Five Days of Fall in Vermont
Vermont in October has always been on my travel bucket list. 🍁
Ever since I saw the Queen of Fall, Caitlin Covington, gush about Woodstock, it’s been at the top of my must-visit list. So when my girlfriends and I started planning our next getaway, Vermont was a no-brainer—and it did not disappoint.
For five days, we leaned into the cozy charm of Woodstock and Stowe. From peaceful mornings sipping coffee on a porch with golden-tree views, to the quiet warmth of small-town bookstores and fire-lit evenings with friends—this trip was everything I’d hoped a fall escape would be.
Here’s a recap of our girls’ trip, packed with foliage, flannels, and all the maple syrup a girl could want.
Click here to watch my Travel Vlog.
My Trip Overview:
Dates of Travel: October 18-22, 2024
Trip Duration: 5 Days
Local Airport: Patrick Leahy Burlington International Airport (BTV)
Cities Visited: Stowe and Woodstock
Carry-On: Roam Expandable Carry-On
Day 1
Arriving in Woodstock
Our adventure began with an early flight, and after landing at Patrick Leahy Burlington International Airport (BTV)—the closest airport to Stowe (30 minutes away) and not too far from Woodstock (about 1.5 hours)—we picked up our rental car and were ready to hit the road. I definitely recommend getting a rental car if you’re flying into Vermont to explore. It lets you roam around at your own pace, so you can soak up Vermont’s countryside and visit all the scenic stops without a schedule.
With our carry-ons in tow, we set off for Woodstock, making a quick detour to the picture-perfect Sleepy Hollow Farm on our way into town. You’ve probably seen this Farm pop up on the ‘gram or on your Pinterest board before—it’s the classic Vermont postcard shot!
💡 TRAVEL TIP:
Sleepy Hollow Farm is a private family residence nestled on a narrow neighborhood road. In recent years, this picturesque backdrop has become so popular that the road is often closed to tourists during peak fall season to help manage crowds and ensure safe passage for locals. If you’re visiting during peak foliage, you may find the road closed for this reason. If you’re lucky enough to find it open (as we were post-peak season), please be respectful: do not pull into the driveway or disrupt traffic. Enjoy the view quietly and respectfully. 📸🍁
Once we arrived in Woodstock, we made a stop at the Woodstock Farmers' Market to pick up essentials for the Airbnb. They have everything from local produce to prepared foods and snacks, so it’s the perfect spot to stock up. By the time we checked in, it was golden hour, and the view from our backyard was pure magic—surrounded by autumn hues, it felt like we’d stepped into a painting.
After settling in, we walked downtown to explore some of Woodstock’s charming shops and spots. We passed the Middle Covered Bridge on our way—a classic wooden bridge that’s as picturesque as it sounds. Our stroll continued with stops at Woody’s Mercantile for a few cozy home decor finds and Clover Gift Shop for cute trinkets.
For dinner, we had reservations at Worthy Kitchen, a farm-to-table spot known for its delicious New American eats and craft beers. After a day of traveling and exploring, their rustic comfort food was the perfect end to our first day.
Day 2
Woodstock Wandering
We started our day slow, taking in the crisp Vermont air as we strolled into town for breakfast at Mon Vert Café. This charming little spot is a popular choice, so be prepared to wait for a table, but trust me—it’s worth it. I went for the breakfast burrito paired with a local cider, and it hit the spot.
From there, we walked through some of the nearby streets and neighborhoods that were filled with New England charm. Each house was dressed up in full Halloween spirit, with every house and shop adding its own festive touch. We spent some time shopping through the cute boutiques that lined downtown Woodstock, starting with The Vermont Flannel Co. for cozy souvenirs and then making our way to FH Gillingham & Sons, an old-school general store where I found a Christmas ornament to add to my travel tree back home.
Of course, we had to try the local favorite—a Maple Creemee. This maple-flavored soft serve, from Woodstock Scoops, lived up to every bit of hype. Don’t skimp on the maple sprinkles on top. 🍦 I’m still dreaming about it.
In the afternoon, we made our way to Sugarbush Farm for a true taste of Vermont. This family-run farm walked us through the maple syrup-making process, and we got to sample all the varieties (plus some local cheeses!). It was everything you’d want in a fall farm experience—cozy, educational, and delicious. To work off the treats, we headed to Quechee Gorge, where a short, scenic trail led us to beautiful views of the gorge and its vibrant fall colors reflected on the water. It was gorge-ous, literally.
Before dinner, we made one more stop at Bourdon Maple Farm, a smaller, quieter farm where we tasted even more maple varieties and browsed their charming shop.
Then, it was time for our dinner reservation at The Ransom Tavern in South Woodstock. This rustic Italian spot is set within an inn and had a cozy, welcoming vibe that was perfect for our group. I ordered a wood-fired pizza, and we all agreed that this meal was one of the highlights of the trip.
