Daniel Boone Pioneer Festival

This three day event has a little something for everyone.  The Festival kicks on Friday night with a Street Dance in downtown.  There is a 5K run & Walk with Friends Saturday morning and Arts, Crafts and Food all weekend!  The finale is an outdoor concert featuring nationally renown country musicians.  We just wrapped up our 37th festival…hope you’ll join the fun for the 38th! 

Beer Cheese Festival

Beer Cheese lovers converge in downtown Winchester annually the 2nd weekend in June!  Mark your calendar and join us!

Civil War Living History Event

The Civil War Living History event is traditionally  held at the Civil War Fort at Boonesboro each May.  A variety of re-enactors share their knowledge of the Civil War in engaging ways.  Fun for the entire family!

Scenic Winchester

Whether you are driving through our scenic countryside or strolling down our Main Street,  Winchester offers some incredible views that provide not only  great photo opportunities but also lasting memories!