Vermont Fall Travel Guide: The Best 5-Day Itinerary

GUYS VERMONT IS THE MOST MAGICAL FALL DESTINATION OF ALL TIME. I’m not sure how I’ve lived in New York my entire life and haven’t made it up to Vermont, but now that I have I think it needs to be a yearly tradition. If you haven’t visited add it to your “must visit” list immediately and plan you trip using this COMPLETE Vermont Fall Travel Guide.

The 1954 classic ‘White Christmas’ might have coined Vermont as “America’s winter playground”, but I can assure you it’s the perfect place to visit no matter what time of year it is. Once you finish reading this guide you’ll probably agree with me in saying Fall in Vermont is the absolute best time to visit. Spectacular fall foliage, apple picking and plenty of outdoor activities are just a few of my favorite things about Fall in Vermont.

Vermont Fall Travel Guide

Best Time to Visit Vermont for Peak Fall Foliage

We timed our Fall Foliage trip PERFECTLY and we arrived in Vermont just a few days after peak (the foliage peaked a little early the year we visited because of the cold weather, wind and rain), but it was still perfect. I highly recommend tracking Vermont’s fall foliage maps to properly time your trip. If that’s not possible and you’re planning your trip well in advance I suggest aiming for the last week in September or first week in October if you’re visiting Northern Vermont. And the first or second week in October if you’re visiting Southern Vermont. Lower elevations in the southern part of the state may still have beautiful colors into late October, but for the best fall foliage I would stick to the earlier part of October.

Best Towns to Visit in Vermont

While Vermont is one of the smallest states in the United States, it’s seems much bigger than it actually is because of it’s terrain. It’s home to the Green Mountains (part of the Appalachian Mountains), Taconic Mountains and Coolidge Range which makes Vermont a little harder to get around than a “flatter” state. I suggest when planning your trip to Vermont you either visit Southern Vermont or Northern Vermont so you don’t stretch yourself too thin and end up spending too much time in the car.

Northern Vermont’s most popular towns include Stowe, Burlington, Woodstock, Montpelier and Killington. Southern Vermont’s most popular towns include Brattleboro, Manchester, Bennington and Grafton.

On our fall road trip the main towns we visited were Stowe, Woodstock and Burlington and each town was more perfect than the last. We chose to stay in Stowe and make the short drive to the other towns for day trips which worked out great, but you can also break up your trip and stay in different places.

5 Day Itinerary Northern Vermont in the Fall

While you can easily spend a week or two traveling around Vermont, after reading my 5-Day Vermont Itinerary you’ll see exactly how much you’ll be able to do, see and eat in a relatively short amount of time. I broke down this guide day by day so you can see the best things we did in each small town, where we ate and why it deserves a spot on your fall trip list! 

Day 1

The drive from the New York City area to Stowe, Vermont takes around 5 hours. We left Westchester County, New York around 1pm and arrived in Stowe right around 6pm. If you’re driving from anywhere outside the immediate New England area I would allot a majority of your first day to driving.

We quickly checked into the Field Guide Lodge which we were SO happy we got a room at. It’s located just a short walk from the Stowe’s cute downtown and a great price point for peak season in Vermont.

We had 6:45 reservations at the HIGHLY recommended Edson Hill Restaurant and it was the PERFECT time to eat because it was just getting dark and the back patio looked magical with all the string lights. We ate inside the tavern and was beyond delicious! Their menu changes seasonally so I can’t promise all of the items I recommend will be available when you visit, but I can promise you won’t be disappointed with anything that you order.

Order the Purple Haze to drink (though the Maple Run Margarita sounded VERY appealing too), get the Fried Brussel Sprouts (they’re actually FRIED) and Maple Ginger Salad to start, and then the Seared Salmon or Crispy Duck for your main dish. And save room for dessert because the Dark Chocolate Tart with PUMPKIN CHEESECAKE ICE CREAM was insane! If you’re a foodie like me, Edson Hill Restaurant is one of the best places to eat in Stowe, I can’t recommend it enough

Day 2 – Stowe

One of my favorite perks of staying at a Lark Hotels property is free breakfast. They offer small breakfast bites, fruit and coffee in the lobby and it’s the perfect snack for when you’re getting ready in the morning.

If the Gondola SkyRide at Stowe Mountain Resort is open during your visit it’s a MUST DO! It usually operates from mid June to Mid October, weather depending, and such a unique experience. You can book tickets in advance or get day of tickets in person (I suggest booking in advance). The gondola takes you to the top of Mt. Mansfield, Vermont’s highest peak, where you can dine at the Cliff House restaurant, visit the Summit Retail Gift Shop or enjoy at sweet treat at the Waffle. The peak also offers the best views in the entire state in my opinion, so take your time wandering around and snap plenty of photos.

