Enjoy the stunning colors of Vermont in the fall

A Spectacular Trip Through Southern Vermont in the Fall

Select Registry - August 12, 2021

See Stunning Southern Vermont!

Enjoy the stunning colors of Vermont in the fall

Though there are many wonderful places to enjoy Vermont in the fall, there is perhaps nowhere more beautiful than the southern hills of Vermont.  It’s an area filled with beautiful villages, charming history, and stunning vistas. Though this area is wonderful in all 4 seasons of the year, it’s particularly magical during the fall, when peak fall foliage is on full display. 

Between the towns of Bennington and Manchester, the area of southwestern Vermont has been lovingly referred to as “The Shires of Vermont.” It’s a picturesque region nestled between the Taconic and Green Mountains, and it’s one of the prettiest places to enjoy Vermont in the fall. 

These 15 charming towns are connected by a scenic stretch of Historic Route 7A, now called the Shires of Vermont Byway. Three towns here, Manchester, Sunderland, and Dorset, also happen to be home to some of the most charming Vermont Bed and Breakfasts. 

It’s hard to go wrong with a visit to this area in September and October. Peak fall foliage usually occurs sometime in late September through mid-October, but truly there’s plenty of beauty to enjoy in the surrounding weeks as well.

To enjoy the best of Vermont in the fall, you’ll need to start planning now, as it’s an exceptionally popular time of year to visit! Browse through our collection of Select Registry Bed and Breakfasts in Vermont below.

Enjoy the stunning colors of Vermont in the fall

See Southern Vermont in the Fall

As we said previously, southern Vermont in the fall is a magical place. No matter how much or little you do, you’ll see the vibrant reds, oranges, and yellows of fall everywhere you turn. 

The southwestern corner of Vermont is also easy to access. It’s just a few hours outside of New York City and Boston, which means in no time at all, you can escape the city and embrace the rural beauty of Vermont in the fall! As you begin planning your adventure, take the time to know three of our favorite towns in southern Vermont.


From historic Inns and great shopping to plentiful opportunities to get outside for some biking, Manchester is a wonderful place to see Vermont in the fall. Manchester also happens to be one of the best shopping destinations in Vermont. It’s even been called the Fifth Avenue of the Green Mountains! 

Manchester is also home to Bromley, a popular ski area that also happens to be an excellent place to enjoy the best of Vermont in the fall. There’s even a new adventure park there for the young at heart to enjoy. Consider taking the scenic drive from Manchester to Poultney on the Stone Valley Scenic Byway for even more of those classic Vermont in the fall views. 

Don’t miss the Southern Vermont Arts Center while in Manchester, either. It’s nestled on 100 acres in the Green Mountains. It offers various activities, including art exhibitions, a sculpture park, woodland hiking on the Boswell Botany Trail, and several beautiful art galleries. Altogether, it’s a great place to enjoy a bit of Vermont in the fall. 


All you need to do to enjoy the beautiful views of Vermont in the fall is to hop in the car and head out for a drive.  There are few drives prettier than Skyline Drive in southern Vermont, which takes you up Equinox Mountain near Sunderland. This 5.2-mile climbs to a height of 3,248 feet, offering breathtaking panoramic views of the area. 

With great access to the Green Mountain National Forest here, there’s no shortage of hiking. Sunderland is also a great place to get out on the water for a bit of kayaking or canoeing. The Battenkill River runs right through the heart of the area, offering a unique angle from which to enjoy Vermont in the fall.  


The historic town of Dorset is home to a thriving arts scene and what seems like a never-ending list of outdoor activities. It’s a lovely place to enjoy the scenery of Vermont in the fall. 

There is plenty of great mountain biking and hiking trails in the Dorset area to explore. For some truly great fall views, head to The Pinnacle and Cutler Memorial Forest. The Mad Tom Notch Trail, a spur trail from the Appalachian & Long Trails, is also great. 

One of the best ways to truly appreciate Vermont in the fall is to head to the top of the mountains for a birds-eye view of the colorful valleys below.  In Dorset, you can do that at Stratton Mountain Resort

As great as these towns are, there’s more to enjoy about Vermont in the fall. Here’s a great road trip guide to southern Vermont, combining some of the other top areas and attractions into a gorgeous road trip. 

Enjoy the stunning colors of Vermont in the fall

Plan Your Cozy Vermont Getaways

Vermont in the fall is the perfect place to enjoy cozy, romantic getaways. Between the crisp mountain air of southern Vermont and the bold colors surrounding you, we have little doubt you’ll feel the magic in the air.  Add to it a stay at our Select Registry Bed and Breakfasts in the area, and you have the perfect recipe for cozy Vermont getaways. 

Fall isn’t the only great time to visit our southern Vermont Bed and Breakfasts, however. Winter also happens to be a beautiful season, and another wonderful time to plan cozy, romantic Vermont getaways. Just as fall in Vermont isn’t the only great time to visit, there are other wonderful towns and areas around the state worth exploring, too – each filled with its own collection of Vermont Bed and Breakfasts!

Wherever you stay and whenever you choose to plan your Vermont getaways, you can expect nothing but the finest accommodations, sumptuous breakfasts in the morning, luxuries like jacuzzi tubs or warming fireplaces, extra touches that make your stay memorable, and exceptional hospitality.

