There are so many Holiday Festivities in Annapolis and the surrounding area to choose from.
Macaroni KID Annapolis is here to save you time in the search to find family fun happening between November 15, 2023 and January 1, 2024. Use the list below to find festivities that your family will enjoy. Check back often because new events will be added as we hear about them.
The events are sorted by date. Click on event names to be taken to the webpage or social media page for specific details. Many events require tickets or pre-registration so check each event listing carefully.
Below the dated list, you will find events that are on-going such as Light Displays, Santa Visits, and a few others
HAVE FUN!
If you know of an event we missed, send us an email.
NOVEMBER - HOLIDAY FESTIVITIES |
November 17 - Friday
November 18 - Saturday
November 20 - Monday
November 23 - Thursday
November 24 - Friday
November 25 - Saturday
November 26 - Sunday
November 27 - Monday
November 28 - Tuesday
- Giving Tuesday: Donate money to your favorite non-profit organizations and make a difference in our community.
November 29 - Wednesday
November 30 - Thursday
December - Holiday Festivities |
December 1 - Friday
December 2 - Saturday
- Lights of Kindness: Homestead Gardens, Davidsonville, 9am - 6pm
- Colonial Yuletide: William Paca House, Annapolis, 2-6pm
- Special Historic Holiday Tour: Hammond-Harwood House, 3-5pm
- West Annapolis Holiday Market
- Vintage Christmas Market: Wildberry Farm, Crownsville, 2-6pm
- Holiday Show: by Muddy Creek Artist Guild, Edgewater, 10am-7pm
- Breakfast with Santa: Woodland Beach VFD, Edgewater 9am - Noon
- Quaker Holiday Market: Annapolis Friends Meeting, 9am - 2pm
- St. Anne's School Holiday Bazaar: Annapolis, 2-5pm
- Handel's Messiah: USNA Chapel, Annapolis, 7pm
- DFC's Holiday Cabaret With Santa: Children's Theater of Annapolis, 2-5pm
- Jingle Bell 5K Run/1M Walk: Quiet Waters Park, benefits the DeCesaris/Prout Cancer Foundation
- Sugar Plum Tea: by National Ballet Company at Captain Avery Museum, Shady Side, 1pm
- Wreath Workshop: Historic London Town and Gardens, Edgewater, ages 12+, 2 sessions
- Special Historic Holiday Tour: by Watermark Tours, Saturdays Nov 25 through December 30
- Winter Wonderland: Festival at Riva Shopping Center, Annapolis, 1-3pm
- Stories and Art in the Galleries "Blizzard": Chesapeake Arts Center, Brooklyn Park, 10-10:45am
December 3 - Sunday
- Lights of Kindness: Homestead Gardens, Davidsonville, 9am - 6pm
- Chocolate Binge Festival: Inner West Street, 11am-4pm
- Handel's Messiah: USNA Chapel, Annapolis, 3pm
- Italian Christmas Market: Annapolis, 10am - 4pm
- Nutcracker Tea: Graduate Annapolis Hotel, 10am, 2pm
- A Cantori Christmas: Live Arts Studio, Annapolis, 3-4:15
- Holiday Craft Fair: South River High School, Edgewater, 9am-4pm
- Nutcracker Storytime and Preview: Discoveries: Te Library at the Mall, Annapolis, 2-3pm
- Sugar Plum Tea: by National Ballet Company at Captain Avery Museum, Shady Side, 1pm
- A Peter White Christmas - 20th Anniversary (Featuring Mindi Abair and Vincent Ingala): Rams Head on Stage, Annapolis - all ages show
December 4 - Monday
December 5 - Tuesday
December 6 - Wednesday
December 7 - Thursday
December 8 - Friday
December 9 - Saturday
- Holiday Jazz Fest: "Pip" Moyer Rec Center, Annapolis, 2-6pm
- Eastport Yacht Club Lights Parade: Annapolis Harbor area along Spa Creek, 6-8pm
- Mrs. Claus Book Club and Cookies: Annapolis Town Center
- Holiday Spirit Tour: Yuletide Traditions at the William Paca House, Annapolis, 11am-Noon
- A Colonial Christmas: Hammond-Harwood House, family friendly, 10:30am - 12:30pm
- Maryland Government House Open House: Annapolis, 10am - 1pm
