The Well Worn Shoes

Wanderlust Welcome

  • Home
  • Start Here
    • About
    • Contact
    • Work With Me
    • Disclaimer
    • Affiliate Disclaimer
  • National Parks
    • Acadia
    • Yellowstone
    • Great Smoky Mountains
    • Grand Canyon
    • Utah National Parks
    • Badlands
  • Dog Friendly
  • Road Trips
    • One Day In Guides
  • Destinations
    • United States
      • New England
      • Southwest
      • South
      • Mountain West
      • Midwest & Great Lakes
      • Mid-Atlantic
    • Canada
  • Gear
  • Shop

October 10, 2023

8 Charming Vermont Towns To Visit In Fall

Vermont in the fall means vibrant forests bursting with reds, yellows, and oranges. It means nature, mountains, and all things apple cider. But there is even more to this pristine part of New England that includes historic covered bridges, maple syrup, and an abundance of hiking trails. Vermont has many charmingly beautiful small towns to explore during the fall season. Keep reading for the top 8 Vermont towns to visit in the fall. 

Top 8 Vermont Towns To Visit In The Fall
 [show]
  • Best Time To Visit Vermont For Fall Foliage
  • 8. Burlington
  • 7. Waitsfield 
  • 6. Peacham 
  • 5. Brattleboro 
  • 4. Grafton 
  • 3. Manchester 
  • 2. Stowe *My Favorite*
  • 1. Woodstock *My Second Favorite*
    • Like This Post? Pin It For Later

Best Time To Visit Vermont For Fall Foliage

While peak foliage is different every year, Vermont reliably sees its best fall colors beginning in late September in the northern part of the Green Mountain state. The leaves slowly transition through mid-October in the southern part of the state. 

Check Out the Vermont Fall Bucket List

Top 8 Vermont Towns To Visit In Fall 

8. Burlington

The beautiful lakeside town of Burlington is bustling with outdoor activities and fantastic urban culture. Not to mention, it is surrounded by the most impressive fall foliage. You will find everything from apple picking to art galleries to live concerts in Burlington, there is truly so much to see and do. Check out the long bike path for the perfect place to go riding or take a stroll among the spectacular foliage. Or get a different vantage point and take in the beautiful leaves from the eastern shores of Lake Champlain. 

7. Waitsfield 

If you are looking for a storybook town for your fall foliage escape to Vermont, you will love Waitsfield. Nestled in the Mad River Valley, Waitsfield is located between the Northfield Mountains and Green Mountain Range, and it offers some of the most spectacular fall foliage in Vermont. Waitsfield is also home to some of the Green Mountain State’s famous covered bridges.

This includes the beautiful Pine Brook and Big Eddy bridges. Make sure to take a laid-back stroll along the Mad River Path for truly epic autumn scenes. Take the 9-mile path to the south of the town, where you can feast your eyes on a gorgeous waterfall. As an added bonus Route 100 is the main road through town (backlink to the Guide To Driving Route 100 article in the PLR pack). 

6. Peacham 

Peacham is located in the Northeast Kingdom of Vermont and is filled with quaint cottages and charming stories. Peacham is one of those places where if you’ve been in the fall once, you just keep wanting to come back for more. One of the best ways to explore the town’s most impressive fall trips is catching Peacham’s Fall Foliage Day, usually held in early October (but this varies every year). This is a sleepy small town that is surrounded by epic fall colors. Head to the Peacham Fire Station and explore the field behind the station. You can enjoy the magnificent foliage views from any one of the hills, gorgeous mountains, or rolling fields.

5. Brattleboro 

If you are looking for a quintessential Vermont experience, you will absolutely love Brattleboro and its location in the middle of vibrant and flourishing forests.  The town offers many fall experiences and activities. There are several amazing hikes and walks through the gorgeous forests, and rolling hills, or you can visit one of the beautiful historic farms that surrounds the town. If you are looking for magnificent vistas and amazing wildlife you’ve come to the right place. Make sure to check out Pisgah State Park, and Mount Wantastiquet, to get panoramic views of the town and the river valley during your time in Brattleboro. 

4. Grafton 

In the rolling hills of southern Vermont, you will discover the must-visit town of Grafton. Fall in Grafton means gorgeous foliage, rich history, incredible dairy, and a fantastic art scene. There is so much to experience during the fall thanks to the spectacular nature that surrounds the town. This includes beautiful gardens and hiking trails leading to stunning forests and parks. Start your adventure at the Grafton Trails & Outdoor Center where you can enjoy over 2,000 acres of natural beauty bursting with fall colors. Make sure to visit the Nature Museum to enjoy some of the most breathtaking fall views in Grafton.

3. Manchester 

You will find Manchester nestled in the southern Great Mountains, the town offers some truly spectacular fall foliage, as well as fall activities. The entire town is surrounded by mountains, making it a perfect leaf-peeping paradise. The picturesque rolling hills offer a magnificent display of vibrant colors, and beautiful trails with 360-degree views of the Green Mountains, the Manchester Riverwalk, and the Taconic Mountains. Of course, you do not want to miss the seasonal favorites cider donuts, apple pies, or pumpkin-inspired desserts.

2. Woodstock *My Second Favorite*

Do you want to feel like you’ve walked into an episode of Gilmore Girls? How about Practical Magic or a Halloween Hallmark movie? Welcome to charming Woodstock, a town offering the quintessential fall experience. From the historic Billings Farm & Museum to the Marsh-Billings Rockefeller National Historic Park there is no shortage of things to do in Woodstock.  Fall is the perfect time to see Mount Tom ablaze in beautiful colors, and there is no better way to experience foliage than hiking this mountain. Don’t forget to stop a few of the town’s idyllic-covered bridges along the way. 