After coming down it was time to explore downtown Stowe. Stowe has a very walkable downtown with well-preserved historic buildings, boutique shopping, local dining and lots more! We popped into Butlers Pantry for brunch, it’s one of Stowe’s breakfast hotspots and I highly recommend popping in, everything we got was amazing, but whatever you do make sure to order a side of MAPLE SAUSAGE!

After make sure to explore near the Stowe Recreation Path and around Main Street for the best photo opps!

Beer Tasting in Stowe and Exploring Waterbury Center

Another thing Stowe is know for is it’s incredibly breweries! Idletyme Brewing, The Alchemist Brewery, von Trapp Family Brewing, just to name a few and if you like beer I can’t recommend visiting one of these enough. We went to Idletyme Brewing (but looking back I wish we went to The Alchemist). We both got the Brewski Sampler to drink (it’s served on a ski), which had 6 samples of the beer they brew in house. And we split the Fried Pickles (INSANELY GOOD) and the Idle Fries.

During late afternoon we headed towards Waterbury, because we were last minute able to snag a dinner reservation at an insanely popular Vermont restaurant, and stopped at Waterbury Center State Park, if you’re into hiking or canoeing this is a great place to bookmark.

If you go to one restaurant in Northern Vermont have it be, Hen of the Wood! We tried to make reservations there from the second we booked our trip, but had no luck so we set up an alert on Resy so that we would get alerted if anything opened up while we were visiting and were able to nab a 5pm reservation. Though it was definitely earlier than we were hoping we were so happy when we got there because we got to see the beautiful waterfall all the back of the restaurant in the daylight. Hen of the Wood is another restaurant that changes their menu with the season and since our meal was so delicious I can’t imagine ANYTHING being a bad choice. If you see the Cauliflower Agnolotti with Butternut Squash, Romanesca & Breadcrumbs ORDER IT!

Day 3 – Woodstock

We took scenic Route 100 from Stowe to Woodstock because we read it was one of “the most scenic drives in New England” and while it absolutely was, I don’t necessarily think it was worth the extra hour it took to get from Stowe to Woodstock. Everywhere in Vermont is beautiful and unless you plan on stopping along the way I don’t think you need to take it.

Once we got to Woodstock we headed straight Worthy Kitchen for lunch. I highly recommend ordering a local Vermont beer and either the Worth Chikwich or the Kitchen Burger (or both if you’re sharing like we did). So so good and the staff was amazing!

After lunch we drove to Downtown Woodstock, parked near the central square, know as the Green and explored. Woodstock is often called “the quintessential New England town” and once you arrive you’ll understand why. One of the best ways to truly experience it is to just take your time walking around, absorb it all and take lots of photos. Don’t miss the Woodstock Inn & Resort, Middle Covered Bridge, the Ardmore Inn and Pleasant St. Every inch of the little town is picture perfect and absolutely worth spending a few hours in.

Explore Woodstock Farms and Enjoy Dinner in Stowe

If you have time make sure to visit Billings Farm & Museum, a working farm and museum just a scenic stroll from the village center of Woodstock that is dedicated to scientific farming history. Or stop by Sugarbush Farms where you can do a free sampling of 15 cheeses, learn how maple syrup is made, interact with farm animals and more.

Instead of staying in Woodstock for dinner, we drove back to Stowe headed to dinner at Cork. Another AMAZING dinner! We ordered Roasted Corn & Poblano Dip, Dirty Potatoes and Chopped Kale Salad as appetizers and Herb Roasted Chicken and Sticky Shiitake Mushrooms & Broccoli for entrees.

Day 4 – Burlington & Shelburne

We decided to stop along the way to Burlington in Waterbury to pick up sandwiches from Hender’s Bake Shop & Cafe so that we could explore once we got there. If you happen to stop there, get the Salami Sandwich, it’s salami, tomato herb sauce, pepperoncini and ricotta salata and it is out of control good.

Burlington, Vermont is a city in northwestern Vermont, on the eastern shore of Lake Champlain, just south of the Canadian border. The downtown area in Vermont’s biggest city offers a vibrant mix of shops, restaurants and entertainment venues. It is also home to the University of Vermont and is very much a “college town”. It’s progressive and artsy is the best ways possible and a great place to spend the day.

Walk along the Burlington Waterfront or if you’re more adventurous bike the Burlington Bike Path, a scenic 8 mile trail that offers stunning Adirondack views and passes right through downtown.

Explore Shelburne’s Vineyards and Orchards

After exploring Burlington, head just a few miles south to Shelburne. The most popular tourist attractions in Shelburne include Shelburne Farms, Shelburne Museum and the Vermont Teddy Bear Factory, but I recommend visiting Shelburne Vineyard or Shelburne Orchards while you’re in the area!

Shelburne Vineyards is a picture perfect vineyard that crafts responsibly-made Vermont wines and ciders. We reserved a table on the lawn and drank wine flights (we both got the “Rachel”) and local cheese! It was truly the most perfect fall day! Shelburne Orchards is home to a distillery and a great place to go apple picking in the area. Enjoy apple cider, cider donuts and a cute pumpkin patch and even rotating food trucks.

