State Circle, Annapolis
Jennifer Casey

Merry-land Holiday Festivities

Get into the spirit of the season with these festivities full of Maryland cheer

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State Circle, Annapolis
Jennifer Casey

There’s no place like Maryland for the holidays! Get into the spirit of the season at Parades and Festivals, great holiday Train Events dazzling Light Displays and Candlelight Tours, memorable Performances of holiday classics, unique Arts & Crafts Shows, and spectacular New Year's Eve Celebrations.

Make this year special with a Home for the Holidays hotel package.

1
Midnight Madness - Historic Ellicott City
holiday shoppers

December 4, 2020 4pm-midnight
Bring the family to Historic Ellicott City for the  42nd annual Midnight Madness Celebration! Catch a glimpse of  Santa, watch the tree lighting and sip hot treats while strolling Ellicott City's picturesque historic district. Shops will be well stocked and will stay open late so that you can find unique gifts, plus local restaurants will be serving festive culinary delights late into the evening! Strolling carolers, period actors and more make this an evening not to miss!
 

2
Six Flags America - Holiday in the Park, Bowie
kids with santa
Six Flags America

November-January Weekends & select days
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.

3
Christmas on the Square and Annual Tree Lighting in Leonardtown
Christmas tree lighting

November 27, 2020
The Town of Leonardtown will ring in the holiday season with the traditional "Christmas on the Square and Annual Tree Lighting Ceremony".  Event activities include live entertainment, rides, face painting, a living nativity, food and much more!  Don't miss Santa's arrival  at 7pm and the lighting of the Town Christmas Tree! 

4
Chesapeake City's Winterfest
Christmas lights
Dave Scarbrough

December- January 2020
The month-long holiday season begins with the lighting of the town's many seasonal figures.  Come to Pell Gardens on Saturday December 5th to shop at the Olde World European Christmas Market. On Saturday December 12th enjoy Christmas on the Canal  a modified version of Chesapeake City's Candlelight House Tour. 

5
Cambridge & Dorchester Christmas Parade & Crab Tree Lighting
parade float
Cambridge-Dorchester Christmas Parade

December
Get caught up in the swirl of light and sound during the 71st annual Cambridge-Dorchester Christmas Parade -- one of Maryland's largest nighttime parades. Marching bands, floats, classic cars, horses, and more fill the streets with energy and excitement. Shortly before the parade kicks off at 5pm, Cambridge's Crab Basket Tree will be lit. This tree is constructed of  200 crab baskets -- the very bushel baskets that local watermen use to harvest blue crabs.
 

6
Christmas in Princess Anne
holiday street
Main Street Princess Anne

December 5, 2020
Celebrate Christmas in Princess Anne with a great line-up of events including: pop-up shops, parade, Christmas house tour, and for the finale, a candlelight reception at Historic Teackle Mansion in Princess Anne (reservations are required for reception and dinner).
 

7
Frostburg Storybook Holiday
Frostburg Storybook Holiday
Frostburg, MD's Annual Storybook Holiday

Returning December 2021
This is a very unique event in Mountain Maryland and Maryland as a whole. Storybook Holiday is in its 16th year and is sponsored by Frostburg State University’s Children’s Literature Centre. The event includes a Parade, Elk Olympics, Breakfast with the Elves, Storybook Readings, Elves’ Secret Workshop (letter writing to Santa, Photo with an Elf, arts and crafts), Festival of Trees and much more!

8
Colonial Christmas at Historic St. Marys City
woman walking through snow in red cape
VisitStMarysMD.com

Returning December 2021
Celebrate Christmas the way the first Marylanders did with a walking tour of holiday traditions. Tours depart hourly beginning at 11am the last tour is at 3pm.

9
Cecil County Christmas Parade - downtown North East
pinecone and holly

December
The  tradition continues with floats, marching bands, animals, antique and classic automobiles and SANTA CLAUS!  Get in the holiday spirit, arrive early and stay late to enjoy the yummy goodies and great deals from North East Main Street Merchants.
More info...

