Your Catskills Area Guide

The Best of the Northern Catskills, Curated by Bear House Catskills

Bear House Catskills sits in Cairo, NY — a village locals call the Crossroads of the Catskills because it sits at the intersection of the Hudson Valley and the Northern Catskill Mountains. It's one of the most strategically located spots in all of upstate New York. Within 30–45 minutes, you can be at a world-class waterfall, a ski mountain, a renowned farm-to-table restaurant, or the iconic arts village of Woodstock.

We've spent years exploring this region and these are our genuine favorites — the places we actually recommend to every guest.

🥾 Best Hikes Near Bear House

Kaaterskill Falls — 30 min from Bear House Catskills

The most iconic hike in the Catskills, and for good reason. Kaaterskill Falls is the tallest two-tiered waterfall in New York State, and the trail through the gorge is one of the most beautiful walks in the entire Northeast. The lower falls are accessible on a relatively easy 1.5-mile round trip; adding the upper falls makes it more of a workout. Go in summer for the full flow or fall for the color. Arrive before 10am on weekends — parking fills up fast.

North-South Lake — 30 min from Bear House

The jewel of the Catskill Forest Preserve. North-South Lake is a gorgeous campground and day-use area with two connected lakes, a sandy beach, and access to some of the most dramatic views in the Catskills. The Escarpment Trail from here looks out over the Hudson Valley far below — it's a view that stops conversations. The Pine Orchard area near the lake was where Thomas Cole and the Hudson River School painters came for inspiration in the 1800s.

Overlook Mountain — 40 min via Woodstock

A beloved Woodstock hike that climbs through the ruins of a historic hotel to a fire tower at the summit with sweeping 360-degree views. At 2.5 miles each way, it's a solid workout but very achievable. The ruins and tower make it feel like an adventure, not just exercise. Go at sunset if you can.

Windham High Peak — 20 min from Bear House Catskills

One of the Catskills' 35 High Peaks, offering a moderate-to-challenging hike through hardwood forest to a partially open summit. Part of the Catskill 3500 Club's list of required peaks. Beautiful in fall.

Elm Ridge Trail / Peekamoose Blue Hole — 60 min

The Blue Hole is one of the most stunning swimming holes in New York — a crystal-clear pool on the Rondout Creek with a vivid blue-green color that has to be seen to be believed. It's a modest walk from the parking area. Permits required on weekends in summer; check DEC website before you go

🍽 Best Restaurants Near Bear House

Woodstock (40 min)

• Garden Cafe on the Green — beloved vegan café right on the village green, serving Woodstock since the 1990s. Wonderful for lunch, casual dinner, or weekend brunch. One of the most authentic spots in town

• Silvia — wood-fired, farm-to-table dinner in a beautifully renovated space. Nordic-Asian-fusion menu with an open kitchen, a vine-wrapped pergola outside, and a gorgeous bar room inside. One of the best meals in the region — reservations essential

• Good Night — Silvia's pan-Asian sister restaurant a few doors down, with shareable plates, outdoor seating, and creative cocktails. More relaxed, equally delicious

• Pearl Moon — a family-run restaurant, bar, and live music venue on Mill Hill Road. Farm-fresh comfort food, craft cocktails, and buttermilk biscuits baked fresh every morning. Dog-friendly patio in warmer months

• Tinker Taco Lab — margaritas by a stream, excellent tacos, and a fun al fresco vibe. Perfect for a casual lunch after a hike

• Medo — a genuinely surprising Japanese restaurant in the heart of Woodstock. Fresh sushi, yakitori, and katsu sandwiches. Locals love it; don't skip it

Catskill & Cairo area (5–20 min)

• See & Be Kitchen (Cairo, 5 min) — a husband-and-wife sourdough bakery and café right on Main Street in Cairo. Beloved for long-fermentation bread, pastries, creative breakfast and lunch dishes, and genuinely warm hospitality. Your first stop most mornings

• Julia's Local (Round Top, 15 min) — farm-to-table with a Scandinavian twist, opened by a Norwegian chef whose menu changes weekly based on what's in their one-acre garden. One of the most exciting restaurants in Greene County. Dinner only; reservations recommended

