The Perfect Cozy Vermont Fall Itinerary: 3 Days in Vermont!

Are you planning a mini fall foliage road trip through Vermont and wondering how to fit it all in?

There’s no better place to lean into the cozy fall season than in upstate Vermont: crisp air, apple cider donuts, maple-flavored everything, Halloween porch displays, and drives through fiery hillsides so bright it feels like the trees are glowing.

This 3 day Vermont itinerary is built around the state’s most charming towns — Burlington, Stowe, and Woodstock — and packs in iconic foliage views, fall treats, and some local spots I’ve discovered after visiting Vermont over 20 times!

You’ll need a rental car to make the most of this route, since it’s all about scenic drives and small-town stops. The easiest option is to fly round-trip out of Burlington airport (BTV) for this itinerary. However, you can also fly home out of Manchester Boston Regional (MHT) if it’s cheaper, since the drive time is the same!

My husband and I did this exact trip (plus a few days in New Hampshire) in late October instead of peak foliage season earlier in the month, and we hit the perfect balance of beautiful leaves, local Halloween events and fewer crowds.

I’ve packed as much into this itinerary as 3 days will allow to maximize your time off. So keep reading to discover how to spend the perfect long weekend exploring Vermont in the fall!

Vermont Itinerary Route with Map

This Vermont fall road trip is structured as a loop through three classic Vermont towns — Burlington, Stowe, and Woodstock — with one overnight in each area!

The trip is short enough for a long weekend and hits all of the best parts of Vermont, in my opinion!

Below is a quick overview of the itinerary with drive times.

• Day 1: Fly into BTV and explore Burlington
  • Stay: Hotel Vermont in Burlington
• Day 2: Drive 45 min to Stowe. Explore + Overnight in Stowe
  • Stay: von Trapp Family Lodge
• Day 3: Drive 1 hr 30 min from Stowe to Woodstock. Explore + Overnight in Woodstock
  • Stay: Woodstock Inn & Resort
• Day 4: Option to fly out of BVT or MHT – both are around 1.5 hours away from Woodstock

I’ve also created a map of all the places mentioned in this itinerary to make trip planning a breeze! I highly recommend saving it to your phone for offline use — some of Vermont’s most scenic roads are also the most remote, meaning you may lose cell phone service at some points.

To make the most of this route, you’ll definitely need a rental car since you’ll be hopping between different cities each day. Plus, driving in Vermont is half the fun, thanks to its rolling hills, fiery orange trees, and spontaneous roadside maple stands (not kidding!).

The easiest thing to do is just pick up and drop off your rental car at the airport, whether that’s Burlington or Manchester.

Note: Fall in Vermont is extremely busy. I highly recommend booking your rental car a few months in advance to ensure they have availability! 🚗🍁

When I did this trip, my husband and I traveled in a campervan and stayed just outside each town. If you’re doing the same, I’ll share our exact campsites as we go. But if not, I’ve also included hotel recs for every stop so you can cozy up indoors after a full day of exploring!

Day 1: Explore Burlington, Vermont’s Largest City

Morning: Arrive at BTV, Coffee, & Farmer’s Market

Welcome to Vermont! As mentioned, you’ll be flying into Burlington International Airport (BTV) — a small, easy-to-navigate airport just ten minutes from the downtown area. I recommend arriving as early as possible to maximize your time!

After picking up your rental car, you’ll have the rest of the day to explore the city and ease into the trip with great food, lake views, and fall color right in town.

If you’ve arrived in time for breakfast, make sure to start your day at Speeder & Earl’s Coffee shop. This coffee is a Vermont-staple, and we were absolutely obsessed with their maple blend after trying some at Cold Hollow Cider Mill (more on that later!).

The coffee shop is located just south of downtown, about 10 minutes from the airport! They have some pastries here, or you can head next door to Great Harvest Bakery for even more choices + some lunch options if you’re arriving later in the day.

From there, start making your way towards the downtown area. If you’re visiting Burlington on a Saturday, don’t miss the Burlington Farmer’s Market nearby!

Afternoon: Explore Downtown + Breweries or Bike Ride

After the market, head downhill toward the Lake Champlain waterfront, where you can walk along the boardwalk or just sit and take in the view of the Adirondack Mountains across the lake.

There are benches, grassy areas, and often street performers or pop-up markets. If you’re into biking and the weather is warm enough, you can also rent bikes and cruise along the Island Line Rail Trail, which runs right along and then across the lake.

