We’ve compiled the region’s most cherished holiday attractions, events, parades, and light shows. May you have a very Merry Christmas, Happy Hanukkah, Blessed Kwanzaa, New Year’s, and the happiest holiday season!
Handel’s Messiah
Live Arts Maryland’s annual performances of “Messiah” are another Annapolis tradition. On December 15th and 16th at 8 p.m., and on December 17th at 3 p.m., view the performance of the season at St. Anne’s Church in Annapolis. A world-class soloist, the Chamber Orchestra, and the Annapolis Chorale come together for a beautiful presentation of this timeless work. Get your tickets at liveartsmd.org.
Christmas at the Mall
Looking for the perfect place to get pictures with Santa? Reserve a spot at Santapolis: A Magical Holiday Experience at the Westfield Annapolis Mall to enjoy time with Santa and immerse yourself in the holiday spirit like never before. Santa's elves will welcome you to a world of twinkling lights and festive decor. Photos with Santa are available through December 24th. On December 4th and 11th, our four-legged friends will have the opportunity to take photos with Santa as well. After getting your family's picture taken, stop by the CPK Court and in the food court for the Salvation Army's Angel Trees. Choose an angel from the tree, shop for them and bring unwrapped gifts to Salvation Army on Hilltop Lane by December 11th. Find more information about all things Santapolis at westfield.com
Midnight Madness
The shopping festivity of Downtown Annapolis is back for three nights! The first two Thursdays of December, from 4 p.m. until midnight, and the third Thursday of the month from 4 to 11 p.m. Downtown Annapolis Partnership and Historic Downtown Annapolis promote this tradition. These nights support local businesses and help our community thrive. Find more information at downtownannapolispartnership.org.
Annapolis Holiday Market
Annapolis’ Holiday Market is free this year in Downtown Annapolis on December 7th through 10th. The town is decorated with holiday greens, wreaths, and beautiful storefront windows for the season, so why not add to the cheer by shopping the town market full of arts, crafts, food, and handmade gifts from local and regional vendors. Last year, for the inaugural Annapolis Holiday Market, 45 artisans and 25,000 visitors enjoyed the market over four days. Find more information and a list of vendors at annapolisholidaymarket.com.
Celebration of Christmas
For one night only! On December 8th at 8 p.m. at Maryland Hall in Annapolis, it’s the most wonderful time of the year, especially for this community tradition—Live Arts Maryland’s Celebration of Christmas. The concert will feature a sleigh full of holiday cheer provided by the Annapolis Chorale, Chamber Orchestra, Artistic Director J. Ernest Green, and special musical guests like audience favorite Mark Berman at the piano. Find more information and get tickets at marylandhall.org.
Photo by Joe Heimback
Annapolis Chocolate Binge Festival
Inner West Street Association is back with the popular tradition, the Annapolis Chocolate Binge Festival. From 11 a.m. to 4 p.m. on December 3rd, visit the first block of West Street in Annapolis for family-friendly entertainment, shopping, chocolate, chocolate, and more chocolate. Enjoy a chocolate gingerbread decorating contest and visits from Willy Wonka, Oompa Loompas, Santas, Elfie, live music, and more. Find more information and buy your tickets at IWSAnnapolis.com.
Christmas with the Celts
Christmas with the Celts is celebrating 12 years of national touring with timeless Irish Christmas Carols and Irish dancing. On December 4th, Christmas with the Celts will be performing at Rams Head On Stage in Annapolis. Even though the group has been touring for 12 years, they vow that no two concerts are the same. So be sure to get your tickets at ramsheadonstage.com.
Tuba Christmas
Gather in front of St. Anne’s Church on December 9th for Annapolis’ Tuba Christmas! Holiday music will be performed by instruments of the tuba family, including baritone horns and euphoniums at 3 p.m. Bring your tuba and register for $10 by 1:30 p.m. to perform in the concert. This outdoor concert is free for the audience. Find more information, visit the Facebook page: TubaChristmas Annapolis!
