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Holiday Festivals and Special Events

The holidays are approaching quickly and many places are already in the holiday spirit! Start to enjoy the season with tree lightings, holiday decorations, and holiday special events!

rsz tree lighting national harbor

Updating for 2020. List is updated regularly. Check back often! Attractions may be closed certain days or are now virtual. Call ahead or check their website to verify.

Holiday Festivals, Open Houses and Special Events

The B&O’s First Tree Lighting Ceremony & Evening Train Ride – 2020
Nov. 20, 6 p.m.-8 p.m.
Join us as we light the beautiful 35-foot Christmas tree, tour through Santa’s Winter Village shops and model train layouts, enjoy a visit from Santa and Frosty the Snowman, and delight in delicious cookies with spiced cider or spiked cider for the grown-ups. borail.org/holiday/

Santa’s Official Arrival in Baltimore by Train
Nov. 27, 9–10 a.m. The holiday season is officially here when Santa arrives back in Baltimore aboard the B&O No. 6944! Santa’s locomotive will pull into the B&O Railroad Museum’s spacious Roundhouse, creating the perfect opportunity to take the first festive photos of the season. Your ticket includes all-day access to the entire Museum, including the chance to enjoy the B&O Holiday Festival of Trains with Santa’s Winter Village shops and model train layouts. borail.org/holiday/

Festival of Trees – 2020
Nov. 27–Nov. 29. Festival of Trees 2020 will be a hybrid event, but will still feature beloved traditions, such as designer-decorated trees and wreaths for sale, Santa, entertainment, and a not-to-miss online silent auction with many unique items. Free. festivaloftrees.kennedykrieger.org

Six Flags Holiday in the Park – 2020
Nov. 21–Jan 3. Open weekends and select weekdays. More than 1 million glittering lights, holiday entertainment, delicious seasonal treats, visits with Santa and theme park rides. $49.99. Six Flags America, Upper Marlboro. sixflags.com

Breakfast with Santa & a Train Ride on the Reindeer Railway
Saturday, November 28, December 12 & 19 (8:15am – 10am) 
Sunday, November 29, December 6,13 & 20 (9:15am – 11am)  
Join us for the annual breakfast buffet with Santa! Santa will join you and your family during breakfast and be available for socially distant photo sessions inside the spacious Roundhouse that is transformed  into a festive wonderland featuring the B&O’s signature 35-foot Christmas tree, model train layouts, and Santa’s winter village. Families will then ride the Reindeer Railway train and children will be given reindeer antlers for the trip.
B & O Railroad Museum, Baltimore. Borail.org

Gingerbread House Show and Contest – 2020
Dec. 9–18. 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. history.pgparks.com

Festival of Lights- 2020
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. 5–9:30 p.m. Watkins Regional Park, Upper Marlboro. mncppc.org/742/festival-of-Lights

Christmas on the Square – 2020
Nov. 27. A modified holiday event is being planned for 2020. Please stay tuned for details. Free. 4:30-8:30pm. Leonardtown Square, Leonardtown. leonardtown.somd.com/christmas

Click here for light displays and tree lightings

Nightly Holiday Tree Light Show – 2020
Nov. 14-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 weekends (Friday, Saturday and Sunday) there will be snowfall over the tree during the light show.
National Harbor Waterfront District, nationalharbor.com

Holidays at Homestead Gardens – 2020
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 – 2020
Dec. 5. 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 – 2020
Fridays, Saturdays and Sundays in Dec.; except Dec. 12. 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. $13-23. 6, 7 and 8 pm. Annapolis City Dock, Annapolis. watermarkjourney.com

Chocolate Binge Festival – 2019
No info for 2020 yet
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. Suggested donation of $5; children are free. First block of West Street, Annapolis. Annapolischocolatefestival.com

Christmas in St. Michaels – 2020
Dec. 12. St. Michaels will light up the night with a Lighted Boat Parade 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 – 2020
The race has been canceled for 2020 but you can still donate to a great cause and support their annual Toy Drive. New and unwrapped toys and books can be dropped off at both Homestead Gardens locations (Davidsonville and Severna Park) through Dec. 6 and The Federal House in Annapolis will be accepting donations Dec. 3 through Dec. 6. 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.

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