Downtown Bennington Vermont covered with snow.
Bennington covered with a fresh dusting of snow

January 31, 2023

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.

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.

We recommend hanging your hat in Bennington for the weekend and exploring farther afield on day trips.

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

Where to Stay in Bennington

Four Chimneys Inn covered with snow.
Winter at Four Chimneys Inn

You’ve got lots of spectacular lodging choices 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.

We’ve got even more ideas in this round-up post featuring Bennington’s most sought-after lodging.

Day One: Exploring Bennington, Vermont

Holiday decorations at night in Bennington, Vermont.
Holiday decorations in downtown Bennington

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.

Gravestone of Robert Frost.
Photo credit: Phil Holland

For dinner, head into downtown Bennington and choose from several great restaurants right on Main Street.

Here are a few suggestions (check out all of Bennington’s restaurants):

  • 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.

Day Two: Bennington and Manchester

A snowy scene featuring the Burt Henry Covered Bridge in North Bennington, Vermont
Burt Henry Covered Bridge in the winter

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.

Hildene covered with snow 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).

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.

Inside Northshire Bookstore in Manchester, Vermont.
Inside Northshire Bookstore in Manchester, Vermont.

To end your day, head to one of Manchester’s local eateries before driving back to your Bennington hotel. 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.

Day Three: Choose Your Own Adventure

Snowshoeing near Bennington Vermont
Snowshoeing at Lake Shaftsbury State Park, just north of Bennington.

Fuel your morning adventures with breakfast at The Angry Egg 2 or the iconic Blue Benn Diner.

If you’re itching to spend the day outside, don a pair of snowshoes, cross-country skis, or Microspikes and visit a local trail.

This post includes a nice collection of local trails that are fun to explore in the winter.

For an indoor adventure, consider exploring one or more of the half-dozen antique shops in and around Bennington. You never know what you’ll come across!

Looking for even more things to do?

Check out these Southern Vermont posts:

—Tara Schatz is the author of the third edition of AMC’s Best Day Hikes in Vermont and a writer at Vermont Explored.