10 Vermont Road Trip Ideas for Your Next Adventure
Planning a road trip in Vermont is a great way to see small towns, scenic views, and local spots you might miss otherwise. Vermont’s winding roads take you through mountains, farms, and charming villages filled with unique things to do.
With so much to see, having a list of road trip ideas helps you make the most of your time and discover the best parts of Vermont. Whether you’re looking for nature, food stops, or relaxing drives, you’ll find plenty of options for every kind of traveler.
1) Explore Stowe’s charming downtown and local breweries
If you love small towns, you should stroll through downtown Stowe. Main Street is full of local shops, bookstores, and cozy cafes. There’s always something interesting to pop into or a spot to grab a quick snack.
You’ll find plenty of places to sample Vermont made treats. Many stores sell local maple syrup, jams, and chocolates. Take your time to explore and maybe find a souvenir or two.
Stowe is also known for its local breweries. Grab a craft beer at one of the town’s brewpubs or tasting rooms. The atmosphere is relaxed, and you can often chat with the friendly staff about the different flavors.
If you visit in the afternoon or evening, breweries are popular hangouts. You might catch some live music or food trucks outside. Afterward, you can walk off your meal by taking a quick walk through the rest of downtown.
Whether you’re into shopping, relaxing, or trying new drinks, Stowe’s downtown has something to offer. It’s a great way to start your Vermont road trip. And if you have time, visit Smugglers Notch Vermont as well, which is the main hiking area nearby.
2) Drive scenic Route 100 from Wilmington to Ludlow
Take a drive on Route 100 between Wilmington and Ludlow to see some of Vermont’s classic sights. This two-lane road runs through forests, small towns, and open valleys. It’s a great drive if you want a peaceful day out or want to explore at your own pace.
Along this route, you’ll pass through quiet villages like Dover and Weston. You can stop for coffee, shop at a country store, or stretch your legs at a local park. Make sure to look out for classic barns and covered bridges along the way.
If you’re traveling in the fall, the trees along Route 100 put on a great show of color. In spring and summer, you’ll see green hills and wildflowers everywhere. Winter travelers will notice ski areas and maybe catch some snow scenes.
There are plenty of places where you can pull off for a picnic or a photo. The road is easy to follow and has lots of gentle turns. Whether you’re driving for a few hours or most of the day, Route 100 is a relaxing, scenic option.
3) Visit Woodstock for covered bridges and quaint shops
If you love small towns, you’ll want to stop in Woodstock. This Vermont town has a cozy downtown with local shops and pretty streets. It’s an easy place to walk around and take in the classic New England road trip experience.
You can check out covered bridges right in town. Woodstock has four covered bridges, including the Middle Covered Bridge and the Lincoln Covered Bridge. They cross over the Ottauquechee River and look beautiful in every season.
Follow the quiet roads for views of rolling hills and historic buildings. Stop by a bookstore like Yankee Bookshop, open since 1935, or browse other unique shops on the main street.
While you’re there, grab a bite at a local café or bakery. You might also spot small art galleries or markets with handmade goods. Woodstock makes for a simple and relaxing stop on your Vermont road trip. Also worth considering is taking a look at the following post I have on Vermont covered bridges to check out.
4) Hike the Appalachian Gap for stunning mountain views
If you love hiking and nature, the Appalachian Gap is a spot you don’t want to skip. It’s located in the Green Mountains, right along the classic Route 17. You’ll feel surrounded by forests, ridges, and fresh mountain air.
The Appalachian Gap trail climbs steeply in places, so be ready for a bit of a workout. You might even find ladders and caves along the way. The trail offers several lookout points where you can pause and enjoy the views.
On a clear day, you can see far across the valleys. The mountain peaks stretch out around you on both sides. It’s a great place for photos or just relaxing while you look out over Vermont.
This hike brings you close to nature, but make sure to wear good shoes and bring water. You may also want to check the weather or trail conditions before you go.
If hiking isn’t your thing, you can also enjoy the views right from the roadside at the Gap. There are places to park and take in the scenery without walking far.
5) Stop at Quechee Gorge for a quick, scenic walk
Quechee Gorge is known as Vermont’s “little Grand Canyon.” It’s a great spot to stretch your legs and take in some natural beauty.
You can start your visit at the Quechee Gorge Visitor Center. There’s a well-trodden path that takes you along the edge of the gorge. The views of the rocky cliffs and the Ottauquechee River below are worth the short walk.
If you stop at the bridge, you’ll get a nice view looking straight down into the gorge. The water at the bottom looks especially pretty in the fall when the leaves change color.
This walk isn’t too long or difficult. It’s perfect for everyone, whether you want to snap a quick photo or just enjoy the fresh Vermont air.
Parking is usually available near the visitor center. You can also find a few picnic spots nearby if you want a snack before you get back on the road.
6) Check out Lake Willoughby
Lake Willoughby is one of the most popular lakes and visitor spots in the state to do a road trip through. The lake spans for over 10 miles and is accessible from the north and south ends where visitors can swim, boat and stay at nearby hotels and campsites in.
Located all across the lake are stunning hiking trails, waterfalls and picture perfect views of the area. My favorite time to visit Lake Willoughby is in the fall, when the colors are extremely vibrant and the lake itself is stunning to behold with the autumn leaves.
7) Browse independent bookstores in Brattleboro
If you enjoy reading and seeing more Covered bridges, then Brattleboro is a great stop for your Vermont road trip. The town has several independent bookstores close to each other downtown. You can easily visit more than one shop in a single visit.
Everyone’s Books is a popular spot known for its wide selection and friendly staff. Brattleboro Books also offers a mix of new and used books. Both are easy to find if you take a walk down Main Street.
