Top Vermont Fall Foliage Towns

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Top Vermont Fall Foliage Towns

A person can spend years wandering the scenic backroads of the small state of Vermont and never get to see everything in every magical season. I truly enjoyed my time exploring the gorgeous state during the leaf-peeping season and made a list of the best towns to see in Vermont in the fall.

Roadtrip through Vermont

United States Fall Foliage Map

Also, when planning a time to start your travels, consult the fall foliage map that Smoky Mountain National Park provides. This map shows you the color stages throughout the United States in which the leaves will be during each week of the fall.

Camera Gear Needed to Capture Colors

A circular polarizer is essential for capturing fall colors because it reduces glare and helps enhance color. One of my go-to’s is the Polar Pro Circular Polarizer

Another must-have is a really good tripod. If you are like me, I hate lugging around a bunch of stuff that just seems to get in the way. This tripod from Peak Design is a perfect size for travel and is very lightweight. 

The last piece of equipment that is useful is a versatile camera lens. One of my favorites is the Canon RF 24-70mm f/2.8 lens

Start in Bennington

Top Vermont Fall Foliage Towns

Full of revolutionary war history and scenic mountain views this town ranks at the top for one of the best towns to visit in Vermont. Thomas Jefferson and James Madison actually stayed at the Walloomsac Inn, the oldest inn in Vermont, which has long since been sliding into ruin.

Old First Church

Top Vermont Fall Foliage Towns

Originally built in 1762 as the first Protestant church in Vermont, it has served as a place of worship, school, court, school, and a meeting house. During the battle of Bennington in the Revolutionary War in 1777, the structure served as housing for wounded Hessian mercenaries. The current church was built in 1805 and was designated as “Vermont’s Colonial Shrine” in 1935.

Top Vermont Fall Foliage Towns

Robert Frost, the poet, spoke at the rededication and is buried with his family behind the church. Plaques honoring prominent Vermonters are located throughout the structure.

Location: 1 Monument Circle, Bennington, VT 05201

Hours: Monday through Saturday 10 a.m. – 4 p.m., Sunday 1 p.m. – 4 p.m.

Old Bennington Cemetery

Wandering through the oldest cemetery in Vermont is like wandering through the pages of history. Beautifully preserved headstones and memorials are scattered around a gorgeously sloping hill intertwined with stunning fall foliage.

Top Vermont Fall Foliage Towns

The cemetery is one of true character. Casualties, from all sides, during the Revolutionary War are buried here. There are also five Vermont governors and even a victim of the Titanic, Charles Cresson Jones. There is even a stone memorializing David Redding, a Loyalist, that was executed in 1778.


Home of the earliest gravestones that were carved by Ebenezer Soule, a fourth generational carver. His stones are recognized by wigged heads that stare blankly back at you with wings spread underneath them. The most prolific carver is Zerubbabel Collins who was the son of a stone carver and had moved to Vermont in 1778. Stone carvers charged by the letter so markers could get very expensive.

One of the most prominent graves is that of Robert Frost and his family. I absolutely love the inscription in the stone, “I had a lover’s quarrel with the world”. Frost was born in San Francisco in 1874 and moved to the New England area in 1912 to pursue his literary career. He attempted farming but did not have much success. Instead, he put all his energy into constructing beautiful poetry.

Top Vermont Fall Foliage Towns

When his wife, Elinor, passed away her wishes that her ashes be scattered at a farm Derry, New Hampshire was denied. Robert located and visited the farm and found it to be in total disarray and not a suitable resting place. Instead, he waited for a plot to come available in Bennington for him and his wife. He was not known to be a devoutly religious individual which is why it has been speculated, that his headstone faces away from the church. While you are in this town leave time to check out Robert Frost’s home that is nearby.

Top Vermont Fall Foliage Towns


Four Chimneys Inn  

21 West Road

Bennington, VT 05201

(802) 447-3500 extension 1


Norman Rockwell chose this town to be his home between 1939 and 1953. It was here that he actually painted some of his more famous works including, The Four Freedoms.

The Norman Rockwell Exhibition can be found on Route 7Awhere not only his artwork can be found but also history on the more than 200 Arlington citizens that served as his muses.

While in the area, check out the Sugar Shack. This shop offers locally sourced maple syrups and homemade goods.

Top Vermont Fall Foliage Towns

Do not miss the beautiful covered bridges in the vicinity. One of the oldest surviving covered bridges in the state is the Arlington Green Covered Bridge. Built in 1852, this bridge spans approximately eighty feet over the Battenkill River.


This town makes for a perfect fall day experience in Vermont. There are local breweries, art galleries, hiking trails, and a quaint downtown.

Top Vermont Fall Foliage Towns

Check out Bromley Mountain to see sweeping views of the fall colors over the mountains. Pick any country lane to explore, you will not regret it.

Top Vermont Fall Foliage Towns

Also, of interest, is the Hildene House which is the former estate of Todd Lincoln, President Abraham Lincoln’s son. The home covers over 400 acres and includes gardens, a carriage barn, a 1903 Pullman train car. Inside the mansion, visitors can see President Lincoln’s stovepipe hat.


