Drinks + Food
Ze Windham Wine Bar
5369 Main StreetWine and tapas
Chicken Run Family Restaurant and Steak House
5639 NY-23Alpine-themed watering hole with a cozy vibe serving Bavarian cooking with beer & house cocktails.
105 locals recommend
Jagerberg Beer Hall and Tavern
7722 Main StAlpine-themed watering hole with a cozy vibe serving Bavarian cooking with beer & house cocktails.
Good variety of beers on tap & bottles. Not your average pub food. Great burgers
72 locals recommend
Tap House Grille
5359 NY-23Good variety of beers on tap & bottles. Not your average pub food. Great burgers
Food + Drinks
Nana Gail's
387 NY-296local cheap greasy spoon!
Family friendly restaurant. Great outdoor spot in the summer for kids and adults. Also good place to grab a drink with live music on weekends.
214 locals recommend
Chicken Run Family Restaurant and Steak House
5639 NY-23Family friendly restaurant. Great outdoor spot in the summer for kids and adults. Also good place to grab a drink with live music on weekends.
Mama's Boy Burgers
6067 Main St Ice Cream & Burgers! nuff said :)
Maggie's Krooked Cafe
6000 Main St Vegetarian Options
Recent addition to the area. Great Cafe with local spirits and live music on weekends.
129 locals recommend
The Windham Local
5410 NY-23Recent addition to the area. Great Cafe with local spirits and live music on weekends.
The Prospect
13 Scribner Hollow RdHigher Grounds
61 NY-296The go to place for bagels, sandwiches & coffee.
Michelin-starred local cuisine. Great food, rustic, romantic spot. Also great to sit at the bar or patio for a cocktail.
122 locals recommend
Deer Mountain Inn
790 Co Rd 25Michelin-starred local cuisine. Great food, rustic, romantic spot. Also great to sit at the bar or patio for a cocktail.
Millrock Restaurant
5398 NY-23Italian restaurant
Vesuvio
49 Co Rd 65Nice Italian restaurant. Close to the house.
Being at the bottom of the gorge (Palensville) it's one of our go to stops on the way home! Great sandwiches, coffee, deserts and sm section of organic items and local gifts for purchase.
113 locals recommend
Circle W Market
3328 NY-23ABeing at the bottom of the gorge (Palensville) it's one of our go to stops on the way home! Great sandwiches, coffee, deserts and sm section of organic items and local gifts for purchase.
Family friendly restaurant with local gifting items. Windham's version of Cracker Barrel. Popular brunch spot!
105 locals recommend
Catskill Mountain Country Store - Windham
5510 NY-23Family friendly restaurant with local gifting items. Windham's version of Cracker Barrel. Popular brunch spot!
Neapolis
5330 NY-23Jagerberg Beer Hall and Tavern
7722 Main StMa-Ma's Pizza Parlor
7730 Main StFellow Mountain Cafe
7883 Main StGreat little coffee, bakery, breakfast and lunch spot
Parks & Nature
One of the Catskills main attractions in the summer or winter!
There are two access points. Upper trail (head to North-South Lake) has parking and easy walk to view falls from the top. Lower trail is a hike, but worth it!
668 locals recommend
Kaaterskill Falls
One of the Catskills main attractions in the summer or winter!
There are two access points. Upper trail (head to North-South Lake) has parking and easy walk to view falls from the top. Lower trail is a hike, but worth it!
Nice lake to cool off in the summer. Free parking. Short walk to lake.
120 locals recommend
Colgate Lake
Nice lake to cool off in the summer. Free parking. Short walk to lake.
Nice to walk around the lake, swiming, and hiking. Entrance fee in the summer season.
146 locals recommend
North-South Lake
Nice to walk around the lake, swiming, and hiking. Entrance fee in the summer season.
Elm Ridge Wild Forest
360001 Town Of WindhamEasy paved hiking trail close to the house. Nearest entrance- Park behind the Windham Pharmacy off 296. Main entrance is off RT23.
114 locals recommend
The Windham Path
4982 NY-23Easy paved hiking trail close to the house. Nearest entrance- Park behind the Windham Pharmacy off 296. Main entrance is off RT23.
Entertainment & Activities
Windham Theatre
11 Vets RdMountain Cinema
7971 Main StMountain Trails Cross Country
6198 Main StCross-Country Ski
4-wheel in the summer. Snowmobile in the winter.
Good for beginners.
26 locals recommend
Rip Van Winkle Ranch
5305 NY-23A4-wheel in the summer. Snowmobile in the winter.
Good for beginners.
Windham Mountain Resort
19 Resort DrSki, snowboard, tubbing, food, drinks & live music.
Ski, snowboard, tubbing, zip line, food, drinks & live music.
71 locals recommend
Hunter Mountain Resort
8827 NY-23ASki, snowboard, tubbing, zip line, food, drinks & live music.
snow tubing, x-country ski, ice skating, snowshoe, fat bikes
48 locals recommend
Bearpen Mountain Sports
1491 Co Rd 2snow tubing, x-country ski, ice skating, snowshoe, fat bikes
Arts & Culture
The Orpheum Performing Arts Center
6050 Main StEssentials
Tops Friendly Market
6350 Main StThe place to get all your Grocery Essentials
Small grocery store to get the basics. Selection of Italian goods or to get a quick sandwich at the deli.
64 locals recommend
Todaro's Salumeria
5344 NY-23Small grocery store to get the basics. Selection of Italian goods or to get a quick sandwich at the deli.
Windham Pharmacy
61 ST NY-296Windham Liquor Store
5448 NY-23Hunter Village Wines & Liquors
7261 NY-23AGetting Around
Hudson
69 S Front St45 min Drive to Amtrack