Best Entertainment events in Annapolis This Weekend | December 27 - 28

Q: What are the upcoming Entertainment events in Annapolis?

Here are the upcoming events in Annapolis: Jimmie's Chicken Shack Holidaze Show, Military Bowl, 2nd Generation @ Dark Horse!, 12/27 - ilyAIMY @ Dark Horse Annapolis (full band!), Sinners at 49 West , Blackwall Hitch Annapolis

Q: Which kind of events are trending in Annapolis?

Here are the top trending events in AnnapolisFestivals, Live Music, Free Events, 🎄 Christmas , 🥂 New Year

Entertainment events in Annapolis this Weekend

Fri, 26 Dec, 2025 - 08:00 PM

Jimmie's Chicken Shack Holidaze Show

Rams Head On Stage

192+ Interested
Fri, 26 Dec, 2025 - 07:00 PM

Military Bowl

Navy Marine Corps Memorial Stadium
Fri, 26 Dec, 2025 - 08:00 PM

2nd Generation @ Dark Horse!

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

25+ Interested
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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Sat, 03 Jan Onwards

Brian Curry The Good Liar

Capital Hilton

81+ Interested

|

USD 50
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Sat, 03 Jan Onwards

Brian Curry The Good Liar 5 PM

Capital Hilton

55+ Interested

|

USD 50
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Fri, 06 Feb • 07:00 PM

Samay Raina "Still Alive" - Washington DC - 6th Feb, 2026

Cramton Auditorium

394+ Interested

|

USD 55
Wed, 31 Dec • 07:00 PM

BADAL SARI US TOUR 2025/26 SWAR Live in Virginia

The Michael & Son Sportsplex at Dulles

USD 25
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Fri, 26 Dec • 07:00 PM

Comedy Night in Manassas!

Aroma Wine Tasting Room

Newly Added

|

USD 13
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Wed, 31 Dec • 08:30 PM

New Year's Eve International Gala at the Omni Shoreham Hotel

Omni Shoreham Hotel

8+ Interested

|

USD 109
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Wed, 31 Dec • 10:00 PM

D.C. BollyWood NYE 2026 @Wilson Hardware

Darna

20+ Interested

|

USD 30
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Sat, 28 Feb • 09:00 PM

THE LUXE GRAND FINALE

Guilford Hall Brewery

Newly Added

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USD 20
Sat, 17 Jan • 06:30 PM

Limousine Adventure and Race: THE 20th CENTURY COLD WAR RETURNS

Rosslyn

Newly Added

|

USD 74

Frequently Asked Questions

Which Entertainment events can I attend in Annapolis today?

Here are the best Entertainment events happening in Annapolis today:

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
Blackwall Hitch Annapolis is happening on 26 Dec 2025 from 9:00 PM onwards at Blackwall Hitch Annapolis

What are the upcoming Entertainment events in Annapolis?

Here are the upcoming Entertainment events in 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
Military Bowl is happening on Fri 26 Dec 2025 from 7:00 PM onwards at Navy Marine Corps Memorial Stadium, 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
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
Blackwall Hitch Annapolis is happening on Fri 26 Dec 2025 from 9:00 PM onwards at Blackwall Hitch Annapolis

Which kind of events are trending in Annapolis?