- Annapolis Holiday Market: Downtown Annapolis, 11am-9pm
- The Nutcracker: by the Ballet Theatre of Maryland, Maryland Hall, Annapolis, 7pm
- The Nutcracker: by the Chesapeake Ballet Company at the Children's Theater of Annapolis, 1pm and 4pm
- Vintage Christmas Market: Wildberry Farm, Crownsville, 2-6pm
- 47th Annual Christmas Bazaar: Deale VFD, 9am - 2pm
- Kwanzaa Celebration: Banneker-Douglas Museum, 11am - 3pm
- Special Historic Holiday Tour: by Watermark Tours, Saturdays Nov 25 through December 30
- Santa on the Trail: B and A Trail, (see website for times and locations along the trail) 10am - 3pm
- TubaChristmas Annapolis: St. Anne's Episcopal Church in downtown Annapolis, 3-4pm
- Merry Grinchmas: Main Street at South River Colony, Edgewater, 11am-2pm
- Process Art - Winter: Eastport-Annapolis Neck Library, 10:30-11:30am
- Free Family Makerspace - Snowflake Stamped Clay Bowls: Chesapeake Arts Center, Brooklyn Park, 2 sessions 10:30am and 11:30am
- How the Grinch Stole Christmas in Concert: Baltimore Symphony Orchestra at Joseph Meyerhoff Symphony Hall, Baltimore, Dec 7-9
December 10 - Sunday
- Parade of Light, Annapolis, Parade starts at Safeway on Housley Rd at 5pm and ends at City Dock around 5:45pm, followed by Menorah Lighting
- Menorah Lighting, City Dock, Annapolis, 5:45pm
- Annapolis Holiday Market: Downtown Annapolis, 11am-5pm
- Tuscan Prime Brunch with Santa: Annapolis Town Center
- Annapolis Fire Santa Run: throughout Annapolis
- The Nutcracker: by the Ballet Theatre of Maryland, Maryland Hall, Annapolis, 1pm and 4:30pm
- The Nutcracker: by the Chesapeake Ballet Company at the Children's Theater of Annapolis, 1pm and 4pm
- Nutcracker Tea: Graduate Annapolis Hotel, 10am
- Honey's Holiday Market: Honey's Harvest Farm, Lothian, 11am-3pm
- Gift Making Workshop: Chesapeake Children's Museum, 1-3pm
- The Chesapeake Arts Center and the 229th Maryland Army National Guard Band Presents "The Adjutant's Own" Holiday Concert: Chesapeake Arts Center, Brooklyn Park, 3-4:30pm
- Jolly Express Cruise: City Dock Annapolis, 45-minute cruises on Spa Creek between 3-7pm
December 11 - Monday
December 12 - Tuesday
December 13 - Wednesday
December 14 - Thursday
- Midnight Madness: Downtown Annapolis, 4pm-Midnight
- City of Annapolis Holiday Open House: City Hall, Annapolis, 4-6pm
- West Street Artisan Market: Inner West Street, Annapolis, 5-9pm
- Family Movie Night - Home Alone 2, Lost in New York: Deale Library, Deale 6-8pm
- State Ballet Theatre of Ukraine Presents The Nutcracker: The Modell Lyric, Baltimore
- 2023 Gospel Holiday: Worship Live!: Joseph Meyerhoff Symphony Hall, Baltimore, 7pm
December 15 - Friday
- Storytime with Mrs. Claus: Homestead Gardens, Severna Park, 2-4pm
- Holiday Spirit Tour: Yuletide Traditions at the William Paca House, Annapolis, 4-5pm
- Season of Joy: by The Talent Machine Company, at Indian Creek School, Crownsville, 7pm
- The Nutcracker: by the Chesapeake Ballet Company at the Children's Theater of Annapolis, 7pm
- ASO Holiday Pops: by Annapolis Symphony Orchestra at Maryland Hall, 7:30p
- Handel's Messiah: Live Arts Maryland's annual performance, St. Anne's Church, Annapolis, 8-9:30pm, Dec 15-17
- Winter Wonderland Sensory Play: Deale Library, Deale, 10:30-11:30
- Living Nativity: Heritage Baptist Church, Annapolis 6:30-8pm
- A Charlie Brown Christmas Live: The Modell Lyric, Baltimore, 7:30pm
- Baroque Christmas: by the Baltimore Symphony Orchestra (BSO), Joseph Meyerhoff Symphony Hall, Baltimore, 7:30pm
- Mariah Carey - Merry Christmas One and All: CFG Bank Arena, Baltimore
December 16 - Saturday
- Storytime with Mrs. Claus: Homestead Gardens, Davidsonville, 10am-noon
- Holiday Spirit Tour: Yuletide Traditions at the William Paca House, Annapolis, 4-5pm
