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Middlebury is an amazing town. The community is supportive and friendly - a great place for families and pets. There is a lot to do outdoors, but it is quite rural. It's easy to be vegetarian or vegan here, and there are always interesting lectures and events going on, frequently on Middlebury College's campus. There's also a movie theater in town and the Town Hall Theater. It's only a couple hours from Montreal and one hour from Burlington.
Middlebury is very small and quaint, which is a bonus if you enjoy community. The college adds wealth and jobs, so the town is full of fairly wealthy people and what comes with them, like a nice natural foods coop. The college is beautiful but many students are privileged and generally don't see Vermont outside of Middlebury. If you go just outside of the town you will find wonderful places to hike and ski.
Middlebury is an eclectic town filled with activities. Whether you visit the college, go to the Natural Foods Co-op, or sit on the green the town has a way of inspiring awe with its beauty and welcoming environment.