For a wonderful summertime day trip, weekend getaway or impromptu vacation, it’s hard to beat Southwestern Vermont, where I’m a full-time member of the creative community. From the Capital Region, it’s such an easy trip across the border to see our picturesque rolling hills, phenomenal cultural attractions, and delightful shops and restaurants.
To start your breathtaking drive, take New York Route 7 northeast from Troy. As you cross over the Vermont border, take in the awe-inspiring mountain views on all sides. First stop: North Bennington. Pop into The Roasted Bean Espresso Bar on Prospect Street for a revitalizing beverage and delicious pastry. Or for upscale dining, Pangaea on Prospect Street offers tasty farm-to-table fare in a refined, yet casual setting. In the mood for sightseeing? Pay a visit to the Park-McCullough Historic Governor’s Mansion on Park Street. This extraordinary Victorian mansion features a vast collection of antique artifacts, informative exhibits and a wonderful outdoor flower garden. Afterwards, stretch your legs with an energizing stroll through the Mile-Around Woods, which is accessible through nearby entry points on Woods Lane.
Then head south to the lively and inviting town of Bennington. For delicious Vermont-brewed beer and pub fare, stop in at Farm Road Brewing or Madison Brewing Company Pub & Restaurant on Main Street. Or hit The Coffee Bar for live concerts in a stylish and rustically modern setting. For additional historic sightseeing, head to the Bennington Monument, a tall and majestic obelisk that pays tribute to The Revolutionary War’s famed Battle of Bennington on Monument Circle. The Bennington Museum on Main Street hosts an impressive collection of art and sculpture, and the Four Chimneys Inn on West Road provides comfortable and elegant lodging.
If you are a musician, you will not want to miss Old Mill Road Recording in my hometown of East Arlington, which is en route to Manchester—just head north on Route 7 from Bennington. The world-class destination recording studio is housed in two beautifully renovated 18th century townhouses next to an historic gristmill. Inside, a 48 Channel SSL Duality (state-of-the-art mixing board) is manned by Grammy Award-winning engineer Benjamin J. Arrindell. The main “live room” and recording booth overlook a waterfall and river through oversized glass windows, so clients who book a recording session are able to relax, rejuvenate and record in sublime comfort while taking in the gorgeous Vermont view.
Proceeding down Old Mill Road, stop into Bonnie and Clyde’s Corner Market for a delectable sandwich, then browse the assortment of artisan Vermont-made products. With your shopping bags and bellies full, take a left and meander east on East Arlington Road and across the famous Chiselville Covered Bridge to Manchester.
At the intersection of West Road and Main Street beckons the elegant, dinner-only Silver Fork restaurant. Continuing onward on Main Street, you will pass by the Orvis flagship store, as well as the American Museum of Fly Fishing and the Orvis Fly Fishing School. Southern Vermont is home to some of the most legendary fly fishing spots in the world, including the venerated Battenkill River, which runs through Manchester and West Arlington.
Shoppers, rejoice! Manchester is also home to the Manchester Designer Outlets. Throughout Main and Depot streets, visitors will find amazing deals at world-famous clothiers such as Polo Ralph Lauren, Armani, Theory and Brooks Brothers. Shopping made you hungry? You’re in the right spot. The Copper Grouse at the luxe Taconic Hotel offers wonderful American bistro fare, the Avocado Pit is great for fast-casual Mexican food, and the chefs at Thai Basil create Asian fusion delicacies with flair and panache—all right there on Main Street.
Artistically inclined travelers will no doubt savor a trip to Manchester’s preeminent art galleries, such as Helmholz Fine Art on Depot Street and Tilting At Windmills on Highland Avenue. Nearby Southern Vermont Arts Center (SVAC) hosts beautiful sculpture and art exhibitions at its breathtaking hillside campus, and its on-site CurATE Café offers beautifully plated, delicious food.
For additional fun and frolic, consider an expedition to Bromley Mountain Ski Resort, which in the summer months boasts a kid-friendly adventure park, treetop ropes course and disc golf course. Taking Route 11 east from Manchester, you will pass by a series of fantastic restaurants: Social House, Zoey’s Double Hex, The Raven’s Den, Garlic John’s and Pearl’s Pantry.
Regardless of the season, no trip to Southwestern Vermont is complete without a visit to Stratton Mountain Resort. In the summertime, the mountain transforms into an Elysian haven for mountain bikers, hikers and nature lovers; and mountaintop yoga classes and guided hiking tours are perfect for immersion into Vermont’s beautiful natural scenery. Then head into the village to the shops and restaurants for fun for the whole family.
Benjamin Lerner is a staff writer for VERMONT Magazine, Stratton Magazine, Berkshire Magazine and Manchester Life. He is also a musician, composer and recovery advocate. His debut album, CLEAN, was released in 2020, and he recently made his Carnegie Hall debut with the Indie Collaborative.