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Plan A Perfect Winter Weekend in Vermont: Bennington and Manchester

The holidays are over and you’re ready for a relaxing weekend in Vermont where you can enjoy snowy days and peaceful nights. Wondering where to go for your winter getaway? We’ve got lots of suggestions, but one of our favorite Vermont destinations for a winter escape is the southwest corner of Vermont.

A snowy view of Main Street in Bennington Vermont in the winter.

Bennington County in Vermont has two county seats – Bennington in the southern part of the county and Manchester, about 30 minutes north. Between the two towns, there is no shortage of things to do in the winter, whether you’re into outdoor recreation, shopping, or cultural and historical attractions.

The towns are separated by a 25-mile narrow valley and flocked by mountains to the east and west, making for beautiful scenery in all directions.

Manchester makes a great 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, and snowshoeing. Both towns have a rich history, beautiful New England architecture, and tasty dining options.

Both Bennington and Manchester are within a day’s drive of major metropolitan areas in the Northeast. Bennington is three and a half hours from both NYC and Boston, five hours from Philadelphia, four hours from Montreal, and an hour from Albany and the closest international airport.

Where to Stay in Bennington and Manchester

We recommend spending a night in Bennington and a night in Manchester so you can explore both towns properly.

In Bennington, consider staying at the luxurious Four Chimneys Inn with its beautiful classic decor and premium location in historic Old Bennington. For a more budget-friendly option, check out the Hardwood Hill, which features eclectic local artwork in every room.

You’ve got a lot of different lodging choices in Manchester. Here are our recommendations.

The Barnstead Inn in Manchester Vermont in the winter.
The Barnstead Inn in Manchester, Vermont
  • Inn at Ormsby Hill: For incredible luxury and attention to detail, you really can’t beat this gorgeous historic inn. Bedrooms all have luxurious jacuzzi tubs, fireplaces, and high-end linens and decor.
  • The Barnstead Inn: Modern luxury with different configurations of rooms and suites to meet your needs. The Barnstead includes an amazing breakfast, outdoor fires, and pop-up events indoors and out. The Barnstead Inn is within walking distance of downtown, which is always a plus.
  • The Kimpton Taconic: We don’t often recommend chain hotels on these pages, but we always recommend the Kimpton Taconic, which is beautifully decorated, within walking distance to many shops and restaurants, and it’s dog-friendly!

Here’s a perfect weekend itinerary for your Vermont winter getaway in Bennington and Manchester.

Day One: Exploring Bennington, Vermont

A snowy view of North Street in downtown Bennington Vermont in the winter.
A snowy night in Bennington, Vermont

Friday in Bennington, VT

After checking into your Bennington hotel, take the afternoon to meander around Old Bennington. Check out the Bennington Monument at the top of Monument Avenue and then stroll past 18th-century homes as you make 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 and beautifully decorated headstones, many from well know stone carvers of the time, including featuring the work of noted stone carvers including Ebenezer Soule, Josiah Manning, and Zerubbabel Collins. The oldest headstone belongs to Bridget Harwood, who died in 1762.

The gravestone of Robert Frost in Bennington, Vermont.
Robert Frosts’s grave in the Bennington Centre Cemetery

For dinner, head into downtown Bennington and choose from several great restaurants right on Main Street. Here are a few suggestions:

  • Allegro Ristorante: Upscale Italian in a cozy atmosphere. Reservations suggested. We’ve never had a bad meal here and it’s where we go to celebrate milestones or just treat ourselves.
  • 421 Craft Bar and Kitchen: Great beers on tap, wood-fired pizza, and casual, but unique entrees. This is a newer restaurant that we are really enjoying. My only beef with 421 is that it is loud inside because of the weird acoustics, but the yummy food and festive atmosphere make it all worth it. Also, they don’t take reservations.
  • 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 you’re in Bennington. Definitely make a reservation, as it fills up on most weekend nights.

Saturday in Bennington and Manchester, VT

The Burt Henry Covered Bridge in Bennington, Vermont during a snowstorm.

Start your morning at Sunny Side Diner in Bennington, where you’ll meet all the locals over coffee and pancakes with real maple syrup. 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 certainly stroll the grounds before walking up to the Mile Around Woods.

Driving north on Route 7A toward Manchester is the road you want to take to check out the two covered bridges in Arlington that are part of the tour mentioned above. Next, stop at Hildene, the former home of Robert Todd Lincoln (son of President Lincoln).

This historic Georgian Revival estate was created in 1905 as a summer residence and has been lovingly preserved as a museum, farm, and education center on 412 acres.

A winter view of Hildene in Manchester, Vermont.
Hildene in Manchester. Photo credit

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 happen to visit before Christmas, you will experience the estate as it was decorated for the holidays in 1912. The holiday display is usually up until the weekend after the New Year holiday.

After leaving Hildene, stop for lunch at Sam’s Wood Fired Pizza or Seasons (fresh American fare) before checking into your lodging.

If it’s not too late in the day, spend some time exploring the shops in Manchester. Not only is Manchester home to more than 40 designer outlet stores, but it’s also got 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:

  • Ye Old Tavern: Housed in a 1790 Inn, this historic and cozy restaurant features a cozy fireplace, creaky wood floors, and an awesome early-bird menu. Choose from classic New England dishes, but don’t pass up the cranberry fritters with maple butter that are served with every meal.
  • 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.
  • Depot 62: A unique home decor boutique that also houses a bistro and cafe, Depot 62 is not your typical restaurant. The small, but robust menu features unique Mediterranean-style dishes that will transport you from snowy Vermont to the sultry shores of Turkey for a brief, but memorable hiatus.

Sunday in Manchester, VT

A later winter view of an outdoor sculpture of a larger-than-life woman made of steel. Located on the grounds of Southern Vermont Arts Center in Manchester, Vermont.

Time for breakfast in Manchester. Looking for really awesome 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.

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.

The view from Robin's lookout on the Equinox Preserve in Manchester Vermont in the winter.
Snowy view from the Equinox Preserve. Photo credit
  • 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 do 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 of your own, you can rent a pair at the Mountain Goat in Manchester.
  • Downhill Skiing at Bromely: 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 47 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 on the town.

More Things to do in Bennington and Manchester this Winter

If you’ve got more than a weekend to spend during your Vermont winter getaway, this area has more to offer. Here are some suggestions for beefing up your itinerary.

  • Cross-country skiing at Prospect Mountain in Woodford: Welcome to the highest-elevation nordic ski area in Vermont. Located just east of Bennington, Prospect maintains more than 30 kilometers of trails that are groomed for classic and skate skiing. As long as there’s snow on the ground, the mountain is open daily from 9 am – 5 pm. Rentals are available onsite.
  • 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 60 top-rated pinball machines that you can play with a single admission fee, this is perfect for days when you just don’t want to be outside.
  • 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? Check out these Southern Vermont posts:

More Things to Do in Vermont

Grab our five-page printable bucket list that includes all the best things to do in Vermont!

Tara Schatz is a freelance writer, and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, which was released in May 2023.