Enjoying Vermont in Winter When Most of the Town Is Closed

I needed to get out of the city, at least for a couple days, but finding a destination within driving distance in the winter is as easy as it sounds. After searching around, I decided to take a couple days in southern Vermont — I just wasn’t quite prepared for the lack of things to do, though it wasn’t such a problem.

I hadn’t been to Vermont in about 20 years — my last trip was to go camping with a friend in the Green Mountains. That previous summer trip included some terrible rain (it was so bad that I was driving about 25 mph on the NY Thruway). It was a great trip, but muddy hiking isn’t much fun.

vermont winter
View of the Green Mountains from the small Normal Rockwell Exhibit

This time around, I had a little less time to plan. The travel plan was set less than 24 hours before I got in my car and drove the 200 miles north to Manchester. I figured it’d be a relaxing couple days in the Green Mountains, and there might be an opportunity for winter hiking. Beyond that, I did little research of the area just north of Bennington. Along the drive up, I passed by a few things that were of interest, including a small Normal Rockwell Exhibit and the Robert Frost Stone House — I discovered the following day that both are closed for the winter. I could’ve gone to the American Museum of Fly Fishing, right next to the huge Orvis store, but it wasn’t of interest.

robert frost stone house
The Robert Frost Stone House was closed

I booked my hotel just outside the town the morning before I departed — it looked quiet and included a bar, so I thought I might meet some other travelers while having a drink. It’s not quite that easy when you’re the only guest at the hotel (alright, there were two other people the first night, but I only met them briefly as they left early the following morning).

vermont winter
Revolutionary War memorial in Manchester Village

On the day I arrived, I wandered around the town of Manchester — it’s a quaint town of fewer than 5,000 with beautiful views of the Green Mountains (maybe not so beautiful in winter with all the bare trees). There’s a bit of history in town, particularly in the village, dating back to the Revolutionary War as it was a region served by the Green Mountain Boys.

The newer town, officially known as Manchester Center, just north of the village isn’t much bigger. I parked and walked around in less than an hour — fortunately, it wasn’t that cold on that January day. Manchester would be more appealing if I was interested in shopping as there are quite a few high-end outlet stores around town, which made me wonder whether the shops were for tourists or locals.

vermont winter
It was a grey day when I arrived

The main part of town is in a loop that is easily walkable in under an hour. Along the walk, I stopped in the liquor store to check out some Vermont spirits and beer that I could bring home (they only had a few single beers for sale, most of which were not from Vermont). I also looked around the grocery store and a Vermont tourist shop for some local delicacies.

The most important stop on my walk through Manchester was Northshire Bookstore — a shop the owners of North Shire Lodge suggested. It was well worth checking out. This is a big, beautiful independent bookstore with new and used books as well as some other items of interest. I could’ve spent hours in this store, but settled for a short walk through and some coffee in the cafe before searching for dinner.

northshire bookstore
Great design in Northshire Bookstore

I took another walk around town the following day when the weather was better — it was surprisingly warm for winter. The park around Mill Pond provided some pleasant views. It would’ve been nice to check out the historic buildings around there if they were open to the public. In hindsight, I should’ve stopped at The Equinox hotel, a luxury hotel that dates back to the 18th century.

vermont sign
A sign in the sidewalk outside the bookstore

On the first morning in town, I decided to take a hike up Mt. Equinox, a 3840-ft peak in the Green Mountains and the highest in the Taconic Range (it’s also the second highest mountain in Vermont). I was told that it’d take a few hours to hike and that I might not make it all the way up due to icy conditions and some significant mud due to the warm winter weather. I didn’t even make a third of the way up — I was overdressed and exhausted from my heavy coat.

mt equinox vermont
This doesn’t look like winter in Vermont

Despite my failure, I’d give it a try again in better conditions. It’s a well-marked trail, and I’m sure the scenery is much nicer in spring and autumn. There’s a toll road to the peak as well, but it’s closed in the winter.

Following my failed hiking attempt, I headed back to the hotel and got a discounted ticket for Hildene, a home owned by Robert Lincoln, Abe Lincoln’s only child to survive to adulthood. Unfortunately, the warm winter damaged the driveway to the house and it was closed for the entire week for repairs. I was 0-4 on sightseeing in Vermont.

vermont winter
Walking along the creek in Manchester

With little else to do in the area, I settled on spending time enjoying the silence at the hotel, at which I was the only guest, and having a few drinks with the owner at the bar. It was the most relaxing and rewarding failure of a trip I could have imagined.

Have you ever failed so spectacularly in your travel plans that it turned into a great trip?

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