The importance of trees in a streetscape can be observed even in the dead of winter; the trees lining the sidewalk, seen here, are important to the integrity of the Old Bennington Historic District. Trees must be respected in addition to the historic architecture.
Preservation in Pink 
So true! Trees are an important part of historic streetscapes and landscapes. In Canada, they can even be designated because of their cultural value: http://www.historicplaces.ca/en/results-resultats.aspx?m=1&Keyword=trees
Kayla, thanks for the link! I don’t know much about Canadian HP, but it’s completely relevant here in Vermont.
Spending a lot of time in Bennington lately Kaitlin? Some of my best friends in high school lived on Monument Ave, one actually right next door to the Walloomsac Inn. Anyway, if you are looking to do some more exploring the Park-McCullough House in North Bennington is nice. The house is closed in the winter but you can XC Ski or snowshoe in the area, and depending on the route you take to get there, you may cross a covered bridge or two!
Luke – actually only one day in Bennington. I love Monument Ave. What do you know about the Walloomsac Inn? Have you been inside? I’ve heard of the Park-McCullough house too; we considered it for our wedding at first. Thanks for the XC skiing tip – hopefully I’ll get to try some skiing soon!
I don’t know much about the Inn. The condition you saw it in has basically been the same since I was in 6th grade. We went on a field trip to the Bennington Museum, The Congregationalist Church (built by the same architect as Middlebury’s, Lavius Fillmore) and the cemetery where Robert Frost is buried. The the Inn was kind of mentioned in passing as “famous people spent the night here” type spheel. It has always been a less than welcome building to investigate.
In regards to zoning and demolition by neglect, its important to note that the building is within Old Bennington, which is its own incorporated village that shares some services with the Town of Bennington (like road maintenance and police) however I do not believe that the Town of Bennington’s zoning, design review or preservation commission would have any jurisdiction there. This is at least the case with North Bennington, which is also a village within the town, so I imagine it is similar with Old Bennington. (Confusing I know.)
Thanks for the information. I’m still surprised that, regardless of which officials have jurisdiction, that voters and lawmakers wouldn’t want to adjust zoning to keep such an important landmark in the district. Sad. If you find out any other information in passing, please share.