Explore Bennington and Manchester, Vermont This Winter
Note: Advertising is how we keep this site free for you to enjoy, and we earn a commission from affiliate links that may be included in this post. Thank you for supporting Vermont Explored!
Wondering where to go for your winter getaway? We have lots of suggestions, but one of our favorite Vermont winter escapes is the southwest corner of the state.
Spend Friday night in Bennington and Saturday night in Manchester, 25 miles up the valley, and you get Colonial history, covered bridges, Hildene, and your pick of downhill or Nordic skiing in one weekend.
Bennington and Manchester are at two ends of a 25-mile narrow valley in southwestern Vermont and framed by mountains to the east and west, making for beautiful scenery in all directions.
The natural beauty is why I live in this part of Vermont, and I’d love to entice you to visit when the winter winds blow across the mountains and the snow blankets the ground.
Manchester is the perfect home base if you want to spend the weekend skiing, and Bennington is a beautiful spot for other types of recreation, including Nordic skiing, winter hiking, snowmobiling, and snowshoeing. Both towns have a rich history, beautiful New England architecture, and tasty dining options.
No matter which town you choose to hang your hat, you won’t run out of things to do! Here’s a complete weekend guide for winter in Manchester and Bennington, Vermont.
Bennington and Manchester Winter Weekend at a Glance
- When to go December through March. Visit in December to catch Hildene dressed for Christmas Eve 1912.
- Where to stay One night in Bennington, one night in Manchester.
- How to get there Route 7 connects the two towns in about 30 minutes. Route 7A is the slower, prettier way with a slower speed limit.
- Getting around You’ll need a car. Downtown Manchester is walkable from the Barnstead Inn and the Kimpton Taconic.
- Top 3 highlights Robert Frost’s grave in Old Bennington, Hildene, and snowshoeing the Equinox Preserve.
- Dog-friendly? Very. My dog Malinda has hiked the Equinox Preserve, the Park-McCullough grounds, and Prospect Mountain’s dog-friendly trails, and she’s welcome at Northshire Bookstore and Charlie’s. Hildene is the exception: dogs aren’t allowed on the trails.
Last checked by Tara: [October, 2026]
Tara’s take
Only have one night? Sleep in Manchester. It has far more places to stay and eat, and Hildene and the Equinox Preserve will fill a whole day on their own.
But First, Where to Stay in Bennington and Manchester, VT
Base your stay in either town, or spend a night in Bennington and a night in Manchester, so you can explore both towns properly.
Stay in Bennington
Boutique
South Shire: A Little Hotel
Victorian architecture, classic decor, and a short walk to downtown Bennington.
- 124 Elm Street, Bennington
- Dogs: Yes
Budget
The Harwood Hill
The budget-friendly pick, with eclectic local artwork in every room.
- Bennington, on Route 7A
- Dogs: Yes
Stay in Manchester
Tara’s pick
Kimpton Taconic
Dogs aren’t just tolerated here, they’re celebrated. I got the feeling our dogs were very welcome.
- Walk to shops and restaurants in Manchester
- Dogs: Yes, no pet fee and no size limits
Dog-friendly
The Barnstead Inn
Modern rooms and suites, a homemade breakfast, and fire pits two blocks from downtown.
- Breakfast included; no children under 12
- Dogs: Yes, in select rooms (one dog, one-time cleaning fee)
Splurge
Inn at Ormsby Hill
A historic inn with ten rooms, each with a jetted tub, and a hot country breakfast with mountain views.
- Fireplaces: in every room!
- Dogs: No
A Winter Weekend in Bennington and Manchester, VT
Every Stop on This Winter Weekend
| Stop | Day | Town | Time to spend | Winter note | Dogs |
|---|---|---|---|---|---|
| Bennington Monument and Old Bennington | Friday | Bennington | 1 hour | Monument and Bennington Museum closed in winter; grounds open | On-leash, outdoor walk |
| Old First Church and Robert Frost’s grave | Friday | Bennington | 30 minutes | Cemetery open year-round | On-leash, outdoor walk |
| Covered bridge tour | Saturday | Bennington and Arlington | [1 to 2 hours] | A driving tour, fun in any season | Yes, on-leash |
| Park-McCullough grounds and Mile Around Woods | Saturday | North Bennington | 1 hour | House closed; grounds open dawn to dusk | Yes, there’s an off-leash area in the upper fields |
| Hildene | Saturday | Manchester | At least a few hours | Open year-round; holiday display in December | No |
| Northshire Bookstore and Manchester shops | Saturday | Manchester Center | 1-2 hours | Bookstore open daily 10 am to 7 pm | Yes, at Northsihire |
| Southern Vermont Arts Center | Sunday | Manchester | 1-2 hours | Open Wednesday to Sunday | On the grounds, but not in the buildings |
| Equinox Preserve snowshoe | Sunday | Manchester | 2 hours | Rent snowshoes at the Mountain Goat for $15 | Yes, on-leash |
| Bromley Mountain | Sunday | Peru | Full day | 48 trails, lessons for all levels | No |
| Prospect Mountain Nordic | Extra day | Woodford | 2- 3 hours | Open 9 am to 5 pm as snow allows | Leashed, on snowshoe trails and some ski trails |
Friday in Bennington, VT
After checking into your Bennington hotel, spend the afternoon meandering around Old Bennington. Visit the Bennington Monument at the top of Monument Avenue, then stroll past 18th-century homes on your way to the Old First Church.
