Fall in Vermont is the stuff of fairy tales, and there’s no better way to experience the magic of the season than on a road trip. This fall road trip itinerary will take you to some of the most pristine landscapes in the state, following Vermont’s scenic Route 100 from Montgomery to Manchester.
You’ll start north where the leaves turn colors first and meander south through picturesque towns. Hilltop apple orchards, roadside farm stands, quaint covered bridges, and quintessential country stores are somehow even more charming against splashes of red, orange, and gold. Pull-over views greet you around every turn as you drive through the Green Mountains that are anything but at this time of year.
The best time to take this road trip for peak fall foliage in Vermont is typically the first two weeks of October, when you won’t find better leaf peeping anywhere else in the world. It’s up to you how long to make it. Driving this entire route straight through without stopping would take only three hours. But of course I’d recommend breaking it up over a few days or even a full week to really linger at each destination. And more importantly, in between – after all, it’s about the journey!
Follow along to discover my favorite places to stop and stay along Vermont’s Route 100 in this ultimate fall foliage road trip itinerary.
Stop 1: Montgomery
Just north of Route 100, Montgomery is the perfect place to start your Vermont fall foliage road trip. It’s about a four hour drive from Boston, two hours from Montreal, and six hours from New York City. This tiny town boasts more covered bridges than any other place in the nation. You can hit at least six of my favorites all within 30 minutes of each other.
What to do in Montgomery
Start your covered bridge tour just north of Montgomery at Hopkins Covered Bridge. It was built in 1875 by Sheldon and Savannah Jewett, brothers who are credited with building most of the area’s covered bridges. Keep following the Trout River just a little ways down the main road to Longley Covered Bridge. Built in 1863 by the same Jewett brothers, it is the oldest of their surviving bridges.
Right before you get back to Montgomery, take a turn down West Hill Road and pull over at West Hill Covered Bridge. The road as it approaches the bridge from either direction is little more than a one-lane, gravel path. Enjoy a peaceful moment in this secluded spot, where the only sounds to disturb your thoughts are the crunching of leaves underfoot and the babbling of the West Hill Brook.
Once you’re ready to pull yourself from your reverie, head back to the main road for a spectacular view of Comstock Covered Bridge. Then tuck back in to see Fuller Covered Bridge, which crosses the unassuming Black Falls Brook. Finally end your whirlwind tour at Hutchins Covered Bridge. It carries the dead end Hutchins Bridge Road over the south branch of the Trout River a short way west of the main road.
Where to Stay in Montgomery
If you choose to stay overnight in Montgomery, this Airbnb is a great option. It’s dog friendly, is set on 24 acres with gorgeous mountain views, and is within walking distance to West Hill Covered Bridge. It’s pretty remote and there aren’t a ton of restaurants in Montgomery, so I’d recommend stocking up on groceries and settling in to enjoy your meals in front of the home’s cozy fireplace.
Stop 2: Stowe
When you’re ready to get back on the grid, follow Route 100 south to the iconic mountain town of Stowe. Stowe is best known for its winter skiing, but my favorite time of year to visit is in the fall. In fact, it’s even nicknamed New England’s “Fall Color Capital”!
things to do in Stowe
There are so many fun fall activities in Stowe. One of my favorites is to bike or stroll the Stowe Recreation Path. This five mile paved trail runs between the West Branch Little River and Mountain Road, with plenty of scenic stops along the way. I like starting at the northwestern-most access point near Top Notch Resort. One of the first sights you’ll encounter is the Brookdale Bridge, an iconic red covered bridge that stands out against the brilliant fall foliage.
Heading southeast toward town, the next stop you’ll come across is the Percy Farm Corn Maze. The maze is directly accessible from the Stowe Recreation Path, or there’s parking at nearby Thompson Park. It generally takes 30 to 40 minutes to navigate, and it’s great fun for the whole family (even leashed dogs are allowed!)
There are also several great breweries to visit along the Stowe Recreation Path. The first one you’ll come across when following my suggested route is Idletyme Brewing Company. On a crisp fall day, I’d recommend sitting at the outdoor bar built around a tree, which remains comfortable even when temperatures start to dip thanks to roaring fire pits and ample heaters. The next and most famous is The Alchemist, whose signature Heady Topper is one of the most sought-after and rewarded craft beers. Finally, for something a little different, pull off at Stowe Cider to enjoy crisp, fresh-pressed hard cider made from local fruits.
Another must-do when visiting Stowe in the fall is Smuggler’s Notch. You can the hairpin turns of this narrow pass for an experience in and of itself, or get out and stretch your legs. One of my favorite fall hikes is the Sterling Pond Trail, a moderate, 2.3 mile out-and-back trail with rewarding views.
