A Romantic Weekend at the Historic Four Chimneys Inn (VT)

Article by contributor Mindy Briar

About Mindy: California native, Mindy Briar moved to Connecticut with her husband Cameron in 2017 when they decided they needed a change of pace. Mindy is a full-time professional wedding and lifestyle photographer and travel blogger and has a deep love for the New England area and its history.

*Please note that we followed all CDC Vermont travel regulations to visit the state. We encourage you to quarantine and get a test prior to your arrival at this time. Together we can keep our states healthy.*

Recently Cameron and I headed north to Bennington, Vermont to stay at the beautiful Four Chimneys Inn. A beautiful mansion nestled in the shires of Vermont.


* Photo from The Four Chimneys Inn*

The Four Chimneys Inn was built in 1783 when it was the home of the Reverend David Avery, second pastor of the Old First Church (the beautiful church right down the road from the inn). The inn has had several owners in its history and was a residence, general store, boarding house, and restaurant.

In the 1950s the mansion became a well-known fine dining restaurant that even celebrities such as Elizabeth Taylor and Walt Disney visited! The home was owned by James Rollis at this time.

The current owners Lynn and Pete Green did an amazing job of showing the inn’s history throughout the home with old photos and descriptions. I loved these thoughtful touches throughout the home!
The original menu at The Four Chimneys
* “Norman Rockwell painted this scene of an impatient boy and his dog anxiously looking for Santa at the Four Chimneys Inn.”*

The current owners are Lynn and Pete Green (pictured above). They restored the inn in 2005 and were married at the inn prior to owning it. Their love for the inn and Old Bennington lead them to the decision to leave their corporate jobs behind and head to a charming and more relaxed lifestyle in the beautiful shires of Vermont. You can often find them around Old Bennington or at the inn visiting with their guests. They are the kindest people and I can’t think of better owners to care for this beautiful historical property.

You may have seen The Four Chimneys Inn in Yankee Magazine last year – they were voted the best B&B in all of New England!

Inn Tour

The beautiful grand entrance of the inn.

We stayed for two evenings at this beautiful inn and felt that it was the perfect amount of time to lounge around and take in the property as well as head into town to do some shopping and sightseeing. Though we fully admit – we truly didn’t want to leave charming Bennington and the Four Chimneys Inn!

Our Suite

We stayed in Room #1 the Deluxe King – which is a stunning suite that is perfect for a relaxing couples getaway!

The entrance to our suite…right up the grand staircase. There was hand sanitizer and lysol wipes in every room and even right outside of our guest room! The owners didn’t skip a beat on the covid-19 safety protocols and we felt so safe during our stay,

“This spacious guest room at our Bed and Breakfast in Bennington, VT has newly refurbished hardwood floors, a four-poster mahogany king bed, cable TV, and a gas fireplace. Decorated in soft, soothing blues, there isn’t a week that goes by that we don’t get a request for the paint color! Relax in on a comfortable couch looking out a seven-bay window onto the South lawn and 150-year-old stone wall. Adding to the romance of this enchanting room at our Vermont bed and breakfast is a beautiful marble and tile bathroom with an oversized jetted tub, separate shower, and chandelier. The perfect room for a special anniversary, honeymoon, or romantic getaway.” – The Four Chimneys Inn

We loved that the room had a large couch to lounge on and a beautiful warm fireplace. The views out the front windows were stunning and when it snowed outside – it was so dreamy to watch it fall out the window. We also loved the relaxing jetted tub and super soft king bed!

The inn has 11 stunning rooms for you to pick from – all of them are so beautiful you just can’t go wrong!


Each morning you will be greeted by a friendly innkeeper and hostess to serve you your delicious breakfast. They will give you a menu the day prior to pick out your selection and the time that you would like to eat. When you come downstairs in the morning it will be all ready for you – it’s also great because you can request to get a dining spot when no one else will be eating for extra caution during this time. When we ate both mornings, we were the only ones in the dining room and felt very safe! The hostess also always wore a mask.

