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
    • Road Trip Itineraries
  • 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 Ultimate Dog Hiking Gear List For National Parks
  • The Ultimate New England Fall Road Trip: A Six-State Foliage Loop (2026)
  • The Girls Trip Guide to Bar Harbor & Acadia National Park
  • Acadia National Park October Guide: Fall Colors, Weather & What to Pack
  • The Bar Harbor Cheat Sheet: Everything You Need To Know Before You Visit

Categories

  • Destinations
  • History
  • National Park Love

Reader Favorites

Things to Do in Salem, MA in October: An Honest Guide to the Witch City in Fall (2026)

6 Best Dog-Friendly National Parks to Visit This Winter

18 Best Things to Do in Bar Harbor, Maine - sunset over a tranquil harbor near Acadia National Park captures the magic of Maine's coast, from lobster boats at anchor to pink granite shores and golden skies

The 18 Best Things to Do in Bar Harbor, Maine

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

October in Acadia is Disney World busy. Most peopl October in Acadia is Disney World busy. Most people lose the day to it because they do things in the order the map suggests, not the order the crowds do.

So steal my one fall day in Acadia. This is the one fall day I’d plan for a friend: sunrise from the cliffs instead of the summit, one real hike before 9, east side or quiet side, your pick, out of the park when it peaks, tide pools in the afternoon, and a sunset nobody else is at.

Every date, reservation window, and closing is in the Acadia & Bar Harbor In Fall guide in 16 pages, $27, written after six months on the island.

Comment 🍁 FALL 🍁 and I’ll send you the link! 

Happy Adventuring! 😁
Everyone books Cadillac for sunrise. While I under Everyone books Cadillac for sunrise. While I understand why, if you don’t get that reservation, I promise there are other amazing spots to see sunrise at Acadia! 

My personal favorite: Otter Cliffs. Park at Otter Point, walk two minutes on Ocean Path, and you’re standing on 110 feet of pink granite with the Atlantic doing the whole show below you. 

No $6 reservation, no 10 am refresh two days out, no line of headlights up the summit road at 5:30. Just you, the rocks, and whoever else figured this out, which in October is almost nobody.

The light hits the cliffs from the side instead of coming up over a parking lot. Dogs on leash are fine on Ocean Path. Bring the headlamp and a real jacket; the wind off the water in the dark is a different temperature than the forecast said.

Sunrise is around 6:30 right now and slides toward 7 by late October. Be there at least 20 minutes early, and take it from someone who is always racing the sun, 30 mins early is even better. The 10 minutes before the sun clears the horizon are the ones you’ll remember the most, I promise 🌅☀️

☀️ Save this for your Acadia trip ☀️
🌲🦉 Targhee National Forest, Idaho side. The stretc 🌲🦉 Targhee National Forest, Idaho side. The stretch between West Yellowstone and everything else, which most people do at 65 with the cruise on.

We turned onto a dirt road at sunset because that’s the whole point of living the lifestyle we do. But to be totally honest, we’ve been doing this since our 3rd date. 

Skies like this, the back side of the Tetons, and a Great Gray Owl sitting in a field watching. 

You don’t need a reservation for this. You need to slow down on the way to the famous thing.

✨Save it for your next Yellowstone drive✨
🍁🍂 Some of my favorite days are never the perfect 🍁🍂 Some of my favorite days are never the perfect ones.

This one started with the Artists Bluff hike, coffee, and a pup cup for Bama. Then we put on something moody and drove the Kancamagus straight into the fog.

You couldn’t see a thing from the overlooks. No sweeping views. No postcard-perfect October day. Just gray skies, wet roads, and Bama beside me.

And somehow, it’s still one of the best days I ever had in the White Mountains.

Bama’s been gone since 2020 🐾🪽, but I think about that drive more than almost any bluebird day since. Maybe because the day wasn’t perfect. It was just ours.

7 New England autumns taught me this: fog isn’t ruining the mountains. It IS the mountains. Embrace it. 

The postcards are the exception. In October, the Whites can be gray, moody, wet, and ridiculous in the best way. The road itself is worth the drive, 34 miles of color in layers, neon maples against the gray, and empty pullouts because everyone else is waiting for the fog to burn off.

It usually does by 10. Don’t wait for it.

Fill the tank in Lincoln. There’s nothing for 34 miles, and the fog does not care about your gas gauge.

🍁✨🍁 Save this for October. 

🍁 For the full six-state route, closure dates + Google Map Companion for when your signal drops, comment LEAVES
I lived in New England for 7 years, and every Octo I lived in New England for 7 years, and every October I watched people make the same mistakes.

Wrong direction. Too many towns. A gate closed 3 days before arrival. And that one farm photo everyone swears you can still get…except you can’t.

Every year I also had a handful of visitors who wanted to see this town or go to that festival in the fall, and I’ve explored SO many of them. Fall was my favorite in New England

So I made the version I’d actually hand a friend or tell them over coffee, because that’s why I do here 🍁🧡

🍁 A six-state clockwise route
🍁 7-day + 10–14 day itineraries
🍁 2026 closures + reservation windows in one place
🍁 Dog-friendly stops (and the four that absolutely are not)
🍁 What to do when your trip slips a week and the mountains have already moved on

🍁✨Plus a Google Map companion with every stop, because “no service” and “where the hell are we?” tend to arrive together.

The Ultimate New England Fall Road Trip Guide is 19 pages of all of the best New England has to offer in the fall. 

🍁🍂 Comment LEAVES and I’ll send you the direct link.
Follow on Instagram

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