Lookout Mountain Rd Tuxedo Park, NY

This Orange County community derives its name from the Lenape word “Tucseto,” translating to “place of the bear”—but you’d be correct to draw the connection to men’s formalwear. Once a fashionable getaway for New York’s Gilded Age elite, Tuxedo Park was sensationalized in the 1880s when a coterie of mischievous socialites began entering its country clubs in coats with no tails, a sartorial move then as controversial as clip-on ties. The trend, of course, is largely unchanged, not unlike the innate draws to this storied corner of the Hudson Valley. The Town of Tuxedo, wherein Tuxedo Park lies, is easily reached via Route 17 and the New York State Thruway, and there’s a quaint Victorian train station on Metro-North’s Port Jervis Line complete with an old-fashioned waiting room. With just a few thousand residents, there’s plentiful room for nature to run its course, both at public venues like Sterling Forest and right in your backyard.