Nov 6, 2019

CCC Escapes: Windham

Ah, Upstate, the delightfully bucolic middle finger to Montauk. A place where you’ll find comfort, world-class eats, bocce, badminton, hiking, foraging and actual relaxing. It all makes for a weekender that’s less of a schlep and more of (shocker) a reprieve. Let’s jam.

Pass by Wappingers Falls through Balsam Lake Mountain Forest and on into charming Windham.
Click here for your driving road map

STAY: Remember summer camp? Erase the awkwardness and add a really rich uncle with an eye for tasteful design, and you’ve got the Eastwind. A 1920s bunkhouse stylishly rebuilt, it’s design-forward but not at all hoity-toity. There’s a small sauna, but no pool. The experience is about actual escape, not posing for pictures of one. There’s a main house (good for peeps who want to be close to the bar), a bunkhouse and three trés intimate A-frame cabins for maximum romance. Each experience is special and worth it. Kids welcome. Only cool ones. No jerks.

EAT: Forget fine dining and stay on-site. The Eastwind serves up a blend of German, Ukrainian and Dutch fare, along with a minimalist, European-style breakfast. At night, you’re in for homestyle meats and potatoes that are better than you mother’s (don’t tell her we said that). Should you need to soak up a late Friday night with a big brunch, the Chalet Fondue and iconic Phoenicia Diner are in driving distance. Rock-paper-scissors for who takes the wheel.

PLAY: Prior to this adventure, we rated the appeal of foraging somewhere between knitting and “this sucks, let’s do something else.” But this trip changed us. You MUST forage, ideally with the awesome folk at Woodland Pantry as your guide. Do it at the Eastwind, and they’ll even make cocktails with your mugwort (prepare for lucid dreams). Beyond that, throw some bocce, take out a bike, play shuffleboard and get some stinkin’ rest. In the afternoon, there are board games aplenty. In the morning, soak up those sins and ask the owners where the lesser trodden waterfall hike is; bandwagon Kaaterskill Falls is littered with city mice at this time of year.