Robert Frost is buried in the graveyard behind the church, and you’ll also spot some very old, beautifully decorated headstones, many by well-known stone carvers of the time, including Ebenezer Soule, Josiah Manning, and Zerubbabel Collins.
The earliest recorded burial here is Bridget Harwood, a widow who died in the fall of 1762.
If you roll into Bennington by lunchtime, grab a sandwich at Your Belly’s Deli on Pleasant Street, which also does deli salads and quiche. It’s open 11 am to 3 pm most days and until 7 pm on Fridays.
For dinner, head downtown and choose from several great restaurants on Main Street. Here are a few suggestions:
- 421 Craft Bar and Kitchen: Great beers on tap, wood-fired pizza, and casual but unique entrees. No reservations accepted.
- The Miller’s Toll: Offering fantastically unique cocktails, a changing menu featuring American-style tapas, and private dining nooks, this is a lovely spot to unwind while in Bennington. Make a reservation, as it fills up on most weekend nights.
Saturday in Bennington and Manchester, VT
Start your morning at Papa Pete’s on Woodford Road, the self-proclaimed Home of the Giant Pancake, and come hungry. Another option? The Angry Egg 2 on Main Street in Bennington, where you’ll meet all the locals over coffee and a varied and robust menu.
Next, embark on a covered bridge tour of Bennington County, which is fun no matter what time of year you visit.
If you want to work off some of your breakfast before driving north, stop at Park McCullough House in North Bennington for a hike through the farm fields and woods. The Victorian-era mansion is closed for the winter, but you can stroll the grounds before walking up to the Mile Around Woods.
Take Route 7A north toward Manchester to see the two Arlington covered bridges on the tour, just a short detour from your route north.
Next, stop at Hildene, the former home of Robert Todd Lincoln (son of President Lincoln).
This historic Georgian Revival estate, built in 1905 as a summer residence, has been lovingly preserved as a museum, farm, and educational center on 412 acres.
Plan to spend a few hours exploring Hildene.
Take a guided tour of the house, meander the 12+ miles of trails, and visit the Hildene Farm. If you visit before Christmas, you will see the estate as it was decorated for the holidays in 1912. The display is usually up until the weekend after New Year’s.
After leaving Hildene, stop for lunch at Depot 62, where the wood-fired Turkish and Mediterranean menu is served inside a home decor shop (closed Tuesdays), or slurp a bowl of ramen at Neighborhood Noodle, the ramen shop and izakaya that opened on Main Street in March 2026. You order at the counter, and there’s sake and beer if the snow has you settled in.
If it’s not too late in the day, explore the shops in Manchester.
Manchester is home to more than 40 designer outlet stores, plus a great variety of local boutiques and gift shops. Our favorite Vermont bookstore, Northshire Bookstore, is a local hub where book lovers can spend hours, and it’s dog-friendly.
To end your day, head to one of Manchester’s local eateries. Here are our recommendations:
- Mystico Cucina Italiana: Handmade pasta and focaccia from local ingredients, right on Main Street. Dinner runs Monday through Saturday, 5 to 9 pm, and you can book on Resy.
- Lola Mediterranean Woodfire: Greek and Mediterranean dishes from a wood-fired copper oven, opened in October 2025 by the family behind Christos’ Pizza & Pasta. Weekend tables go fast, but the bar and pizza counter are first come, first served.
- Ye Old Tavern: Housed in a 1790 inn, this historic, cozy restaurant features a fireplace, creaky wood floors, and a fantastic early-bird menu. Choose from classic New England dishes, but don’t pass up the cranberry fritters with maple butter served with every meal.
- The Silver Fork: Housed in what was once the local library in Manchester Village, this posh restaurant features a changing international menu of eclectic delicacies. It’s a charming spot to celebrate a special occasion.
Sunday in Manchester, VT
It’s time for breakfast in Manchester. Looking for really outstanding coffee?
Head to Charlie’s Coffee House on Bonnet Street (if you’re staying at the Barnstead Inn, you can walk there in five minutes). I take my coffee very seriously, and this is my favorite spot in Manchester. The beans are locally roasted in Brattleboro, and they make the coffee nice and strong. You can also get pastries, bagels, and quiche to fuel the rest of your adventures. Oh, and did I mention that Charlie’s is dog-friendly?
If you’d rather sit down for eggs and pancakes, head to Up for Breakfast, a quirky upstairs spot on Main Street. Bring cash, because that’s all they take.
For the last day of your Vermont winter getaway, you have a few options, depending on your mood. Do you want to relax a bit before heading home? Recreate? Shop? You can do all of that and more in Manchester. Here are some ideas.
