Annapolis Comedy Shows January 2027
Stand-up comedy, touring comedians, and live comedy shows in Annapolis and nearby areas.
- Updated: November 13, 2026
Annapolis comedy shows in January 2027 include stand-up comedians, improv performances, podcast tours, and live comedy events. Comedy performances take place across clubs, theaters, arenas, and entertainment venues throughout the city during the month.
- 4 Upcoming Shows
- Next Show Starts In:
- Jessica Michelle Singleton
- Jan 23 · 8:00 PM · Annapolis, MD
- View Tickets
Comedy Shows By Dates
Upcoming Comedy Shows in January
Browse comedy shows by date and venue in Annapolis during January 2027.- Jan 23, 2027, 8:00 PM Sat — COMEDY, Weekend Event, Pay Later Available: Jessica Michelle Singleton at Rams Head On Stage • 300 seats,
33 West Street, Annapolis, MD 21401, US. From $157, Avg. price ~ $181, 2 tickets remaining! Select Seats - Jan 24, 2027, 7:30 PM Sun — COMEDY, Best Value, Weekend Event: Tyrus - Comedian at DoubleTree by Hilton Hotel Annapolis, 210 Holiday Court, Annapolis, MD 21401, US. From $57, Avg. price ~ $137, Tickets Available: 52. Select Seats
- Jan 28, 2027, 8:00 PM Thu — COMEDY, Best Value: Jessica Kirson at Maryland Hall For The Creative Arts, 801 Chase Street, Annapolis, MD 21401, US. From $60, Avg. price ~ $94, Tickets Available: 433. Select Seats
- Jan 30, 2027, 7:30 PM Sat — COMEDY, High Demand, Weekend Event, Pay Later Available: Gary Gulman: 7th Hour at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $137, Avg. price ~ $252, 23 tickets remaining! Select Seats
All Comedy Shows in January
Comedy Clubs & Venues
Comedy Shows FAQ
What comedy shows are happening in Annapolis during January 2027?
Comedy schedules may include stand-up comedians, touring comedy acts, improv performances, podcast tours, and live comedy specials across Annapolis and nearby areas.
Are comedy schedules updated regularly?
Yeah. New comedy performances and additional dates are added often as venues announce updated schedules and special events throughout January.
What types of comedy performances are included?
You’ll commonly find stand-up comedy, improv shows, podcast recordings, sketch comedy, and performances by touring comedians.
Where are comedy shows usually performed in Annapolis?
Comedy events are often hosted at comedy clubs, theatres, casinos, bars, resorts, and entertainment venues throughout Annapolis.
Do comedy shows happen during the week?
Absolutely. Many comedy venues host performances throughout the week, while weekends are usually the busiest nights for live comedy.
Do major comedians tour through Annapolis?
Yes. National touring comedians and comedy acts regularly perform in Annapolis during January 2027.