Windham Mountain Outfitters

When Cave Mountain Ski Area opened in 1960, it transformed this corner of the Catskills into ski country. Today, that legacy lives on in family-owned outfitters like this one, where a fire-engine red roof and bold italic signage announce their purpose with zero subtlety. The shop is owned by the same family that runs Higher Grounds Coffee next door, and there’s a rescue dog named Wiggles who greets customers at the door, proof that even in stoic upstate New York, a little personality goes a long way.

The mountain that built the town has changed its name four times since 1960: Cave Mountain became Ski Windham in 1981, then Windham Mountain in 2001, then Windham Mountain Club in 2023, when a group of hospitality investors bought in with plans for a $70 million overhaul. Windham Mountain Outfitters, by contrast, has kept things simple. Same red roof, same family, same dog.

That dog earned her spot the hard way. Wiggles was found on the side of the road with a broken tail and a fractured spine before the family took her in; she now greets customers as if none of that ever happened. It’s a fitting mascot for a town that’s reinvented itself before: Windham’s first industry wasn’t skiing but tanning leather, starting with a hemlock-bark operation built around 1803, one of dozens that once processed hides across the Catskills before the trees ran out and the business collapsed by the 1860s. The mountain keeps changing its name. The dog keeps wagging her tail. The town just keeps finding something new to sell.