Travel

Vermont Fall Travel Guide

The lovely Woodstock Inn.

For years I’ve seen gorgeous photos of Vermont on Instagram and I’ve been dying to visit. Especially through the eyes of those who live in New England! (Some of my favorites IGers include @jackiegreaney, @pjhavel, @theyellownote, @kjp & @abbycapalbo)

This year Emma and I were lucky enough to plan a fun 4-day trip to the Green Mountain State (which looked more orange & red when we were there) and we LOVED every minute of it! We flew into Burlington and began our road trip. We visited Stowe, Woodstock, Manchester, and Bennington – and drove through some of the most scenic routes along the way. We decided to write a ‘Vermont Fall Travel Guide’ to help you plan a New England getaway of your own!

Fall Foliage Planning

You definitely want to think ahead if you’re planning on visiting Vermont during the fall foliage season. There’s a window of around 4-5 weeks where the leaves are bright and beautiful throughout the state.. usually from mid-September through the first 2 to 3 weeks of October. Before we planned our trip we followed THIS Vermont fall foliage tracker which really helped us settle on dates. This year the foliage was at peak while we were there during October 7-10.

Important to note: Foliage peaks at different times throughout the state. The Northern sections peaks a couple weeks earlier than the southern, and higher elevations peak earlier than lower elevations.

Where to Stay

There are so many cute places to stay along your Vermont road trip… from the North to the South there are plenty of adorable towns filled with bed & breakfasts, AirBnB’s and Inns to choose from. In Vermont I am a bigger fan of the Inn-style accommodation – I prefer the more personalized attention from Innkeepers. They always know the best places to go, scenic routes to take, etc.

Northern

  • The Green Mountain Inn – Located in Stowe. Built in 1833, this Inn is gorgeous and so cozy. Love the decor they offer during the holidays.
  • Inn at Shelburne Farms – Located in Shelburne, about 20 miles north of Burlington. Beautiful property located at the extremely popular Shelburne Farms.
  • Edson Hill – Beautiful Inn located in Stowe. Sits on 38 acres, 22 guest rooms, elegant and beautiful. Wish we had stayed here while visiting Stowe!

Southern

  • Four Chimneys Inn – Located in Bennington. We stayed here and fell in LOVE! Click here to read our entire review on it & the local area.
  • The Equinox, A Luxury Collection Hotel – Located in Manchester. Built in 1749, elegant accommodation & 5 restaurants on-property!
  • Barrows House – Located in Dorset. Gorgeous 9-building Inn with lots of room options. Dorset is a super cute village/resort town and close to many other locations.
  • The Woodstock Inn – Located in Woodstock. This inn is beautiful & in the classic town of Woodstock. All of the homes here and stores are Instagrammable & everyone needs to stop here.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!

Where to Go/What To Do/Eat

There are so many places to stop along the way while leaf peeping in Vermont! I will be getting into detail about each place we loved & places we we have heard are amazing but didn’t get the chance to stop at below.

Must-See Towns

Stowe: a charming town located between all of the different mountain ranges in the north. It is famous for skiing, and family fun. 200 year old village. Easy to get to from Burlington and a great first-stop on the fall foliage trip.

Things to do near Stowe:

  • Cold Hollow Cider Mill – One of Vermont’s most popular tourist attractions. Adorable place – they make amazing apple cider donuts and delicious cider (we had both and loved them!). Lots of local goodies to be purchased for friends & family.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Smuggler’s Notch Drive – We ran across this road by accident and fell in love with it. A beautiful mountain drive with lots of stop-offs to take photos. Gorgeous fall foliage and dramatic views.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Gondola Skyride at Stowe Resort – Head to the top of Mt. Mansfield, Vermont’s highest mountain, and enjoy the view of the colorful fall foliage. We were amazed by the beauty here! At the top they have quite a few different hiking trails.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Drive around & take in the views – We loved driving around in our rental and stopping off at random little farms, roads, fall foliage views, and more. This area is beautiful and one of the more scenic spots we visited.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Visit the Von Trapp Family Lodge – yes, the same family from The Sound of Music! They settled here after the war and built a lodge. The original lodge burnt down in the 80s. They built a larger and updated lodge in it’s place. Lots of little sheep, walking trails, and beautiful scenery.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
One of our favorite little shops.
  • Stop off at cute shops along the way – We loved visiting little family-run stores like Stowe Maple Products (yum!) and antique stores around the area.
We loved The Bench in Stowe.