- Mr. Paca's Garden Storytime: Winter Holidays Around the World, 10-11am
- Season of Joy: by The Talent Machine Company, at Indian Creek School, Crownsville, 2pm and 7pm
- Handel's Messiah: Live Arts Maryland's annual performance, St. Anne's Church, Annapolis, 8-9:30pm, Dec 15-17
- The Nutcracker: by the Ballet Theatre of Maryland, Maryland Hall, Annapolis, 7pm
- The Nutcracker: by the Chesapeake Ballet Company at the Children's Theater of Annapolis, 1pm and 4pm
- Everyone Eats Cookbook Club 5th Annual Cookie Exchange: Busch Annapolis Library, 12:30-1:30pm
- Snowy Day Crafts: Eastport-Annapolis Neck Library, 2-3pm
- Flicks with Sticks: Miracle on 34th Street: Busch Annapolis Library, knitting and a movie, ages 11+, 2-4:30pm
- Kids Crafternoon - Holiday Cards and Gifts: Discoveries: The Library at the Mall, Annapolis, 2-3pm
- Wreaths Across America, Annapolis National Cemetery: Annapolis, noon
- Wreaths Across America, Crownsville Veterans' Cemetery: Crownsville, noon
- Santa Paws: at the American K9 Dog Ranch, Davidsonville, 9am-1pm
- Special Historic Holiday Tour: by Watermark Tours, Saturdays Nov 25 through December 30
- Naptown Half Marathon and 10K/5K, Annapolis
- Cirque Nutcracker: Joseph Meyerhoff Symphony Hall, Baltimore, Dec 16 at 7:30pm and Dec 17 at 3pm
- SoCo Farmers Holiday Market: Deale Library, December 16, 10am-2pm
- The MD Theatre Collective Presents Home for the Holidays: A Cabaret: Chesapeake Arts Center, Brooklyn Park, 7-8:30pm
December 17 - Sunday
- Season of Joy: by The Talent Machine Company, at Indian Creek School, Crownsville, 2pm and 6:30pm
- The Nutcracker: by the Ballet Theatre of Maryland, Maryland Hall, Annapolis, 1pm and 4:30pm
- The Nutcracker: by the Chesapeake Ballet Company at the Children's Theater of Annapolis, 1pm
- Handel's Messiah: Live Arts Maryland's annual performance, St. Anne's Church, Annapolis, 3-4:30pm, Dec 15-17
- Santa Paws: at the American K9 Dog Ranch, Davidsonville, 9am-1pm
- Trio Galilei Winter Solstice / Christmas Concert: The Barn House, 1730 Crownsville Road, Annapolis, 3pm
- Winter Solstice Celebration: Odenton Library, 11am-noon
- Cirque Nutcracker: Joseph Meyerhoff Symphony Hall, Baltimore, Dec 16 at 7:30pm and Dec 17 at 3pm
- STEAM Sunday, Winter Wonderland: Chesapeake Arts Center, Brooklyn Park, 10:30am - 12:30pm
- Maryland Concert Series Presents Home for the Holidays! - Anne Arundel Community College Holiday Show: Chesapeake Arts Center, Brooklyn Park, 3-5pm
December 18 - Monday
- Holiday Spirit Tour: Yuletide Traditions at the William Paca House, Annapolis, 11am-Noon
- Festival of Lights Menorah Car Parade and Lighting: Parade, 5:30pm; Menorah Lighting 6-7pm, near Market House, Downtown Annapolis
- Trio Galilei Winter Solstice / Christmas Concert: The Barn House, 1730 Crownsville Road, Annapolis, 3pm
- Winter Solstice and Other Holidays Storytime: Busch Annapolis Library, 10:30-11:30am
- Time Tours: Winter Solstice Traditions: Discoveries: The Library at the Mall, 4-7pm
- Movies at the Library: The Nightmare Before Christmas: Severna Park Library, 6:30-8pm
December 19 - Tuesday
December 20 - Wednesday
- Season of Joy: by The Talent Machine Company, at Indian Creek School, Crownsville, 7pm
December 21 - Thursday
December 22 - Friday
December 23 - Saturday
December 24 - Sunday
December 25 - Monday
December 26 - Tuesday
December 27 - Wednesday
December 28 - Thursday
December 29 - Friday
December 30 - Saturday
December 31 - Sunday
January 1, 2024 - Monday
OTHER EVENTS with MULTIPLE DATES |
- Holly-Days: The Maryland Zoo, Baltimore, four weekends of holiday events, storytimes, crafts, photo ops, Hanukkah traditions, Elf on the Shelf scavenger hunts and, of course, the Zoo’s beloved animals.
