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September 14, 2021

Vermont Fall Bucket List

Vermont Fall Bucket List

So, you are thinking of visiting Vermont this fall? Vermont is nothing short of spectacular during the fall season. It’s one of those states that makes you want to come back time and time again. Incredibly clean, stunningly beautiful, and friendly, there really isn’t anything about Vermont that isn’t amazing. Honestly, there isn’t a more magical time to visit Vermont than during fall, and there are so many awesome things to do! But what should be on your Vermont fall bucket list?

Vermont Fall Bucket List
 [show]
  • The Basics: 
    • Where Is Vermont?:
    • What Is Vermont Known For?:
    • How Do I Get To Vermont?:
    • When Is Fall Foliage At Peak?:
  • Vermont Fall Bucket List
    • 1. Stay In A Cozy Cabin 
    • 2. Drive Route 100 
    • 3. Have At Least 20 Cider Donuts 
    • 4. Visit Covered Bridges 
    • 5. Drive To The Top of Mt. Mansfield In Stowe, Vermont
    • 6. Try True Vermont Maple Syrup 
    • 7. Visit A Working Farm 
    • 8. Eat So Much Cabot Cheese 
      • Cabot Farmers’ Store
      • Cabot Farmers’ Village Store
      • Prohibition Pig
    • 9. Visit As Many Breweries As You Can 
      • Von Trapp Brewing
      • The Alchemist
      • Fiddlehead Brewing Co
      • Prohibition Pig 
    • 10. Ben & Jerry’s Factory Tour 
    • 11. Take A Hike And Enjoy The Foliage 
      • Quechee – Quechee Gorge 
      • Pittsford – Bald Mountain 
      • Woodstock – Mount Tom 
      • Groton – Owlshead Mountain Trail 
      • Stowe – Stowe’s Pinnacles Trail 
    • 12. Try Some Cider
      • Stowe Cider 
      • Vermont Hard Cider 
      • Boyer’s Orchard And Cider Mill 
    • 13. Enjoy The Foliage From A Ski Lift 
      • Smugglers’ Notch Resort 
      • Stowe Mountain Resort 
    • 14. Have Fun At A Fall Festival 
      • Smugglers Notch Applefest 
      • Stratton Harvestfest Weekend 
      • Wagon Ride Weekend – Woodstock 
      • Stowe Foliage Art Festival 
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The Basics: 

Where Is Vermont?:

Vermont is in the northeastern United States, and is known for its natural landscape. Part of the New England region, Vermont is the only state in New England that does not touch the Atlantic Ocean. 

What Is Vermont Known For?:

It’s known for being home to more than 100 19th-century covered wooden bridges, as well  as being a major producer of maple syrup.

How Do I Get To Vermont?:

Air: The largest airport is in Burlington, Vermont. They service major air carriers including JetBlue, United, American Airlines, and Delta. 

You will need a rental car. 

Drive: Vermont is an easy road trip for much of the east coast. I highly recommend visiting this way because you need a car to get to all of the awesome things Vermont has to offer. 

When Is Fall Foliage At Peak?:

This differs every year but typically the first and second week of October are peak for foliage in Vermont. 

Vermont Fall Bucket List

1. Stay In A Cozy Cabin 

Is there a better way to enjoy your fall trip to Vermont? Nope! Just imagine a homey log cabin, flannel, a steaming cup of coffee in the morning, and a crackling cozy fire at night. Perfect, right? I love these options: Dream Log Cabins, Cozy Rustic Cottage,Rustic Retreat.

2. Drive Route 100 

Running along the eastern edge of the Green Mountains, the Scenic Route 100 Byway is located in south-central Vermont. It’s been recognized as one of the most scenic routes in New England, and for good reason. This route is particularly scenic during the fall season and the foliage is epically gorgeous. 

3. Have At Least 20 Cider Donuts 

There are many options for cider donuts in Vermont, but arguably the best can be found at Cold Hollow Cider Mill. 

