Winter Skiing
To some folks from the city, the Catskills is just one big, undifferentiated place "up there." Yes, there is good downhill skiing in the Catskills, but further north and not in Sullivan County. Unfortunately, no part of the Catskills has everything. In Sullivan County, you get wonderful lakes, rolling farmland and the Delaware River — but not great downhill skiing. Northeast of here, in Delaware and Greene counties, you do get downhill skiing at Belleayre, Windham and Hunter Mountains, but not the lakes or the Delaware River.
The closest "real" ski areas to Sullivan County are Belleayre in the northern Catskills, about 44 miles from Roscoe (1 hour driving) and Elk Mountain in Pennsylvania. Elk is a nice mountain with a 1,000 vertical (it's where I ski.) Elk is 31 miles west of Callicoon, about a 45 minute drive.
For smaller, closer mountains, there's Big Bear at Masthope Mountain in Lackawaxen, Pennsylvania, just across the Delaware River from Barryville. Big Bear is a smaller mountain, good for an occasional day or to try out those new skis. And in Sullivan County itself, we have Holiday Mountain near Bridgeville with a 400 foot vertical (they're tag line, "Where Great Skiers Begin" sort of says it all) and the Villa Roma Ski Area near Jeffersonville with a mind-boggling 250 ft. vertical.
So you can see, Mount Snow or Killington we ain't. There's enough skiing close by for an occasional day trip to schuss down the slopes (and an hour drive on a Saturday to Belleayre is a heck of a lot faster than a 2 1/2 hour drive from the city to ski.) But if you're looking for looking for the Sullivan County equivilent of being just off the Killington access road, this isn't the place.
While we don't have a lot of downhill action right here, cross country is BIG. In the farm areas of western county, many farmers open up cattle fences to permit snowmobilers to travel through (and some of those trails cut by snowmobilers go for miles and miles). Those snowmobile trails make great cross country trails. The Frost Valley YMCA, just over the Ulster County line northeast of Claryville, offers some of the best 'formal' cross country trails in the east.
If downhill skiing is your thing, you're probably better off heading to the northern Catskills or over to the Poconos. But — and I'm sticking my neck out here — I will venture that Sullivan County, with our lakes, rivers, golf courses and woodlands, offers more recreation options the rest of the year.