- The Polar Express Train Ride: B and O Railroad Museum, Baltimore
- Christmas Village in Baltimore: West Shore Park at Baltimore's Inner Harbor, Dec 18-24, Noon to 8pm
- ICE! Christmas at Gaylord: Gaylord Harbor Resort, National Harbor, Maryland, Nov 21 - Dec 31
- Holiday Candlelight Stroll: Downtown Annapolis, starts Nov. 24
- Ice Skating at Quiet Waters Park
- Miracle on 34th Street: Toby’s Dinner Theatre, Columbia, Nov 10 - Jan 7
- Gingerbread House Making: Annapolis Town Center, Dec 2-16
- White Christmas: Classic Theatre of Maryland, Annapolis, weekends Nov 24 through Dec 24
- A Christmas Carol: Classic Theatre of Maryland, Annapolis, select dates Nov 30 through Dec 24
- Jolly Express Cruise: by Watermark, Annapolis City Dock, 45 min tours between 3-7:45pm, select dates between Nov 24 and Dec 31
- Holiday Decor at the Hammond-Harwood House: Annapolis, throughout December, see website for exact dates and times.
- Holiday Candlelight Stroll: by Watermark, Meets at Annapolis Market House, 7-8:30pm, select dates between Nov 24 and Dec 30
- Season of Joy: by The Talent Machine Company, at Indian Creek School, Crownsville, Dec 15-17 and Dec 20-23
- A Christmas Carol: Ford's Theatre, DC, for ages 5+, runs Nov 17-Dec 31
- Maryland State House Holiday Trees: Maryland State House, everyday (except Christmas Day and New Years Day) 8:30-5 Display of decorated holiday trees from all Maryland Counties and Baltimore City.
- Nightly Tree Light Show: National Harbor, Fort Washington, MD, daily, runs every half hour from sunset to 9pm
LIGHT DISPLAYS |
- Christmas Lights of MD: Facebook page listing addresses of decorated homes you will want to see
- Lights on the Bay: Sandy Point Park, Annapolis, Nov. 19 - Jan.1
- Fair Family Christmas: Anne Arundel County Fairgrounds, Crownsville, Nov 25-26, Dec 1-3, Dec 8-10
- Festival of Lights: Watkins Regional Park, Upper Marlboro, Nov 24 - Jan 1
- Symphony of Lights Drive Through Display: Merriweather Post Pavilion, Columbia, Nov. 23 - Jan. 1
- Enchant Christmas: Nationals Park, DC, Nov. 24 - Jan. 1
- Garden in Lights: Annmarie Garden, Solomons, Nov. 24 - Jan. 1
- North Pole Lights Walk: Willow Oak Flower and Herb Farm, select dates Nov. 24 - Dec 30
SANTA VISITS AND TRACKING |
- Annapolis Town Center: Santa's Cottage - Photos with Santa, special dates/times for pets, visits with Mrs. Claus, and sensory friendly visits with Santa. Nov 18 to Dec 23
- Westfield Annapolis Mall: Santapolis: A Magical Holiday Experience - Photos with Santa, special dates/times for pets. Nov 10 to Dec 24.
- Homestead Gardens: Davidsonville - Photos with Santa, No walk-ins, Nov. 26-Dec. 18 (weekends only), Santa Paws for pets on Dec. 1
- Google Santa Tracker: Online 24/7 - Explore, play, and learn with Santa's elves all December long.
- Norad Tracks Santa - Track Santa on Christmas Eve as he travels around the world.
- Shady Side Community Center, 5444 Muddy Creek Rd., 410-867-2599, benefits community events, Scout Troop 853, and local non-profit organizations
PARKING and GETTING AROUND ANNAPOLIS |
- Free Parking: The City of Annapolis offers free parking between Thanksgiving and New Year's Eve.
- Two hours of free parking at metered and kiosk spaces.
- One hour of free parking at Hillman Garage.
- You must use the ParkMobile app or website and enter code ParkDTA
- Garage parking:
- Circular Trolley: free shuttle between the downtown business district and four downtown parking garages. The Circulator runs on a 20-minute interval. Times: Monday through Saturday - 7:30am to 11pm and Sunday - 8am to 8pm.
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