24 Hours in Bennington, Vermont | A Mini Travel Guide

If you follow along on Instagram, you know the affinity Tom and I have for Vermont.  And if you know us in “real life”, you may be one of the many people who’ve asked when we’re moving there.  It’s hard not to love (but we won’t be leaving our beloved hometown of Glens Falls in upstate NY any time soon!).  Lucky for us, we can have our cake and eat it too with the Vermont border just a quick 45 minute drive from our back door.  

While we tend to frequent Woodstock and Manchester, we know there are plenty of hidden Vermont gems yet to be explored - Bennington being one!  It was our first time, and it definitely won’t be the last (we may be headed back sooner than later to pick up a couple of antique pieces we can’t stop thinking about!).  If you’re looking to explore a new Vermont town, read on for the scoop on Bennington (...and if you’d like to see, we made a short video of some of our favorites from the trip using my favorite app - scroll to the bottom or click here to watch!).

Bennington Vermont Four Chimneys Inn.JPG

W H E R E  T O  S T A Y

The Four Chimneys Inn:  This inn is quintessential Vermont with its lush expansive lawn, meandering brick path and stately white exterior (all tucked behind a charming old stone wall!).  The best of both worlds, you instantly feel miles away and yet you're walking distance to the Bennington Monument and Old First Church, and minutes away from antique shops and downtown restaurants.  

Bennington Vermont Four Chimneys Inn

Our room (Room 10) was perfect with the adorable blue and white wallpaper, an old door repurposed as a headboard, and a bright and airy sunroom overlooking the lawn.  Each of the eleven rooms is unique, and I'm already thinking about Room 1 with its big seven-bay window overlooking the foliage in the fall, and the wood burning fireplace in Room 2 for a winter stay.  

Bennington Four Chimneys Inn Room
Four Chimneys Inn Bennington hotel

Breakfast was delicious (and so many choices!), and the staff were so very kind.  We can't wait to go back!

W H A T  T O  D O

Stroll through Old Bennington:  Just around the corner from the Four Chimneys is the village of Old Bennington.  A stretch of beautiful historic homes line the street starting with the Old First Church and cemetery (where Robert Frost is buried) and leading up the hill to the Bennington Battle Monument.  At the monument, take the elevator up to the top for gorgeous views of the hills and valleys of Vermont, New York, and Massachusetts - already thinking about the view in the fall.

old bennington vermont
old bennington vermont house
bennington monument

Go Hunting for Covered Bridges: Is any trip to Vermont complete without laying eyes on one of these beauties?  Lucky for us, there are 5 within striking distance of Bennington (here is a good overview on all five).  We visited 3 on this trip, all within a few minutes of the Four Chimneys Inn.  Our favorite of the three was Henry Bridge - it's tucked a bit further away from the main roads than the others, and also has a park and picnic area overlooking the bridge (perfect for an impromptu cider donut picnic).

covered bridge bennington vermont
covered bridges bennington

Visit Bennington Potters:  Take a tour, meet the potters, and shop the gorgeous stoneware and pottery in their beautifully curated home goods store.  I wanted one of everything, and the colors were so good.  

bennington potters

Get Mini Cider Donuts at The Apple Barn:  A must.  We picked up two dozen and they were gone in an embarrassing amount of time.  We missed berry picking by just a few days, but their blueberry fields are open for picking now!

Tour the Park-McCullough House:  We arrived a bit late to tour the House, but luckily the grounds are open until dusk, and we had the gorgeous gardens and wrap around porch to ourselves.  There is an adorable carriage house on property which hosts concerts and theatre and we would've loved to stay for that evening's show.  Next time for sure!  

park mccullough house bennington vermont

Antique Shopping:  There are no shortage of antique shops in Bennington, and we probably could have used another day to see everything.  Our favorite was Green Mountain Antiques (bonus points for the cute shop dog!), and there were rooms upon rooms (...upon rooms!) of treasures at Camelot Village

On our list for next time:  Bennington Museum, Covered Bridge Museum, Hemmings Motor News Vehicle Display

W H E R E  T O  E A T

Aside from the delicious breakfast at Four Chimneys Inn, of course... 

South Street Cafe:  Went in for a coffee, left with a coffee and a warm cinnamon roll (fresh out of the oven!) which we devoured within 1 minute of returning to the Jeep.  Delicious.

south street cafe bennington vermont

Allegro:  With only one night in town, we wanted to make sure we went to the place in Bennington.  A little online research and a lot of recommendations from locals once we arrived pointed us toward Allegro and it did not disappoint.  We had delicious pasta and wine, and enjoyed a great atmosphere with most folks at nearby tables lingering over drinks for a long while after their meals.  

allegro bennington vermont restaurant

Powers Market:  Just like covered bridges, I can't leave a Vermont town without a visit to the local country store.  A quick search turned up Powers Market, and turns out it is the oldest country store in Vermont, having been built in 1840.  We ordered a grilled cheese, sat on the porch, and never wanted to leave.

powers market bennington

Vermont Confectionery & Dairy Bar:  Affectionately known as the sweetest place in Vermont, this is home to the very best maple creams I've ever had.  Do yourself a favor and get a pound before you head home, and if you plan on sharing, get another ;)  

On our list for next time:  Madison Brewing Company, Pangaea, The Grille at Mt. Anthony Country Club

So long for now, Bennington!  We'll be back for more of your charm (and your cider donuts and maple creams) very soon.

A short video with some of our favorite moments from the trip, if you'd like to see!

*This travel guide was in partnership with Vermont Tourism and The Four Chimneys Inn.  Thank you to The Four Chimneys Inn for welcoming us as their guests.  As always, all opinions are my own.