A few additional thoughts as I was running out the door before…
I personally really loved the rural area around Middlebury. Very pretty. Bowdoin is attractive too but it doesn’t have that wow factor of the endless seemingly undeveloped mountains barely in the distance. Though at Bowdoin you are very close the incredible Maine Coast and the school and Outing Club each own parts of or entire islands there. Middlebury owns a small ski resort.
Bowdoin is known for its ourdoorsy culture and it’s student-run Outing Club is incredibly well-resourced and produces many activities that are virtually free (after a $500 annual membership). Middlebury is outdoorsy too with the ski resort and rural location.
Bowdoin is famous for its food (though that is mostly lost on my non-foody son).
Where Bowdoin has a distinct advantage between the two is convenience to major transportation options. There’s an Amtrak station across the street from the school that can get you to/from Boston or the nearly city of Portland, Maine which is about 30 minutes away and is a great city for restaurants, culture, shopping. Portland also has an airport with tons of direct flights to the New York area (I can’t speak for other locations). I was shocked how many daily direct flights. Also, Bowdoin is about 15 minutes from the shopping mecca of Freeport, Maine which is also the headquarters of LL Bean which operates a massive 24 hour/365 day store there (the doors don’t even have locks and the only time they closed was for the memorial service of their founder, when the local police guarded the unlocked doors out of respect). And it’s about a 1 hour flight. By comparison, Middlebury is about 45 minutes from Burlingame, VT, and that’s about it for major urban areas. Midd is close to endless recreational and rural locations, including Lake George, Lake Champlain, etc.
Neither of these schools, in my opinion, are in the same league as Wesleyan or Vassar when it comes to organizing a variety of entertainment activities on campus. Wesleyan is insane in that regard with usually numerous competing activities every single Thurs-Sat among other days. Bowdoin seems pretty sleepy by comparison with a handful of plays, dance, art or concerts over a semester; the social houses (the school-controlled former frats that every student is affiliated with as a Freshman) dominate the party scene. I’m not criticizing – to each their own – just observing.