If it’s too cold for biking, I highly recommend spending your afternoon checking out the Burlington craft beer scene! Burlington is known for some incredible brews, and visiting in fall means you can try some seasonal beers! I had a “Leaf Peeper” flight at Switchback that I loved!

Foam Brewers sits right by the lake and is probably the most atmospheric. It’s a great place to grab a flight and chill outside if the weather is warm enough. Their inside was fun too though and decorated for Halloween when we visited!

From there, I recommend driving a bit south to explore the other top breweries in the area.

Luckily, Switchback Brewing and Burlington Beer Company are right next to each other, so I recommend visiting both! Switchback is a lot more laid back, with a small tasting room and some outdoor seating.

Burlington Beer Company has a much larger selection of beers, and the brewery itself is huge! They had so many yummy beers to try, even tropical sour beers which are my favorite. We loved this spot and stayed for a while thanks to their old school arcade room.

Lastly, Zero Gravity Brewery is one of the most popular breweries in Burlington (and all of Vermont). Unfortunately we didn’t make it here on our trip, but I will definitely be going back! The inside looks very Vermont-coded, with a large fireplace and cozy vibes!

In addition to a full draft list, they also have wine, cider, cocktails, and N/A beverages, plus a full food menu! This is a great place to grab lunch, so maybe visit here first depending on your timing for the day.

Optional Fall/Halloween Events

And if you’re visiting in late October, keep an eye out for Halloween events — downtown often hosts themed activities, pop-ups, and costume-friendly bar nights. Even if there’s nothing formal, the storefronts are decked out with pumpkins, spooky displays, and lots of fall flair!

On that note, if city life isn’t for you, you can also head drive 15 minutes south of Burlington to Shelburne Farms — a 1,400-acre working farm and nonprofit that’s open to the public from mid-May to mid-October. This place is part historic estate, part sustainability campus, and it’s one of the best fall experiences in the area.

At the farm, you can walk scenic trails along Lake Champlain, visit the animals at the Children’s Farmyard, watch cheesemaking in action, and go on a guided farm tour! The ultimate Vermont experience.

➡️ Read Next: Your Ultimate Packing Guide for New England in the Fall🧣

Evening: Dinner in Downtown Burlington

To wrap up your day in Burlington, spend a few hours wandering around Church Street Marketplace, Burlington’s pedestrian-only downtown hub. It’s lined with shops, bookstores, cozy cafés, and little nooks that feel extra magical in fall.

Finally, end your day with dinner at Honey Road, which was one of my favorite meals in Vermont. It’s a Mediterranean small plates spot with an ever-changing menu of bold, seasonal dishes.

I’m not lying when I say our meal here was to die for. Just try to make reservations if you can!

If you still have some energy, Burlington also has a great nightlife scene thanks to its student atmosphere. There’s plenty of dive bars and cocktail bars to choose from, depending on your style!

Where to Stay in Burlington:
🏕️ Campsite: Shelburne Camping Area or North Beach Campground (we actually drove to Stowe instead of staying overnight in Burlington, but it’s up to you!)
🏨 Hotels: Hotel Vermont ($$) or Hotel Champlain Burlington ($$) are both great options and centrally located in Burlington!

Day 2: Explore Stowe, The Adorable Mountain Village

Morning: Drive to Stowe + a Cozy breakfast

After breakfast or coffee in Burlington, start your morning with the 45-minute drive to Stowe!

Your first stop once you arrive in Stowe is breakfast at Round Hearth Café — a super unique café that doubles as a lodge and antique store.

This historic restaurant is an old ski lodge with creaky wooden floors, mismatched chairs, and a big round hearth in the center of the room. The food is hearty and affordable, and it’s the kind of spot where you’ll want to linger over coffee and enjoy the vibes (we did!!).

After breakfast, head into town to explore the streets of Stowe. The village area is tiny but packed with charm — boutique shops, cafés, and fall decor on every corner.

There’s usually something happening in the town square, especially in October. I’d budget an hour or two to walk around, pop into local stores, and soak up the Hallmark vibes.

Late Morning: Scenic Views

Once you’ve explored town, it’s time for some light adventure. If you want to get some exercise, I highly recommend Sunset Rock — a quick trail that starts right in town and gives you beautiful views over Stowe’s steepled rooftops and fiery trees.

