Twinkling lights, magical events, and wintery wonderlands - Annapolis is a great place to enjoy time with family while soaking in the holiday spirit. Consistently ranked one of the best cities in America to visit during the holiday season, there are a handful of events for everyone to enjoy. Check out this must-see list of holiday events in Annapolis & Anne Arundel County.

Holiday Season

Lights on the Bay

November 17 through January 1 Don’t miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 70 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit SPCA of Anne Arundel County. 5:00 p.m. to 10:00 p.m. nightly, weather permitting.

American Indian Heritage Day

November 23 The Cedarville Band of Piscataway Indians returns to London Town for its annual celebration of native peoples in Maryland. Join in a dance, talk with an elder, and enjoy the state holiday alongside the Piscataway. 10:00 a.m. to 4:30 p.m.

Grand Illumination – Annapolis Tree Lighting

Holiday Season

November 25 With support from the Annapolis business community, the Annapolis Jaycees (Junior Chamber of Commerce) host the Lighting of the Tree in Annapolis during the City’s Grand Illumination event. Watch Santa arrive in town and enjoy singing and dance performances by area youth. The Jaycees provide refreshments and ornaments children can use to decorate the tree. Attendees are invited to bring nonperishable food items and new, unwrapped toys for the Jaycees’ annual Angel Tree Project. 5:00 p.m. to 7:15 p.m.

State House by Candlelight

December 1 Enjoy this annual open house featuring performances by young musicians and vocalists from throughout Maryland. The oldest State House in continuous legislative use in the nation will be adorned with 24 Christmas trees representing every Maryland county and Baltimore City. Photo identification is required for individuals age 16 and older. 5:00 p.m. to 9:00 p.m.

72nd Annual U.S. Naval Academy’s Handel’s Messiah Concerts

December 1 – 2 A long-standing Naval Academy tradition, the U.S. Naval Academy Men’s and Women’s Glee Clubs join the Annapolis Symphony Orchestra and soloists from the Metropolitan Opera Company to present selections from Handel’s beloved Messiah. Conducted by Dr. Aaron Smith, USNA Director of Musical Activities, the elegant concert has been broadcast on public television stations regionally and nationwide. Saturday, 7:00 p.m.; Sunday, 3:00 p.m.

Holiday Candlelight Stroll

December 1, 7, 14-15, 21-22 Stroll through Annapolis alongside a festively attired colonial guide and learn about holiday traditions. Includes tour inside the historic Hammond-Harwood House for additional seasonal spirit. 7:00 p.m. to 8:30 p.m.

Jolly Express Cruises

Holiday Season

Fridays-Sundays, December 1 – 31 (except Saturday, December 8) Take a holiday-inspired “sleigh ride” cruise aboard Watermark’s Miss Anne, adorned with reindeer spirit. 6:00 p.m., 7:00 p.m. and 8:00 p.m.

4th Annual Chocolate Binge Festival

Holiday Season

December 2 Are you a chocoholic in need of a fix? You won’t want to miss the 4th Annual Chocolate Binge Festival! More than 35 chocolate vendors will be selling chocolate specialties, including: chocolate caramels, cakes, bars, truffles, fudge, cookies, candies, hot chocolate and more. Enjoy live music, roasting s'mores with the Fire Department, a gingerbread house moon bounce, Cocoa with the PoPo, a holiday market, the lighting of the Holiday Lights Canopy and a visit from Santa. Noon to 5:00 p.m.

Midnight Madness Holiday Shopping

December 6, 13 & 20 Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that’s open to all. Enjoy outside musical performances as well as food and refreshments at many stores as you stroll along Main Street, Maryland Avenue, West Street, State Circle and City Dock in search of that perfect gift. Sponsored by the Downtown Annapolis Partnership. December 6 and 13, 6:00 p.m. to midnight; December 20, 6:00 p.m. to 11:00 p.m.

Illuminated London Town

Fridays & Saturdays, December 7 – 22 Experience the magic of a winter evening at Illuminated London Town! Sip hot cider and roast s'mores beside roaring fires in the Historic Area. Explore the gardens illuminated with festive holiday lights. Discover colonial nighttime festivities and holidays at a candlelit William Brown House, decorated for the season. Enjoy special performances in the gardens each week. 6:00 p.m. to 9:00 p.m.

36th Annual Eastport Yacht Club Lights Parade

Holiday Season

December 8 More than 30 brightly lit boats bedecked for the holiday season parade around the Annapolis waterfront and Spa Creek. Themes including Santa Claus, Polar Bear Christmas, a Christmas Angel and the Abominable Snowman have delighted young and old in this traditional Annapolis holiday event. Thousands of lights and a host of jolly revelers make this a fun Christmas event for the entire family. Prime viewing areas include: Eastport, Spa Creek, City Dock and Naval Academy seawall. Sponsored by the Eastport Yacht Club. 6:00 p.m. to 8:00 p.m.

Holiday Open House

December 15 Celebrate a merry holiday with Declaration of Independence signer William and his wife Mary. Take a break from the busy holiday season and enjoy an afternoon of history and family-friendly activities. Visit with the Pacas and their friends in a home filled with laughter, games, music and sweet treats to share. Stroll down to Hogshead to continue the celebration with the middling sort, where more music, dancing and merriment is destined to put a holiday spring in your step. 3:00 p.m. to 6:00 p.m.

11th Annual Military Bowl

Holiday Season

December 31 The Military Bowl presented by Northrop Grumman, benefitting the USO of Metropolitan Washington-Baltimore (USO-Metro) will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC) in its 11th Anniversary game.

City of Annapolis New Year’s Eve Celebration

Holiday Season

December 31 Family activities fill the day, while music and dancing fill the night at this annual celebration welcoming the New Year. For the third year, kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Activities will include kids’ crafts, obstacle courses, moon bounces and music performed by kids’ rock bands. The afternoon festivities wrap up with on-site fireworks at approximately 5:15 p.m. Then it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks. Sponsored by City of Annapolis. 3:00 p.m. to 5:15 p.m.

For a more complete list of holiday events, visit the VAAAC website.

Holiday Event Parking 

Noah Hillman Parking Garage - 150 Gorman Street South Street Lot - South St. off of Church Circle Gotts Court Parking Garage - 25 Northwest Street Knighton Parking Garage - 1A Colonial Avenue Park Place - 1 Park Place


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