Best Music events in Annapolis December 2025

Q: What are the trending Music events in Annapolis?

Here are the trending events in Annapolis: Siren's Call, Jimmie's Chicken Shack Holidaze Show, Pressing Strings, 2nd Generation @ Dark Horse!, 🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷, Slugs & Special Guests - New Year’s Eve at Dark Horse!

Music events in Annapolis in December

Fri, 26 Dec, 2025 - 05:00 PM

Siren's Call

The Westin Annapolis

Free
Fri, 26 Dec, 2025 - 08:00 PM

Jimmie's Chicken Shack Holidaze Show

Rams Head On Stage

192+ Interested
Sun, 28 Dec, 2025 - 08:00 PM

Pressing Strings

Rams Head On Stage

76+ Interested
Fri, 26 Dec, 2025 - 08:00 PM

2nd Generation @ Dark Horse!

985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States

25+ Interested
Wed, 24 Dec, 2025 - 06:30 PM

🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷

7 Church Cir, Annapolis, MD, United States, Maryland 21401
Wed, 31 Dec, 2025 - 09:00 PM

Slugs & Special Guests - New Year’s Eve at Dark Horse!

Dark Horse Annapolis

68+ Interested
Fri, 26 Dec, 2025 - 06:00 PM

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis
Fri, 26 Dec, 2025 - 09:00 PM

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis
Fri, 26 Dec, 2025 - 08:00 PM

Live Music with Guava Jelly

Rams Head Roadhouse

4+ Interested
Tue, 23 Dec, 2025 - 05:00 PM

Tides & Tunes

The Westin Annapolis

Free
Sat, 27 Dec, 2025 - 08:15 AM

CC @ Military Bowl 2025

Navy-Marine Corps Memorial Stadium
Sat, 27 Dec, 2025 - 09:00 PM

12/27 - ilyAIMY @ Dark Horse Annapolis (full band!)

Dark Horse Annapolis

26+ Interested
Sat, 27 Dec, 2025 - 07:00 PM

Sinners at 49 West

49 West Coffeehouse, Winebar & Gallery

6+ Interested
Fri, 26 Dec, 2025 - 09:00 PM

Blackwall Hitch Annapolis

Blackwall Hitch Annapolis

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Upcoming Music events in Annapolis

Date	Event	Venue
26 Dec 2025	Jimmies Chicken Shack Holidaze Show	Rams Head On Stage, Annapolis
23 Dec 2025	Tides & Tunes	The Westin Annapolis
28 Dec 2025	Pressing Strings	Rams Head On Stage, Annapolis
26 Dec 2025	DJ VER1TAS at Charthouse Prime Restaurant Annapolis	Charthouse Restaurant Annapolis
26 Dec 2025	LIVE MUSIC with Timmie Metz Band	Blackwall Hitch - Annapolis
26 Dec 2025	Live Music with Guava Jelly	Rams Head Roadhouse, Annapolis
27 Dec 2025	CC Military Bowl 2025	Navy-Marine Corps Memorial Stadium, Annapolis
27 Dec 2025	1227 - ilyAIMY Dark Horse Annapolis (full band)	Dark Horse Annapolis
27 Dec 2025	Sinners at 49 West	49 West Coffeehouse, Winebar & Gallery, Annapolis
26 Dec 2025	Blackwall Hitch Annapolis	Blackwall Hitch Annapolis

Date

Event

Venue

26 Dec 2025

Jimmies Chicken Shack Holidaze Show

Rams Head On Stage, Annapolis

23 Dec 2025

Tides & Tunes

The Westin Annapolis

28 Dec 2025

Pressing Strings

Rams Head On Stage, Annapolis

26 Dec 2025

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis

26 Dec 2025

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis

26 Dec 2025

Live Music with Guava Jelly

Rams Head Roadhouse, Annapolis

27 Dec 2025

CC Military Bowl 2025

Navy-Marine Corps Memorial Stadium, Annapolis

27 Dec 2025

1227 - ilyAIMY Dark Horse Annapolis (full band)

Dark Horse Annapolis

27 Dec 2025

Sinners at 49 West

49 West Coffeehouse, Winebar & Gallery, Annapolis

26 Dec 2025

Blackwall Hitch Annapolis

Blackwall Hitch Annapolis

Frequently Asked Questions

Which Music events can I attend in Annapolis today?

Here are the best Music events happening in Annapolis today:

Siren's Call is happening on 26 Dec 2025 from 5:00 PM onwards at The Westin Annapolis
Jimmie's Chicken Shack Holidaze Show is happening on 26 Dec 2025 from 8:00 PM onwards at Rams Head On Stage, Annapolis
2nd Generation @ Dark Horse! is happening on 26 Dec 2025 from 8:00 PM onwards at 985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States
LIVE MUSIC with Timmie Metz Band is happening on 26 Dec 2025 from 9:00 PM onwards at Blackwall Hitch - Annapolis
Live Music with Guava Jelly is happening on 26 Dec 2025 from 8:00 PM onwards at Rams Head Roadhouse, Annapolis
Blackwall Hitch Annapolis is happening on 26 Dec 2025 from 9:00 PM onwards at Blackwall Hitch Annapolis

Which Music events can I attend in Annapolis this weekend?

Here are the best Music events happening in Annapolis this weekend:

Pressing Strings is happening on Sun 28 Dec 2025 from 8:00 PM onwards at Rams Head On Stage, Annapolis
CC @ Military Bowl 2025 is happening on Sat 27 Dec 2025 from 8:15 AM onwards at Navy-Marine Corps Memorial Stadium, Annapolis
12/27 - ilyAIMY @ Dark Horse Annapolis (full band!) is happening on Sat 27 Dec 2025 from 9:00 PM onwards at Dark Horse Annapolis
Sinners at 49 West is happening on Sat 27 Dec 2025 from 7:00 PM onwards at 49 West Coffeehouse, Winebar & Gallery, Annapolis

What are the trending Music events in Annapolis?

Here are the trending Music events in Annapolis:

Siren's Call is happening on Fri 26 Dec 2025 from 5:00 PM onwards at The Westin Annapolis
Jimmie's Chicken Shack Holidaze Show is happening on Fri 26 Dec 2025 from 8:00 PM onwards at Rams Head On Stage, Annapolis
Pressing Strings is happening on Sun 28 Dec 2025 from 8:00 PM onwards at Rams Head On Stage, Annapolis
2nd Generation @ Dark Horse! is happening on Fri 26 Dec 2025 from 8:00 PM onwards at 985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States
🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷 is happening on Wed 24 Dec 2025 from 6:30 PM onwards at 7 Church Cir, Annapolis, MD, United States, Maryland 21401
Slugs & Special Guests - New Year’s Eve at Dark Horse! is happening on Wed 31 Dec 2025 from 9:00 PM onwards at Dark Horse Annapolis