Where to Eat/Drink in Stowe:

  • The Bench – Amazing food & great drinks! Loved the atmosphere of this place. Cozy with great service. Extremely popular with locals. Definitely order something woodfired – if they offer the Salmon, it’s to die for!!
  • The Dining Room at Edson Hill – Many of my friends have stayed at this property and raved about the dining. Beautiful and yummy food with a lovely atmosphere.
  • The Bistro at 10 Acres – Delish food, lots of Vegetarian options. Cozy atmosphere and popular in the area. Casual dining.
  • Cork Wine Bar – Cutest little place to taste wine & snack on appetizers.
  • Vermont Artisan Coffee & Tea Co. – Cool spot outside of the main area of Stowe. Emma and I stopped here on our way out and LOVED the coffee.. so amazing. Huge compound where they roast their own beans as well, they also offer classes on coffee here.
  • Idletyme Brewing Co – Vermont surprisingly has a lot of great craft beer options locally and this place looks awesome and casual. A perfect spot to grab a beer.
Lovely hydrangea in Woodstock.

Woodstock – This town is absolutely adorable and looks like it came straight out of a movie. It has a traditional town square, historic buildings, covered bridges, adorable shops, and beautiful homes located in neighborhoods throughout.

Things to do in/near Woodstock:

  • Visit the Woodstock Inn – Not only one of the cutest places to stay in Vermont, but it’s also one of the most insta-grammable! Especially in the Fall when they place a ton of gorgeous warm-colored mums in the iconic front yard. A must-do while traveling through Woodstock.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
The Middle Bridge.
  • See the Covered Bridges – There are 4 covered bridges around the Woodstock area. 1 of which is actually in town – the Middle Covered Bridge. A Vermont staple (there were over 600 at one point in the state!) and it’s fun to walk across the bridge and see the traditional methods in which is was built.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Window Shop – Tons of cute shops line the streets in Woodstock, and we fell in love! Some of our favorites include the Clover Gift Shop which was established in 1928 and is filled with lots of local home goods, Yankee Bookshop which has been open since 1935, and The Vermont Flannel Company.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
Gorgeous homes.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
The residents go all out in Woodstock for Fall/Halloween..
  • House Stalk – There are so many quaint and historic homes in the area. Emma and I loved walking around taking pictures. If you visit during the Fall you’ll notice that many of these homes go all out decorating their front porches, fences, and anything they can place a pumpkin on.
  • Visit Simon Pearce – Located in nearby Quechee, you can stop in and see all the talented glassblowers at work. Very beautiful location on the river!
  • Hiking – If you hike up Mt. Tom (which is just 30 minutes from town – the trail begins on Mountain Ave behind the covered bridge) you can see a beautiful view of Woodstock from the summit. There are crazy amounts of gorgeous trails back there and snow-shoe opportunities during the winter.
  • Visit Billings Farm & Museum – This farm is adorable with sheep-shearing and butter churning.. it’s a blast from the past! Lots of fun activities and it’s very pretty.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!

Where to Eat/Drink in Woodstock:

  • The Prince and the Pauper Restaurant – Long regarded as one of Vermont’s finest restaurants. Request a reservation in advance – amazing food and adorable atmosphere.
  • Melaza Bistro – Casual dining where New England cuisine meets tropical flavors. Relaxing front patio.
  • Mon Vert Cafe – Cute café located on one of the main shopping streets. Always packed and it has busy offering both breakfast & lunch!
  • The Mill at Simon Pearce – Located in nearby Quechee – super popular place to eat dinner and lunch. It was voted “One of America’s most romantic restaurants” by Travel + Leisure. Make reservations in advance!
  • Mangalista – Delicious food and dining experience. Voted #1 restaurant in Woodstock according to yelp!

Manchester – Upscale shops, Inns, and restaurants fill this town. It’s also a beautiful skiing area with 2 popular resorts w/ ski runs nearby. Relaxed ambiance. beautiful foliage. We spent a day here and enjoyed it.

Things to do in/near Manchester:

  • Visit the Vermont Country Store – Only 30 minutes away.. this store is one of the most popular spots in the whole state. Located in Weston. Huge compound with the best Vermont goods.. cute photo ops, and more. Family owned since the 40’s.
  • Explore Hildene, the Lincoln Family Summer Home – Emma and I toured this beautiful estate and it was a highlight of our trip. We loved every minute of it.. so much history here. The home is in beautiful condition and it’s a Vermont must-do! The views from behind the estate of the mountains and fall foliage are to die for.

  • Take one of the beautiful day hikes – So many amazing hikes throughout this stunning region to choose from. If you’re more of an outdoorsy person then this is the spot for you!

