Middletown, NY (≈30,000) is a lively Hudson Valley hub with a compact downtown full of ethnic eateries, bars, the historic Paramount Theatre, SUNY Orange, seasonal draws like the Orange County Fair, nearby Highland Lakes State Park and easy access to Shawangunk hikes—comfortable and interesting for multi‑week stays rather than a lonely outpost.
You also get easy day‑trip options: it’s about 71 miles from New York City for weekend culture and airports, roughly 44 miles from Poughkeepsie for extra dining/riverfront activities, and Middletown sits close to Newburgh for more local options.