The Catskills are a 700,000-acre mountain region in southeastern New York, 2 hours from midtown Manhattan — making them the most accessible mountain destination for the 20 million people living in the New York metro area. The region has experienced a genuine renaissance since 2015, with a new wave of boutique hotels, farm-to-table restaurants, and artisan shops transforming towns like Woodstock, Phoenicia, Narrowsburg, and Hunter from sleepy hamlets into weekend destination communities. For reunion organizers from the NYC-Philadelphia-Hartford corridor, the Catskills offer a rare combination: real mountains (peaks to 4,180 ft), clear trout streams, swimming holes, and a sophisticated food and arts culture.
The vacation rental market in the Catskills has exploded to become one of the deepest in the Northeast. Sullivan County, Delaware County, and the Ulster County corridors now have thousands of listings on VRBO and Airbnb, including many converted farmhouses, mid-century modern retreats, and architect-designed 'design hotels' that sleep 6-20 people. A 10-BR farmhouse in Sullivan County with a pool runs $3,000-6,000/week in summer — significantly cheaper than comparable properties in the Berkshires or Hamptons. Groups of 30-60 can rent adjacent properties on the same road. The Catskills Center maintains a lodging resource guide at catskillscenter.org.
The outdoor activity anchor is world-class swimming holes: Peekamoose Blue Hole, Peck's Falls, and the Plattekill Clove pools are iconic and free. Kaaterskill Falls (the highest two-stage waterfall in New York) is a 2.4-mile round trip hike that every reunion group should do. Woodstock is 15 minutes from most Catskill rentals and functions as the region's cultural village, with galleries, live music, and farm-to-table dining every night of the week.
Where it is
Things to do (with the family)
Hand-curated. Every entry links to its official source so you can plan without guessing.
Kaaterskill Falls hike
New York's highest waterfall (260 ft in two tiers) — 2.4-mile round trip with 1,000 ft elevation gain. Moderate difficulty; the upper tier viewpoint is mandatory. Parking fills by 9 AM in summer — use the Laurel House Road lower trailhead.
Official source ↗Peekamoose Blue Hole swimming
Emerald-green swimming hole on the Rondout Creek in the Catskill Wilderness — the most famous and most beautiful in the region. Free but timed-entry permit required (recreation.gov in season). Arrive early or reserve permits.
Official source ↗Woodstock village
Legendary arts village — galleries, live music at the Bearsville Theater, farm restaurants, and the town green. The Woodstock Artists Association & Museum is free. The 1969 festival was actually in Bethel (50 mi away), but Woodstock has been the arts heart of the Catskills for 120 years.
Official source ↗Minnewaska State Park Preserve
Sky Lakes wilderness with two cliff-top lake beaches (Lake Minnewaska and Lake Awosting) — free swimming, easy trails, and the Trapps climbing area. $8-10/vehicle parking. One of the most beautiful parks in New York.
Official source ↗Delaware River tubing and kayaking
Kittatinny River Trips and Landers River Trips run Delaware River float trips in Sullivan County — half-day and full-day tubes/canoes/kayaks. $25-45/person. Group discounts for 20+. Gentle Class I-II, suitable for all ages.
Official source ↗Hunter Mountain and Belleayre ski areas (summer activities)
Both ski areas run summer gondola rides, festivals, and mountain biking in season. Hunter Mountain's scenic gondola is open July-August. Belleayre Beach on Belleayre Lake is the most accessible mountain swimming.
Official source ↗Bethel Woods Center for the Arts (original Woodstock site)
Outdoor amphitheater on the original 1969 Woodstock festival field in Bethel — summer concerts, the Museum at Bethel Woods (Woodstock era history). Worth a half-day trip from Catskill rentals (45 min).
Official source ↗Farm-to-table dining in Phoenicia and Hudson
The Phoenicia Diner (retro, excellent), River Cafe Woodstock, Peekamoose Restaurant, and Graham & Co. hotel bar are the reliable reunion dinner anchors. Hudson (45 min) has a James Beard-level restaurant scene.
