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Octoberfest is held the first four weekends in October, is focused on celebrating the region’s German heritage. Hermann, MO a beautiful place to visit. This is the famous Stone Hill Winery . People from far and near stop in, buy a bottle of wine and maybe some cheese and just sit on the hilltop to relax, ponder and reminisce of good times. A fall festivity that's been going on for generations. Cheers!