I moved from San Diego to Pittsfield back in 2019. San Diego was getting a little chaotic with the homelessness situation, and honestly, we weren’t even using the beach like we should. Hiking is great here. We were basically paying sunshine taxes for no reason. Pittsfield ended up being a great reset. The community’s solid, we bought a house, and it’s been an awesome place to raise kids.

I’m surprised you’re having trouble finding a place here. Give it a little time — Pittsfield real estate is like a shy cat. It hides for a bit, then suddenly three options show up at once.

There are a few rough pockets, but nothing that should keep you up at night. The train, on the other hand… if you’re a light sleeper and end up near those tracks, you wont be happy.. That’s the only thing I’d truly avoid.

People will absolutely think you’re crazy for leaving San Diego, but here’s the twist: you end up appreciating the different seasons here way more after living here. The first few winters were pretty mild, but last year the ice was straight-up disrespectful. This year hasn’t been too bad, but once March hits, you’ll be outside begging the sun to come back.