1. Stowe *My Favorite*

Located on the slopes of the state’s highest peak, is the picturesque village of Stowe – the perfect spot for a fall getaway. Plan your trip from late September to mid-October and enjoy the town’s colorful blanket of leaves while grabbing some fantastic cider donuts at the famous Cold Hollow Cider Mill. Stowe is brimming with vibrant colors and breathtaking views. The village of Stowe boasts over 45 hiking trails and over 65 miles of biking trails to allow for an epic fall adventure. Make sure to drive through Smuggler’s Notch for the amazing foliage views. 

To read more about Stowe check out my Stowe Vermont: A Charming New England Day Trip

Whether you want to explore Vermont’s great outdoors, shop in charming small towns, or learn about the rich history of the quintessential Green Mountain State, you will surely leave a small piece of your heart in Vermont during the fall. With brilliant foliage, quaint B&Bs, covered bridges, and panoramic mountain views the Vermont towns listed above truly exemplify everything the region has to offer.

Have you been to Vermont? Which of these small towns is your favorite?

Like This Post? Pin It For Later

Vermont| Vermont Fall| Best Vermont Towns| Best Vermont Towns Fall| Fall Travel| Fall Travel Guide| Charming Towns Vermont| 8 Can't Miss Towns| The Most Charming Towns To Visit In Vermont This Fall

Posted In: New England · Tagged: Fall, Fall Colors, Fall Travel, Fall Travel Guide, New England, Vermont

Get on the List

Leave a Reply Cancel reply

You must be logged in to post a comment.

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!

Join the List

Let's be friends! I know e-mails can suck but mine won't and I promise cute pup photos too!

Connect

Recent Posts

  • The Bar Harbor Cheat Sheet: Everything You Need To Know Before You Visit
  • The Complete Guide to the Best Bars in Bar Harbor, Maine
  • The Complete Guide To Getting Out On Frenchmans Bay
  • The Best Sunset Spots in Acadia National Park
  • One Day In Acadia With Dogs: A Local’s Itinerary

Categories

  • Destinations
  • History
  • National Park Love

Reader Favorites

One Day At Zion National Park

The First Timers Guide To Grand Canyon National Park

5 Things Not To Miss On Your First Visit To The Grand Canyon

Lamar Valley, Yellowstone: The Wild Heart of the Park

On the Blog

  • Destinations
  • History
  • National Park Love

Join the List

The Well Worn Shoes is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.

Connect

We came around a bend and saw what looked like fog We came around a bend and saw what looked like fog settled across the prairie. So, naturally, we pulled over.

It wasn’t fog.

It was the biggest bison herd either of us has seen in @theodorerooseveltnps. Slowly materializing out of the mist while the sunset turned everything gold.

Stay a little longer and the whole prairie starts telling stories. Young bulls running and shoving each other around like brothers. Calves curled up in the grass for a nap. Massive bulls hanging back while the herd kept moving.

An entire world, unfolding right in front of us.

And there was almost nobody else there.

Named after my favorite president, Theodore Roosevelt National Park somehow still flies under the radar. Fine by me.

Some places don’t need bigger crowds. They just need people willing to pull over when something looks a little different.

What’s the most underrated national park you’ve ever been to?
6 months on Mount Desert Island changed my perspe 6 months on Mount Desert Island  changed my perspective on Bar Harbor and Acadia 🦞✨🦞

I’d already written about Acadia. Then I stayed there and found out how much of it was wrong, or right in a theoretical way that falls apart the second you try to park at Sand Beach in August.

So I rewrote everything, every post, and the guides I wish I had in 2011 on my first visit. 

The guides are live today. Day plans, real distances, dog access mapped trail by trail, 2026 dates, and the parts I’d tell you to skip.

Link in bio - Message me with any questions! 🦞✨

Where are you headed - the town of Bar Harbor, the park, or both? Hopefully both 😁
Six months on Mount Desert Island changes the way Six months on Mount Desert Island changes the way you see Acadia.

You stop chasing the busiest overlooks. You stop fighting for parking. You find the hikes you don’t have to wait in line for. You learn that the park before breakfast and the park at noon might as well be two different places.

Comment LOBSTER and I’ll message you a direct link the Bar Harbor/Acadia Cheat Sheet! 

👀 Keep your eyes peeled tomorrow for the Bar Harbor and Acadia Guides that I WISH I had for my first 10 trips into Bar Harbor and the park.

What’s one place you’d love the “here’s what I’d tell my best friend” guide for? 🧡
The free Bar Harbor/Acadia Cheat Sheet 🦞 It’s got The free Bar Harbor/Acadia Cheat Sheet 🦞

It’s got the places worth your time, the ones I’d skip, the sandbar you have to time with the tide, the trail almost nobody talks about, the bar hidden inside a gift shop, where to eat, and where your dogs are actually welcome.

Download it to your phone before you go, no cell service needed.

I didn’t just visit Bar Harbor. I lived there for six months, wandered the side streets, chased way too many sunrises, and learned the difference between the places everyone recommends and the ones you’ll still be talking about after you get home.

🦞 Grab the free cheat sheet at the link in my bio, or comment LOBSTER and I’ll send you the link.

The full Bar Harbor and Acadia guides are coming soon (next week-ish), but this is where I’d start.

Who’s got Bar Harbor on their road trip list? 👇
3 years of chasing sunsets from the road… …and the 3 years of chasing sunsets from the road…
…and they still ruin my schedule.

This Ruidoso sunset at Alto Lake did not disappoint. What made it even better? Wild horses showed up with a colt! See video in stories 😍

Every single time the sky starts showing off, I’m pulling over like it’s my first road trip. 

Some things are worth being late for.
Follow on Instagram

Copyright © 2026 The Well Worn Shoes · Theme by 17th Avenue