The holidays are approaching quickly! Start to enjoy the season with tree lightings, holiday parades and decorations, and holiday special events!
Updating for 2023. List is updated regularly. Check back often!
Attractions dates and time will vary. Call ahead or check their website to verify.
Holiday Festivals, Open Houses and Special Events
Festival of Trees – 2023
Nov. 24–Nov. 26. Complete with hundreds of one-of-a kind trees, wreaths and gingerbread houses decorated by local designers, corporations and schools. We also have shopping, entertainment and delicious holiday treats! Don’t miss the family-friendly entertainment on our Rosemore Main Stage! Our entertainment lineup includes everything from dance groups and singers to magicians and comedians! festivaloftrees.kennedykrieger.org
Polar Express Train Ride
November 24-25 & December 1-3, 8-10 & 15-19, 2023
Climb aboard The Polar Express to create a Christmas memory that you and your family will cherish forever! Come in your pajamas as a family to watch the live performance of The Polar Express. Once on the train, the classic Christmas tale will be performed and little ones will have the opportunity to meet Santa and receive their first gift of Christmas! Santa’s helpers will greet you upon arrival to the North Pole, where you can take pictures with Santa and have lots of holiday fun.
B & O Railroad Museum, Baltimore. Borail.org
Gingerbread House Show and Contest – 2023. Nov 24-26. Dec 1-3. Dec 8 – 10. View displays of edible gingerbread houses virtually and vote on your favorite in the Viewer’s Choice Award Competition. $2. Noon–5 p.m. Darnall’s Chance House Museum, Upper Marlboro. Register in advance to compete. All entries must be delivered to the Museum in completed form on Sunday, November 19 between 12 – 3 pm. Drop-off times will be scheduled in advance. The Museum will contact contestants to schedule. history.pgparks.com
Festival of Lights- 2023
Nov. 27–Jan. 1. This spectacular drive-through event features dazzling displays with more than 2.5 million lights and a giant, 54-foot LED musical tree! $10 per car in advance. $15 at the gate. Free Admissions: December 25th. 5–9:30 p.m. Watkins Regional Park, Upper Marlboro. mncppc.org/742/festival-of-Lights
Christmas on the Square – 2023
Nov. 24. Free. 4:30-8:30pm. Holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, hot drinks, food, holiday treats and other fun activities! Leonardtown Square, Leonardtown. https://www.visitleonardtownmd.com/christmasonthesquare
Click here for light displays and tree lightings
Nightly Holiday Tree Light Show – 2023
Nov. 11-Jan. 3, 5:30 p.m.-9 p.m. ignite your holiday spirit with the nightly lighting of the 56-foot tree and two million twinkling lights. The tree light show takes place nightly, every half hour from sundown to 9 p.m. On Saturday nights the light show is followed by fireworks.
National Harbor Waterfront District, nationalharbor.com
Holidays at Homestead Gardens – 2023
Sat. and Sun. Themed trees, live music (on weekends) and magical main street decorated with lights, colors and sounds of the season. See holiday trains and “Santa’s Workshop” themed animatronic sets, pick your own tree, shopping and more. 10 a.m.–6 p.m. Homestead Gardens, Davidsonville. homesteadgardens.com
Solomons Christmas Walk – 2023
Dec. 9. Lighted Boat parade, gazebo lights, and a beautiful 18 ft Christmas tree. Free. 6 p.m. Riverwalk at Solomons, Solomons. solomonsmaryland.com
Jolly Express Cruise – 2023
Fridays, Saturdays and Sundays starting Nov 24. Forty-five minute Spa Creek cruise aboard the Miss Anne. Miss Anne will be adorned with reindeer spirit for an intimate cruise including hot cocoa, holiday music, and good cheer. Bring your own blankets and enjoy the cruise with “Captain Santa” at the helm. $13-25. On the hour 2 – 7 pm. Annapolis City Dock, Annapolis. watermarkjourney.com
Chocolate Binge Festival – 2023
Dec 3. 11am-4pm. Family friendly entertainment, chocolate, holiday shopping and the lighting of the new West Street Light Canopy. Other activities include giant gingerbread moon bounce, marshmallow roasting, pictures with Lady Godiva, visits with Santa and more. $5-$15; children are free. First block of West Street, Annapolis. Annapolischocolatefestival.com
Christmas in St. Michaels – 2023
Dec. 8-10. St. Michaels will light up the night with a Lighted Boat Parade Dec 9 at 6pm in the harbor and houses decorated for the holiday season. Virtual events and videos starring Santa will be available, online auction and marketplace. St. Michaels. christmasinstmichaels.org
Santa Speedo Run – 2023
Dec 16. Meet at O’Brien’s Oyster Bar & Seafood Tavern in Annapolis at 11am. Toy drive combined with fun, live music, great food, dancing and crazy costumes. Participants run through Annapolis in skimpy festive outfits. santaspeedorunannapolis.com
Need to get started on your holiday shopping? Check out our roundup of Maryland Holiday Shopping and Craft Shows here. And check out our complete guide to Christmas fun and holiday events in Maryland here.