We wrapped up the night with post-dinner drinks at Au Comptoir, a little outdoor cocktail lounge with fire pits and blankets. We cozied up around the fire with our drinks, sharing laughs and enjoying the perfect end to a day full of Vermont magic.
Day 3
Farewell Woodstock, Hello Stowe
The next morning it was time to say goodbye to Woodstock and head north to Stowe - with a quick breakfast pitstop along the way at Wit and Grit. This place was a few minutes off the highway, but it was so cozy and had some incredible breakfast eats that it definitely made the off-the-path trek worthwhile.
Our first stop in Stowe was Mount Mansfield, Vermont’s highest peak. We took the gondola up to the summit, and wow—the views stretched on forever. Vibrant red and gold leaves blanketed the valley, and with the sunshine on our side, it felt like autumn perfection. At the top, we grabbed a drink at the Cliff House Restaurant and relaxed at the picnic tables, soaking in the crisp mountain air and sweeping views.
After we took the gondola back down from the mountain and picked up our car, we made the quick drive along Smuggler’s Notch which was a trip highlight for me! Every twist in the road revealed another breathtaking scene, with hidden waterfalls and beautiful lookouts perfect for quick stops and photos. If you’re in the area, this drive is a must-do for its endless scenery and autumn colors.
Finally, after an afternoon of exploring, we checked into our new Airbnb in Stowe—a beautifully converted schoolhouse that just might be one of my favorite Airbnb stays to date. The owners preserved so much of its charm, with musical instruments on the walls, a grand piano in the entry, and a cozy back porch where we had our morning coffee.
As evening approached, we set out for a quick hike up to Sunset Rock, which was just a short walk from our Airbnb. Watching the sun dip below the hills of Stowe was the perfect way to end the day, and it made us fall even more in love with this charming town. For dinner, we headed to Cork Wine Bar. The vibe was relaxed and inviting, and their butternut squash pasta was a standout dish—one I haven’t stopped thinking about since.
Day 4
Small-Town Magic in Stowe
We started our morning with coffee and cozy vibes at the Airbnb, then set out to explore downtown Stowe. Our first stop was Shaw’s General Store, a local gem filled with everything from classic Vermont souvenirs to practical outdoor gear. We meandered through some cute boutiques and stumbled upon the sweetest chocolate shop, where I snagged some maple pecan bark that I instantly regretted not buying more of. The highlight, though, was an art gallery at the end of the main street, showcasing pieces from local artists—a beautiful mix of craftsmanship and Vermont charm.
After shopping, we had brunch at Butler’s Pantry. This place is a can’t-miss, with classic breakfast options and a cozy, welcoming atmosphere.
Fueled up, we drove over to Moss Glen Falls. The short and easy hike led us to one of the prettiest waterfalls, with cascades tumbling over rocks framed by fall foliage—a true autumn dream.
Next up was Cold Hollow Cider Mill, where we found the ultimate stash of Vermont souvenirs. We sampled apple cider and stocked up on fresh maple syrup to bring a bit of Vermont home with us. It was like stepping into cider heaven, complete with hard ciders, freshly baked cider donuts, and everything maple.
Later in the day, we couldn’t resist a visit to Ben & Jerry’s HQ for dessert. After grabbing our favorite flavors, we took a stroll through the quirky Flavor Graveyard, where retired flavors are laid to rest with witty epitaphs—a fun, nostalgic detour.
We capped off the day with a reservation at Hen of the Wood, a highly recommended farm-to-table restaurant known for its locally sourced menu. Every bite was packed with flavor, and it was the perfect way to close out our final night in Stowe.
Day Five
Farewell to Vermont
Our last morning in Vermont was all about soaking up the peaceful, quiet moments before heading home. We enjoyed coffee on the porch of our cozy schoolhouse Airbnb, taking in the crisp air and autumn scenery one last time. After a slow start, we packed up our bags, loaded the car, and took a final look at the charming town of Stowe!
With everything packed up, we hit the road back to Burlington Airport. This trip was everything we could have hoped for—full of cozy mornings, scenic drives, and maple-flavored treats.
Thank you so much for coming along with me on this incredible journey through VERMONT!
From quaint towns and scenic drives to fall flavors and hidden gems, this trip was everything we’d hoped for in a fall getaway. Whether you’re a leaf-peeper, a food lover, or just looking for a peaceful escape, Vermont has a little autumn magic for everyone.
I hope you found some inspiration for your own travels and maybe discovered a few spots to add to your list. And if you’re ready to skip the planning and dive right in, don’t forget to download my full Vermont itinerary! It’s packed with maps, a road trip plan, and all the details to make your own Vermont adventure as effortless as possible. 🍁