Restaurants and Breweries in Stowe
There’s no shortage of top-notch dining and drinking options in Stowe. Start your day with a hearty, home-cooked breakfast at Butler’s Pantry. Or check out Woodland Baking and Coffee, where fresh-ground coffee and baked goods are made from scratch on site. Another good breakfast option is the Kaffeehaus Bakery & Deli at the Trapp Family Lodge. Here you can enjoy a strong cup of coffee and fresh-baked pastries overlooking the beautiful mountain views that reminded the Von Trapp family of their home in the Alps.
For more substantial meals, grab a table at The Bistro at Ten Acres in a restored 1820s farmhouse with lovely views of Stowe’s rolling countryside. Doc Ponds is favorite among locals for delicious comfort food and an extensive local craft beer list. And Stowe Sandwich Company is a go-to spot for lunch, located right off the Stowe Recreation Path.
No fall visit to Stowe would be complete without sampling a local brew. Stop by The Alchemist‘s state-of-the-art facility to stock up on their signature Heady Topper, or stay a while to sip on free, unlimited samples from their rotating taps. Idletyme Brewing Company‘s deck located right off the Stowe Recreation Path is the perfect place to unwind after a long day of exploring. Another great option is Von Trapp Brewing, located at the Trapp Family Lodge, which brings the crisp, clean style of Austrian lager beers to the craft beer movement in Vermont. Rock Art Brewery in nearby Morristown is one of the few places where you can sip beer while perusing incredible work from local artists. And while beer might be the name of the game in Vermont, cider is not to be overlooked at Stowe Cider. Bonus – all of these options are dog friendly!
Dog Friendly Breweries in New England
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Where to Stay in Stowe
Regardless of how you break up your fall foliage road trip on Vermont’s Route 100, I’d recommend spending the night in Stowe. This is where you’re going to find the most options for lodging. My favorite places to stay in Stowe are The Stowehof, a warm and welcoming lodge built around raw wooden beams and stunning mountain views, and Field Guide Lodge, a stylish boutique hotel run by Lark Hotels. Bonus, they’re both dog friendly!
Dog Friendly Guide to Stowe, VT
Discover even more things to do with your dog in Stowe, Vermont.
Stop 3: Waitsfield & Warren
Continue your fall foliage road trip south on Vermont’s Route 100. Drive through Waterbury Center, where you can pull over for a scoop and factory tour at the flagship Ben & Jerry’s. Cross over to the other side of I-89 and enter the Mad River Valley, named for the winding waterway that sometimes floods the region in the springtime.
Pull over at Waitsfield Covered Bridge, also known as the Great Eddy Bridge. Built in 1833, it’s the oldest operating covered bridge in the state and has the longest clear span of any Burr truss bridge in Vermont, spanning an incredible 105 feet. You can get a great view of it while enjoying a cup of coffee and a pastry at The Sweet Spot.
The historic town of Warren has all the makings of a quintessential New England destination for fall foliage. You can find everything you might ever need and more at the Warren Store, an authentic Vermont country store. If you choose to stay overnight in Warren, The Pitcher Inn is an upscale resort with comfortable rooms. There’s even a few that are dog friendly!
Stop 4: Killington & Woodstock
Next up is the town of Killington, home to one of Vermont’s biggest ski resorts. At this point, you’ll want to turn off Route 100 for a detour that’s well worth it. Just 30 minutes east on Route 4 is the postcard-perfect town of Woodstock.
Things to Do in Woodstock
Start in the heart of Woodstock, where the bucolic village green is infused with an extra dose of charm thanks to the vibrant colors of fall. From here, you can walk over to get a great view of Middle Bridge. This single-lane span over the Ottauquechee River is one of the most-photographed covered bridges in New England.
Be sure to hit the shops on Central and Elm Streets in downtown Woodstock. Discover local wares at F.H. Gillingham & Sons, a general store that has been family-owned since it first opened its doors in 1886. Get a head start on your holiday shopping list at Clover Gift Shop. Stock up for cozy season at Vermont Flannel Company. Lose yourself in the well-curated selection at the Yankee Bookshop. Venture a little outside of town to browse artisan home goods at the popular Farmhouse Pottery. Or head to nearby Quechee to watch master glass artisans at work at the Simon Pearce flagship store.
While in Woodstock, don’t miss your chance to experience Vermont’s only national historic park while it is bejeweled in fall colors. At Billings Park, you can explore an extensive network of trails through vibrant sugar maples, across historic covered bridges, and alongside rambling stone walls.
