Notch

We did a hike in Smugglers Notch, but the real highlight of the area was driving the winding mountain road surrounded by a tunnel of fall color. We hiked the Sterling Pond Trail (2.3 miles), which leads to a serene mountaintop pond. I was a little disappointed that there wasn’t much foliage around the pond itself, but the trail getting there was gorgeous.

After looking into it later, I realized most people stop at the pond and begin their descent (just like we did) but there are additional viewpoints just a short hike away. If you ever do this trail, make sure not to miss them! No matter which route you take, you really can’t go wrong. Smugglers Notch is one of the most beautiful areas to experience Vermont’s fall scenery.

Stowe

After driving through the dramatic twists of Smugglers Notch, we made our way to Stowe Mountain Resort, home to the famous Stowe Gondola SkyRide. This area feels straight out of a postcard in the fall, with the slopes lined in fiery shades of burnt orange, golden yellow, and deep red.

The gondola takes you up to Mount Mansfield, Vermont’s highest peak, where the views stretch endlessly over the valley and surrounding mountains. At the top, you can step out to enjoy the crisp mountain air, grab a bite or a drink at The Cliff House restaurant, or take a short trail walk for even more viewpoints.

Afterward, we wandered into the charming village of Stowe, where covered bridges, local shops, and inviting cafés make it the perfect spot to stroll around with a warm drink. Between the mountain scenery and small town charm, Stowe truly captures that quintessential Vermont fall experience.

We made our way to Stowe's downtown for lunch and then headed back home. We had a packed full two days and I got to see a state I haven't seen before. All in all, our Vermont trip was a lot of fun and I'm so glad we finally made it happen!

Thanks for reading!

- The Maine Chick