It’s super easy and a great option if you’re not up for a big hike but still want to get into nature.

If you’d rather drive than walk, take the Stowe Mountain Auto Toll Road instead. It’s a 4.5-mile drive up to the summit ridge of Mt. Mansfield (Vermont’s tallest mountain), with panoramic views the whole way.

At the top, you can explore some short trails or just soak in the scenery. The road usually closes mid-October due to weather, so double-check if you’re visiting later in the month.

And while you’re in the area, you can’t miss the Stowe Gondola SkyRide — a scenic lift that whisks you to the top of Mt. Mansfield for even more incredible foliage views.

This was high on my list, but unfortunately it was closed for the season when we went! But it’s something I’ll absolutely come back for!!

🍁 For more ideas on things to do in Stowe, plus other tips and recommendations, check out my full guide on visiting Stowe, Vermont in Fall! 🍁

Afternoon: Ben & Jerry’s Factory

Once you’ve wrapped up your mountain time, head west to Waterbury (about 15 minutes from Stowe) for one of the most iconic Vermont stops: the Ben & Jerry’s Factory.

Open every day from 10:00am to 8:00pm, the Ben & Jerry’s Factory is a must-do on any Vermont itinerary, no matter the season.

Here, you can take a 30-minute tour of the factory to learn about the history of Ben and Jerry and their company, as well as a look at the production floor and of course, an ice cream tasting!

If you’re interested in doing the tour, you absolutely need to buy tickets in advance, especially during the fall season! Unfortunately, we just showed up on a Friday afternoon and the tour was sold out for the next few days (luckily, I had already done it on a previous trip!).

Even if you’re not doing the full tour, the factory still worth visiting! We both grabbed a scoop of ice cream, wandered through the Flavor Graveyard, and browsed the gift shop full of tie-dye and punny merch.

Evening: Sunset Dinner at Von Trapp Brewery

End your day with dinner and beers at von Trapp Brewing & Bierhall, just outside of Stowe. This was my husband’s favorite stop of the entire trip!!

Perched on a hillside with alpine views and an Austrian menu, this beerhall is run by the actual von Trapp family from The Sound of Music. They settled in Vermont after fleeing Austria during WWII and opened a ski lodge that has grown into a full resort, restaurant, and beer hall. How cool is that?!

We sat in the glassed-in patio, as it was way too cold to sit outside and enjoy the large lawn, though they did have fire pits to keep you warm! The traditional Austrian food we had (bratwurst, sauerkraut, and schnitzel) was soo yummy, and the house-brewed beer felt straight out of Europe!

This is the perfect place to end your time in Stowe! I recommend trying to visit around sunset for the best views from the top of the mountain.

Where to Stay in Stowe:
🏕️ Campsite: Smugglers’ Notch RV Village (This is where we stayed — the drive in is intense but beautiful! It’s a bit out of the way though)
🏨 Hotels:
– Trapp Family Lodge (Gorgeous property in the mountains with stunning views)
– Green Mountain Inn (Right off Main St in the heart of Stowe Village)
– The Lodge at Spruce Peak (Luxe ski resort with mountain views)

Day 3: Explore Woodstock, Vermont’s Most Beautiful Town

Morning: Cold Hollow Breakfast + Maple Stop

Time to say goodbye to Stowe — but not before breakfast! Just 10 minutes outside of town is one of Vermont’s most iconic fall stops: Cold Hollow Cider Mill.

This spot is equal parts breakfast café, cider house, gift shop, and local attraction. Because this is a very popular place to visit thanks to Instagram, I recommend arriving as early as possible – they open at 8am!

Start on the café side, where you can grab Vermont-style breakfast sandwiches and the fluffiest biscuits ever (I’m still dreaming about them). They serve Speeder & Earl’s maple coffee here too, which, if you remember from Day 1, is the best coffee in the state!!

After you eat, head over to the mill side to check out the cider press in action, browse shelves of maple syrup, jams, sauces, and cookbooks, and of course — try the famous apple cider donuts. I’ll be honest, I thought they were just okay, but the experience was still 100% worth it.

Once you’re finished up at Cold Hollow, it’s time to make your way to Woodstock. Before going all the way there, I highly recommend one last maple stop on your way south — either Bragg Farm Sugar House or Morse Farm Maple Sugarworks.

