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Vermont gets a lot hype for being a cool Winter destination, but have you considered visiting in the summer? (Side note: how is skiing in Vermont nowadays? I don’t ski, but I’ve heard that some resorts have had to close trails in recent years because there hasn’t been enough snow).
I’m fortunate to have an uncle who has a small house in Weybridge, Vermont, a (very) small town outside of Middlebury, VT. Downtown Weybridge consists of one store and a church. I and my family, and sometimes my friends, when permitted, have traveled to the house in the summertime.
Here’s the house. A bit small, but for a second home it works just fine. It’s about 1100 square feet. In 2022, it was appraised for $375,000.
Upstate New York, or the Hamptons, get a lot of hype about being good destinations outside of the city to travel to. And they are nice places to go — good escapes and easy to get to, about two hours each way. The drive to Vermont — Middlebury specifically — which is an hour south of Burlington, VT, is a bit of schlep — about four and and a half hours.
But I think this area is a great place to travel to (I’m not so familiar with other parts of the state). There are few roads and few people, a nice change of pace from NYC (not that I don’t like people). The views — wide open landscapes with mountains in the background — are really breathtaking. There is great hiking, swimming, and biking (but with a lot of hills, if you’re into that).
I also think the general vibe in Vermont is kind of special. It seems to be generally a relaxed, fun place — think Ben and Jerry’s (you can visit the Ben and Jerry’s factory in Waterbury, VT), and just overall calm energy. Burlington is the biggest city in the state (population around 45,000), and offers some decent restaurants and some other fun activities, and for the most part is a pretty place overlooking Lake Champlain.
Country houses are a definite luxury, but seem to require a bit of maintenance. I am not a one-home homeowner so I can’t attest to the headache of owning one home let alone two, but my uncle has insisted on keeping the house rented during winter months when he is not able to be in the house regularly. He lives in New York City full-time with an occasional inflexible work schedule, and doesn’t like to make the commute to and from Vermont super often. Because the winters can be harsh and things at the house can go wrong (there was an issue with the water system last winter), he likes to keep the house occupied with tenants when he isn’t able to be there consistently. Thankfully, because the house is close to Middlebury College, there is solid demand for renting. He hasn’t had a problem keeping it occupied during the winter months, and keeps it available for his own use in the summer and early fall – arguably the best time to be there (but I don’t think there is a bad time to be in Vermont).
So, long story short, if you’re looking for a good escape from NYC that is a little different than the usual, easy destinations, but is still drivable, I’d recommend visiting the Green Mountain State: Vermont!
The frontyard / view from the front of the house.
Here’s the one store in “downtown” Weybridge: it’s a dairy store open Monday-Thursday 1pm-5pm
Front of the store.
Church in “downtown” Weybridge
I forgot to mention that in “downtown” there is also this monument in addition to the one store and church.