Official source ↗Catskill Center's High Peaks loop
The 35 "Catskill 3500" peaks above 3,500 ft — hiking with a dozen worthy objectives for active family members. Slide Mountain (4,180 ft, 5 mi round trip) is the highest and most popular.
Official source ↗Resorts World Catskills casino
Full-scale casino resort in Monticello (Sullivan County) — hotel, restaurants, and a spa. Not the typical Catskills vibe, but a rainy-day option for the adults.
Official source ↗Find more things to do for your The Catskills, New York reunion
The picks above are general. Inside the Reunly app, Rosi tailors local activities, meals, and printables to your actual dates, group size, ages, and budget — and saves them straight to your reunion plan.
Good for
- NYC-area families wanting mountains without a long drive
- Design-forward and food-oriented reunion groups
- Swimming hole and outdoor adventure fans
- Groups wanting a sophisticated small-town arts experience
- Fall foliage (spectacular mid-October)
Practical logistics
- Nearest airport
- Stewart (SWF, Newburgh) — 45 min · Newark (EWR) — 2 hr · JFK — 2 hr
- Drive times
- Manhattan 2 hr · Brooklyn 2 hr · Philadelphia 2.5 hr · Hartford 2.5 hr · Boston 3.5 hr
- Best rental sites
- VRBO, Airbnb — deepest inventory in Sullivan County, Delaware County, and Ulster County
- Best months
- June-September (peak summer) · October (foliage) · some December-February for ski reunions
- Cell service
- Variable — good in towns like Woodstock and Windham; spotty in hollows and remote properties
- Groceries
- Adams Fairacre Farms (Kingston, 20-30 min from most rentals) is the go-to. Price Chopper and Hannaford in various towns.
- Key areas
- Ulster County (Woodstock, Phoenicia, Kingston) · Sullivan County (Livingston Manor, Narrowsburg) · Delaware County (Margaretville, Andes) · Greene County (Hunter, Windham)
When to go
Memorial Day through Columbus Day for the full experience. Summer weekends (July-August) are peak — swimming holes require permits, and parking fills by 9 AM. September is excellent for hiking and dining without the weekend crunch. Mid-October peak foliage is spectacular but lodging books out 6-9 months ahead.
Best for your group size
Small group · 10–25
Groups of 10-25 are perfectly served by the Catskills' abundant 6-10 BR farmhouse and chalet rentals in Sullivan and Delaware Counties.
Medium group · 25–60
Groups of 25-60 should book 2-3 adjacent properties (common in the Catskills, where property managers often hold clusters). Graham & Co. in Phoenicia has 20 rooms ideal for a medium-group hotel block.
Large group · 60+
Groups of 60+ need a resort hotel or a full buyout. The Emerson Resort & Spa in Mt. Tremper (50 rooms), Full Moon Resort, or Resorts World Catskills hotel are the main options.
Sample 3-day Catskills New York family reunion
A starter agenda you can copy into Reunly's Schedule and customize for your group.
Day 1 — Arrival + Woodstock
- Drive 2 hours from NYC; stop at Adams Fairacre Farms (Kingston) for groceries
- 2:00 PM check-in at rental farmhouse
- 4:00 PM Woodstock village — town green, galleries, ice cream at Woodstock Country Club
- 6:30 PM group dinner at Peekamoose Restaurant (reserve ahead)
- 8:30 PM bonfire at the rental
Day 2 — Kaaterskill Falls + Swimming Holes
- 8:00 AM early breakfast
- 8:30 AM depart for Kaaterskill Falls trailhead (arrive by 9 AM)
- 9:00 AM hike to Kaaterskill Falls (2.4 mi round trip, 1.5-2 hours)
- 11:30 AM Peekamoose Blue Hole (timed-entry permits reserved)
- 1:00 PM swimming and picnic lunch
- 3:30 PM return to rental — pool time
- 6:30 PM dinner at the Phoenicia Diner
Day 3 — Delaware River + Departure
- 9:00 AM Delaware River kayak or tube trip (Kittatinny River Trips)
- 1:00 PM end of float — lunch in Narrowsburg at the Heron
- 3:00 PM farewell stop at Bethel Woods Center for the Arts (original Woodstock site)
- 5:00 PM drive home
Reunion organizer tips
Book Peekamoose Blue Hole timed-entry permits at recreation.gov the moment they open (4-6 weeks ahead in summer). They sell out within hours. Without a permit, the access road is gated — no permit, no entry.
