By Monica Vanover on January 15, 2026
With smartphones, it’s easy to stay connected from afar. Finding time to be together is what makes all the difference, especially for these five friends.
Now’s the time for that Vermont road trip your crew is always talking about on the group chat and The Shires of Southwestern Vermont is the perfect destination.
Stunning outdoor adventures, internationally-inspired cuisine, craft breweries and distilleries, and unique historical and cultural events—The Shires has it all, plus the iconic covered bridges that made this region of Vermont famous. In and around picturesque Bennington and Manchester, you and your besties will find plenty to do, see and experience in a breathtakingly beautiful and culturally inclusive setting.
Follow five friends as they spend a long weekend in The Shires, discovering places to eat, hang out, and explore. Expect the kind of moments that turn into inside jokes and keep the group chat going long after the trip.
Some experiences are universal, like the feeling of freedom that comes with road-tripping with friends. Other experiences can only be had in The Shires. From moving historical narratives to one-of-a-kind Americana stops, these are the places to hit on your roadtrip that you can only see here.
Only in The Shires
Now’s the time to get outside before winter hits. Exploring the forests, waterfalls and lakes interwoven within The Shires of Southwestern Vermont offers access to hiking trails and scenic beauty that’s great for the ‘Gram but better shared with friends in person.
Lye Brook Falls: There’s nothing like the majestic beauty of a waterfall. Lye Brook Falls is one of Vermont’s highest waterfalls, tumbling 125 feet down ancient granite steps. The Insta opportunities in front of the falls are worth the hike through the Green Mountain Wilderness just outside Manchester. It’s free, dog-friendly, and gorgeous year-round, making it one of the best spots to snap that memory of all your friends in one place.
Emerald Lake State Park: In a region historically known for its marble quarries, Emerald Lake shimmers like a gem. This 20-acre lake and surrounding woodlands is a place for unplugging and enjoying the company of friends in a peaceful setting. Paddle out on its glassy waters or sit and take in the views from the sandy beach. With access to both the legendary Appalachian Trail and Dorset Mountain, this 430-acre state park is as ideal for a weekend of off-grid camping as it is a simple afternoon away from looking at your notifications.
Explore the Covered Bridges: The Shires are world-famous for its covered bridges. Painted iconic red with lattice-design architecture, these bridges built in the mid- to late-19th Century are recognized by the National Register of Historic Places. Three bridges—Silk Road, Paper Mill Village, and Burt Henry—are all within two miles of each other along the placid Walloomsac River. The Paper Mill Village Bridge is the longest covered bridge, while Silk Road is the oldest. The Burt Henry offers nearby river access so you can cruise in a canoe below the iconic span. All three (and more!) are worth a stop.
Accessible Adventure
SPONSORED BY Southwestern Vermont Chamber of Commerce
Finally Make that Vermont Trip Real. Here’s What to Do in The Shires.
Lye Brook Falls
Emerald Lake State Park
Hildene, the Lincoln Family Home, sits at one of the southernmost stops on the Vermont African American Heritage Trail. This 412-acre estate is an insightful look at American history’s past and present. Make sure you check in with the ‘Many Voices’ exhibits, an exploration of the legacy of the Black Pullman porters who played an integral role in both the labor union movement and the Civil Rights movement. The property features 14 historical structures including a Georgian Revival mansion built in 1905, formal gardens designed by Lincoln's granddaughter, and a restored 1903 Pullman railcar.
Explore living history:
A short jaunt from downtown Bennington, the Chocolatorium at the Village Peddler combines the quirky charm of Americana roadside attraction with delectable, irresistible chocolate. Housed in a renovated wagon shed, the historic building oozes kitsch, while inside you can immerse yourself in a world of artisan chocolates and specialty foods. Don’t forget to take a selfie with Cocoa, the world's largest chocolate teddy bear!
Indulge at The Chocolatorium:
Manchester is home to Northshire Bookstore, a universally beloved bookstore and literary hub that Publisher’s Weekly once hailed as the best bookstore in country. Family-owned and proudly independent since 1976, Northshire Books has everything for a culturally-informed shopping experience: over 300,000 new, used and rare books plus a curated selection of vinyl records. The location is a vibe, located in the historic Colburn House, a continuously running inn for over a century before it became a bookstore.
Get lost in a book forest:
Only in The Shires
The Shires’ two central hubs—Bennington and Manchester—are packed with delicious, farm-to-table restaurants, boutique cafes, craft breweries and local distilleries. If your group likes to eat, drink and be merry, these are some of the must-eat spots in The Shires.