- Southern Vermont Arts Center: The campus of Southern Vermont Arts Center sits on 12 acres at the foot of Mount Equinox. It features a state-of-the-art museum complex with an outdoor sculpture park and rotating indoor exhibits that feature nationally acclaimed and local artists. Plan to spend several hours here and have lunch at the curATE Cafe.
- Snowshoeing the Equinox Preserve: Strap on snowshoes and explore more than 914 acres on the side of Mount Equinox. Meander through a mature hardwood forest around Equinox Pond or climb the short but steep trail to Robin’s Lookout. If you don’t have snowshoes, you can rent a pair at the Mountain Goat in Manchester.
- Downhill Skiing at Bromley: Located seven miles east of Manchester, Bromley Mountain is big enough for full-day adventures on the snow and small enough for families just starting out. Discover 48 trails for all levels of skiers, or take a lesson and find your snow legs.
- Retail Therapy at Manchester Designer Outlets: We’ve already talked a bit about Manchester’s shopping experience, but you may need more time to explore all that this little town has to offer. For a complete listing of outlet stores, visit MDO and plan your perfect day in town.
Snowshoeing the Equinox Preserve? Download the trail map to your phone before you go, since cell service can drop on the mountain. I use AllTrails Plus so I can follow the trail without cell service. Use my referral link to get 30% off AllTrails Plus or Peak.
Read Next: A Local’s Guide to 23+ of the Best Things to Do in Manchester
More Things to Do in Bennington and Manchester Yhis Winter
If you have more than a weekend for your Vermont winter getaway, this area has so much more to offer. Here are a few ideas to beef up your itinerary.
- Cross-country skiing at Prospect Mountain in Woodford: Prospect bills its base lodge as the highest Nordic base lodge in Vermont. Located just east of Bennington, it grooms about 40 kilometers of trails for classic and skate skiing and is open 9 am to 5 pm in season, as conditions allow. Rentals are available onsite, and leashed dogs are welcome on the snowshoe trails and the ski trails north of the lodge.
- Pastime Pinball: If you have kids, or a kid-at-heart in your family, you may want to spend a few blissful hours at the family-friendly museum arcade that is Pastime Pinball in Manchester. Featuring 66 pinball machines that you can play all day for a single admission fee, this is perfect for days when you just don’t want to be outside. It’s open Thursday through Sunday.
- Ice Skating at Riley Rink: Another great indoor option for families is indoor ice skating at the Northshire Civic Center. The rink schedule varies, so be sure to check online before planning your visit. Skate rentals are available.
Looking for even more things to do in the area? Check out these Southern Vermont posts:
- Winter Hiking at Haystack Mountain in Wilmington. Wilmington is about a half hour east of Bennington
- Lake Shaftsbury State Park in all Four Seasons. Lake Shaftsbury is located between Bennington and Manchester.
- Four Seasons of Beauty in Woodford State Park. Woodford State Park is located 15 minutes east of Bennington.
- Hike to Lye Brook Falls in Manchester. This is a summer trail guide, but the hike would work for snowshoeing, too.
Winter Weekend FAQ
How far is Bennington from Manchester, Vermont?
The two towns sit at opposite ends of the same valley, about 25 miles apart. Route 7 gets you there in about 30 minutes. Route 7A takes longer but passes through Arlington so you can detour to the two covered bridges.
Is Manchester, Vermont worth visiting in winter?
Yes. You can ski 48 trails at Bromley, snowshoe more than 900 acres on the Equinox Preserve, and tour Hildene, which stays open all winter and is decorated for Christmas Eve 1912 in December. On a stormy day, Northshire Bookstore and 66 pinball machines at Pastime Pinball keep you warm.
Where can you ski near Manchester and Bennington?
For downhill, Bromley Mountain in Peru, just east of Manchester, has 48 trails and lessons for all levels. For cross-country skiing, Prospect Mountain in Woodford, just east of Bennington, grooms about 40 kilometers of classic and skate trails and rents equipment.
Is Hildene open in winter?
Yes, Hildene is open year-round. Last winter it was open Thursday through Monday, 10 am to 4:30 pm, and closed December 23 to 25. Check hildene.org for this season’s holiday display dates.
What is there to do in Bennington in winter besides skiing?
Walk Old Bennington and visit Robert Frost’s grave at the Old First Church, drive the covered bridges, and stroll the Park-McCullough grounds into the Mile Around Woods. The Bennington Monument’s observation level is closed until late May, but you can still walk the grounds. For a snowy hike, try White Rocks Overlook.
Are Bennington and Manchester dog-friendly in winter?
Yes. The Kimpton Taconic in Manchester welcomes dogs with no pet fee and no size limits, and the Barnstead Inn has a few dog-friendly rooms. The Equinox Preserve, the Park-McCullough grounds, and Prospect Mountain’s snowshoe trails are all good winter walks with a dog, and Northshire Bookstore and Charlie’s Coffee House welcome dogs inside. Dogs aren’t allowed on the Hildene trails.
Follow us on social media for more Vermont inspiration!
