Living in Massachusetts, we haven’t always made the best use of our beautiful surroundings in New England. Since travel is not advisable during the COVID-19 pandemic, we’ve started taking more quick trips in the area. Over Columbus Day Weekend, we drove up to Vermont to check out the foliage. Here’s the perfect three day Vermont fall foliage itinerary.

Day 1: Explore Woodstock and a Scenic Drive Up North

This itinerary starts in Woodstock, Vermont. We checked into the Woodstock Inn late on a Thursday so we had the full day Friday for activities.

Explore Woodstock on Foot

The Woodstock Inn is located right in the middle of Woodstock so it’s easy to walk around the town. We took a morning walk before grabbing breakfast from Mont Vert Cafe.

Woodstock Inn

Sleepy Hollow Farm

Sleepy Hollow Farm is one of the most photographed places in Vermont during fall foliage. Located on Cloudland Road in Pomfret, Vermont, you’re sure to see amateur and professional photographers alike pulled over for a chance to photograph this private residence. You can read more about why Sleepy Hollow Farm is so popular here.

Sleepy Hollow Farm

Sugarbush Farm

Next, head to Sugarbush Farm for a cheese and maple syrup tasting. Both the cheese and syrup are so good, you’ll surely want to take some home! Stopping here was one of the highlights of our trip.

Sugarbush Farm

Quechee Gorge

After your cheese tasting, head over to nearby Quechee to hike down to Quechee Gorge. First, get some aerial shots of the gorge from the Quechee Gorge Bridge. You can then park just before the bridge to hike down to the gorge.

Quechee Gorge

The full Quechee Gorge Trail is 2.7 miles total, but if you choose to hike down to the bottom of the gorge only, it’s much shorter.

Quechee Gorge

Lunch at Simon Pearce

Head down the road to Simon Pearce for lunch. Simon Pearce is a well-known glass store with a restaurant overlooking a mill.

Simon Pearce

The scenery is beautiful and the food is even better!

Simon Pearce Lunch

Drive Through Smugglers Notch

You’ll spend a decent portion of your afternoon leaf peeping from the car. First, drive to Waterbury either on the highway or taking scenic Route 100. Make a pit stop at Cold Hollow Cider Mill for some apple cider donuts.

Cold Hollow Cider Mill

Continue through Stowe and onto Smugglers Notch for one of the most scenic drives in the area. Stay on the road until Jeffersonville before changing course and heading to Burlington for the night.

Smugglers Notch

Overnight in Burlington

We checked into the Hilton Burlington Lake Champlain for the night before walking over to Church Street Marketplace, a pedestrian-only area with shops and restaurants. Visit Lake Champlain Chocolates for an afternoon treat. When you’re ready for dinner, you might want to try American Flatbread or Hen of the Woods.

Church Street Marketplace

Day 2: Head South to Manchester

On Day 2, you’ll spend the morning in Burlington before continuing onto your last stop, Manchester.

Lake Champlain Waterfront

Start your morning with a walk along Lake Champlain’s waterfront park. Be sure to stop at the Skinny Pancake for breakfast.

Lake Champlain Waterfront

After breakfast, it’s a slow drive down to Manchester along scenic Route 7. This was one of the prettiest drives in terms of fall foliage.

Route 7 Vermont

Lunch in Manchester

Upon arriving in Manchester, pick up lunch from Zoey’s Deli. This place is super popular so be sure to order ahead!

Equinox Pond

We spent the night at the Equinox, a Luxury Collection Resort with close proximity to Equinox Pond and Mount Equinox.

Equinox Resort

Walk up to the Equinox Preservation Trust from the hotel to take a short mile-long hike around Equinox Pond.

Equinox Pond

Dinner at Ye Old Tavern

For dinner, head to Ye Old Tavern for some good old fashion New England comfort food. The restaurant dates back to the late 1700s! Ye Old Tavern is known for its prime rib, but they only have a limited amount so make an early reservation if you want to try it. We ate later and still had delicious options…the turkey dinner is excellent!

Ye Old Tavern

Day 3: Last Stops in Manchester

Spend your last day in Vermont fully exploring Manchester before heading home in the afternoon.

Equinox Mountain

Breakfast at Little Rooster Cafe

Little Rooster Cafe is a no-frills diner that gets extremely busy. If you arrive before 8:30 am, you shouldn’t have a problem getting in. Otherwise, you may have to wait a bit.

Little Rooster Cafe

Skyline Drive to Mount Equinox Summit

Skyline Drive is the longest privately owned paved toll road that takes you up to the summit of Mount Equinox. You will need to stop at the toll house to pay. It’s $20.00 per car and driver and $5.00 for each additional passenger. I recommend doing this drive early in the morning to avoid long lines at the toll house in the afternoon.

Mount Equinox Skyline Drive
View from Skyline Drive

Lye Brook Falls Hike

After Skyline Drive, head over to the Lye Brook Falls trailhead for a 4.7 mile out and back hike. This is a popular hike so it’s also recommended to start early!

Lye Brook Falls

Lunch at Bonnet & Main

The last stop before heading home is Bonnet & Main for lunch. Their spicy tofu bahn mi is amazing!

Final Thoughts

Vermont is the place to be during the fall. Not only are there so many amazing outdoor activities, but doing them with a beautiful fall foliage backdrop makes them even better. This three day Vermont fall foliage itinerary is the perfect introduction to first-timers in Vermont.

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