The Winchester Recreation & Community Education department is on Main Street in a majestic building, which is surrounded by large fields, a playground and basketball courts. The department has activities for adults, children and summer-specific classes. Adult programs include business and finance, creative arts, dance, health and fitness, music and personal development. For the youths of Winchester, the department offers SAT prep classes, babysitting training and for elementary school children it hosts a track meet.

Over the summer the activities vary from swimming programs to soccer and sport camps to adventure and art camps. There are also a number of tennis programs adults and youths can choose from.

The Winchester Youth Center is committed to cultivating leadership skills and a devotion to community service through healthy social and learning activities for teens.