Our Innkeepers know just how to help you create the perfect getaway, and they also know when to leave you alone for some of that coveted “you” time. Moreover, each of the Vermont Bed and Breakfasts below have passed the most rigorous inspection in the industry, ensuring you have the safe and high-quality getaway you deserve.  

Learn more about what it means to Stay Select, get to know our cozy Vermont B&B’s, and then start planning your getaways to these charming southern Vermont towns today!

Vermont Bed and Breakfasts

The Inn at Manchester

Tucked away in the breathtaking landscape of the Green and Taconic Mountains, the Inn at Manchester provides an idyllic home base for exploration of Vermont’s cultural haven of Manchester. This year-round destination has something for everyone, including shopping, theatre, art, golf, skiing, hiking, fishing, and more.

As always, there is no rule you ever have to leave the Inn! Unwind beside the hearth in the living room or over a game of chess in the cozy den. Maybe take a stroll around our beautiful grounds, a dip in the pool, or relax in a rocker on the porch. Then join us for cocktail hour in our cozy, living-room-style pub – one of the places where guests gather to relax and socialize.

Hill Farm Inn

Tucked away on fifty picture-perfect acres, this boutique inn and retreat offers a collection of impeccably renovated guest rooms and cottages for an authentic, upscale Vermont escape. Distinguished by thoughtful details, luxurious amenities, and stunning valley views, with on-site opportunities every season; stroll the River Loop, lounge poolside, or stargaze by the outdoor fire. Relax on one of the inn’s rambling porches. Begin your day with a farm-to-table breakfast in the cheerful dining room. End with a crisp cocktail from the Battenkill Pub. 

In between, discover our beckoning mountains, play a round of world-class golf, or explore southern Vermont’s charming towns and villages.

West Mountain Inn

Luxurious rooms, splendid meals, refreshing outdoor pursuits, relaxing afternoons, and convivial evenings – now imagine having your own Country Estate, and you will understand what a visit to the West Mountain Inn is like. Set high on a mountainside overlooking the historic village of Arlington and the Green Mountains beyond, the century-old West Mountain Inn has been hosting guests for over thirty years.

Visitors are surrounded by spacious, antique-filled guest rooms, fantastic views, and 150 acres of gardens, lawns, woodlands, and meadows. Without having to leave the Inn’s property, guests can hike or snowshoe on miles of trails, fly fish, swim or canoe in the famous Battenkill River and read or relax in the Adirondack chairs on the front lawn. The Inn’s wood-paneled dining room provides the perfect setting for the lavish country breakfasts and sumptuous 5-course dinners created daily by our award-winning chef.

The Inn at Ormsby Hill

Step across the massive marble threshold of this beautiful, historic property, drop your bags and breathe a sigh of relief. Welcome to a house that has been a home away from home to many.

Stop first in the heart of our home – the conservatory dining room. With magnificent views of the Green Mountains, an intricately carved mahogany mantle surrounding an immense fireplace, snacks, and beverages day and night, and our amazing three-course breakfast every morning, this room will nourish your body and soul. Our enormous patio and porch are Steps away with Adirondack rocking chairs, patio tables, porch swings, and views you will never forget. Plan some time out here with your book, tablet, wine, or favorite beverage, and let yourself dissolve into the surroundings. Stroll around the exquisitely landscaped grounds and expect a few surprises: a labyrinth in the meadow or a cozy gazebo hideaway. 

The Dorset Inn

For more than 224 years, the Dorset Inn has offered traditional New England Hospitality. As Vermont’s oldest continually operating inn, we pride ourselves on offering travelers gracious lodging, gourmet dining, fine wines, and great spirits! Travelers who we’ve had the pleasure of hosting enjoy our welcoming atmosphere and exceptional cooking.

No matter when you plan your stay, there’s something to do all year long in Vermont! Imagine spending the day downhill skiing at Bromley and Stratton during the winter months. Or shop Manchester’s designer outlets and attend summer stock theater at our own Dorset Playhouse! In the fall, enjoy Vermont’s unparalleled foliage season. From the quiet getaway to the outdoor adventure vacation.

Barrows House

Barrows House is the epitome of the quintessential historic Vermont charm! We are proud to be one of the first lodging accommodations in Dorset. Today, we offer guests a place of rest and relaxation with the distinct ambiance and character from a bygone area!  

In 2012, Barrows House was purchased by the owners of the Historic Dorset Inn and was completely renovated before opening in the summer of 2013. The inn’s 27 guest rooms, restaurant, and taproom have been modernized and reconfigured to include a new large outdoor dining terrace and a local marble bar. Today, Barrows House boasts several cottages, a swimming pool, tennis courts, and beautiful gardens and grounds, as well as the finest of accommodations and superb American cuisine!

exterior inn

Thanks for looking around!

Want to learn more about our distinguished collection of inns? Sign up to receive the latest with Select Registry.

white cottage

Stay in the know with Select Registry!

Want the latest offers, news, and specials from Select Registry? Sign up for our newsletters to get inn-sider updates from our collection of distinctive properties!