While browsing, you can find fiction, local authors, or even books about Vermont. Many stores have cozy corners to sit and flip through a book before you buy.
Some shops have small gift sections, too. You might find cards, bookmarks, or Vermont-themed souvenirs stacked near the register.
Stopping at Brattleboro’s bookstores is a simple way to slow down and enjoy the town’s relaxed vibe. These shops welcome readers of all ages, so bring your friends or family along.
8) Taste fresh Vermont cheese and maple syrup in Middlebury
If you love food, Middlebury has plenty to offer. This small Vermont town is known for its delicious cheese and locally-made maple syrup.
You can visit nearby farms to see how cheese is made, and many of them offer samples. Grab some cheddar or try something new, like goat cheese, from local producers.
Make sure to also stop by a sugarhouse. Here you’ll find fresh maple syrup, often made right on site. Some places let you watch how they turn sap into syrup, especially in spring.
Don’t miss a visit to a local market or farm store. You can pick up cheese, syrup, and other Vermont treats to take home or enjoy as a snack during your road trip.
Middlebury’s food stops are an easy way to try real Vermont flavors. It’s a simple, tasty part of your drive.
9) Take the Mount Ascutney Parkway drive for fall colors
If you want to see some bright Vermont fall colors, the Mount Ascutney Parkway is a great choice. This scenic drive is about 3.7 miles long and takes you up the mountain to around 2,800 feet.
You get really good views of the Connecticut River Valley as you drive. There are a few pull-offs where you can stop, look out, and take photos.
The parkway is usually open from mid-May to mid-October, so fall is a perfect time to visit. You can take the drive slowly and enjoy the changing leaves all the way up.
At the top, you can park and even find some hiking trails for a closer look at the fall scenery. It’s a quiet spot, and you don’t have to hike to enjoy the views if you don’t want to.
Don’t forget to bring a camera or your phone. The colors can be really nice, especially on a clear day.
10) Explore Bennington Monument
Bennington Monument is an amazing historic area to visit. Besides the near 13 story tower you can explore from the inside and out, the surrounding area and city nearby is also stunning, especially in the fall. I’ve personally visited this place 3 times so far and each time it’s an absolute treat.
Tips For Planning Your Vermont Road Trip
Good planning makes a Vermont road trip way more fun and stress-free. You’ll want to know what season is best, what items to bring, and how to get around the state’s scenic roads.
Best Times Of Year To Visit
Fall is usually the most popular. Vermont’s foliage hits its peak from late September to mid-October. The changing leaves make even short drives unforgettable.
Summer is warm and full of local events, hiking, and swimming. June through August means all the ice cream and maple creemees you can handle.
Winter brings snow, skiing, and cozy inns. Expect icy roads but also lots of fun if you’re into winter sports.
Spring can be muddy but is quieter. Maple sugaring happens then, and the waterfalls really come alive.
Vermont road trip packing list:
Vermont weather is never boring. Pack layers, even during summer, because temperatures drop at night. A waterproof jacket is handy in all seasons.
Bring comfortable walking shoes or hiking boots for exploring towns and trails. In fall and spring, extra socks and a hat help if it’s chilly or wet.
Don’t forget a reusable water bottle. Rural Vermont has limited shops in some areas, so pack snacks, especially if you take backroads.
If you visit in winter, insulated boots, gloves, and a warm coat are musts. Toss in sunscreen and bug spray for summer, since you’ll spend lots of time outside.
A printed map or downloaded offline map helps in case cell service drops.
Navigating Vermont’s Scenic Byways
Vermont has many winding state highways and scenic byways. The best views often mean sharing the road with slow-moving farm vehicles or cyclists.
Be prepared for spotty cell reception, especially in the mountains. GPS can cut out, so bring a physical map or download routes beforehand.
Gas stations aren’t always frequent outside bigger towns. Fill your tank early and keep an eye out for fuel stops.
If you want local tips, ask at farm stands or general stores. Locals often know fun detours or secret swimming spots.
Watch for wildlife, especially at dawn and dusk. Deer are common, and roads can get slippery in wet or cold weather.
Making The Most Of Your Drive
Road tripping in Vermont is about what you taste and discover along the way. Small towns and back roads offer unique foods, fun stops, and chances to see the real Vermont.
Must-Try Vermont Eats Along The Way
You’ll want to stop for Vermont cheddar, which you can find at places like Cabot Creamery or local farmers’ markets. Try a classic syrup-topped stack at a roadside pancake house—many have their own maple syrup. Grab an apple cider donut at cider mills or orchards, especially in the fall. Sugar & Spice is a popular spot for maple treats in Mendon.
Farm stands sell fresh apples, berries, and homemade jams. Many general stores have deli counters for sandwiches made with local bread and cheese. If you love ice cream, Ben & Jerry’s Factory in Waterbury is a fun stop. A sample itinerary might include pancake breakfasts, market snacks, and a scoop of Vermont-made ice cream in the afternoon.
Local Experiences Beyond The Beaten Path
Get off the main roads and you’ll find places like the Hathaway Farm corn maze, especially fun with kids in fall. Stowe and Woodstock have scenic walks and small museums. In some towns, you can see barns with old quilts painted on them.
You might visit Mendon Orchards to pick apples or take a self-guided farm tour to meet cows and goats. Local craft shops and art galleries showcase pottery, woodworking, and paintings made by Vermonters.
List of activities for your trip:
- Explore corn mazes at Hathaway Farm
- Visit local orchards for apple picking
- Walk art trails or view murals in small towns
- Browse farmers’ markets for handmade crafts and fresh food
By taking these side trips, you can experience everyday Vermont life. Many activities are seasonal, so check what’s open before you go.
