Winterberg has a railway station on the Ruhr–Sieg line, with regular connections to Dortmund (about 2 hours) and Siegen (about 1 hour). In winter, Ski-Express trains run direct from Düsseldorf and Cologne on weekends.
By car, Winterberg is about 1.5 hours from Cologne and 1 hour from Dortmund via the A46 and B480. Driving is more flexible for reaching the outlying ski areas and trailheads. Parking in town can be tight during peak winter weekends.