Apple picking & pumpkin carving: Greig Farm in Red Hook and Kedler Farm in Kerhonkson have great apple picking and fun fall activities. Sunfrost Farms, sells perfect pumpkins for carving.
Catskills Mountain Railroad: Take a step back in time and enjoy the foliage from the open carriage of a steam train. Fall Foliage Specials depart from Mt Tremper Station (5401 Route 28, Mt. Tremper, NY 12457) from September 26-October 26, each Friday, Saturday & Sunday as well as October 13 (Columbus Day) on the hour from 10AM to 3PM.
The foliage: Some of the best places to view fall foliage in the Woodstock area are the Ashokan reservoir, Overlook Mountain & Cooper Lake. Belleayre Mountain, Overlook Lodge also offers fantastic views. The skyride to the lodge operates Columbus Day Weekend, otherwise you can hike up to the lodge in about an hour. The lodge is open daily from 7AM to 3PM. A little further afield (40 minute drive from Woodstock) the Catskill Escarpment Loop from Schutt Road (North/South Lakes) is one of the most spectacular foliage hikes in NY.