  • 3600 Waterbury Stowe Road, Waterbury Center, Vermont 05677
  • Daily 8 am – 6 pm

In case it needs to be said – DO NOT skip cider donuts especially at Cold Hollow Cider Mill. 

4. Visit Covered Bridges 

There are more than 100 19th-century covered bridges in the state of Vermont. Historic, beautiful, and unique some of these bridges date back to 1820. 

5. Drive To The Top of Mt. Mansfield In Stowe, Vermont

Another great scenic drive is Stowe Mountain Toll Road. 

Vermont Fall Bucket List
  • Cost: $33 for the two people and 2 dogs
  • They accept both cash and cards
  • Dogs are allowed at the top parking lots as long as they are on a lead 

The drive itself is gorgeous and takes about 20 minutes to arrive at the top with a max speed of 15 mph. Once you reach the 3rd parking lot at the Mount Mansfield Visit Center it’s an easy 5 min walk to gorgeous 360-degree views. 

Check Out: Stowe, Vermont: A Charming New England Fall Day Trip

6. Try True Vermont Maple Syrup 

Did you know that Vermont is the nation’s leading producer of maple syrup, the state produced more than 2 million gallons last year. So, you’ve gotta try some maple syrup during your fall trip to Vermont. Spring is the season to visit sugar houses but you can still purchase pure Vermont maple syrup during fall. 

Check Out: 

Sugarbush Maple & Cheese Farm – 

  • 591 Sugarbush Farm Rd, Woodstock, VT 05091

7. Visit A Working Farm 

Check out Shelburne Farms. It’s a nonprofit educational organization that inspires  learning for a sustainable future. The farm is  located on a 1,400-acre, that include:  forest and National Historic Landmark along the shores of Lake Champlain, on the ancestral land of the Abenaki.

  • 1611 Harbor Rd
  • Shelburne, VT 05482
  • Find more HERE
Vermont Fall Bucket List

8. Eat So Much Cabot Cheese 

In case you didn’t know, the famous Cabot Cheese is made right in Vermont. You will find cabot cheese on many Vermont restaurant menus. There are also two retain shops of Cabot products…

Cabot Farmers’ Store

  • 2657 Waterbury-Stowe Road, Waterbury Center, VT 

Cabot Farmers’ Village Store

  • 3075 Main Street, Cabot, VT 05647 

Or have lunch or dinner at…

Prohibition Pig

  • 23 S Main St, Waterbury, VT 05676
  • Find Out More HERE

Prohibition Pig is one of my absolute favorite restaurants, and I love their Cabot mac-n-cheese 

9. Visit As Many Breweries As You Can 

Vermont is craft brewery heaven and you have to visit as many as you can during your fall visit! 

Von Trapp Brewing

  • 1333 Luce Hill RD, Stowe, VT 05671

The Alchemist

  • 100 Cottage Club Road, Stowe, Vermont 05672

Fiddlehead Brewing Co

  • 6305 Shelburne Road, Shelburne, Vermont

Prohibition Pig 

  • 23 South Main Street, Waterbury, Vermont

10. Ben & Jerry’s Factory Tour 

1281 Waterbury-Stowe Road, Vermont Rte 100, Waterbury Village Historic District, VT 05676

Vermont Fall Bucket List

Take a tour of the famous Ben & Jerry’s Factory in Waterbury, Vermont. It’s such a fun experience and you get a free sample at the end of the tour. Don’t forget to try some of these famous crazy concoctions afterward. 

And don’t miss the Flavor Graveyard where retired flavors reside.   

11. Take A Hike And Enjoy The Foliage 

There is no better way to take in all of those fall colors than hiking in Vermont. 