  • Shop ’til you drop – There are many adorable local shops and stores here to enjoy. Some of the cutest? Northshire Bookshop, Miss Phyllis Fine Linens and Frocks, and Mother Myrick’s Confectionary.

Where to Eat/Drink in Manchester:

  • Ye Olde Tavern – 1790 colonial restaurant featuring New England fare. Located in a historic home. Delicious food and cozy ambiance.
  • The Copper Grouse – Comfort-food located in a tavern. Very casual and yummy.

Old Bennington – Emma and I stayed at the Four Chimneys Inn and loved the area. Everything is darling and picturesque. So many fun things to do nearby.. It’s a great place to stop through if you’re on your way to New York or Massachusetts. The town borders both states.

Things to do in/near Bennington:

Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!
  • Old First Church – Make sure to visit Old First Church. This beautiful and historic church is a short 5 minutes walking distance from the Four Chimneys Inn. It’s the first church built in Vermont in the early 1800’s. If you’re a fan of poets, the cemetery is where Robert Frost’s gravesite is located.

  • Bennington Potters – 1 mile away from Four Chimneys Inn. Visit the largest working craft pottery in the U.S.

  • Bennington Museum – Walking distance from the Inn. Bennington is rich in history and there is so much to learn about the area here.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!

  • Hildene, the Lincoln Family Home – Lynn recommended that we visit Hildene and we’re so happy that she did! Abraham Lincoln’s oldest son, Robert Todd Lincoln built the estate as his summer home in 1905. It’s stunning and full of history with many famous people visiting over the years. Today you can see the estate with over 90% of the original furnishings. They’ve made sure to keep the interiors designed the way the family kept them. The gardens are formal and the surrounding mountains are the perfect backdrop for photos.

  • Robert Frost Stone House Museum – around 7 miles from the Inn. Literary landmark, Frost resided in the home from 1920-1929 during which he composed the extremely famous poem, “Stopping by Woods on a Snowy Evening.”
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!

Where to Eat/Drink in Bennington:

  • Pangaea – Delicious food and cozy atmosphere. You can choose whether to eat at the ‘fine dining’ restaurant side (We ate here, you can wear jeans. Just really good food!) or head next door to the Lounge.
  • The Country Club – Beautiful views of the local golf course with great food. Decorated beautifully around the holidays.
  • Allegro Ristorante – Located in Downtown Bennington. When you walk in you might not be impressed by the decor.. but the food is out of this world! Make reservations the day before – SO popular. Can’t emphasize how good the food is.
Vermont Fall Travel Guide | Fall Foliage guide, best inns & hotels, top restaurants to eat at, and all the cute towns/places to stop along the way!

Best Scenic Drives in Vermont

One of the major draws to visiting Vermont is that it’s an easy state to navigate. It’s smaller size allows you to reach state line to state line within a few hours and with it’s small population driving is enjoyable. :) The state has many beautiful scenic driving routes to explore.. especially during the fall when the trees are putting on a show. We loved renting a car and driving everywhere our hearts desired. Here are some of the most popular scenic drives:

  • Scenic Byway 100 – The most well-known scenic drive in Vermont. It runs the length of the state from the south to central Vermont for 146 miles. It is the most popular foliage drive in Vermont.
  • Smuggler’s Notch – A gorgeous 18-mile scenic road from Stowe. Closed in the winter due to snow. We took some of our most favorite shots here.
  • Middlebury Gap – Route 125 is a stunning road full of fall foliage in the middle of the state.

We hope that this Vermont Fall Travel Guide helps you plan for your next trip to the Green Mountain State! We fell in love with the beautiful fall foliage, adorable towns, and all the sweet people we met along the way. Comment below & let us know what some of your Vermont favorites are.. we love hearing from you!

xo,
Kristy & Emma

Thoughts?

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13 thoughts on “Vermont Fall Travel Guide

  1. Dear Kristy & emma,

    This is perfect! Just what I needed. You could trun this guide into a book. :) I will refer to this guide when I plan my trip. Thank you so much. Stunning!!
    Hugs,
    Cassy

  2. What an amazing guide. You reallY got EVERYTHING exactly right! And those photos!! Beautiful! And thank you so much for including our inn and ouR little town. So hAppy you are planning a trip back next year!!!! Yay!! Lynn

  3. It was a pleasure to read your article and to look at These beautiful Pictures. I would like to visit Vermont in one day.
    What camera or phone do you use to take these great PICTURES?
    Kisses

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