Winningen is a gateway to the Terrassenmosel (Terraced Mosel), the portion of the river characterized by steep, terraced vineyards. Winches help haul miniature monorails, with the winegrowers and their tools aboard, up the steep incline, but tending and harvesting the vines are all done by hand. For a bird's-eye view of the valley, drive up Fährstrasse to Am Rosenhang, the start of a pleasant walk along the Weinlehrpfad (Educational Wine Path).
As you head upstream toward Kobern-Gondorf, you'll pass the renowned vineyard site, Uhlen. In Kobern, the Oberburg (upper castle) and the St. Matthias Kapelle, a 12th-century chapel, are good vantage points. Half-timber houses reflecting the architectural styles of three centuries ring the town's pretty market square.