#Bennington, Local Impact

Southwestern Vermont Autumn: A Dozen Destinations

A leisurely drive on the scenic byways of Vermont in the fall is an event all its own. The road winds through red, orange, and yellow mountains dotted with charming farm houses, white steeples, and covered bridges.

Two people walking on a paved path beneath yellow leaves

But the full Vermont experience is only available to those willing to stop a while. Here are a dozen places that turn Vermont from “a beautiful place to visit” into an all-out feast for the senses.

A Frosty morning

Visit Poet Robert Frost’s final resting place and run your fingers across his well-crafted epitaph at the beautiful Old First Church in Old Bennington, Vermont. Photos of the church and grounds turn up on postcards and in calendars, so be sure to conduct your own mini photo shoot. Those interested in learning more about the poet should not miss a visit to Bennington College’s Robert Frost Stone House Museum in Shaftsbury. There, Frost’s poems, including "Stopping by Woods on a Snowy Evening,” resound. It’s open 10 am–4 pm Thursday to Monday until October 31.  

Out-stand-ing Donuts

Continuing north on scenic Route 7A will take you past farm stands stocked with chrysanthemums and pumpkins and flooded with the delicious smell of apple cider donuts cooking. (They sell so fast, you will most definitely find them warm!) If they are out at one stop, the next is sure to be closeby. There are no fewer than 260 places to purchase fresh apple cider donuts in New England. And if you’re especially interested in donuts, don’t miss the King Bakery Donut Cart on Main Street in nearby Cambridge, New York. 

Traveling through time

Plan to stop at Hildene, the former summer home of President Abraham Lincoln’s son Robert Todd Lincoln and his wife Mary Harlan Lincoln. The house, historic exhibits, farm and farm animals, gardens, and trails create an exceptional experience. They have hay rides and other special events this time of year. All will put you in a classic autumn state of mind. 

Becoming a market expert 

If you happen to be nearby on a Sunday, you cannot miss the Dorset Farmers Market. The market features beautiful local produce, hand-crafted breads and baked goods, stunning crafts, and delicious prepared foods. Grab a bite and listen to one of the many talented folk and traditional music bands who play. Bonus: the market is held on the grounds of an authentic country store, H.N. Williams Store, until October 8 and on the factory floor of J.K. Adams, an incredible kitchenware store, during the colder months. 

Views, views, views

There’s no better way to see the fall foliage than from the top. Quarry Hill Trail in Pownal, Vermont, and Zaphod’s Run, a new trail from the Bennington Area Trail System, are both great short hikes with big views. For a longer, spookier hike, try Bald Mountain. The trail, which starts on North Branch Street in Bennington, takes you into the reputedly haunted Glastenbury Wilderness. The most stunning view in Southwestern Vermont, the White Rocks, is about three miles up. From there you can see the iconic buildings of the Bennington College campus and other local landmarks. 

Harvest Festivals

Lots of Southwestern Vermont towns and organizations host family-friendly harvest festivals this time of year. Visit the Merck Forest & Farmland Center Harvest Festival on September 16 to learn more about forests and their impact. For music, food, artisans, and more, you can’t beat the Peru Fair on September 23. Wing and a Prayer Farm, which produces beautiful naturally dyed wool and yarn, is holding an Open Farm with tons of fun activities on October 8, and Bennington’s Harvest Festival, which closes Main Street each year, is on October 14. 

Bennington meets Britain

Now that you’ve experienced New England, you might be hungry for the original. Luckily, Bennington boasts its very own fish and chips shop. Lil’ Britain will satisfy hearty cravings for Britain’s famously rich and salty fare, including Bangers and Mash and Mushy Peas. 

These and other stop-worthy spots—quirky antique shops, epic bookstores, handcrafted warm and cold beverages, and more—celebrate Vermont’s simple goodness, its unique sensory experiences, and the fleeting sweetness of the season.