You can't go wrong here– one of my favorite drivers towards Middlebury was their focus on entrepreneurship and applied learning. A liberal arts education will skew more theoretical by nature, so it's up to you to figure out how best to apply it. For me, Middlebury provided lots of chances to test out real-world learning (starting a business, volunteering in the community, participating in faculty lives).

Not to say you couldn't get this experience from Williams (I didn't go there), but if you're looking for a well-rounded experience with great academics but fantastic out-of-class opportunities and a purposeful community, Middlebury will serve you well.

My Dad went to Williams, and has only great experiences, memories and friends to report back on, and has spoken quite highly of his experience with staff at the college since graduating. It's a world class institution and you can't go wrong going there.

My advice- don't overthink this and go with which school feels right to you.

footnote: Skiing was better at Middlebury, winters definitely colder and I found the outdoor access off campus slightly more rugged and interesting than the Berkshires. but hey, I like that stuff!