Planning a fall trip to Vermont? This 4-day itinerary hits all the essentials. From foliage and scenic hikes to covered bridges, cozy small towns, and maple everything. Whether you’re chasing peak color or simply craving crisp air and cider donuts, this road trip loops through the best parts of Vermont during its most magical season.
I did this exact itinerary in late September and early October. Trust me, it’s a stunner. Here’s how to make the most of 4 perfect fall days in Vermont.
Day 1: Arrival in Burlington, Church Street, and Waterbury Wonders
Fly into Burlington in the morning to kick off your adventure in one of Vermont’s most vibrant cities. After picking up your rental car from Enterprise, take some time to explore Church Street Marketplace. It’s a pedestrian-only zone lined with boutiques, bookshops, and cafés. This area has small-town charm with a college-town buzz. Take a stroll through the brick-lined streets.
Next, head about 40 minutes southeast to Waterbury, where you can’t miss a tour of the original Ben & Jerry’s Factory. It’s fun, nostalgic, and yes, you get free samples. Don’t forget to stop by the flavor graveyard! Not far from here is Cold Hollow Cider Mill, a quintessential Vermont stop! Sip cold or hot cider and try their legendary cider donuts.
Before the day ends, stretch your legs with a moderate hike at Mount Elmore. The 4.3-mile trail offers a mix of forest trails, lake views, and a fire tower at the top with sweeping fall foliage vistas. In the evening, dine at Hen of the Wood in Waterbury. You’ll need to make a reservation as they are often booked out. I got lucky and was able to grab a seat at the bar. This cozy farm-to-table restaurant is known for its seasonal Vermont-inspired dishes and romantic ambiance.
Day 2: Stowe’s Scenic Trails, Smugglers’ Notch, and Alpine Views
Start your morning in nearby Stowe with breakfast at Green Goddess Café. A beloved local spot offering hearty bowls, wraps, and delicious beverages to get the day started. Then, hit the trail at Stowe Pinnacle, one of the area’s best short hikes. It’s a bit steep, but the panoramic views from the top are stunning, especially in the fall when the trees are ablaze with red and gold.
From there, take a leisurely drive through Smugglers’ Notch, a narrow mountain pass lined with massive boulders and bursting with fall color. This drive alone is worth the trip. If you’re up for it, take the Gondola Skyride at Stowe Mountain Resort for a bird’s-eye view of the valley and mountains.
If you still have energy, hike part of the Sunset Ridge Trail at Mount Mansfield for even more spectacular views. Cap off the day with dinner at the von Trapp Family Lodge, a unique alpine lodge run by the descendants of the von Trapp family (yes, those von Trapps from The Sound of Music). The property has several dining options to choose from: the Main Dining Room for Austrian-inspired dishes with mountain views, the lively Bierhall serving house-brewed lagers and hearty fare, and the cozy Kaffeehaus with European-style pastries and light bites. Since it’s one of the most popular spots in Stowe, reservations are highly recommended, especially during peak foliage season.
Day 3: Sunrise, Sugar Shacks, and Covered Bridges in Woodstock
Start your third day with an early sunrise hike at Mount Philo State Park, a relatively short but rewarding climb just south of Burlington. It offers sweeping views of Lake Champlain and the Adirondacks. After your hike, head south to Maple Sugar & Vermont Spice, a charming roadside spot perfect for pancakes and, you guessed it, fresh maple syrup.
Make your way toward the Woodstock area, stopping at the Original General Store in Pittsfield for snacks or souvenirs. If you’re craving more outdoor activity, hit the Killington Peak Loop, a challenging trail with serious elevation but breathtaking rewards. In the fall, this area is a kaleidoscope of color.
Once you arrive in Woodstock, take time to browse F.H. Gillingham & Sons, a historic general store full of Vermont-made goods, and visit Sugarbush Farm to learn about cheese and maple syrup production. Before sunset, don’t miss Quechee Gorge, also known as “Vermont’s Grand Canyon.” End your day with a comforting dinner at Worthy Kitchen, a local favorite known for its burgers and laid-back vibe.
Day 4: Covered Bridges and Pumpkin Patches in Southern Vermont
On your final day, take the scenic drive south toward Manchester, soaking in every last bit of foliage. Once there, enjoy a slow morning walk around town and pop into Northshire Bookstore, a local gem with two floors of books, gifts, and cozy nooks.
Next, visit the Arlington Covered Bridge, one of Vermont’s most photographed fall spots, and then head to Equinox Valley Nursery for their annual Pumpkin Patch Fall Festival. It’s family-friendly, but even as an adult, it’s hard not to smile surrounded by pumpkins, cider, and hayrides.
For lunch, settle into Ye Olde Tavern, a historic 18th-century restaurant that feels like stepping back in time. After your meal, begin the drive back to Burlington (about 2 hours) to catch your evening flight home. Hopefully with a phone full of foliage photos and a heart full of autumn magic.
Four days is just enough time to fall in love with Vermont in the fall. Between the hikes, scenic drives, local flavors, and small-town charm, this itinerary gives you a little bit of everything that makes New England so special. Whether you’re going with friends, your partner, or solo, Vermont’s cozy corners and foliage are waiting.
Don’t forget to check out my Best Fall Hikes in New England guide.