10
Bethesda's Winter Wonderland
students singing
Bethesda.org

December

This community event features live performances, ice sculpting and Santa Claus too.  Wander over to Veterans Park in downtown Bethesda and enjoy the festivities.

More info...

11
Christmas in Crisfield
Crab pot  Christmas tree
delmarvanow.com

December 4-5, 2020
Don't miss the lighting of the Crab Pot Christmas Tree!  There will be entertainment, food, vendors and Santa will be there too!  Plenty of fun events for the kids so bring the family to this free holiday event.
 

12
Midnight Madness - Annapolis
Midnight Madness - Annapolis
VisitAnnapolis.org

December 3,10 & 17, 2020
Lights, garland, action! Historic Annapolis' shops throw open their doors in a glorified block party that is open to all. Enjoy musical performances as well as food and refreshments at many stores as you stroll along Main Street, Maryland Avenue, West Street, and State Circle in search of that perfect gift. Explore the uniqueness that makes downtown Annapolis special.

13
December Saturdays in Downtown Frederick
Carolers

December 5, 2020
December's First Saturday means all day activities, holiday lights, late-night shopping and dining, and a free trolley to guide your way. During each of the first three Saturdays in December, celebrate the holiday season by shopping and dining local.

14
Annual Solomons Christmas Walk
Calvert Marine Museum winter painting
Calvert Marine Museum

Stroll through Solomons luminaria streets  and enjoy the sights and the sounds of the season. This is a fun-filled day of special children’s activities including "open house" at many local businesses, a live puppet show, Santa’s arrival and the Lighted Boat Parade! 
Calvert Marine Museum, Solomons.

15
Yuletide Festival at Mount Harmon
Colonial room decorated for the holidays
MountHarmon.org

December 5-6, 2020
The Yuletide Festival features holiday decorations inspired by Colonial Williamsburg, hearth cooking demonstrations, children’s holiday craft activities, and holiday decorations  and greens sale. Visitors enjoy hearth cooking demonstrations, hearth-made gingerbread and Wassail punch in the colonial kitchen, and children’s holiday craft activities in the Education and Discovery Center.

16
Annual Christmas Open House at Ladew Gardens
Don't be afraid of a little snow! Ladew's 100 larger-than-life topiary farms sparkle in winter.

Returning December 2021
Seasonal resplendence as floral designers and Garden Clubs decorate the rooms of the circa 1747 Manor House, adorning walls, tabletops and fireplace mantels in festive holiday decor. Holiday arrangements, greens and gifts are available for sale. The Ladew Café will be open for lunch and will be serving wine and beer. 
More info...

17
Mayor's Christmas Parade - Baltimore
Christmas Parade
Gerard M Buckleman

Returning December 2021
The Annual Mayor's Christmas Parade will feature about 160 marching units, floats, local TV and radio personalities, over 100 Harley Davidson motorcycles, a steam calliope, great bands, Mummers of Philadelphia, Miss Yuletide and Jr. Miss Yuletide and of course - the big man himself - Santa!

18
Old Tyme Holiday Gathering, La Plata
horse drawn carriage

Returns December 2021
A seasonal celebration of friends, community, and good cheer. Enjoy horse-drawn carriage rides, holiday music, activities, refreshments, and a visit from Santa.

19
Christmas in St. Michaels
horsedrawn carriage
Christmas in St. Michaels

Returning December 2021
Celebrate the arrival of the Christmas season St. Michaels! Both ticketed and free events including the Tour of Homes, Holiday Gala, Breakfast with Santa and the largest Holiday Parade on the Eastern Shore.

20
Kris Kringle Procession - Frederick
Courtesy of VisitFrederick

Returns December 2021
This walking procession features German/English characters of yesteryear.  The procession concludes at the Baker Park Band Shell for the lighting of the City Christmas tree and a concert of the Carillon Bells.  It's Old World magic. in the heart of Frederick.

