


The Catskills are full of character-packed bars—from dim taverns in Woodstock to mountaintop cocktail lounges in Windham. Local favorites include The Pines in Mt. Tremper for classic cocktails, Rip Van Winkle Brewing Company in Catskill for casual pints, and West Kill Brewing for scenic drinks among the peaks.
Yes, several. West Kill Brewing overlooks rolling ridgelines and forest trails, Upward Brewing Company in Livingston Manor has its own hiking path that leads to a lookout, and Catskill Brewery pairs small-batch beers with woodland charm right off Main Street.
Many Catskill inns have their own bars worth visiting even if you’re not staying overnight. The Deer Mountain Inn near Tannersville serves craft cocktails beside the fire, Urban Cowboy Lodge mixes après-style drinks in a rustic lodge setting, and The Roxbury Motel is known for its playful, themed bar experience.
You sure can. Most Catskills wineries and cideries have tasting rooms or patios for sipping. Try Whitecliff Vineyard near Gardiner, Hudson-Chatham Winery, or Wayside Cider in Andes for small-batch pours with local flavor.
It’s relaxed, social, and grounded in good company. You’ll find live music at Tubby’s in Kingston, late-night conversation at Phoenicia Diner After Dark events, and local festivals that keep the mountain towns buzzing well past sunset.
Fall and summer are peak seasons — patios open, live music fills the evenings, and mountain views stretch for miles. Winter brings fireplace bars, ski-town après spots, and quiet tasting rooms perfect for small gatherings.
