I’m so excited to FINALLY share my travel guide for Vermont… it took me months to plan the perfect fall itinerary. I’m happy to say that all of the planning paid off and the trip was absolutely magical! It’s one of my favorite trips we have ever been on and we are thinking about making it an annual thing! You could definitely fly to Vermont (I’d recommend flying into Burlington) or make it a road trip, like we did! We decided to drive because we had a new Jeep Grand Cherokee, perfect for long road trips! Driving enabled us to pack all of the necessities, including chairs, a cooler filled with snacks, a picnic basket, and more. I shared a post previously with everything you need for the perfect fall road trip.
We left Richmond at 4am Saturday morning and barely hit any traffic on the way up to Burlington, Vermont. We arrived at Hotel Vermont in Burlington at 2pm. Check in was super easy, they have a free parking garage, and everything was very clean in the lobby. The room was nice, nothing super special, but it had a lovely view of Lake Champlain on the corner. After napping and freshening up, we walked to dinner at nearby Leunig’s Bistro, on Church Street (the busy downtown area of Burlington). Dinner was so delicious (beef bourguignon and pan seared salmon).
The next morning we drove to Kountry Kart Deli, Tristan’s favorite spot from college (he went to Saint Michael’s College near Burlington). We had the best breakfast sandwiches (bacon, egg, & cheese with a hash brown on the sandwich – so good!) After breakfast, we drove to Shelburne Orchards for apple picking. We bought apple cider and a basket to fill when we drove in, then parked in the orchard. It was windy that day but not too cold, so we enjoyed walking through the orchards and picking apples.
When we left the orchards, we headed to the nearby Shelburne Museum. Many of their buildings were closed due to the pandemic, but we decided to walk around the grounds. It was gorgeous and so peaceful. We headed back to Burlington and grabbed a quick lunch at Burlington Bay Market and Café on the water. We walked around Church Street and watched the sunset over Lake Champlain (breathtaking!) Our dinner reservation was at American Flatbread, where we sat outside and enjoyed live music. The flatbreads were great. After dinner, we decided to grab maple creamee (maple soft serve in a cone) from Burlington Bay Market and Café.
On Monday morning, we walked from the hotel to The Skinny Pancake for breakfast. It’s a must try but reservations are necessary! After breakfast, we packed up the car and checked out of Hotel Vermont. We drove to Stowe, about 40 minutes away, but took the long route along Smuggler’s Notch Drive (Route 108). Smuggler’s Notch is one of the most stunning drives in the state of Vermont during the fall. It was raining that day but still beautiful.
Once we arrived in Stowe, we stopped at Idletyme Brewing Co for lunch. It was great and I loved the atmosphere of their outdoor patio and bar. From there, we drove to Warren Falls (a recommendation from our waiter at Idletyme). It took us along the Mad River Byway through Waterbury, so we stopped at the Ben and Jerry’s Factory. There was a short line to get in and order ice cream, and we sat outside and enjoyed it. Tristan worked there in college as an ice cream tester. I got my favorite, half baked, and it was so much more fresh and delicious than from the grocery store.
We made our way to Warren Falls which was a short .3 mile hike from the parking area. It was raining but very pretty and peaceful. After that, we drove back to Stowe and checked into The Lodge at Spruce Peak. We had a room with a balcony and mountain view… I kid you not, it was one of the most spectacular views I’ve EVER seen! The leaves were at peak color and absolutely breathtaking. That night we had dinner at Cork Wine Bar & Market.
The next morning we got up early and did the 3.7 mile Stowe Pinnacle Trail hike. It was SO windy at the top you could hardly stand up, but the views were incredible. The hike itself is relatively easy except for the last little climb to the top. Afterwards we had breakfast at Cafe on Main. We got ready at the hotel and headed to Cold Hollow Cider Mill. For lunch, we had sandwiches at their onsite restaurant, Apple Core, and got apple cider doughnuts (delicious!) On the way back to town, we passed by Thompson Park and stopped to take a stroll, admiring the beautiful leaves and fields of horses and cows. We walked around downtown Stowe and stopped into a bookstore, then had dinner at Piecasso.
On Wednesday morning, we had breakfast at Solstice then drove from Stowe to Pomfret along Cloudland Rd. It’s one of the most picturesque roads in Vermont. The main stop along the way was at Sugarbush Farm, for maple syrup and cheese tasting. It’s a family run farm and the tasting is free. We stocked up on maple syrup and cheese to bring back to friends and family. The next stop was at Sleepy Hollow Farm, a private family farm known as one of the most beautiful in Vermont. We continued on to Woodstock and checked into 506 On The River Inn. It was so peaceful and serene, with a beautiful backyard overlooking the river.
That afternoon, we did a little shopping in town and stopped by the Farmer’s Market, before heading to dinner at The Mill at Simon Pearce. That was one of the best meals we had the entire trip and the restaurant and shop are gorgeous.
Thursday morning we had breakfast at Soulfully Good Cafe, then walked around town, over the covered bridge, and enjoyed our coffee on the village green. We walked around Kelly Way Gardens at the Woodstock Inn then headed to Gillingham’s, Vermont’s oldest store. For lunch we grabbed sandwiches from the Village Butcher and ate them on the back lawn at the historical society, overlooking the river.
The next morning we grabbed breakfast at Mon Vert Cafe, then drove to Quechee Gorge Bridge. We checked out the Woodstock Farmer’s Market before heading to Walpole, MA to visit Tristan’s family.
The trip was absolutely wonderful overall, filled with beautiful scenery, delicious food, and LOTS of maple lattes and apple cider doughnuts. I absolutely fell in LOVE with Stowe and Woodstock. I had been to Burlington before and loved getting to visit again in the fall. Below I’m listing my top must do’s for each. Comment with any questions about fall in Vermont, or tell me your favorite fall destination in the US!
Top Things to do in Burlington, Vermont:
- Dinner at Leunig’s Bistro
- Breakfast at Kountry Kart Deli
- Apple picking at Shelburne Orchads
- Shelburne Museum
- Breakfast at The Skinny Pancake
- Maple creamee from Burlington Bay Market & Cafe
- Dinner at American Flatbread
Top Things to do in Stowe, Vermont:
- Smuggler’s Notch Drive
- Lunch at Idletyme Brewing Co
- Drive the Mad River Byway through Waterbury
- Ben & Jerry’s Factory for ice cream
- Stowe Pinnacle Trail Hike (3.7 miles)
- Cold Hollow Cider Mill
- Thompson Park
Top Things to do in Woodstock, Vermont:
- Drive through Pomfret on Cloudland Rd – stop at Sugarbush Farms for maple syrup & cheese tasting
- Dinner at The Mill at Simon Pearce
- Breakfast at Soulfully Good Cafe
- Stroll through town, over the covered bridge and through the village green
- Sandwiches from Village Butcher (eat them on the back lawn at the historical society across the street)
- Coffee from Mon Vert Cafe
- Quechee Gorge Bridge