Merry-land Holiday Festivities
Get into the spirit of the season with these festivities full of Maryland cheer
There’s no place like Maryland for the holidays! Get into the spirit of the season at Holiday Celebrations, great holiday Train Events, memorable Performances, dazzling Light Displays and spectacular New Year's Eve Celebrations.
Make this year's holiday season extra special by taking advantage of our "Open for the Holidays" Deals and Hotel Packages.
November 20 - January 3, 2022 Select Dates
This dazzling, winter spectacular will make your holiday shine with more than a million glittering lights, holiday entertainment, delicious seasonal treats, visits with Santa and theme park rides. Combine holiday traditions with a thrilling family experience that is uniquely Six Flags.
December 3-4, 2021
As an arts-rich community with strong literary, musical, and theatrical talents, Chestertown invites visitors to enjoy a memorable weekend filled with authentically themed holiday fun. The charm of our historic 313-year-old river town will be the backdrop to a lively display of Dickens-era holiday attractions: carriage rides, street theater, live music, food vendors, decorated house tour, and more!
December 10-12, 2021
The Tour of Homes, the Talbot Street Parade, the Boat Parade, Marketplace, Santa, Breakfast with Santa, the Ornament, and the Old Fashion Christmas Dinner will all be back with determination. As a result of the restrictions last year, some events will take a rest this year – Santa’s Wonderland, Gingerbread Competition and Display and Cocktail Party, the Yuletide Party and the Celebration of Choirs will not be held.
Be on the lookout, there may even be a couple of new events.
November 26, 2021
The Town of Leonardtown will ring in the holiday season with a modified "Christmas on the Square and Annual Tree Lighting Ceremony." Event activities include Santa's arrival at 7pm and the lighting of the Town Christmas Tree!
December 2, 2021 - 5-8pm
Illuminating the historic Washington Monument is a holiday tradition that DPOB has been involved in for decades. The night includes caroling, food and good cheer. Fireworks cap the evening marking the official start of the holiday season.
December 3, 2021 from 6pm-midnight
Our 70+ one-of-a-kind shops and restaurants have decked their halls, and stocked their shelves with treasures to make your holiday merry and bright. Find sidewalk sales, festive cocktail & food offerings, plus specials galore.
December 3-4, 2021
On December 3, Main Street hosts the Christmas Parade at 6:30pm.
December 4, it's Miracle on Tenth Street from 4 - 7pm along Tenth Street. The Lighting of the Crab Pot Christmas Tree, with Vendors and Pictures with Santa take place around 5pm.
December 4, 2021
Each year, the town of St Michaels is transformed into a picture perfect holiday postcard, the shops, restaurants and B&B’s are decorated with stunning greenery, lights and festive cheer. The holiday spirit is felt throughout town, which makes coming to St Michaels during the holiday season a special experience, year after year, and provides a wonderful backdrop to shop for the holidays. Stored will be open late with special sales all day and night.
December 2, 9 & 16, 2021
A Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garland, snowflakes, bows, and lights to create a Downtown Winter Wonderland.
Residents and visitors are invited to stroll along Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street from 4 PM until Midnight to support our local businesses. When we Shop Local, we reinvest in our community and help our downtown businesses thrive. Check out all the stores, galleries, and boutiques throughout the downtown area.
November 26, 2021, 6-8pm
Santa's Arrival & the Lighting of Chestertown
Welcome Santa back to Chestertown by firetruck to Fountain Park. Kids can meet with Santa at a safe distance and get their picture taken. The Fountain Park Christmas Tree will be lit to open the holiday season.
November 27, 2021, 10am
Kick off the holiday season with Chestertown's annual Parade! One of Kent County’s favorite holiday traditions! Line up on High Street to see all of your favorites ring in the holiday season. The annual parade will begin at Dixon Drive and commence at the intersection of High and Spring Street. Enjoy marching bands, classic automobiles, floats and your favorite holiday characters.
December 4, 11 & 18, 2021
First Saturday means holiday lights, late-night shopping and dining. During each of the first three Saturdays in December, celebrate the holiday season by shopping and dining local. Shopping with an independent retailer, eating at a local restaurant, and supporting local artists really matters.
Whether you’ve lived here for years, or you’re a first time visitor, First Saturday (and every Saturday in December) is a great time to discover something new about our beautiful downtown.
December 4, 2021
The museum is open and free to the public from 6:00 - 9:00 p.m. Enjoy musical entertainment, Santa, the Otter mascot, holiday crafts, model train display, and shopping in the Museum Store.
Christmas celebrations kick off with the fabulous Lighted Boat Parade at 6 pm, weather permitting. The Lighted Boat Parade, begins at dusk at the Solomons Yachting Center and ends along the Riverwalk at approximately 7:15pm. Sail and power boats are welcome. The parade can be viewed from many places in Solomons and from the Patuxent Riverwalk.
December 4-5, 2021
Mount Harmon’s Open Air Yuletide Festival & Holiday Marketplace has been re-imagined for pandemic times. The Festival features an Open Air Yuletide Decorations & Greens Sale, Open Air Artisan Marketplace & Holiday Gift Shops, Hearth Cooking Demonstrations, and Self-Guided Open Air Yuletide Walking Tours of our beautifully decorated historic buildings and grounds, featuring our carriage house visitor center, serpentine-walled boxwood garden, colonial outbuildings, and manor house grand outside entrances.
December 10, 2021 6:30 pm
As the nights grow dark and cold, it's time to celebrate winter, colonial style! Join us for an evening learning how colonists celebrated Christmas, Yule, and other winter holidays on a candlelight tour of the ca. 1760 William Brown House, followed by glasses of warm chocolate port, game play, and winter festivity.
Sunday, December 13
Join Chabad Anne Arundel County for the annual Menorah Car Parade. The parade departs Safeway (2635 Housley Rd, Annapolis). Parade participants arrive by 5pm. At approximately 5:45pm, event organizers kindle a giant Menorah and celebrate the Festival of Lights at City Dock. Individually wrapped chocolate gelt (coins), prepackaged latkes, and Chanukah kits will be given out while supplies last. All are welcome!
December 26, 2021 - January 1, 2022
Honor African heritage and rich African-American culture and traditions during the seven days of Kwanzaa. Join celebrations at the Reginald F. Lewis Museum in Baltimore, at the Wiley H. Bates Legacy Center and virtually at the Banneker-Douglass Museum in Annapolis.