Restaurants and Breweries near Woodstock
You’ll find plenty of great spots to eat and drink in Woodstock. Fuel up for the day at Abracadabra Coffee Co. Just down the road from the Woodstock trailhead for the Appalachian Trail, this unassuming spot serves up smooth, single origin coffee and delicious waffles. For farm to table without the fuss, visit Mountain Creamery. This unassuming local breakfast and lunch spot draws tourists from all over New England. The ingredients are fresh and local (the owner has a farm just up the road that supplies the diner when in season) but the dishes are comfortable and familiar.
In nearby Queechee, I’d highly recommend making a dinner reservation at the award-winning restaurant the Mill at Simon Pearce. The views overlooking the Ottauquechee River waterfall and Queechee covered bridge are not to be missed. And Long Trail Brewing Company is located on the banks of the Ottauquechee River just down the road from Woodstock. Named for the 273-mile hiking trail that winds through the Green Mountains of Vermont, it’s the perfect place to hang out after a day of adventure.
Where to Stay near Woodstock
This is another great area to spend the night when breaking up your fall foliage road trip on Vermont’s Route 100. You can either stay right in the heart of Woodstock at the luxurious Woodstock Inn & Resort. Or head back towards Killington and stay at the Mountain Top Resort. Set on 700 acres of land amidst the Green Mountains, this resort has incredible fall foliage views overlooking the Chittenden Reservoir.
Stop 5: Plymouth & Weston
The next stop on this fall foliage road trip on Vermont’s Route 100 is the historic town of Plymouth. Fall is such a wonderful time to visit, when the maples growing across the 360-degree hills surrounding Plymouth are at their peak foliage colors.
Plymouth was the birthplace of Calvin Coolidge, the 30th President of the United States. Today, you can visit his childhood home at the Calvin Coolidge State Historic Site. Considered one of the best preserved Presidential sites in the nation, the historic village looks much the same as it did in during Coolidge’s lifetime. While in town, you’ll also want to stop by Plymouth Cheese for a tour and some provisions. Makers of “America’s oldest cheddar,” the shop was first opened in 1890 by Calvin’s father, John Coolidge.
Next you’ll pass through Ludlow, home to Okemo Mountain Resort, until you get to the charming town of Weston. Weston’s claim to fame is The Vermont Country Store. Started in 1946 by the Orton family, it has become a destination for visitors from near and far. Find something for everyone among a dizzying array of uniquely Vermont items, children’s toys and candy, and nostalgic treasures from bygone years.
Stop 6: Manchester
End your epic fall foliage road trip on Vermont’s Route 100 in Manchester. This idyllic southern Vermont town is nestled at the foot of Mount Equinox in the picturesque Battenkill River Valley. Manchester is a favorite for leaf peepers who also seek world-class dining, luxury accommodations, and first-rate shopping.
Things to Do in Manchester
You might be surprised at the level of luxury in this seemingly small town. Stroll the white marble sidewalks in the historic Manchester village. Shop an abundance of designer outlets in Manchester center. For book lovers, Northshire Bookstore is one of the finest destinations in the Northeast. For outdoor enthusiasts, the flagship Orvis store reads more upscale country estate than chain retailer.
Of course, you came to Manchester for the fall foliage, and there is no shortage of scenic spots for great views. Pack a picnic and drive to the summit of the highest peak in the Taconic Range via the Mount Equinox Skyline Drive. Or explore the picturesque Lake Shaftsbury State Park. Best known for its sandy swimming beach, you’ll likely have it to yourself during its off season.
Restaurants & Bars in Manchester
What better way to witness the change of the season than dining al fresco in Southern Vermont’s culinary mecca. Pearl’s Place & Pantry has incredible fall foliage views from their outdoor patio, where roaring fire pits, snug blankets, and homestyle Southern cooking will keep you cozy on even the chilliest autumn evening. Enjoy contemporary tavern fare on the front porch of The Copper Grouse in the heart of Manchester village. Or celebrate Oktoberfest in the beer garden of the Brownyn on Battenkill overlooking the beautiful Battenkill River in nearby Arlington.
where to stay in manchester
Manchester is another central hub with plenty of lodging options. I recommend splurging on an overnight stay at the luxe Kimpton Taconic. This Kimpton boutique hotel right in the heart of Manchester village is the perfect New England escape. Bonus: it’s dog friendly!
Do you have additional suggestions for things to do on a fall foliage road trip on Vermont’s Route 100? Share in the comments below!