A picturesque town in Orange County's Hudson Valley with beautiful street-level views of the wooded Shawangauk foothills, Middletown is a traditional, old rail-stop community. The town sprung up near the Wallkill River and with the railroad’s arrival, Middletown boomed. Most businesses from that period are long gone. Rocky economic times hit home in Middletown in the 1970s and ‘80s as they did in many of the Hudson Valley's small communities. This little city has recovered and continues to thrive.