Welcome to stick season in Vermont. This period of late fall — when the trees are mostly bare, the frenzy of foliage tourism has subsided and the snow hasn’t started to pile up — can be a great time to explore the state.
We suggest spending some time in southern Vermont, and have highlighted several cozy, spooky, outdoorsy and historical activities to get your itinerary started.
Read our travel guides for northwest Vermont and the Northeast Kingdom, published in June.
Journalists from the New England News Collaborative have been on the road, seeking out the best local spots in the region. Find ideas here for other New England states.
What to do if you’re a…
Book nerd
Southern Vermont is full of literary history, thanks in no small part to students and faculty of Bennington College. This region of the state has been pivotal in the lives of Robert Frost, Bret Easton Ellis, Jonathan Lethem, Donna Tartt, Lucy Terry Prince, John Irving, Rudyard Kipling and Shirley Jackson, among others.
Follow the Brattleboro Words Trail
Download the Brattleboro Words Trail app on your phone — or visit the website — and put on a pair of headphones. This project has dozens of audio stories that you can listen to as you wander through downtown Brattleboro and beyond. You’ll learn about the region’s connections to people like Lucy Terry Prince, who is believed to be the nation’s first African American poet, and author John Irving. Stop by the Brooks House in downtown Brattleboro to listen to the story of Rudyard Kipling, who lived in nearby Dummerston and liked to visit the Brooks House.
- Bonus: Rudyard Kipling’s home in Dummerston, called Naulakha, is owned by Landmark Trust USA and open to the public on select weekends of the year for self-guided tours. For the rest of the year, you’ll have to rent it out for at least three nights if you want to sit at the desk where The Jungle Book came into existence. (There’s also a state historical marker on the corner of Route 5 and Black Mountain Road.)
In North Bennington, explore the world of Shirley Jackson
Jackson is known for the unsettling short story The Lottery and the gothic horror novel The Haunting of Hill House.
The village celebrates Shirley Jackson Day with readings and festivities each June, if you happen to be visiting then, but fall is also an apt time to marinate in Jackson’s work.
Jackson lived at 12 Prospect St. and 66 Main St. The homes are not open to the public, but you can view them while conducting your own Jackson-themed walking tour. The Bennington Museum has several cat figurines that were owned by Jackson. Stop by the McCullough Free Library to find another of Jackson’s cat statues among the shelves — and what better place to sit down with some of Jackson’s literary works or her biography?
More from Brave Little State: What Draws So Many Writers And Poets To Vermont?
More from Vermont Public: Rediscovering Shirley Jackson
Visit Robert Frost’s house in Shaftsbury
Frost wrote Stopping by Woods on a Snowy Evening at the house in June 1922, and he was also living there when he received his first Pulitzer Prize in 1924. The house is now a museum owned by Bennington College and is open select days from spring to early fall. From November to April, you’ll have to make an appointment and perhaps pay an additional fee; see the museum website for more. After exploring the house, drive about 10 minutes south to the Bennington Centre Cemetery to pay respects (and perhaps read some poetry) at Frost’s gravesite.
More from Vermont Public: Bennington College to acquire Robert Frost's Shaftsbury home
Go book shopping
A day in this part of the state wouldn’t be complete without browsing through a bookstore, and there several shops to choose from:
- Bennington Bookshop claims the title of Vermont’s oldest independent bookstore, dating back to 1928.
- Northshire Bookstore in Manchester was a historic inn before it was converted to a bookstore nearly four decades ago. It boasts a whole floor for children’s books as well as a bakery and cafe.
- The staff at Bartleby’s Books in Wilmington are ready with recommendations, and you can browse local art upstairs.
- Everyone’s Books in Brattleboro, founded by peace and anti-nuclear activists in 1984, specializes in books about social change and progressive topics. You’ll also find bumper stickers (covering the walls, and for sale) and T-shirts that match the peace-and-love vibe.
All four of these bookstores are on the Vermont Independent Bookstores Passport, so you can start gathering stamps. If you visit at least five bookstores, you can win prizes — but the real prize is recognizing the value of these bookstores in Vermont’s communities.
Creative
Admire the unsung artistry of stone walls
Walk around Stone Wall Park at Scott Farm in Dummerston any time during daylight hours. This is where experts in dry stone walls have shown off their mastery. You can also stop by Scott Farm Orchard for heirloom apples and other fruit. Rudyard Kipling’s home (see above) is right next door.
More from Brave Little State: Where did all Vermont’s stone walls come from?
Check out the contemporary art exhibits at the Brattleboro Museum and Art Center
Pro tip: The museum has several fun traditions including a Domino Toppling Extravaganza every fall (in 2024, it was on Oct. 6) and a recurring “Glasstastic” exhibit that has glass artists make real sculptures based on kids’ drawings of imaginary creatures.
Steep yourself in even more visual art
Bennington Museum boasts the largest public exhibition of Grandma Moses’ paintings in the world, along with other exhibits of art, pottery and local history. About 40 minutes north is the Southern Vermont Arts Center in Manchester, with another impressive suite of exhibits.
Historian
Explore a restored Pullman railcar and learn about the Black porters
Abraham Lincoln’s son, Robert Todd Lincoln, built an estate in Manchester that’s now known as Hildene, the Lincoln Family Home. You can tour the mansion, formal gardens, farm and trails. Don’t miss the restored Pullman railcar (Robert Todd Lincoln was president of the Pullman company) and explore the exhibit about the Black porters who worked for the Pullman Company. Hildene is a stop on the Vermont African American Heritage Trail.
Learn about the Battle of Bennington
This pivotal Revolutionary War battle prevented British troops from capturing the Bennington supply depot. The fighting took place across state lines, in New York. The former site of the depot is now marked by a tall monument where you can learn the history.
More from Vermont Edition: Examining the Battle of Bennington through history — and music
Take a walking tour of one of Vermont’s oldest towns
Buildings in Bennington date as far back as the 1760s, and the town has shared a self-guided walking tour of 27 historic highlights. Architectural and Revolutionary War history buffs, rejoice.
Nature lover
Take a scenic drive
Try the Molly Stark Byway, which is Route 9 from Bennington to Brattleboro, for some beautiful views. Stop at the Hogback Mountain Country Store in Marlboro for the famous “100 mile view” overlook.
- Want to get a little more elevated? From Memorial Day weekend to Halloween, you can pay a fee to drive the Mount Equinox Skyline Drive in Arlington.
Cast a line into the history of angling
Fly fishing enthusiasts will enjoy the American Museum of Fly Fishing in Manchester, right next to the Orvis flagship store.
Take a walk
There are many options for easy hikes in the region; one is the Hoot, Toot and Whistle Trail in Wilmington, which runs along a former railroad bed and ends at Harriman Reservoir. (If it's warm, you can take a dip.)
Hike, ski, bike or get a ride to the summit of Mount Snow
This ski resort has plenty to offer even when it’s not covered in snow. Several trails take you to the top, where you’ll get a view of Somerset Reservoir. In warmer months you can take the Bluebird Express lift up and down the mountain (or just down the mountain, after you’ve hiked to the summit).
More from Vermont Public: The magic of skipping stones at Lake Paran in Bennington
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