From most areas, take the New York State Thruway to Exit 21, then Route 23 West directly to Windham Mountain.
Amtrak operates between NYC's Penn Station and Hudson, a 40-minute drive from Windham (800-872-7245; amtrak.com).
If you make a rental reservation through Enterprise, they can meet you with your vehicle at the station (518-828-5492; enterprise.com).
The Windham Shuttle is operated by Island Ski Tours and has pick-ups available from Long Island, Queens, Manhattan, and Northern New Jersey every Wednesday through Sunday (631-656-0982; islandskitours.com).
NYC Ski & Board has two pickup locations: 4th Ave & 14th Union Square, and 42nd & Broadway between 7th & 8th (917-692-5222; nycski.com).