Fall is in full bloom here in beautiful Brattleboro, Vermont, and we love it. Whether you’re staying with us this season or not, one of the best ways to immerse yourself in the rich colors of autumn is by exploring one of the many Vermont scenic drives. Several stunning routes near Brattleboro wind through the Green Mountains Vermont, offering panoramic views and a truly unforgettable Vermont scenery experience. These drives are among the most picturesque scenic drives in Vermont, showcasing covered bridges, rolling farmland, and forests ablaze in fall color.
In addition to witnessing the best of Vermont fall foliage, this time of year is perfect for appreciating the region’s heritage and the charming rural character found in towns like Brattleboro. For an iconic Vermont road trip, consider traveling part of the famed Route 100 Vermont—often called the most scenic road in the state. A drive along Vermont Route 100 is ideal for a relaxed day of sightseeing or as a memorable leg of a longer Vermont trip. Be sure to check your Vermont map and plan your stops—local farms, historic villages, and mountain lookouts await.
Southern Vermont is one of the top destinations for fall getaways, and our #1-rated Vermont Bed and Breakfast is the perfect place to start and end each day. Just a short walk from downtown Brattleboro, our inn offers a peaceful escape with access to trails, gardens, and breathtaking seasonal views. Whether you’re heading out for one of the top Vermont scenic drives, enjoying a cozy afternoon by the fire, or planning one of your future Vermont trips, we’re here to help you make the most of fall in this incredible region. Book your stay today!
The Best Vermont Scenic Drives Near Us
Though there are countless ways to experience fall in Vermont, one of the quickest and most rewarding ways to soak in the season’s vibrant hues is by taking one of the many Vermont scenic drives near Brattleboro. Southern Vermont is considered one of the most picturesque areas in the state, offering access to winding backroads, forested mountainsides, and sweeping valley views. These scenic drives in Vermont are a must for anyone planning a fall Vermont trip to see the fall foliage, whether you’re here for a weekend getaway or a longer Vermont road trip.
You will pass through peaceful river valleys and rural farmland famous across the state, and climb into the Green Mountains of Vermont for dramatic views that stretch for miles. With every turn, these Vermont scenic drives showcase why the region is known for its unforgettable autumn color and classic charm. Once you take just one of these routes, you’ll understand why a well-planned drive is one of our favorite ways to experience authentic Vermont scenery each fall.
Our 3 Favorite Vermont Scenic Drives Near Brattleboro:
- Molly Stark Scenic Byway (Route 9) is the southernmost of the officially designated scenic drives in Vermont. It runs from Brattleboro to Bennington, cutting directly through the stunning Green Mountains, and offering a beautiful blend of historic towns, winding forest roads, and sweeping vistas. Along the way, you’ll encounter iconic trails like the Appalachian Trail and Long Trail, ideal for adding a short hike to your scenic journey.
- Brattleboro to Mount Snow (via Route 100 Vermont) drive includes parts of Vermont Route 100, widely considered one of the best fall foliage routes in New England. It’s a highlight of any Vermont road trip, covering nearly 100 miles of breathtaking countryside. Points of interest include Mount Snow, where you can take a fall foliage chairlift ride, and scenic stops like Buttermilk Falls, Jamaica State Park, and the famous Vermont Country Store in Weston. Grab a Vermont map and plan a full-day or even multi-day adventure—you’ll want time to enjoy every stop along the way.
- Connecticut River National Byway is an officially designated National Byway that travels alongside the Connecticut River, tracing the boundary between the Green Mountains of Vermont and the White Mountains of New Hampshire. It offers both natural beauty and cultural richness, making it one of the most unique Vermont scenic drives. Along the route, you’ll find museums, historic towns, riverside views, and plenty of places to pull over and soak in the surroundings. It’s a fantastic option for pairing a scenic route with meaningful stops that reflect the heart of Vermont trips past and present.
Eight More Things to do This Fall in Vermont
The rural, rolling hills and river valleys of southern Vermont are among the most beautiful parts of the state, especially during the vibrant fall season. Whether you’re looking for a cozy retreat to relax or planning a full Vermont trip packed with seasonal activities, our top-rated Vermont Bed and Breakfast is the perfect place to land for a few days. From our location near downtown Brattleboro, you’re ideally situated to explore the region’s best hikes, farms, waterfalls, and the most scenic Vermont scenic drives in the area.
There are so many things to do in Vermont in the fall, including taking scenic drives and exhilarating hikes, to enjoying more traditional fall activities like apple picking and cider sipping. There’s no shortage of great things to do in Vermont in the fall, and we’ve included some of our favorites in the Brattleboro area below.
- Hiking is one of the best ways to enjoy Vermont in the fall, and there’s no shortage of great Brattleboro hikes to take this fall. Consider hiking the famed Mount Monadnock in nearby New Hampshire, for example. You don’t need to take an exhausting hike to enjoy the best of Vermont in the fall; you can do it from right here in our backyard with the popular Retreat Trails.
- Like hiking, biking is a great way to see the scenery of Vermont in the fall. Brattleboro Bicycle Shop has rentals available, and there are multiple cycling tours to take in the area. We’re also happy to pull out a Vermont map and suggest some routes.
- There are plenty of great Vermont ski resorts near Brattleboro, but winter isn’t the only time to visit. You’ll also find scenic chairlift rides and fantastic Vermont fall foliage at many of them, including Stratton Mountain Resort and Mount Snow.
- Tour the top Vermont Covered Bridges around the state, and enjoy these charming structures surrounded by the vibrant foliage of Vermont in the fall.
- Chase waterfalls and enjoy the beauty of Vermont in the fall in an entirely different way. Popular choices nearby include Dummerston Falls, Jelly Mills Falls, and Beaver Brook Falls.
- Enjoy a classic fall afternoon sipping apple cider, picking apples, and more at local orchards like Scott Farm and Green Mountain Orchards.
- Taste your way down the Vermont Cheese Trail. It’s the perfect complement to all of those fall adventures!
- Ride the beautiful Champlain Valley Dinner Train through some beautiful Vermont fall foliage.
Whatever brings you on your Vermont trip this fall, make sure you enjoy a few days of rest and relaxation at the #1 Bed and Breakfast in southern Vermont. Book your room at our Vermont Bed and Breakfast today!