We headed back to Stowe for dinner at Doc Ponds, which was right down the street from our hotel! Order the Charred Broccoli Salad and Salt Cod & Corn Fritters to start, then the Pulled Pork Sammy and Dry Rub Wings for your entree!

Day 5

After a small breakfast at the hotel we packed up the car and went back to the Stowe Mountain area to try and get some drone shots of the fall foliage. There was an easy hiking path off the road at the Barnes Camp Visitor Center that we stopped at.

We stopped in Quechee, VT (just over an hour south of Stowe) to grab lunch at The Skinny Pancake then continued home!

If you have a little more spare time in Vermont before leaving I recommend checking out Smugglers Notch, Ben & Jerry’s (especially the Ben & Jerry’s Flavor Graveyard) and trying one of Vermont’s famous Maple Creemees, a frozen treat made of high-quality milk and high-quality maple syrup.

Restaurants we didn’t get to try but were highly recommended:

Where to Stay in Northern Vermont:

Field Guide Lodge (Stowe)

• Boutique hotel located right in the heart of downtown Stowe.
• Lark Hotel property (one of my personal favorite hotel chains)
• Amenities include free parking, free WiFi, seasonal heated outdoor pool, hot tub open year-round, complimentary light-bite European grab and go breakfast, fire pit area, spacious lounge and more.
• The property has 2 buildings:
  • The Trail House houses luxe suites and cottages, perfect for families and larger parties.
  • The main building, known as the Lodge, has more intimate double-occupancy rooms.
• We stayed here and absolutely loved it!

Outbound Stowe

• Think classic New England meets modern glamping with a mix of cozy rooms, lofts and cabins.
• Amenities include the largest outdoor seasonal pool in the area, year-round hot tub, communal fire pits, free guest parking, pet friendly rooms, free WiFi, etc.
• This is the perfect hotel if your goal is to be outside as much as possible. It has direct access to Stowe’s Recreation Path and West Branch Little River, and they offer on-site bike rentals, solo stoves, stargazing kits and more.

AWOL Stowe

• Boutique hotel tucked into the side of Cady Hill Forest, but just a short walk from Stowe village.
• Another Lark Hotel property.
• Amenities include complimentary Lark Hotel breakfast (the best!), full-service lounge, outdoor cedar hot tub, cold plunge pool, sauna, communal fire pits, on-site library, free WiFi and more.
• 35 rooms and suites, some with working fireplaces.

Woodstock Inn & Resort (Woodstock)

• Upscale resort located right in the center of Woodstock, Vermont.
• This historic property is perfect for a luxury resort getaway.
• Amenities include complimentary WIFi, pet-friendly rooms, free parking and valet parking, seasonal outdoor pool, year-round indoor pool and hot tub, Athletic Club access, complimentary coffee, tea and cookies. 
• The Inn has two restaurants with full bars, an Athletic Club, Country Club, Golf Course, Ski Area, Nordic Center, Spa & more.

The Shire Woodstock

• The Shire is a charming hotel with river views located in historic Woodstock.
• The perfect peaceful escape for family, friends and couples.
• Amenities include high-speed WiFi, backyard games, complimentary parking, fire pits and more.

On the River Inn (West Woodstock)

• A cozy boutique Vermont Inn perfect for couples, families and travelers looking for a relaxing escape.
• Offers both modern hotel rooms with balconies and patios or suites with full kitchens and living rooms.
• Amenities include an indoor pool, sauna, jetted hot tub, fitness center, library, games and entertainment room, complimentary WiFi, free parking, complimentary country breakfast and more.
• They offer cute perks like afternoon cookies and nightly s’mores around the fire.
• Home to 506 on the River, open for dinner 5 nights a week.

AC Hotel Burlington

• Just steps away from the iconic Church Street Marketplace and the shores of Lake Champlain, if you want to stay in the city of Burlington, this is the hotel for you.
• A Marriott property
• The amenities in this brand new hotel include a fitness center, business center, rooftop terrace, onsite restaurant and bar.

Blind Tiger Burlington

• City center B&B housed in a grand brick mansion close to the University of Vermont in the residential neighborhood of Burlington Heights
• Another Lark Hotel property (I stayed in the Blind Tiger Portland and was in love with it)
• Amenities include complimentary continental breakfast, free WiFi, parking, a fully stocked complimentary pantry with snacks plus much more.
• My favorite part about staying in any of the Lark Hotels, but especially their Blind Tiger hotels, are the mixed use gathering spaces and living room like spaces with comfortable seating available for guests to use throughout the hotel. 

PIN my Vermont Fall Travel Guide for LATER:

Need help with what to pack on your fall adventure? Check out my What to Wear in Vermont in the Fall guide!