For my fellow breakfast lovers, get excited – the breakfasts here were amazing! We tried several different menu selections and all of them were outstanding. When we got home from VT, Cameron and I looked at each other and said “I wish we were at The Four Chimneys for breakfast!!” Trust me – it’s some of the best breakfast/brunch you will have. 

Formal Dining

From the dining room, you can head right into another beautiful dining area/sunroom that is perfect for a larger family or to simply enjoy the large festive Christmas tree!

This room is filled with natural light and has elegant decor and the most stunning chandelier.


On the other side of the dining room is the lounge area/bar. Normally the bar would be open but during this time it is closed. This room is so so cozy and has large windows and a big beautiful fireplace. Lynn did such a great job designing these rooms!

I even found custom cards of the inn by one of my favorite artists, Riley Sheehey!

The Grounds

The grounds of the inn are truly stunning. We decided to take a walk around the property one of the days and we were so excited to see it with snow all around!

Doesn’t this lamp post remind you of The Chronicles of Narnia – The Lion The Witch and The Wardrobe?!

We loved this beautiful moose on the property. After doing some research and seeing several of these moose statues in town we came to find that Bennington holds an annual Moose Festival! How charming is that?!

Things To Do

Take a Walk in Old Bennington

One of the best things to do is to take a walk from the inn right onto the main street of Old Bennington. Head down to the Old First Church…look at the amazing old graveyard…say hello to Robert Frost’s grave…and then head down to the historic house-lined street to the Bennington Battle Monument at the very end.

Drive to see the Covered Bridges

There are three red covered bridges in Bennington that are very close together. They are about 8 minutes from the inn and definitely worth the drive! Be sure and get out for the Paper Mill Village Bridge to see a beautiful waterfall.

This beautiful event venue is right past the Henry Covered Bridge.

If you go past this bridge you will also find Bennett’s Tree Farm which is a beautiful and idyllic tree farm and homemade maple syrup store! The owners were so lovely and this truly is a gem in the area.

Go Antiquing

There were quite a few fantastic antique stores in Bennington but our absolute favorite was Main Street Antiques! The service was fantastic and we found so many great items that we went home with!

Go shopping in Downtown Bennington

Downtown Bennington is filled with charming shops and restaurants that will keep you occupied for hours. We loved the Madison Brewing Company for a beer and bite to eat as well as the Bringing you Vermont Country Store for a cup of joe. The shops were beautiful and this area is quickly becoming one of my favorite Vermont towns to visit.

We also visited Mt. Anthony Country Club’s restaurant called the Grille and this was also SUPER good!! It was the perfect spot for a warm cozy meal and a toasty fireside dinner. Definitely check it out!

Visit the Bennington Museum

If you’ve been following me for a while you know that I’m a very big museum lover. When I get to a new place, I always want to know the background and what happened there in the past. Bennington, Vermont is filled with a very rich history – one of which is the Battle of Bennington from the Revolutionary War. The Bennington Museum was a beautiful place to visit and a must-do on your tour of the area.

The museum also has an incredible Grandma Moses exhibit that was a highlight of the museum. We also loved learning the history behind the Bennington flag which is the USA flag with the 76 on it. You will also see the original flag at the museum!

Nearby Towns…

  • Hildene – The Lincoln Family Home (we love this amazing home! I can’t recommend this tour enough. We went on our last visit to VT and can’t wait to return!)
  • Manchester, Vermont
  • Dorset, Vermont
  • Mount Snow

In conclusion…

In conclusion, we just fell in love with this historic town. We loved the natural beauty of the area, small shops, and kind locals as well as the rich history and scenic walks.

When visiting Vermont, I highly recommend this beautiful town! I also 100% recommend staying with Lynn and Pete at their magnificent home, The Four Chimneys Inn Bed and Breakfast.

Thank you Lynn and her team for being so incredibly kind and hospitable to us during our stay – we just had the best time!

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