Quechee – Quechee Gorge 

  • 6800 Woodstock Road, Quechee, Vermont 05049 
  • Daily 9 am – 7 pm 
  • Distance: 2.7 Miles 
  • Rating: Easy 
  • Elevation Gain: 200 ft
Vermont Fall Bucket List

Pittsford – Bald Mountain 

  • Distance: 3.3 Miles 
  • Rating: Moderate 
  • Elevation Gain: 849 ft

Woodstock – Mount Tom 

  • Mount Tom via Faulkner Trail 
  • Distance: 4.2 Miles 
  • Rating: Moderate
  • Elevation Gain: 669 ft

Groton – Owlshead Mountain Trail 

  • Distance: 3.2 Miles 
  • Rating: Easy
  • Elevation Gain: 475 ft

Stowe – Stowe’s Pinnacles Trail 

  • Distance: 3.7 Miles 
  • Rating: Hard 
  • Elevation Gain: 1,604 ft  

12. Try Some Cider

There are so many great ciders to try in Vermont, both alcoholic and non-alcoholic. 

Vermont Fall Bucket List

Stowe Cider 

  • 17 Town Farm Lane, Stowe, Vermont, 05672
  • Daily 12-8 pm 

Vermont Hard Cider 

  • 1321 Exchange St, Middlebury, VT 05753
  • Wed-Fri: 11 am – 5 pm, Sat-Sun: 11 am – 6 pm 

Boyer’s Orchard And Cider Mill 

  • 1823 Monkton Rd, Monkton, VT 05469
  • Daily 9:30 am – 5:30 pm 

13. Enjoy The Foliage From A Ski Lift 

To get a different perspective, marvel at the red, orange, and yellow leaves from the sky (or closer to it). Check out the foliage from one of these awesome ski lifts – 

Vermont Fall Bucket List

Smugglers’ Notch Resort 

  • 4323 VT-108, Jeffersonville, VT 05464

Stowe Mountain Resort 

  • 5781 Mountain Rd, Stowe, VT 05672
  • Mon-Fri: 8 am – 4 pm, Sat-Sun: 7:30 am – 4 pm 

14. Have Fun At A Fall Festival 

There are so many fun fall festivals in Vermont that you don’t want to miss! Check out…

Smugglers Notch Applefest 

  • Sept 17 – Oct 3rd 
  • Find Out More HERE

Stratton Harvestfest Weekend 

  • Oct 9-11
  • Find Out More HERE
Vermont Fall Bucket List

Wagon Ride Weekend – Woodstock 

  • Sept 9-10 
  • Find Out More HERE

Stowe Foliage Art Festival 

  • Oct 8-10
  • Find Out More HERE

There are so many amazing things to do in Vermont in fall! No matter what you end up doing on your fall trip to this gorgeous state, you can’t go wrong. Have you been to Vermont in fall? What was your favorite? 

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Posted In: New England, United States · Tagged: Bucket List, Fall In New England, Fall Travel, New England, United States, Vermont

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Hi! I'm Vanessa, a 30 something, sunset chasing traveler. I'm here to inspire you to travel wherever, whenever, and with whoever you can. My Huskies, Loki and Freya are usually along for the ride. I have a soul that likes to wander, a desire to experience the unknown, and a curiousity to discover things off the beaten path. I hope you'll stick around for awhile!

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Salem questions, round two. I love being your unof Salem questions, round two. I love being your unofficial tour guide for your October witch era. 🧙‍♀️

Which train should you take? Is 9 a.m. too early? (For Salem in October? Absolutely not.) Where did the witch trials actually happen? Can you go inside the Hocus Pocus house? (Nope. People live there. Please don’t be weird.)

We’re also talking coming in from Danvers, the ferry, what your 10-year-old will love, and whether November is too late for a Salem trip.

I lived in Massachusetts for 7 years and made the October pilgrimage more times than I can count. These are the answers I’d give a friend before sending them off to get aggressively distracted by every witchy gift shop in town. 

And if you want the whole game plan, I’ve got you:

🧹 The Ultimate Salem Guide ($): Week-by-week crowd calendar, parking lots by address, a kids’ itinerary, and what’s changed for 2026.

🎃 The Salem Cheat Sheet ($): The need-to-know details without the 47 open browser tabs.

