Winchester Events May 2027
Concerts, sports, comedy shows, Broadway performances, and live events across Winchester, VA.
- Updated: November 13, 2026
Explore upcoming events in Winchester in May 2027, including concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment across the city and nearby areas. Browse events by date, venue, category, and neighborhood throughout the month.
- 11 Upcoming Events
- 7 Event Categories
Browse Events in May By Category
- All Events 11
- broadway 11
- Live Shows 11
Popular Events in May
Winchester Events by Date
Browse events happening each day during May 2027.Winchester Events Schedule – May 2027
Browse concerts, sports, comedy shows, Broadway performances, festivals, and live events across Winchester.- May 14, 2027, 8:00 PM Fri — MUSICAL / PLAY: Sister Act at Winchester Little Theatre,
315 W Boscawen St, Winchester, VA 22601, US. From $32, Avg Ticket Price: ~ $37, 10 tickets remaining! Select Seats - May 15, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 2 tickets remaining! Select Seats
- May 16, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 4 tickets remaining! Select Seats
- May 20, 2027, 8:00 PM Thu — MUSICAL / PLAY: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 15 tickets remaining! Select Seats
- May 21, 2027, 8:00 PM Fri — MUSICAL / PLAY: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 8 tickets remaining! Select Seats
- May 22, 2027, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 7 tickets remaining! Select Seats
- May 22, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 20 tickets remaining! Select Seats
- May 23, 2027, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $38, 2 tickets remaining! Select Seats
- May 27, 2027, 8:00 PM Thu — MUSICAL / PLAY: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $43, Tickets Available: 40. Select Seats
- May 28, 2027, 8:00 PM Fri — MUSICAL / PLAY: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $43, Tickets Available: 74. Select Seats
- May 29, 2027, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Sister Act at Winchester Little Theatre, 315 W Boscawen St, Winchester, VA 22601, US. From $33, Avg Ticket Price: ~ $49, Tickets Available: 74. Select Seats
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About Events in Winchester During May 2027
May 2027 features concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment across Winchester and nearby VA areas. Major arenas, theaters, clubs, and entertainment venues continue to update their schedules throughout the month.
Browse All Events in May
Frequently Asked Questions
What events are happening in Winchester during May 2027?
Winchester hosts concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment throughout May 2027.
Where can I find Winchester events by date?
Use the monthly event calendar and date filters to browse concerts, sports events, comedy shows, and live performances happening across Winchester.
Are concerts happening in Winchester during May 2027?
Yes. Concert schedules include touring artists, arena shows, local performances, music festivals, and live entertainment events throughout Winchester and nearby VA areas.
What are the top event venues in Winchester?
Popular venues include arenas, theaters, comedy clubs, stadiums, music halls, and entertainment venues located across Winchester and nearby areas.
Do event prices change during May 2027?
Yes. Event prices can change based on demand, seating location, performer popularity, venue size, and event date.
Are there weekend events in Winchester?
Yes. Weekends are usually the busiest time for concerts, sports games, comedy shows, festivals, and major live entertainment events across Winchester.