The Rothaarsteig is a 154-kilometre long-distance trail that crosses the Sauerland from Brilon in the north to Dillenburg in the south, with the section near Winterberg passing through the heart of the mountains. Day hikes and multi-day sections both start from the town, where the tourist office provides good maps and route information.
The terrain is gentle by hiking standards — this is low-mountain walking, not scrambling — but the beech forests and open ridgeline sections are genuinely beautiful, particularly in autumn. Mountain bikes are not permitted on the main Rothaarsteig trail, but there are parallel bike routes. Walking poles are useful in wet conditions.