Comment WITCH and I’ll send you the links. Consider it your official invitation to your 90s-kid, Hocus Pocus-loving witch era. 🖤
POV: You’re standing in the front yard of the man POV: You’re standing in the front yard of the man who gave Acadia to the world, and almost nobody knows it 😍

No circling the Park Loop Road looking for parking. Just old stone steps, the Atlantic, and a piece of Acadia history hiding in plain sight.

At the end you’ll find old stone foundations and steps going down to the rocks. That’s Old Farm, George Dorr’s house. Dorr spent his life and most of his money piecing together the land that became Acadia, then handed it to the country. He died in 1944, and the park took the house down a few years later. The story goes he swam off these rocks every morning well into old age.

So you’re standing in the front yard of the person who’s the reason any of this is public land. There’s no sign making a big deal of it. I think that’s the point.

Dogs on leash are fine. Park in the small lot on Route 3 just outside of Bar Harbor.

Then head back into town for dinner. Table Salt on Main Street if you want to sit down somewhere nice, or the Black Friar if you want a pub, a fire, and a bowl of stew. Both are a few minutes from the trailhead, which is the whole argument for doing Compass Harbor late in the day.

✨🍁✨ Save this one for the day you want Acadia without the Park Loop Road.

Heading to Acadia in the next few weeks? Comment Fall and I’ll send you links to my guide and blog post 🍁✨
If Horseman’s Hollow is on your Sleepy Hollow itin If Horseman’s Hollow is on your Sleepy Hollow itinerary, sit down, we need to talk 🎃👻✨

Sleepy Hollow rebuilt its entire Halloween lineup this year, and most of what’s on the internet about it hasn’t caught up. 

Horseman’s Hollow is gone. Kykuit’s paused. Irving’s ‘Legend’ moved outdoors to Sunnyside. Halloween is a Saturday and so is the parade a week earlier.

I lived in New England for 7 years and drove down almost every October. This is the version I’d hand a friend, checked for 2026: the honest week-by-week crowd calendar, every ticket and the order it sells out, the train and the parking lots, parade night and Halloween night hour by hour, one perfect weekday, and the seven real Legend addresses.

The Sleepy Hollow in October Cheat Sheet ($) is six pages you keep on your phone. The Ultimate Sleepy Hollow Guide ($) is the whole year including itineraries, where to actually sleep (RV included), the dog version, the estates, the real history.

Comment HORSEMAN and I’ll send you both links, plus my blog post One Day In Sleepy Hollow!
📰🗞️ It’s called Newspaper Rock, but there’s no hea 📰🗞️ It’s called Newspaper Rock, but there’s no headline. Just 2,000 years of people adding to the story.

Newspaper Rock, on the road into Canyonlands’ Needles district. Hundreds of figures carved into the desert varnish over roughly 2,000 years. Ancestral Puebloan, Fremont, Navajo, Ute, and people whose names we don’t have. Bighorn, riders on horseback (so some of these are after 1600), six-toed footprints. The Navajo name is Tse’ Hone, “rock that tells a story.”

It’s free. No hike. Most people take the photo and keep driving to the park. Stand there long enough and it stops being a photo op and starts being what it is: 2,000 years of people saying “I was here,” on land that was theirs before it was anyone’s park.

It’s worth remembering that the parks are on their land.

No touching, no chalk, no climbing the fence. 

✨✨Save this for your Utah trip✨✨
We took a random dirt road in Idaho with no plan, We took a random dirt road in Idaho with no plan, no destination, and 3 dogs who have opinions. Obviously, we had a great time. 😂

Mud Lake, Idaho. A two-track through the sagebrush, antelope in the distance, a sky that looked like that, and the Harvest Moon rising pink on the other side while we were still watching the sunset.

Not another person in sight. Nothing on the itinerary. Absolutely nowhere we needed to be.

And honestly? This is the whole point of living the lifestyle we do! But we we’ve been doing this since our 3rd date 💚🌲

The national parks are incredible. But some of our favorite memories happen on roads with no signs, no crowds, and no idea where we’re going.

Just us, the dogs, and a whole lot of dirt roads left to explore.

Want more of these little nowhere adventures? Because we’ve got a lot of dirt roads. 🤙
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