The Copper Grouse

3835 Main Street

Manchester, VT 0524


Kimpton Taconic Hotel

3835 Main Street

Manchester, VT 05254


This is one of my favorite towns in Vermont! I absolutely love the quaintness of the town and the quintessential downtown area.

Dorset Quarry

During the summer months, this is a popular swimming hole. However, during the fall it offers a beautiful display of colorful foliage among the large boulders.


White clapboard houses with porches decorated for fall embody this cheerful town.

Local drives

Top Vermont Fall Foliage Towns

Check out the Dorset Hollow road loop which encompasses the Upper and Lower Hollow Road for great leaf-peeping opportunities. If you have time, check out Darby Mountain Road that offers dramatic views of the countryside.


Dorset Rising

Bakery and Cafe

3239 Route 30

Dorset, VT 05251

Top Vermont Fall Foliage Towns
Chantecleer Restaurant

8 Read Farm Lane

East Dorset, VT 05253

Top Vermont Fall Foliage Towns


A Vermont fall foliage trip would not be complete without a stop in this lovely town!

Woodstock, also one of my favorite towns, is considered to be one of Vermont’s most prized possessions. It is truly known as the quintessential New England village. Gorgeous homes, old farms, a covered bridge, and a village green make up this picturesque town. 

It’ll stop you in your tracks.  It may even cause your camera shutter to stutter. 


Visit a farm

The Billings Farm and Museum holds an annual Harvest Weekend each weekend throughout September and October. Visit the apple orchard, walk along the Ottauquechee River Trail, and take in the experience of 19th-century farming.

Check-out farm stands are just outside of the downtown area as well.

Visit a farm


If you enjoy antiquing, Woodstock will provide you with hours of enjoyment as you explore several specialty shops along Main Street. Quechee Gorge Village is host to the annual Vermont Antiques Festival over Columbus Day Weekend. 

The Village is home to shops, a toy museum, and much more.  Before you leave, be sure to sample the local Cabot cheese! Make a stop at FH Gillingham & Sons to see all kinds of Vermont-made specialties such as maple candy, souvenirs, and wine.


I must take a moment to talk about the Vermont Flannel Company. My husband, who is not a flannel fan, absolutely lost his mind in this store! We purchased so much that we actually had to ship it all home!  My favorite find was the blankets that we all enjoy cuddling under on colder evenings.

Historic Places

Make sure you stay at any one of the inns that date back to the 1750s. Almost all of the buildings in the town are on the National Register of Historic Places.

Woodstock has been listed as one of the best places to visit at Christmas and one of the most beautiful towns in America by Conde Nast.

Historic Places

Check out the famous pumpkin display

Follow @houseanddog on Instagram and check out their house that is always decorated in a wonderful pumpkin display. This is an 1826 colonial home that has been renovated and a yoga studio added.


The Woodstock Inn

14 The Green

Woodstock, VT 05091

*This Inn also boasts four amazing restaurants and a relaxing spa

The Jackson Inn

43 Senior Lane

Woodstock, VT 05091



I really enjoyed walking around downtown to visit the shops and galleries. There are several farms and farmers’ markets in the area to check out.

Texas Falls

If you enjoy hiking, check out Texas Falls. Located on the Scenic Route 100 Byway, the recreation area offers viewing points for waterfalls and gorges. The Texas Falls Nature Trail loop is about 1.2 miles and the Hancock Trail is about 1.3 miles long and makes for a wonderful walk in the brisk fall air.

Texas Falls


While Stowe is known for its skiing before the snow season starts, it’s fall foliage is stunning!

Vermont in the News

It is known as fall’s “color capital” and has been listed as a top foliage destination in TripAdvisor, USA Today, Travel + Leisure, and U.S. News Travel. This location is one of the best places to truly Vermont in the fall.

Sound of Music

The von Trapps, yes the Austrian singing family of the famed Sound of Music,  settled in Stowe after touring the United States in the 1940s.  Reportedly, because it reminded them of their native country. They opened a 27 room lodge in 1950 and began welcoming guests.

After a terrible fire in 1980, the original lodge was replaced by a new 96 room lodge with panoramic mountain views and many outdoor amenities. This property is still owned and operated by the von Trapp family and remains open to welcome guests. The resort also hosts an annual Trapp Family Lodge Oktoberfest during which Austrian music, food, and beer are served.

Scenic Drives

Take a cruise on the Green Mountain Byway for gorgeous views of mountains and farmland.  

Another great drive is VT Route 100 connecting Waterbury and Stowe which is loaded with plenty of opportunities to stop along the way to take photos of the scenery.

Mount Mansfield
Mount Mansfield

Take the Stowe Rec Path to scale Vermont’s tallest peak. If hiking to that extent is not your thing, you can also drive up to the top using the Auto Toll Road. This is one of the best ways to enjoy Vermont in the fall and all the colors this state has to offer.

There are so many things to see and do in Vermont in the fall; these are just a few ideas! Get out there and explore, there are plenty of hidden gems!

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Kristal Ham

Hi fellow nomads!

Traveler and Photographer

My name is Kristal and I am so happy to have you visit my site! 

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