Peekskill

We’ve heard people describe Peekskill as the region’s largest town and its smallest city, and both seem about right. It’s got the charm you’d expect from a town, as well as the critical mass necessary for a truly impressive dining and drinking scene. In downtown Peekskill, tables spill out onto the street and musicians start to strum whenever there’s a sunny afternoon. Wander the nearby streets and you’ll find a healthy housing supply of colonials and Victorians.

It's hard to believe that many of the town’s beautiful brick buildings were more or less abandoned by the 1990s, when the Common Council had the brilliant idea to offer them as studios where artists could live and work. Now there are more than 100 art studios, many open to the public. Creative types rub shoulders with hipsters at the dazzling Paramount Hudson Valley Theater, a movie theater dating from the 1930s that now hosts live events.

Where to Get Your Bearings

Make a pit stop at The Central, housed in the former waiting room at Peekskill Station. The massive chandelier, red brick walls, and arched windows give the main room a stepping-back-in-time feel. Operating from morning to night, there’s also an incredibly varied menu, especially for dinner.

What Locals Recommend

One of the area’s largest swaths of green is the 1,538 acre Blue Mountain Reservation, easily accessible from Peekskill. Among the most popular trails for hiking and mountain biking is the three-mile Blue Mountain Summit Loop, which has some great views from the summit.