Mount Anthony / Bennington, VT

Bennington, VT to Great Barrington, MA | Hiking Mount Anthony | July 2024

We were only about two or three hours away from my brothers home near Great Barrington, but didn’t want to arrive too early. So we opted instead to loiter around Bennington, VT for the day. We’ve driven through or around Bennington several times and know it to be a nice historic town with quite a few amenities.

I looked to my peak lists and AllTrails and soon found that Mount Anthony on the South edge of town met my prominence goal AND had an established trail to the top! We left our campsite and drove over the Green Mountains into Bennington, eventually parking at the now abandoned Southern Vermont College. The college was once a private institution located on a large estate but ended up closing in 2019 for financial reasons. While the manor house is currently undergoing a private sale, the manor grounds have remained open and the local hiking organization has maintained the trails.

It was warm out, and I knew the hike would be steep so I made sure Jess and Charlotte were comfortable and then began my hike. And this was a very interesting hike. The trails were very crisscrossed and confusing and more designed for X-Country skiing, but I eventually managed to find my way on the trail network behind the Manor house where I ultimately stumbled upon some of the abandoned ruins that made up the old estate. I’m not sure when they were abandoned – whether in 2019 with the college closure, or sometime during the college’s history – but they really gave a ‘Old World’ and ‘haunted’ appeal. Stone walkways and walls slowly decaying. A fountain overlooking the manor house, choked in vines. Even a cool granite table that felt like it belonged more in a movie about Druidic practices in England than Vermont.

I eventually left all that behind and started up on the trails which were very steep. From what I could gather online, the trails up high on Mount Anthony are relatively new and seldom walked. But between AllTrails and the few trail markers, I managed to make my way to the top following Zaphod’s Run Trail. The summit was tree covered and had a few communications towers and otherwise unappealing, but it was another peak on my goal. I found a geocache then followed a different trail back down stopping briefly at Zaphod’s overlook which did have views overlooking Bennington. Before long I was back down among the ruins and met back with Jessica.

The area of the college was nice, but not really designed for picnicking and loitering so we decided to go check out the Bennington Monument. We had visited before in 2016 and for some reason thought there was a green space with shade and picnic tables. Alas, our memory deceived us, and so we moved off to the other side of town to Willow Park. Here there was a pavilion with outlets, toilets; everything two houseless people need to loiter away an afternoon. And best of all, it had great views of Mount Anthony and the Bennington Monument. The one thing it was lacking in my opinion was letterboxes…all of which were located at the Monument…this hobby.

We had a nice lunch in the shade of the pavilion and then worked on our computers for the rest of the morning and afternoon. Once enough time had passed we headed further South, first into New York, then over into Massachusetts to my brother’s home.

My brother, his fiancée, and their house mates were gracious hosts and allowed us to park the van in the back yard. We ended up taking a day to just relax and take care of some chores and catch up with family over meals, including a delicious dinner at Pleasant and Main Café in Housatonic.