Holiday events in Annapolis

Check out happening holiday events all around Annapolis, MD

Atlanta Rhythm Section in Annapolis

 Sat, 06 Dec at 08:00 pm Rams Head On Stage

Pure Prairie League in Annapolis

 Fri, 05 Dec at 08:00 pm Rams Head On Stage

Summer Sidewalk Sale 2025

 Sat, 16 Aug at 10:00 am 2512 A Solomons Island Road Annapolis, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 14 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

2nd Annapolis Wine and Dine

 Sat, 16 Aug at 01:00 pm Susan Campbell Park USD 29 to 45

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 02 Nov at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 28 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 24 Aug at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 12 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Annapolis Fall Italian Festa

 Sun, 21 Sep at 10:00 am 620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401

Autism-Friendly "Drive-In" Movie Matinee – Proud Moments ABA Annapolis

 Sat, 16 Aug at 11:00 am 900 Commerce Rd Free

Pops in the Park - Quiet Waters Park

 Sun, 31 Aug at 05:30 pm Quiet Waters Park Rd, Annapolis, MD 21403, United States

Eastport Yacht Club Lights Parade

 Sat, 13 Dec at 06:00 pm Historic Downtown Annapolis

Fin Del Verano 2025

 Sun, 31 Aug at 04:00 pm Watermark Tours, Charters, Cruises- Annapolis City Dock USD 151

SAT 9/20/25: BATMAN DAY 2025 AT THIRD EYE

 Sat, 20 Sep at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Rombauer Wine Dinner - Chart House Prime

 Thu, 18 Sep at 07:00 pm Chart House USD 159

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

NJPC Feed the Mids!! Navy vs VMI

 Sat, 30 Aug at 07:00 am Navy–Marine Corps Memorial Stadium

Broadneck Class of 2015

 Sat, 29 Nov at 07:00 pm Metropolitan Kitchen & Lounge USD 66

Ballet Theatre of Maryland presents "The Nutcracker"

 Sat, 20 Dec at 07:00 pm Maryland Hall USD 47 to 72

Jimmie's Chicken Shack HOLIDAZE show at Rams Head On Stage

 Fri, 26 Dec at 07:00 pm Rams Head On Stage

Barktoberfest Annapolis 2025

 Sat, 04 Oct at 11:30 am 1906 Towne Centre Blvd USD 0 to 13

The Brit Pack at Rams Head On Stage

 Sat, 22 Nov Rams Head On Stage

Jon McLaughlin and Friends: Home For The Holidays

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Holiday Parenting: Navigating Challenges with Calm & Connection

 Thu, 13 Nov at 06:00 pm 2158 Renard Ct Free

A Peter White Christmas w/ Mindi Abair & Vincent Ingala (9:30 PM)

Thu, 04 Dec at 09:30 pm Rams Head On Stage

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 14 Dec at 01:00 pm Maryland Hall USD 17 to 72

Evergreen Wreath Workshop

 Tue, 02 Dec at 07:00 pm 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

Speaker: The How of WOW!!! by Karl Gercens, Longwood Gardens Conservatory Manager

 Tue, 04 Nov at 07:00 pm 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

Nutcracker Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland

 Mon, 20 Oct at 01:00 pm 186 Prince George St, Annapolis, MD 21401-1724, United States

Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions

 Fri, 17 Oct at 07:30 pm Maryland Hall USD 120 to 192

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

 Wed, 10 Dec at 09:30 am Maryland Hall USD 12