Pangaea: Looking for that place to eat after a day spent exploring The Shires? Your search ends at Pangaea. North Bennington’s beloved eatery features global-inspired cuisine using farm-to-table ingredients served in a speakeasy style room with tons of moxie. Craft cocktails flow and there’s plenty of local brews on selection. Pangaea proudly reps dietary inclusivity, with gluten-free options, vegan menu items, and a gender-neutral restroom.
International Food Scene
TAAN Cuisine of Siam: Owner and chef Jariya Wannapat ran her own spa in Bangkok for 15 years before opening TAAN Cuisine of Siam, known locally as Niramit in South Shire. She partnered with local area farms to grow fresh Thai ingredients for her elevated take on classic Thai dishes. The experience itself is unique. Located inside the Vistorian-influenced Southshire Inn, TAAN offers a cool blend of East-meets-West aesthetics.
Dorset Bakery: Start your day right at this European-style boutique bakery and café. Dorset Bakery serves scratch-made pastries, artisan breads, made-to-order lunches, and specialty coffee drinks in a Provincial-style setting. If any of your friends need to check in to work remotely, Dorset Bakery is a god spot to enjoy a coffee and a pastry while you do it.
Union South: Located in Bennington’s beautiful and historic Putnam Building, Union South offers modern, approachable American dining inspired by local flavors and quality ingredients paired with Instagramable cocktails and live music.
International Food Scene
In The Shires of Southwestern Vermont, there’s cultural opportunities at every turn. With seasonal festivals like the Garlic Town, USA and the annual Vermont Homebrew Festival there’s always something to do to keep up with local culture on your trip. Other highlights include Green Mountain Bluegrass & Roots Festival and the Dead of Summer music festival in Manchester, the Harvest Fest in Bennington and the old fashioned country Peru Fair.
A stirring calendar of events is always on offer at the Bennington Museum, The Shire’s world-class exhibitor of Revolutionary War artifacts, folk art and American modernism.
This Fall at The Bennington Museum: Grab a special map and go on a tour of the North Bennington Outdoor Sculpture Show. Inspiring, strange, beautiful and everything in between, you’ll want to document this artsy journey.
At the museum, special exhibits run year-round. Current highlights include Green Mountain Magic: Uncanny Realism in Vermont (on exhibit to Nov. 2) and Vermont Vice: Sex, Drugs, Money, and Murder (Nov 15-Dec 30) featuring regional artists whose work explores the seedier sides of humanity.
Get Cultured
Bucket List
Where to Stay
SOUTH SHIRE a Little Hotel: Stay in a historic estate designed by the architect responsible for many of The Shire’s Victorian structures. At South Shire, the restoration and preservation of Gilded Age aesthetics lends a feeling of time travel. This is a living museum, and as a guest, your experience blends these 19th Century environs with the modern amenities of today.
Four Chimneys Inn: This Vermont B&B radiates charm. Intimate yet grand, Four Chimneys Inn is a stately residence close to nearby Bennington College. You’ll easily unwind in an atmosphere of old-world style and new-world comfort, but don’t sleep on breakfast. Four Chimneys is known for its full country breakfast and piping hot coffee. Gluten- and dairy-free and veggie options always available.
The Dorset Inn: End your day of outdoor adventures in the lively tavern of the Dorset Inn then stay the night. Established in 1796, the inn features beautifully appointed guest rooms, each one unique, many appointed with fireplaces, jetted tubs, and four-poster beds. The restaurant on-site offers farm-to-table cuisine perfect after a day hiking the nearby trails.
Barrows House: Travelers searching for elevated lodging look no further than Barrows House. Known as Dorset’s own small resort, Barrows House offers easy luxury throughout its 6-acre historic property. This converted rectory built in 1804 now boasts bespoke rooms, heated saltwater pool, outdoor spaces with lawn games, morning yoga and fine dining on a property built for ultimate relaxation, the Vermont way.
A DM can make or break your day but when it’s time to truly reconnect with friends, hit the road for a visit to The Shires of Southwestern Vermont. It’s an easy trip from the city—and a gorgeous one, too. Hike the forests, take pictures of waterfalls, kayak an emerald lake or stay inside and treat yourself to a shopping experience that may or may not include a visit to a Chocolatorium! When it’s time to plan, visit exploretheshires.com for all you need to know, including ideas on lodging, attractions and a handy travel guide. Don’t go another season without reconnecting with your crew. The Shires are waiting to make your roadtrip the best ever.
"If your group likes to eat, drink and be merry, these are some of the must-eat spots in The Shires. "
One cool thing about a visit to The Shires is the diversity of lodging options. Forget cookie-cutter corporate hotels, these creative inns, boutique hotels and B&Bs are part of an immersive southwestern Vermont experience.