Sullivan County is the best value area: properties are cheaper than the Hudson Valley side but access to the Delaware River, Bethel Woods, and the western Catskill peaks is excellent. Livingston Manor and Narrowsburg are the charming small-town anchors.
Plan one dinner at the Phoenicia Diner (Thursday-Sunday) — the iconic mid-century modern diner on Main Street Phoenicia seats 50+ but waits can be 45 minutes on Saturdays. Make a reservation online.
The Catskill rental market has excellent 6-12 BR farmhouses with pools at significantly lower prices than the Berkshires or Hamptons. A 10 BR Sullivan County farmhouse with pool runs $3,000-5,500/week.
For groups with NYC arrivals by bus: the Trailways and Shortline buses run directly from the Port Authority bus terminal to Woodstock, Rhinebeck, and Kingston. Useful for family members without cars.
How Reunly helps you plan it
Reunly is the all-in-one app made for family reunion organizers. Free to start. No credit card. Cancel anytime.
Smart guest list
Drop in any spreadsheet — Rosi (our AI) reads multi-sheet, color-coded family groups, even handwritten exports. RSVP, dietary, T-shirt, paid status all in one row.
Open in Reunly →Public RSVP link
Share one link with the whole family. They RSVP per event (Friday BBQ, Saturday dinner) without making an account. You see live counts.
Open in Reunly →Budget that adds up
Track estimated vs. actual, who paid, who still owes. Auto-creates per-guest fee rows from your registration cost.
Open in Reunly →Day-by-day schedule
Friday welcome BBQ, Saturday photo, Sunday brunch — with location, meal flag, and per-event RSVPs.
Open in Reunly →Name tags + printables
Avery 5160 sheets color-coded by family, programs, welcome packets, packing lists — auto-filled from your data.
Open in Reunly →Rosi the AI helper
Stuck on a reminder email? A budget? A timeline? Click Rosi anywhere in the app — she drafts it from your live data.
Open in Reunly →Plan your The Catskills, New York reunion with Reunly
Free to start. Build your guest list, share an RSVP link, track payments, and print name tags — no spreadsheets.
Frequently asked
How far are the Catskills from New York City?
Approximately 2 hours by car from Manhattan (via I-87 Thruway North). The western Catskills in Sullivan County are slightly farther (2.5 hours). There is also bus service from Port Authority Bus Terminal to Woodstock, Rhinebeck, and Kingston on Trailways and Shortline, useful for family members without cars.
What is Peekamoose Blue Hole and do I need a permit?
Peekamoose Blue Hole is an emerald-green natural swimming pool on the Rondout Creek in the Catskill Wilderness near Sundown, NY — widely considered the most beautiful swimming hole in the region. Timed-entry permits are required from late June through Labor Day, available at recreation.gov. They sell out within hours of release. Without a permit, the access road is gated.
Are there large vacation rentals in the Catskills for groups of 20-30?
Yes — the Catskills have some of the best-value large group vacation rentals in the Northeast. Sullivan County and Delaware County have abundant farmhouses and mountain homes sleeping 10-20+ people at prices significantly lower than Berkshires or Hudson Valley equivalents. VRBO and Airbnb both have deep inventory. Book 4-6 months ahead for peak summer and foliage season.
When is the best time to visit the Catskills for fall foliage?
Mid-October for peak color — the sugar maples, birches, and beeches create spectacular color in the higher elevations. The peak typically runs from early October at the summits through mid-to-late October in the valleys. Columbus Day weekend is the most crowded and most colorful. Book lodging 6-9 months ahead for that weekend.
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