Every Sunday, the trailer rolls into Winterset, IA and the wonderful Brian and his family bring the sweetest horses for The Pumpkin Ranch’s free Horseback Rides. Every Sunday The Pumpkin Ranch in Winterset, IA offers free horseback rides with paid admission, just like all our other attractions and activities. The horses provided for free Horseback Rides at The Pumpkin Ranch are suitable for all ages. These lead-rope led horseback rides at The Pumpkin Ranch in Winterset, are able to be enjoyed as many times during your visit as time allows. Take in the beautiful pasture views of Winterset, IA as you ride on, Tom, Tiny, Timmy, or Tully, during your free Horseback Ride at The Pumpkin Ranch. The Pumpkin Ranch’s, Horseback Rides are only offered on Sunday’s each open weekend in the fall.