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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*
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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?

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