21
Hometown Holidays - Brunswick
Brunswick Main Street

Returns December 2021
This beloved day takes place in a charming small-town that says "Christmas."  Breakfast with Santa takes place at the Ambulance Company.  Then enjoy a holiday market, children's crafts, and even horse-drawn carriage rides.  
It's tradition and it is magical. 

22
Bel Air Christmas Parade & Tree Lighting Celebration
Boy with Frosty the Snowman
Brand It Images

Returning December 2021
Treat yourself to a traditional parade at 3:30.  Partake in the community bonfire and singalong in Shamrock Park, with free cookies and hot chocolate at 4:00.  A tree lighting completes this family friendly community event at 4:45.

23
Honor African-American Traditions and Heritage During Kwanzaa
Candle Light Ceremony with Sankofa Dance Theater
Jane Yoon

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, the Wiley H. Bates Legacy Center in Annapolis, and the Benjamin Banneker Park & Museum in Catonsville.

24
Grand Illumination--Annapolis City Tree Lighting
Grand Tree With Lights

Returning December 2021
Join all of Annapolis at Market House's Hopkins Plaza as we kickoff the downtown holiday season. Watch Santa arrive by horse and carriage. Sponsored by the Annapolis Jaycees, this popular Annapolis event helps everyone get into the holiday spirit.

25
Frosty Friday in Downtown Frederick
window shopping in Frederick

Returning November 2021
Kick off your holiday season with all day shopping in Downtown Frederick! Parking in downtown will be FREE, shops and eateries will be open early and stay open late, plus there is a free trolley that circulates downtown every 15 minutes to make your day a breeze. Special events include horse-drawn carriage rides, a festive kick-off at 9am, caroling and live music.

26
Kennedy Krieger's Festival of Trees - Timonium
Family looking at gingerbread houses
Kennedy Krieger Institute

November (virtual)
This is the big one:  the East Coast's Largest Holiday Extravaganza!  This Kennedy Krieger fundraiser is full of fairyland forests of more than 800 trees, gingerbread towns, and toy train gardens.  Plus - more than 100 holiday boutiques are on hand for holiday shopping.  Goodies and activities for kids are offered and everyone is in the Christmas spirit!

27
Victorian Christmas in Berlin
Town of Berlin Christmas tree and bike during Victorian Christmas
Town of Berlin

Returning November-January 2021
In Berlin you will find several celebrations of the quintessential Victorian Christmas. The festive season kicks-off with a traditional Christmas tree lighting, caroling, carriage rides. You won't want to miss the Berlin Christmas Parade or the New Year's Eve ball drop!

28
Christmas on the Beach - North Beach
Santa
The Town of North Beach

Returning December 2021

The Town of North Beach begins the festive holiday season by Lighting Up the Town! Gather at the pavilion to see the lighting of the town Christmas tree and holiday displays. The next day, the boardwalk is lined with hundreds of spectators viewing the annual Pat Carpenter Holiday Parade . The best part is when jolly old Santa arrives by fire truck! Santa and Mrs. Claus visit with children and give them a special treat. All are welcomed to warm up around the campfire and enjoy holiday refreshments.

29
Christmas on the Potomac featuring ICE!, National Harbor
National Harbor ice
Christmas on the Potomac

Returns November-December 2021
Enter a magical Christmas wonderland with lavish Christmas decorations, twinkling holiday lights, indoor snowfall and ICE!—Gaylord's signature holiday attraction—is back with Dr. Seuss' How The Grinch Stole Christmas! Watch how the Grinch tries to steal Christmas from the Whos of Who-ville through interactive ice sculptures and displays. 
Experiences include Village Express - a classic children’s train in the heart of Christmas Village, outdoor ice skating in Winter Square, Reindeer Rush Tubing, a live entertainment – Cirque Dreams Unwrapped and much more!