Windham Path – A flat, easy loop right in town along the Batavia Kill, next to the Wylder Hotel, with beautiful views of Windham Mountain. (~2 min from downtown) Kaaterskill Falls – A scenic 1.7-mile moderate hike to one of the Catskills’ most iconic waterfalls. (~20 min from downtown) Sunset Rock – An easy hike to a rocky overlook with sweeping mountain views—perfect for sunset or photos. (~15 min from downtown) Hunter Mountain Fire Tower – A moderate hike to a historic fire tower with incredible 360° Catskills views. (~15 min from downtown) Five State Lookout – A short walk to a viewpoint where you can see five states. (~5 min from downtown) Mountain Top Arboretum – Peaceful gardens and woodland trails ideal for a chill walk. (~8 min from downtown) CD Lane Park – A relaxed spot with a sandy beach, reservoir loop, picnic areas, and playgrounds. (~10 min from downtown) Elm Ridge Wild Forest – Well-marked trails popular for mountain biking and easy hikes. (~5 min from downtown)
Located at Wylder Hotel, this is a great spot for a quick coffee or fresh baked good. Easy, delicious, and perfect for a casual morning start right in town. (0.3 miles, ~1 minute from downtown Windham)
Located at Eastwind Hotel, this all-glass, cozy café is a lovely place to grab coffee or a breakfast sandwich in a bright, relaxed setting. Ideal for a slow morning or casual catch-up. (0.5 miles, ~2 minutes from downtown Windham)
A cute café offering coffee, light bites, and gourmet groceries. A great stop if you’re looking for something simple, local, and thoughtfully curated. (0.4 miles, ~2 minutes from downtown Windham)
A grab-and-go café known for excellent coffee, pastries, and sandwiches. Perfect for fueling up before a hike or heading out for the day. (0.6 miles, ~2 minutes from downtown Windham)
A charming café in the heart of town serving coffee, breakfast, and lunch. A great all-around spot for a relaxed meal or mid-day break. (0.2 miles, ~1 minute from downtown Windham)
Famous for cinnamon rolls, cookies, and baked goods. Highly recommend stopping by for a sweet treat — this one is a Windham favorite. (0.7 miles, ~3 minutes from downtown Windham)
Located at The Henson, this is a great spot for an upscale dinner in a beautiful, thoughtfully designed setting. Perfect for a special night out. (10 miles, ~20 minutes from downtown Windham)
Located at Deer Mountain Inn, this classic, cozy mountain lodge offers excellent food and drinks in a warm, Catskills setting. Ideal for a relaxed but elevated dining experience. (6 miles, ~15 minutes from downtown Windham)
Italian food in the heart of Windham, offering comforting classics and a relaxed local vibe. A great option for an easy, satisfying dinner. (0.3 miles, ~1 minute from downtown Windham)
Laid-back southern comfort food with rustic vibes and live music. A fun, casual spot if you’re looking for something lively and unfussy. (1 mile, ~3 minutes from downtown Windham)
Located in nearby Tannersville, this cute roadside burger and shakes spot feels straight out of a movie. A fun stop if you’re exploring neighboring towns. (10 miles, ~20 minutes from downtown Windham)
A boutique vineyard right in town offering tastings of small-batch New York wines. A lovely, relaxed spot to sip wine and take in Catskill mountain views — perfect for a laid-back afternoon outing. (0.5 miles, ~2 minutes from downtown Windham)
A must-visit Catskills brewery set on a scenic farm just outside Windham. Known for thoughtfully crafted beers made with local ingredients and mountain water, plus a welcoming outdoor space with fire pits and occasional food trucks. (12 miles, ~25 minutes from downtown Windham)
Greene County’s first cidery, producing crisp, locally made hard ciders and meads. A fun alternative to beer or wine, with a casual tasting room and relaxed countryside atmosphere. (16 miles, ~25 minutes from downtown Windham)
A local Windham brewery with a cozy taproom and rotating selection of craft beers. An easy stop right in town if you’re looking for a casual drink without venturing far. (0.6 miles, ~2 minutes from downtown Windham)
A classic Catskills brewery and restaurant offering house-brewed beers and comfort food in a laid-back setting. Great if you’re exploring Hunter or looking for a no-frills spot to grab a drink and a bite. (9 miles, ~20 minutes from downtown Windham)