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Winchester Comedy Schedule
Find the Best Comedy Shows in Winchester for 2026
Winchester is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular comedy shows so you can easily plan your next outing.
Top Comedy Shows in Winchester This Weekend
Planning your weekend? There are 1 comedy shows happening around Winchester this weekend! Here are the most popular comedy shows happening in Winchester from Thursday to Sunday. Don't miss out on the action!
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Dusty Slay | Jul 11 | Hollywood Casino at Charles Town Races | $53 |
Top 2026 Summer Comedy Shows in Winchester
Summer is the perfect time for live events in Winchester! Check out this list of the top comedy shows happening from May through September.
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Dusty Slay | Jul 11 | Hollywood Casino at Charles Town Races | $53 |
| Stand Up Comedy Night | Jul 18 | Mannie's World | $62 |
| Oh Crit Comedy Night | Jul 24 | Maryland Ensemble Theatre | $46 |
| Key City Improv | Aug 7 | Maryland Ensemble Theatre | $50 |
| Steel City Comedy Night | Aug 14 | Ponfeigh Distillery | $72 |
| Jay Yoder | Aug 16 | Jammin Java | $72 |
| Ben Bankas | Sep 5 | Hollywood Casino at Charles Town Races | $38 |
| D.L. Hughley | Sep 18 | Hollywood Casino at Charles Town Races | $75 |
| Jay Leno | Sep 25 | The Maryland Theatre | $161 |
| John Crist | Sep 26 | Capital One Hall | $50 |
Cheap Things to Do in Winchester This Weekend (Under $100)
Looking for fun in Winchester that won't break the bank? You've come to the right place. This list features the best-selling comedy shows this weekend with tickets under $100.
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Dusty Slay | Jul 11 | Hollywood Casino at Charles Town Races | $53 |
Top Venues in Winchester, VA
