Sponsored by The Shires of Southwestern Vermont DMO
As the crisp air of fall sweeps across the Green Mountains, The Shires of Southwestern Vermont transforms into a kaleidoscope of vibrant colors, making it a major destination for autumn enthusiasts and travelers of the soul alike. This year, immerse yourself in the beauty and rich history of this region, where every town and village offers a unique blend of natural splendor, cultural heritage, and outdoor adventure that beckons visitors to slow down and savor every moment.
Begin your journey in Bennington, the southern anchor of The Shires, where history meets contemporary charm in an autumnal setting that feels magical.
The towering Bennington Battle Monument, a proud symbol of Vermont’s Revolutionary War victory, offers a panoramic view of the region, showcasing the vivid fall foliage that blankets the rolling hills and valleys. The surrounding countryside, dotted with historic homes and peaceful farmlands, is a photographer’s dream, especially in the golden light of a fall afternoon. After soaking in the views, wander through the historic streets of Old Bennington, where the past comes alive with every step. Here, the Old First Church, one of Vermont’s oldest congregations, and the gravesite of beloved poet Robert Frost invite quiet reflection amid the rustling leaves.
Head north on The Shires Byway (former Route 7A), a scenic byway that connects the towns of The Shires, each with its own story to tell.
Manchester, nestled at the base of Mt. Equinox, is a four-season destination that shines brightest in the fall. The historic Hildene, the Lincoln family home, is a must-see. Perched on a hilltop, the estate offers a stunning vantage point to admire the vibrant patchwork of autumn colors that stretch across the valley below. Stroll through the meticulously maintained gardens, where late-season blooms mingle with the fiery reds and oranges of the surrounding woodlands. Inside, the mansion’s rich history and connection to President Abraham Lincoln’s family add a poignant layer to the beauty of the setting.
Outdoor Adventures and Local Flavors
Autumn in The Shires is synonymous with outdoor adventure, where the crisp air and breathtaking scenery create the perfect backdrop for exploring the region’s natural wonders. Take a hike up Bald Mountain and rest on the “White Rocks” as you gaze out onto the valley. The state parks in the area, including Woodford State Park and Shaftsbury State Park, are ideal for hiking, fishing, and simply enjoying the serenity of nature. Woodford, with its high elevation, often sees the first hints of snow mingling with fall’s last burst of color, creating a unique and serene landscape. For those seeking a more exhilarating experience, the trails of Long Trail offer challenging hikes with rewarding vistas at the summit, where you can see for miles across the autumn-draped mountains.
For a gentler outdoor experience, take a leisurely drive along the many scenic byways that crisscross The Shires. Stop at roadside farm stands overflowing with apples, pumpkins, and late-season vegetables, or venture into one of the pick-your-own orchards for a classic autumn activity. The sweet scent of freshly pressed apple cider and the taste of warm cider doughnuts are autumnal delights not to be missed.
If you’re looking for a unique way to experience the outdoors, consider exploring The Shires on two wheels. The region offers an array of biking trails, from leisurely rides along country roads to more challenging mountain biking adventures. The quiet backroads provide the perfect setting to take in the stunning fall colors at your own pace. For a truly unforgettable experience, try the rail trails that wind through the countryside, offering a glimpse of Vermont’s rural charm as you pedal past farms, forests, and picturesque villages.
After a day of exploring, indulge in the local flavors that define The Shires. The region is home to a burgeoning farm-to-table movement, with chefs in local restaurants crafting seasonal dishes that highlight the best of Vermont’s produce. For a more refined dining experience, many of the region’s inns and restaurants feature menus that celebrate the bounty of the season, offering dishes that highlight local ingredients with creative flair.
Cultural Riches and Festivities
The Shires is also a hub of cultural activity, especially during the fall, when the season’s beauty inspires festivals and events that draw visitors from near and far. The Dorset Theatre Festival, Bennington Theater, Monument Art & Cultural Center, and Southern Vermont Arts Center host an array of performances and exhibitions, showcasing the region’s vibrant arts scene against the backdrop of stunning autumn landscapes. Whether you’re a theater enthusiast or an art lover, these venues offer a rich cultural experience that enhances your visit to The Shires.
If you’re a history buff, the American Museum of Fly Fishing and the Bennington Museum offer fascinating insights into the area’s past.
The Bennington Museum is particularly renowned for its extensive collection of artifacts related to the Battle of Bennington, as well as its exhibits on regional art and history. The museum’s galleries provide a deep dive into the stories that have shaped this corner of Vermont, from the Revolutionary War to the modern day, making it a perfect stop on your autumn itinerary.
Festivals are another highlight of the season. The Garlic Town, USA festival in Bennington kicks off the season every Labor Day Weekend and is a unique celebration of all things garlic, featuring food, music, and local vendors. It’s an event that embodies the quirky, community-focused spirit of The Shires, drawing garlic lovers from all over to indulge in garlicky treats and enjoy the festive atmosphere. Meanwhile, the Peru Fair and Harvest Fest in October capture the essence of small-town Vermont with its traditional crafts, live music, and a famous harvest decor.
A Warm Welcome Awaits
Wherever your travels take you in The Shires, you’ll find warm hospitality and cozy accommodations that make you feel right at home. From historic inns like the Arlington Inn and Spa, Dorset Inn, The Four Chimneys Inn, or Equinox Golf Resort & Spa where history and luxury meet, to modern comforts at the Kimpton Taconic, Hampton Inn and Suites, or the Hotel Vervana there’s a place for every type of traveler. For a more intimate experience, consider one of the many charming bed and breakfasts or vacation rentals that dot the region. These accommodations often offer personalized touches, such as homemade breakfasts featuring local ingredients, that enhance your stay and provide a deeper connection to the local community.
As you plan your visit to The Shires of Southwestern Vermont this fall, prepare to be enchanted by the region’s stunning landscapes, rich history, and vibrant community. Whether it’s your first time or a return visit, The Shires offers endless opportunities to create lasting memories amid the splendor of autumn. The charm of this region lies not just in its scenic beauty, but in the stories, traditions, and people that make The Shires a truly special place to visit. Come for the foliage, stay for the experience, and leave with memories that will call you back year after year.
A great place to start is to pick up or download our new 2024-2025 Shires of Southwestern Vermont Travel Guide: https://exploretheshires.com/shires-travel-guide
