Best free things to do in Winchester (Virginia)?

There are some great hikes around the Winchester area if you're willing to spend some time driving anywhere from 30 min-1 hr. If you go to hikingupward.com (http://www.hikingupward.com/maps/), you can use the Sortable Hikes map to view and select hikes by distance, difficulty, views/streams, etc. Bears Den is a pretty popular place to watch the sunset and doesn't require any hiking! There are also some nice orchards in the area where you can pick your own apples, berries, etc. like Marker-Miller Orchards. The walking mall downtown is a nice place to relax, also. If you're of age, there are a decent amount of wineries within driving distance, too and places like Barrel Oak Winery have a nice, relaxed environment with pretty cheap wine tastings, I believe. The Alamo Drafthouse Cinema is a fun place to go to the movies; tickets there are cheaper than most places and you can order food while you're there. Hope this helps! :)