4. Bennington, Vermont

Yes, the beautiful town of Bennington is a small town with a population of 5,746; however, the median home value of $207,600 makes it one of the most expensive small towns you can move to.

Bennington has plenty of amazing restaurants, a lot of stunning historical buildings, and maybe most importantly, you can easily access nature. Also, keep in mind that this place is close to three major cities: Boston, Albany, and New York. The town is one hour away from Albany and three hours away from Boston and New York.

As we said before, nature will be close to you since Bennington is located on the Appalachian Trail and in close proximity to Lake Shaftsbury State Park.

The best time to visit this beautiful town is for sure in the autumn. The foliage is top-notch, and you can take a relaxing stroll between the old buildings. Some must-see landmarks in Bennington are the Bennington Battle Monument, which is actually the tallest structure in the state; Robert Frost’s grave; and the Old First Church.

Also, if you plan to go there, don’t forget to try their maple syrup. You won’t regret it!