• Q: What comes to mind when thinking about Vermont?
    A: Vermont tends to bring to mind maple syrup and remote ski resorts, but that's only the beginning of what this wonderful state has to offer.

  • Q: What makes Vermont a great destination?
    A: There's an excellent selection of places to visit, but the state's peaceful back roads and beautiful fall foliage make for a great day trip no matter where you choose to go.

Best Time for Day Trips in Vermont

  • May to June – Ideal for mild weather, blooming landscapes, and outdoor adventures.
  • September to October – Perfect for vibrant fall foliage, scenic drives, and apple picking.
  • July & August – Warm summer days for hiking, swimming, and visiting charming towns.
  • November – Enjoy cooler weather and fewer crowds at cultural and historical sites.
  • December to March – Great for winter activities, cozy retreats, and skiing in the mountains.

Bennington

Explore historic covered bridges, visit charming shops, and admire scenic mountain views.

Bennington

© Kevin Lenaghan/stock.adobe.com

Boasting a vibrant arts community, a rich history, and easy access to outdoor recreation, Bennington offers everything you'd want from a small Vermont town. The charming Main Street is lined with sidewalk cafes and locally-owned boutique shops, and if you head over to the downtown Arts District, you'll find galleries, a theater, and outdoor performance venues. History buffs should also visit the Bennington Battle Monument, a stone obelisk that happens to be the tallest man-made structure in the state. Just outside town, you can hike the steep but worthwhile 3.6-mile Harmon Hill Trail to get fantastic views of Bennington and the surrounding area.

Burke

Bike on world-class trails, explore lush forests, and enjoy a thrilling outdoor adventure.

Burke

© Colin/stock.adobe.com

Tucked away in Vermont's gorgeous "Northeast Kingdom", an area that was once chosen by National Geographic as part of their geotourism program, the tiny town of Burke is a true outdoor playground. Every season offers something unique to do; winter brings the opportunity to ski, snowmobile, and ice climb, while the warm summer weather is perfect for hiking, mountain biking, golfing, and paddling down the Clyde River. Spring is the perfect time to learn about the process of making maple syrup, but autumn is perhaps the most spectacular season, and visitors flock from all over the state to marvel at the incredibly colorful fall foliage.

Chester

Walk along quaint streets, admire historic homes, and explore unique antique shops.

Chester

© Dave/stock.adobe.com

A picturesque town hidden away in the Green Mountains, Chester is one of Vermont's best-kept secrets. The town is best known for its unique "stone village", a collection of pre-Civil War homes made from local granite, which is listed on the National Register of Historic Places. After you've seen the stone village, the Chester Village Historic District is only a few blocks away, and here you'll find an assortment of stately Federal and Victorian style buildings that house boutique shops. If you're visiting in September, you might be here for the annual Fall Craft Festival, when artists sell their wares in the village green.

Dorset

Visit marble quarries, explore scenic hiking trails, and discover charming village life.

Dorset

© lynnealbright/stock.adobe.com

Named after the beautiful Dorset county in England, Dorset is a quintessential New England town that was established in 1761. Several of the businesses in town have been operating continuously since the town was founded, including the Dorset Union Store and the iconic Dorset Inn. The small downtown shops sell locally made handicrafts, including quilts and custom wooden signs, and a farmer's market is held every Sunday all throughout the year. The town is also home to the oldest marble quarry in the entire country, which is now a popular local swimming hole during the summer.

Grafton

See beautifully preserved buildings, walk along peaceful streets, and explore local cheese shops.

Grafton

© lspi138/stock.adobe.com

With its lovely clapboard houses and its white steeple church, Grafton is an inviting little town that looks like something straight out of a movie. In fact, it looks much like it did back in the 1800s; many of the historic buildings have been carefully and lovingly restored by the community, but unlike some other "museum towns", it's home to an active community of residents. Visitors often come here simply to soak in the atmosphere and browse the town's art galleries and shops, but another popular attraction is the Grafton Cheese Co., which sells delicious hand-crafted cheeses.

Hartford

Discover rich history, visit cultural landmarks, and explore scenic riverside trails.

Hartford

© jerdad/stock.adobe.com

Located at the confluence of the Connecticut River and the White River, Hartford is composed of five villages, each with a distinct character. All of the villages are worth a visit, but the highlights include Quechee, an appealing resort town full of beautiful historic buildings, and the rural West Hartford, which offers excellent fishing and is located on the Appalachian Trail. The surrounding area boasts plenty of wonderful attractions as well, including the spectacular 165-foot Quechee Gorge and local maple farms where visitors can learn about how maple sap is collected and turned into syrup.

Hildene

Explore the Lincoln family estate, walk along manicured gardens, and admire historic architecture.

Hildene

© Iriana Shiyan/stock.adobe.com

The former summer home of Robert Lincoln, Abraham Lincoln's son, Hildene is a beautiful Georgian Revival mansion surrounded by landscaped gardens. The mansion is the highlight of the property, but other features include a sustainable goat dairy farm, a restored Pullman car, and a network of walking trails.

Guided tours of the house and property are available on a seasonal basis, but staff are always available to answer questions even when tours aren't being held. Visitors who want to learn even more about the site can book a special behind-the-scenes tour that goes into some of the archive rooms and the Exhibit Prep Room.

Killington

Go skiing on snowy slopes, explore vibrant trails, and enjoy a winter adventure.

Killington

© Francois/stock.adobe.com

If you want to ski, hike, or golf, Killington is one of the best destinations in the area. Located in the Green Mountains, the town is home to both the Pico Mountain ski resort and the Killington ski resort, which is the largest ski area in New England. Both resorts offer trails for skiers and snowboarders of every ability level, and in the summer, these trails are perfectly suited to hiking and mountain biking. Other attractions in the area include the Green Mountain National Golf Course, the beautiful Thundering Falls, and the President Calvin Coolidge State Historic Site.

Lake Willoughby

Admire crystal-clear waters, explore scenic hiking paths, and enjoy a romantic getaway.

Lake Willoughby

© Sonia/stock.adobe.com

Lake Willoughby isn't as well-known as some of the other lakes in Vermont, but that's exactly why it's so appealing. It's not the place to come if you're looking for big-city amenities; the only town you'll find on the lakeshore is the tiny community of Westmore, which has little to offer besides a few small stores selling basic supplies. Instead, visitors come here to enjoy the public beach, take advantage of the lake's excellent fishing, and hike through Willoughby State Forest on the lake's southern end. If you want to see the lake from above, you can climb up Mount Pisgah for some wonderful views.

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Pros and Cons of Day Tripping in Vermont
Pros Cons
Beautiful scenery year-round. Harsh winters in some areas.
Great for outdoor activities. Limited urban attractions.
Friendly and welcoming locals. Remote areas may lack amenities.
Plenty of cultural events and festivals. Seasonal traffic in tourist areas.
Rich history and heritage. Limited public transportation.

Plan Your Trip


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