Four Chimneys Inn- Bennington, VT

Charming, quaint, and cozy, The Four Chimneys is everything a New England Inn should be. I admit my expectations come from watching seasons of Newhart, but I still think they nailed it. It is only missing Dick, Joanna, George, and a few Darryls. It is not missing much else; it is a charming restored mansion that has many of the amenities of a much larger hotel, and an interesting history to boot.

Set just off Main Street in the picture perfect town of Bennington, Vermont, The Four Chimneys started life in 1913 as the home of prominent Bennington businessman, Philip B. Jennings. The site’s original house, dating to 1783 and considered the finest house in Bennington, burned to the ground in 1910. Replacing one grand estate with another, Jennings lived in the house until his death in 1949. Then then fun began.

In the 1950s, the inn was converted to an elegant dinner club, of the Holiday Inn variety. The movie that is, not the hotel chain. Bands entertained while celebrities such as Elizabeth Taylor, Richard Burton and Walt Disney dined. It was a grand party until that era passed and the champagne stopped flowing. Today the Four Chimney’s is bit more sedate, but reminders of the inn’s storied past remain.

The sunny living room lobby is home to a quaint bar, which coupled with the fireplace makes it the perfect place to spend a winter’s night. In the summer, there are several flagstone patios in which to enjoy your libation. The old dining room, sectioned off with glass french doors, makes for a charming place to start the day. Very Stratford Inn, without Stephanie’s attitude. Until recently they still offered an excellent dinner, but that seems to be gone for now.  That is unfortunate, because they really captured the elegance of bygone era.

The rooms themselves are what you would expect in a bed and breakfast. Highly accessorized and antiqued. Ours was up three flights of stairs, under the eaves, and we loved it. The space was a bit tight, but for a single night it worked. It will certainly tide you over until the next Newhart marathon.