Both around 30 minutes from Cold Hollow and just outside Montpelier. At either stop, you’ll get to sample maple products, shop for souvenirs, and learn how Vermont maple syrup is made! This is truly one of the best things to do in Vermont in the fall!

Bragg has been run by the same family for 8 generations, and Morse has a fun maple trail and farm animals!

If you can’t decide which to visit, just make a quick stop at both!

Afternoon: Scenic Drive to Woodstock

From Montpelier, continue the scenic 1-hour drive south to Woodstock. This is one of the prettiest stretches of the trip — winding roads, covered bridges, and little farm stands that beg you to pull over.

If you’re not in a rush, you can add a stop at Worthy Burger in South Royalton for lunch. Their burgers and parmesan truffle fries are chef’s kiss!! Or, you can visit their sister location in Woodstock – Worthy Kitchen – for the same mouth watering food and yummy beer!

For my Gilmore Girls fans: the town of South Royalton was used as the opening aerial shot in the Gilmore Girls intro! This, coupled with the fact that the town was having a Trunk or Treat in the town square, made it the perfect detour on our way to Woodstock.

Another optional stop is Billings Farm & Museum, which you’ll find right before you reach downtown Woodstock. This historic working dairy farm gives a look into rural Vermont life, and it’s especially charming in the fall with pumpkins, hayrides, and cider tastings!!

Once you get into town, park near the village green (there’s metered parking) and start exploring on foot. You’ll immediately feel the difference between Woodstock and Stowe when you arrive!

Woodstock is the kind of place that actually looks like a movie set, and social media doesn’t do it justice. This is especially true in the fall, when its covered bridges are surrounded by golden trees, front porches are overflowing with pumpkins, and boutique shops are filled with fall candles and cozy flannels.

Spend a few hours wandering the shops and side streets, snapping photos of the scenery, and grabbing a maple creemee from the local ice cream shop! Make sure to check out the picturesque general store and the flannel shop across the street too.

The town itself is not very big and very walkable. You could do a loop around the main area in less than an hour.

Note: Woodstock has become very popular in recent years. Please remember that people actually live in this town! Respect their privacy when exploring and taking photos. You can read my full guide to visiting Woodstock in the Fall here!

Evening: Dinner at the Woodstock Inn

For your final evening in Vermont, make dinner reservations at Richardson’s Tavern, located inside the Woodstock Inn & Resort. This is easily one of the most iconic inns in New England — it literally feels like the Independence Inn from Gilmore Girls!!

I used to stay here for work a few years ago, and to this day, it’s one of my favorite hotels in the world. So much so that my husband and I promised ourselves we’d come back every few years for our anniversary.

But even if you’re not staying at the Woodstock Inn (it’s pricey), it’s worth walking around and exploring before your dinner reservation!

We grabbed a glass of wine from the Red Rooster Bar before dinner and strolled around the grounds. We bopped between the front lawn (to die for), the library (quick game of chess), the fireplaces (both inside and out back), and the basement game room (TVs, pool, and life-size Scrabble)!

After exploring, the meal at Richardson’s Tavern was cozy, seasonal, and the perfect way to wrap up the trip!!

Fly Home + Optional Extra Stops

Unfortunately, it’s time to fly home!!!

Before hitting the road, you can grab breakfast at Mon Vert Café in Woodstock if it’s not too busy, or just grab a pastry and coffee from their food truck, usually parked across the street.

If you have time before you need to head to the airport, I recommend exploring Quechee, just 15 minutes from Woodstock. Start with a visit to Quechee Gorge, nicknamed “Vermont’s Little Grand Canyon.”

You can see it just by walking across the bridge on Route 4, but if you want to get closer, there’s a short trail that leads down to the water for a different perspective.

Right down the road, make your final Vermont stop at Simon Pearce, a glassblowing studio, store, and restaurant perched over Mill Pond Falls. This place is such a vibe — you can watch artisans blowing glass in the downstairs workshop, then browse their stunning glassware upstairs (perfect for a splurge souvenir or holiday gift).

They also have a restaurant overlooking the falls if you’re hungry for one last scenic meal.

From there, it’s time to make your way to the airport. Burlington (BTV) is about 1.5 hours northwest, and Manchester-Boston Regional (MHT) is about 1.5 hours southeast. I recommend choosing whichever one is cheaper for you!

Or, if you have more time for this trip, make sure to check out 5 Day New England Fall Road Trip Itinerary, which includes an extra two days exploring the White Mountains area of New Hampshire!