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  • Jolly Express Cruise

    Annapolis City Dock Dock Street, Annapolis, MD

    Jolly Express Cruise Ho, Ho, Ho, and a Bottle of Rum! Well, maybe not the rum, but Santa returns to the shores of Annapolis with his Jolly Express Cruise! Grab […]

    $25

  • Holiday Spirit Tour: Yuletide Traditions at the William Paca House

    William Paca House Garden, 186 Prince George Street 186 Prince George Street, Annapolis, MD

    Celebrate the season and join our new holiday tour of the William Paca House! Bring family and friends to enjoy the elegant decorations, learn about 18th century Maryland holiday traditions, […]

    $2 – $17

  • Annmarie Garden in Lights

    Annmarie Sculpture Garden & Arts Center - 13480 Dowell Road P.O. Box 99 Solomons MD 20688 , United States

    Friday, November 25, 2022 - January 1, 2023, 5-9pm nightly Advance timed-entry tickets required for members & non-members! (Closed November 28 & 29 and December 5, 6, 24, 25) Dazzling […]

  • Lights on the Bay

    Sandy Point State Park 1100 East College Pkwy, Annapolis

    November 20 – January 2, 2023 Lights on the Bay Lights on the Bay is an annual holiday light show featuring a two-mile scenic drive along the shores of the […]

  • SMCM Symphony Orchestra & St. Mary’s College Jazz Band Holiday Concert

    Nancy R. & Norton T. Dodge Performing Arts Center 47855 College Dr, St. Mary's City

    SMCM Symphony Orchestra and St. Mary's College Jazz Band, under the direction of Jeff Silberschlag, will give a holiday-themed concert. The program will include a juxtaposition of Tchaikovsky's Nutcracker with […]

    Free

  • Classic Theatre of Maryland’s A Christmas Carol

    The Classic Theatre of Maryland 1802 West Street, Annapolis

    A CHRISTMAS CAROL December 2 – December 24, 2022 Charles Dickens’ story was created to inspire a spirit of charity toward those less fortunate. This Helen Hayes Awards–recommended original production […]

  • UCVFD Annual Breakfast With Santa

    United Communities Volunteer Fire Department 9604 Romancoke Road, Stevensville

    United Communities Volunteer Fire Department Annual Event - Come enjoy a delicious breakfast and get to meet and take pictures with Santa.

    $4 – $12

  • Quaker Holiday Market

    Annapolis Friends Meeting Hall 351 Dubois Rd., Annapolis, MD, United States

    Come eat, chat, & shop! Quaker Holiday Market                        Saturday, December 3rd, 2022                […]

    Free

  • Glen Burnie High School Winter Craft Fair

    Glen Burnie High School 7550 Baltimore Annapolis Blvd, Glen Burnie

    Get your holiday shopping done at the 39th annual Glen Burnie High School Winter Craft Fair benefiting the GBHS Band Boosters. Join us as over 140 crafters display their unique […]

    Free

  • Regional Textile Showcase

    Montpelier House Museum

    See all kinds of fiber art by local artists. Past exhibitors include the Uhuru Quilt Guild, the Montpelier Arts Center rug hooking class, and the artists of Stitching Pretty. Self-guided […]

    $2 – $5

  • St. Clement’s Island Museum Christmas Doll & Train Exhibit

    St. Clement's Island Museum 38370 Point Breeze Road, Colton's Point, MD, United States

    St. Clement’s Island Museum Christmas Doll & Train Exhibit Dates: Daily, December 1, 2022 – January 1, 2023 (closed Christmas Eve & Christmas Day) Time: 10:00 a.m. – 5:00 p.m. […]

  • Retro Christmas at Piney Point Lighthouse Museum

    Piney Point Lighthouse Museum 44720 Lighthouse Road, Piney Point, MD, United States

    Retro Christmas at Piney Point Lighthouse Museum Dates: Daily, November 27, 2022 – January 1, 2022 (closed Christmas Eve & Christmas Day) Time: 10:00 a.m. – 5:00 p.m. Location: Piney […]

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