02.01 / Monticello
Holiday Mountain
Family-run since 1960. Night skiing, a terrain park and a 350-foot tubing run.



What's on, where to go, and Lake Huntington at the end of the night.
The entire Victorian house on Lake Huntington: three bedrooms for up to eight guests, a year-round private hot tub, indoor fireplace and two fire pits.
Bethel Woods and Sullivan County stops are close by; Mohonk, Ashokan and Cooperstown are longer trips. Dated and linked to the source — confirm before you drive.
Two hills. No lift lines worth complaining about.
Rinks, not the lake. Rental skates at some.
03.01 / Grahamsville
Free weekend skating. Skates available, helmet required.
03.02 / Livingston Manor
Pleasant Street, one block from Main Street.
03.03 / Hurleyville
Free weekday skating.
Deep snow turns an easy trail hard. Bring snowshoes or spikes.
04.01 / Near Livingston Manor
More than 40 miles of trails past frozen ponds. Snowshoe and cross-country ski country.
04.02 / Livingston Manor
Free snowshoeing, then a beer.
04.03 / Hurleyville area
Flat, easy winter walking.
Lake Huntington, from the house.
05.01 / Backyard
Open all year. Best when it's snowing.
05.02 / Up the road
A bald eagle lives nearby. You can see the nest from the shore.
05.03 / Everywhere
Ice-fishing shacks show up across the county. Stay off any ice unless local conditions are confirmed safe.
Warm rooms. Winter hours shrink, so call first.
06.01 / Narrowsburg
A meal with about the best view of the Delaware River you can get.
06.02 / Narrowsburg
Very good French food on the Delaware River, open late.
06.03 / Cochecton
Food and drinks inside an old fire station.
06.04 / Tyler Hill, PA
A proper greasy spoon. Order the pancakes.
06.05 / Livingston Manor
Sunday brunch.
Bars that glow warmer in January.
07.01 / Callicoon
Live music or a game of pool.
07.02 / Narrowsburg
A wine bar in Narrowsburg.
07.03 / Callicoon
A hilltop orchard. Order a cider flight.
07.04 / Roscoe
Its winter festival ran in late January 2026.
Indoor culture, close by.
08.01 / Narrowsburg
Gallery and the winter Ambient Barn Series.
08.02 / Lake Huntington
Opera, comedy and drama, a two-minute walk from the house.
08.03 / Bethel
Shows run all year. The museum is open April through December.
Sunday plans.
09.01 / Callicoon
Sundays, through the winter.
09.02 / Jeffersonville
Readings in a bookshop.
09.03 / Livingston Manor
Sunday mornings.
The Catskills Winter 2027 guide, ready to save or print.
Short answers.