• Log Cabin Cafe (Purling, 15 min) — a classic, cash-only local breakfast and lunch spot known for generous portions and the kind of homefries you'll think about for weeks

• Red Rooster Roadhouse (Cairo) — friendly neighborhood bar and grill with cold beer, solid burgers, and great local atmosphere. Perfect for a casual dinner without a reservation

• Barnwood Restaurant (Catskill, 15 min) — unpretentious homemade food, lunch and dinner, with a loyal local following. Good value, no fuss

Hudson, NY (35 min)

Hudson is a destination in itself — one of the best small-city restaurant scenes in America, packed into a few blocks of Warren Street.

• Wm. Farmer and Sons — farm-to-table at its most sincere, in a beautiful historic building. Craft cocktails, inventive seasonal menu, and a warm bar room with an indoor fireplace. Open Friday–Tuesday for dinner

• The Maker Restaurant — elegant, farm-driven dinner in the boutique Maker Hotel. Speakeasy-esque vibe, art deco meets wilderness lodge interiors, and spectacular cocktails. Dinner nightly

• Governor's Tavern — a beloved neighborhood bar and restaurant with great food, consistent service, and the easy comfort of a true local

• Red Dot Restaurant & Bar — a Hudson staple with a charming garden patio in warmer months. Great for lunch or a relaxed dinner

☕ Coffee, Bakeries & Markets

• See & Be Kitchen (Cairo, 5 min) — fresh sourdough, pastries, and coffee, steps from Bear House. Best morning stop in the area

• Bread Alone (Woodstock) — the definitive Catskills bakery, open daily from 7am. Serious bread, excellent croissants, good coffee

• Catskill Mountain Country Store (Woodstock) — organic groceries, local products, and prepared foods. Great for stocking up on snacks and local goods

• Hannaford Supermarket (Cairo, 10 min) — best full grocery store in the area for stocking the kitchen before your stay

🎨 Arts, Culture & Unique Experiences

•     Woodstock, NY — one of America's most storied arts communities. The 1969 festival was actually in Bethel, but Woodstock has been a center for music, art, and counterculture for over a century. Walk the village, browse galleries, catch live music

•     Catskill Mountain Foundation (Hunter) — hosts concerts, films, art exhibitions, and lectures year-round. Check their calendar before your trip

•     Cairo Fossil Forest — a short walk from a parking area reveals 385-million-year-old fossilized tree stumps, the oldest known forest in the world. Free, uncrowded, and genuinely mind-blowing

•     Opus 40 (Saugerties) — one of the most extraordinary outdoor sculptures in America. Harvey Fite spent 37 years hand-placing bluestone into a 6.5-acre earthwork. A must-see

•     Rail Explorers: Catskills Division — pedal-powered rail bikes through the mountains on a decommissioned railroad. Unique, fun, and available for families and groups

🍷 Wineries & Breweries

•     Old Factory Brewing Company (Cairo) — local craft brewery with great food and cockails - minutes from Bear House Catskills

•     Catskill Brewery (Livingston Manor) — widely regarded as one of the best craft breweries in the Catskills

•     Olivia's Wine and Spirits Liquor Store (Windham) — excellent selection of natural wines in a beautiful shop

•     Hudson Valley Wine Trail — over 30 wineries within an hour of Bear House, many with stunning mountain or river views

❄️ Winter & Skiing

•     Hunter Mountain — 27 min. The premier ski resort in the Catskills, with 67 trails, night skiing, a gondola, and a lively ski village. Lessons available for all ages

•     Windham Mountain Resort — 20 min. More laid-back than Hunter, with excellent grooming and a loyal following

•     Belleayre Mountain — 60 min. State-run and the most affordable of the three. Great for families

•     Plattekill Mountain — 60 min. An independently-owned, old-school mountain with no frills and serious terrain

📍 Getting Here

Bear House Catskills is located in Cairo, NY — approximately 2 hours north of New York City via the Thruway (I-87) to Exit 21 (Catskill) or the Taconic State Parkway to Route 23. No car? The Trailways bus from Port Authority stops in Catskill, about 15 minutes from the house.