🥾 ActiveLong weekend · from New York, NY
Catskills: Slide Mountain, Kaaterskill Falls & the Hudson Valley
The Catskills are the mountains that invented the American concept of wilderness — Hudson River School painters came here first, followed by everyone else. Slide Mountain is the high point; Kaaterskill Falls is the most painted waterfall in American art history; Hudson is the town that quietly became New York's art capital.
Day 1 — Slide Mountain & Catskill EscarpmentDay 2 — Kaaterskill Falls & North-South LakeDay 3 — Olana & Hudson
Day 1 — Catskill Mountains — Slide Mountain
Day 1 — Catskill Mountains — Slide Mountain
🚗 3 hr driving📍 6 stops
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Morning
🚗
Drive
New York, NY → Slide Mountain Trailhead — Big Indian Wilderness
2 hr 30 min8:00 AM → 10:30 AM
Slide Mountain — Wittenberg-Cornell-Slide Trail
★ 4.7The Slide Mountain loop is the crown jewel of Catskills hiking — a ridgeline traverse through ancient yellow birch and balsam fir to the 4,180-foot summit, highest point in the Catskills and one of the best summit views in the Northeast. John Burroughs camped here repeatedly in the 1880s and called it the finest mountain in the Catskills.
10:30 AM📍 See location
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Lunch
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Peekamoose Road — Peekamoose Blue Hole
The most beautiful swimming hole in the Catskills — a series of turquoise pools carved into the Rondout Creek bedrock by snowmelt runoff, accessible via a short trail from the Peekamoose Road. The color of the water is extraordinary; the mountain hemlock forest surrounding the pools is pristine. Entry limited to 25 people on weekends.
11:30 AM📍 See location
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Afternoon
🚗
Drive
Peekamoose area → Woodstock, NY
30 min12:30 PM → 1:00 PM
Woodstock Village Green
★ 4.7The most mythologized village green in American music — Woodstock's small commercial center has maintained its character as an arts community. The independent galleries, record shop, and Tinker Street cafe strip is genuine rather than curated; the Woodstock Film Festival runs every October.
1:00 PM📍 See location
Silvia's Twisted Soul
★ 4.3A Woodstock restaurant with a menu that pulls from Southern, Creole, and Hudson Valley traditions — a surprisingly sophisticated kitchen in a small town known more for its music history than its food scene.
2:00 PM📍 See location
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Evening
Joshua's Cafe
★ 4.5A beloved Woodstock institution on Tinker Street — Middle Eastern and Mediterranean cooking (falafel plates, shawarma, lamb dishes, housemade hummus) in a warm brick-walled room. The go-to dinner spot for the Catskill arts-town crowd after 20 years; the mezze spread is the move.
5:00 PM📍 See location
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The Woodstock Inn on the Millstream
A boutique inn on a Catskill creek in the center of Woodstock village — rooms are tastefully done with mountain-cabin elements, and the creek sound is constant. A short walk to the village green and galleries.
Day 2 — Kaaterskill Falls & North-South Lake
Day 2 — Kaaterskill Falls & North-South Lake
🚗 1 hr driving📍 6 stops
🌅
Morning
🚗
Drive
Woodstock, NY → Kaaterskill Falls Trailhead
40 min8:00 AM → 8:40 AM
Kaaterskill Falls
★ 4.8The most painted waterfall in American art history, subject of Thomas Cole and Frederic Church canvases that hung in London galleries and defined the American landscape for the world in the 1830s. Two-tiered falls dropping 260 feet combined — the approach trail passes through beech-maple forest that was already old when the painters arrived. The short 1.5-mile round trip is essential.
8:40 AM📍 See location
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Lunch
North-South Lake Campground & Beach
★ 4.6The twin lakes at North-South Lake are the gateway to the Catskill Escarpment — the preserved land above the lakes is where the Hudson River School painters set their easels, and the Artist Rock and Sunset Rock overlooks are accessible on a 2-mile rim trail. The swim beach at North Lake is one of the better state park beaches in New York.
9:40 AM📍 See location
Last Chance Antiques & Cheese Café — Tannersville
★ 4.5A Tannersville institution in a Victorian commercial building — an antique shop attached to a cheese and charcuterie cafe that draws everyone who comes through the Catskills. The Kaaterskill Creek flowing behind the building and the hand-painted ceiling inside are both worth attention.
10:40 AM📍 See location
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Afternoon
🚗
Drive
Tannersville, NY → Windham, NY
20 min12:00 PM → 12:20 PM
Windham Mountain Trail — Elm Ridge Walk
★ 4.3The Windham Mountain trail system in summer is a network of hiking and mountain biking trails with a chairlift operating on weekends. The Elm Ridge overlook at the top of the main chair provides a full panorama of the northern Catskills — the broad valley view looking north toward Albany is distinct from the forested ridgeline views further south.
12:20 PM📍 See location
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Evening
Prospect at Scribner's Catskill Lodge
★ 4.2The in-house restaurant at Scribner's Catskill Lodge — seasonal American cooking with Hudson Valley sourcing in a dining room that shares the lodge's mountain-modern aesthetic: exposed timber, wide windows, fire going most evenings. Convenient when you're already sleeping here after a day at Kaaterskill Falls.
5:00 PM📍 See location
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Scribner's Catskill Lodge
A 38-room boutique hotel in Hunter with the best design of any Catskills mountain lodge — clean lines, woodfire pit, swimming pool, and Prospect restaurant serving the most serious kitchen in the mountains. The design is modern without disrespecting the mountain lodge context.
Day 3 — Olana & Hudson
Day 3 — Olana & Hudson
🚗 3 hr 35 min driving📍 4 stops
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Morning
🚗
Drive
Hunter, NY → Olana State Historic Site
1 hr8:00 AM → 9:00 AM
Olana State Historic Site
★ 4.8Frederic Edwin Church, the most celebrated painter of the Hudson River School, designed his own Orientalist-influenced estate on a 250-acre hillside above the Hudson — the house is a visual statement of the same principles Church applied to his landscape paintings. The grounds are open year-round for hiking; the house tours show the studio and collection that Church assembled from his travels in the Middle East. The Hudson River view from the grounds is exactly what Church painted.
9:00 AM📍 See location
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Lunch
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Drive
Olana → Hudson, NY
5 min10:00 AM → 10:05 AM
Hudson — Warren Street
The most concentrated stretch of antique dealers, galleries, and independent restaurants in upstate New York — Warren Street has been Hudson's commercial spine since the 19th century. The whaling money that built these Federal and Greek Revival buildings funded galleries that now show contemporary art. A long, slow walk is the correct approach.
10:05 AM📍 See location
Grazin'
A certified humane, grass-fed burger restaurant in the heart of Hudson — the beef is sourced from Hudson Valley farms and the burger quality reflects it. The honest simplicity of a good grass-fed burger and a pile of hand-cut fries in a town of art galleries and restaurants is exactly right for a lunch pause.
11:05 AM📍 See location
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Afternoon
Hudson Antiques District
★ 4.4Over 50 antique dealers within a few blocks of Warren Street — architectural salvage, American folk art, Federal-period furniture, and the kind of mid-century European pieces that dealers in Paris ship here because New York buyers pay better. A genuinely serious antiques destination.
12:05 PM📍 See location
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Drive
Hudson, NY → New York, NY
2 hr 30 min1:05 PM → 3:35 PM
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