Upcoming Live Music Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025
ART

Richard Thompson in Annapolis

St. John's College - Francis Scott Key Auditorium 2 Nov 2025
ENTERTAINMENT

Najee in Annapolis

Rams Head On Stage 9 Nov 2025
CONCERTS

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Upcoming Food & Drinks Events

2025 Shore Party

Safe Harbor Annapolis 1 Nov 2025
PARTIES

2025 Hall & Friends Oyster Roast

Bay Ridge Marina 1 Nov 2025
MUSIC

Siren's Call

The Westin Annapolis 31 Oct 2025
MUSIC FREE

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Upcoming Halloween Events

Annapolis Halloween Rooftop Party : Haunted Heights

Metropolitan Kitchen & Lounge 31 Oct 2025
HALLOWEEN FREE

Witches of Maryland: a Storytelling Dinner

36 West St, Annapolis, MD, United States, Maryland 21401 31 Oct 2025
WORKSHOPS

Halloween Ghost Hunt in Annapolis

40 Francis St 30 Oct 2025
HALLOWEEN USD 13 TO 40

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Upcoming Festivals Events

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 2 Nov 2025
FESTIVALS

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 7 Dec 2025
MUSIC

The Great Annapolis Gingerbread Houses Contest

26 West St, Annapolis, MD 21401-2421, United States 22 Nov 2025
CONTESTS

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Upcoming Thanksgiving Events

Keb' Mo' in Annapolis

Maryland Hall 21 Nov 2025
CONCERTS

Masquerade…The Phantom of the Opera!

Annapolis Lodge #622, 2 Pythian Drive, Edgewater, MD 21401 22 Nov 2025
WORKSHOPS USD 0 TO 157

Mac Heat @ Blackwall Hitch Annapolis

Blackwall Hitch - Annapolis 21 Nov 2025

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Upcoming Comedy Events

Come Out and Play with Naleighna Kai and the Tribe

210 Holiday Ct 31 Oct 2025
ART USD 0 TO 109

Pete Correale at Rams Head On Stage

Rams Head On Stage 7 Nov 2025

Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon

Stan & Joe's Saloon 15 Nov 2025
COMEDY USD 23

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Upcoming Music Festivals Events

Sister Hazel (matinee)

Rams Head On Stage 15 Nov 2025
MUSIC

Pressing Strings

Rams Head On Stage 28 Dec 2025
MUSIC

Annual Kwanzaa Celebration

84 Franklin St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025
FESTIVALS

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Upcoming Parades Events

Lights Parade Dinner Cruise with Ken's Creative Kitchen

1 Dock St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025
ENTERTAINMENT

Eastport Yacht Club Lights Parade

Historic Downtown Annapolis 13 Dec 2025
PARADES

Maryland Day Week 2026 - filled with fun events!

Anne Arundel County, MD, United States, Maryland 19 Mar 2026

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Upcoming Christmas Markets & Fairs Events

Annapolis Italian Christmas Market 2025

620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 7 Dec 2025
CHRISTMAS

Holiday Craft Fair!

1601 Pleasant Plains Rd, Annapolis, MD, United States, Maryland 21409 22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

Midnight Madness in Downtown Annapolis 2025

Downtown Annapolis 4 Dec 2025
HOLIDAY

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Upcoming New Year Events

The Seldom Scene

Rams Head On Stage 29 Dec 2025
TRIPS-ADVENTURES

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

Dark Horse Annapolis 31 Dec 2025
NEW-YEAR

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Trending Events in Annapolis

Jonathan Butler at Rams Head On Stage

Rams Head On Stage 18 Apr 2026
CALENDAR

A2B Offshore Racing Safety Seminar

317 First Street , Annapolis, MD, United States, Maryland 21403 15 Nov 2025
SPORTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

Chris Isaak in Annapolis

Maryland Hall 7 Dec 2025
CONCERTS

Najee in Annapolis

Rams Head On Stage 9 Nov 2025
CONCERTS

Wishbone Ash: Wishlist Tour

Rams Head On Stage 8 Nov 2025
MUSIC

Nutcracker Tea 2025

DoubleTree by Hilton Hotel Annapolis 7 Dec 2025
ART

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 7 Nov 2025
ENTERTAINMENT

Me Time with Girl Scouts

Michael E. Busch Annapolis Library 10 Nov 2025
TRIPS-ADVENTURES FREE

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
ART

Crack the Sky

Rams Head On Stage 1 Nov 2025
MUSIC

Will Hoge Band w/ July Moon

Rams Head On Stage 16 Nov 2025
MUSIC

More things to do in Annapolis