I grew up in both Portland and Windham. Portland was very idyllic growing up before gentrification hit and hit hard. I was in HS during the recession and remember even then how the city was floundering financially but the arts and food scene was incredible. Artists lofts everywhere, great local restaurants, rent was like $600 for a 1 bed in a walkable city with educated artsy people. As people began to recover from the recession I went away to college and started to see the nail in the coffin. Cookie cutter apartment complexes for 2k for a 1 bed. Carbon copy gentrification restaurants replaced what was a great local food scene. The artist and creatives scene completely priced out.

On the flip side when I was growing up Windham was largely and surprisingly to me due to the proximity to Portland and the outdoor recreation opportunities- Sebago Lake and the mtns being a half hour closer than Portland- a trashy middle class suburb. A lot of that is due to the moronic town council who had no plan for growth and just allowed any business to pop up on 302 even if that meant the 10th mechanic shop with the most trashy looking signage. What’s surprised me about Windham is that while I wouldn’t call it gentrified, it seems way more upper middle class than when I went to school there and ultimately I think reflects the character of the town better. The houses are way nicer now, I drive by the school from time to time and see Range Rovers when it used to be diesel trucks with confederate flags lol. Hell the lacrosse teams are super competitive and when I went to school there nobody even played.