Annapolis Holiday Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Nutcracker Tea 2025

DoubleTree by Hilton Hotel Annapolis 7 Dec 2025

Annapolis Chocolate Binge Festival

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

Annapolis Holiday of Lights Boat Parade

680 Americana Dr 13 Dec 2025

FRI 11/28/25: Black Friday MIDNIGHT MADNESS + ALL DAY DEALS At Third Eye!

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 28 Nov 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

Annapolis Holiday Boat Parade

110 Compromise St, Annapolis, MD 21401-1828, United States 13 Dec 2025

Annapolis Holiday Market 2025

St. John's College 13 Dec 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Holiday Virtual Charity Wine Dinner

36 West St, Annapolis, MD, United States, Maryland 21401 14 Dec 2025

Grand Illumination Tree Lighting - Downtown Annapolis 2025

Market Space, Annapolis, MD 21401, United States 30 Nov 2025

Jon McLaughlin & Friends: Home For The Holidays

Rams Head On Stage 21 Dec 2025

Laura Tsaggaris (Matinee)

Rams Head On Stage 6 Dec 2025

Broadneck Class of 2015

Metropolitan Kitchen & Lounge 29 Nov 2025

Eric Scott's Annual Holiday Celebration with very Special Guest Tony Denikos

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

SOD-O Holiday Party

Acqua al 2 - Annapolis 6 Dec 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

A SQRRL! Holiday (Matinee)

Rams Head On Stage 20 Dec 2025

2025 FRA 24 Holiday Party

Fleet Reserve Club Of Annapolis 6 Dec 2025

Full Moon Celebration - December

Unitarian Universalist Church of Annapolis 5 Dec 2025

Midnight Madness West Street Artisan Holiday Market

60 West St, Annapolis, MD 21401-2434, United States 11 Dec 2025

WTF? & Old Fox Bibliophiles Book Clubs

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 3 Dec 2025

Brunch with the Grinch at CPK!

2002 Annapolis Mall Rd,, Annapolis, MD 21401 7 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Midnight Madness: Author Signing & Irish Music

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 11 Dec 2025

A Colonial Yuletide

186 Prince George St, Annapolis, MD 21401-1724, United States 6 Dec 2025

Annapolis Italian Christmas Market 2025

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

2025 Santa Speedo Run

O'Brien's Oyster Bar & Seafood Tavern 13 Dec 2025

Live Arts Maryland Presents Handel's Messiah

St. Anne's Parish 21 Dec 2025

An Evening of Holiday Radiance

127 Lubrano Dr 3 Dec 2025

Peter Mayer: A Stars and Promises Christmas 2025

Rams Head On Stage 11 Dec 2025

The DeCesaris/Prout Jingle Bell Run/Walk

Quiet Waters Park Annapolis, Md 6 Dec 2025

Midnight Madness in Downtown Annapolis 2025

Downtown Annapolis 4 Dec 2025

Bay Winds Band - 2025 Holiday Concert

St. Martin's Lutheran School of Annapolis 7 Dec 2025

Bay Winds Band Holiday Winter Concert

Unity by the Bay (Maryland) 16 Dec 2025

2025 Bike Doctor Holiday Lights Ride

Safe Harbor Podickory Point 7 Dec 2025

Midnight Madness

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 18 Dec 2025

Lights Parade Dinner Cruise with Ken's Creative Kitchen

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

Storytime with the Grinch

Discoveries: The Library at the Mall - Anne Arundel County Public Library 7 Dec 2025

5th Annapolis Santa Stroll from Peake Social!

Annapolis 6 Dec 2025

East of Maui Santa Paddle

Horn Point Street End Park 13 Dec 2025

Vintage Vibe Finds private holiday shopping experience

40 Hudson St unit 107 14 Dec 2025

Annual Kwanzaa Celebration

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

A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)

Rams Head On Stage 4 Dec 2025

Midnight Madness: Author Signing & Santa Photos

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 4 Dec 2025

Hanging of the Greens

Stan and Joe's Saloon 6 Dec 2025

WED 11/26/25: Third Eye Holiday Homecoming / Games Giving Food Drive

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 26 Nov 2025

🎁 11th Hour Holiday Shopping at The Spice & Tea Exchange of Annapolis! 🎁

The Spice & Tea Exchange of Annapolis 18 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

Black Friday & Small Business Saturday @ The Spice & Tea Exchange of Annapolis

The Spice & Tea Exchange of Annapolis 28 Nov 2025

Bubbles & Baubles

Wrabyn Boutique 3 Dec 2025

Annual Boxwood Wreath Making

Charles Carroll House 7 Dec 2025

Grounding in Grace: A Cacao Ceremony with Sound Therapy

Quiet Waters Park 14 Dec 2025

Anniversay Chocolate & Wine pairing

36 West St, Annapolis, MD, United States, Maryland 21401 7 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 21 Dec 2025

Holiday Tasting Event

1410 Forest Dr, Annapolis, MD, United States, Maryland 21403 6 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

Members Only Holiday Party at Maggiano’s

Maggiano's 2 Dec 2025

Songs of the Season - a holiday concert and sing-along

Eastport United Methodist Church 14 Dec 2025

Thanksgiving - Closed

155 Main St, Annapolis, MD 21401 27 Nov 2025

🎄 MIDNIGHT MADNESS at The Spice & Tea Exchange of Annapolis! 🎄

The Spice & Tea Exchange of Annapolis 4 Dec 2025

4th Annual Peake Irish Experience for Annapolis St Patrick's Day on 3/7

Main Street 7 Mar 2026

Bay Winds Band - Unity by the Bay Holiday Concert

Unity by the Bay (Maryland) 16 Dec 2025

🎄 MIDNIGHT MADNESS at The Spice & Tea Exchange of Annapolis! 🎄

The Spice & Tea Exchange of Annapolis 11 Dec 2025

Run Naptown Running Festival

Navy-Marine Corps Stadium 20 Dec 2025

ANNAPOLIS HOLIDAY MARKET w/ SANTA & The Wish Crackler - St. John's College - Annapolis, Maryland

St. John's College 13 Dec 2025

Christmas - closed

155 Main St, Annapolis, MD 21401 25 Dec 2025

The Gather & Give Holiday Market: A Hallmark-Inspired Holiday Fundraiser for Life of Joy Foundation

201A Ridgely Ave , Annapolis, MD, United States, Maryland 21401 13 Dec 2025

Myra Copus - Holiday Open House

608 Forest Hill Dr, Annapolis, MD 21403-3819, United States 29 Nov 2025

10th Annual Brigade Holiday Market

Dahlgren Hall - United States Naval Academy 9 Dec 2025

Spin It Again at NABSD 10th Annual Brigade Holiday Market

Dahlgren Hall - United States Naval Academy 9 Dec 2025

A SQRRL! Family Holiday Show

Rams Head On Stage - Annapolis 20 Dec 2025

Santa Run & Toy Drive

Hunt Meadow Pool 14 Dec 2025

ANNAPOLIS HOLIDAY MARKET w/ SANTA & The Wish Crackler - St. John's College - Annapolis, Maryland

St. John's College 18 Dec 2025

Maryland Day Week 2026 - filled with fun events!

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

Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions

Maryland Hall 17 Oct 2025

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

Sandy Point State Park 23 Nov 2025

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

Maryland Hall 10 Dec 2025