The Nutcracker
Enjoy the wonder of The Nutcracker, the timeless holiday tradition. Be swept away by the tale of the young heroine Clara and her adventures to rescue her beloved Nutcracker from the Rat Queen’s evil spell. Performances will be Saturdays and Sundays December 9th through 17th at Maryland Hall in Annapolis performed by the Ballet Theatre of Maryland. Order tickets at balletmaryland.org.
Colonial Yuletide Celebration
Celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead property on December 2nd. Learn about holiday traditions of colonial Annapolis and hear stories of Christmases past from living historians as they bring these historic homes to life on this merry day. Enjoy sweet treats, music, and crafts. Admission includes both sites; advance registration recommended. Find more information at annapolis.org.
Holiday Pops
On December 15th, Annapolis Symphony Orchestra will perform their night of cheer, Holiday Pops at 7:30 p.m. at Maryland Hall in Annapolis. The program includes familiar holiday songs you know and love. Artistic Director and Conductor Jose-Luis Novo (pictured) will also bring new and beautiful music from around the world to the performance. The full symphony of more than 72 professional musicians are here to bring the joy of the season! Get tickets at annapolissymphony.org.
ICE! At National Harbor
Each year, National Harbor welcomes Gaylord National Resort’s annual ICE! attraction. Now through December 31st, enjoy the interactive ICE! experience which includes 13 scenes from the classic Rudolph the Red-Nosed Reindeer. Clarice, Bumble, Sam the Snowman, Hermy the Elf, and, of course, Rudolph will be carved out of more than two million pounds of colorful ice. Find more information and get tickets at christmasatgaylordnational.com.
Wreath Workshop
Historic London Town and Gardens is hosting two Wreath Workshops on December 2nd. Join at 10 a.m. or 1:30 p.m. to create your own holiday wreaths and centerpieces. The expert wreath makers will guide attendees in making the perfect natural holiday decorations for your home this holiday season! Find more information and register at historiclondontown.org.
2023 Jingle Bell Run
The Arthritis Foundation’s signature Jingle Bell Run is hitting West Shore Park in Baltimore on December 9th at 9 a.m. Get ready to run with your bells on and the holiday spirit and jingle your way to a cure. Your registration fee and fundraising support will help the fight to conquer arthritis. Find more information and start raising money for your pledge at events.arthritis.org.
Holiday Taste and Sip
Greater Severna Park and Arnold Chamber of Commerce is hosting its 13th Annual Holiday Taste and Sip on December 5th from 5 to 8 p.m. at Chartwell Golf & Country Club. This is one of the most anticipated and well-attended events of the year and full of fantastic food, wine, and music. The event offers samples from local restaurants, bakeries, and liquor stores. Find more information at gspacc.com.
Lights of Kindness
The Rotary Club of South Anne Arundel County is hosting its 10th Anniversary Lights of Kindness charity event during the first weekend of December at Homestead Gardens. Beautifully decorated Christmas trees, sponsored by businesses, in support of local charities, will be displayed from Friday, December 1 through Sunday, December 3. Visitors will have an opportunity to vote and donate in-person then, during business hours, or on-line. Find more information at southcountyrotary.org.
Glen Burnie Gingerbread Festival
’Tis the season for sweetness! Explore the Glen Burnie Gingerbread Festival at Marley Station Mall from December 1st through December 3rd. One can find handmade crafts, a mall-wide scavenger hunt for Gingerbread Men, and the star attraction—the Gingerbread House competition. The festival raises money for needy individuals each year through an auction, gift shop, and people’s choice vote. Come out and explore all the Gingerbread Festival has to offer. For more details check out gbgingerbreadfestival.com.
Dickens of a Christmas
Step back into 1840s London and experience the holiday season as Charles Dickens imagined it. On December 1st and 2nd, enjoy carriage rides, entertainment, home tours, food, book talks, and more on Main Street Chestertown. Santa will be available for pictures. Enjoy Victorian tea and so much more to kick off December. Find more information at mainstreetchestertown.org.
Holiday Marketplace
The Holiday Art & Craft Marketplace is back at the Waterfowl Festival Building in Easton. The event presents the finest local artists and craft vendors. Selections for the show are based on quality, craftsmanship, creativity, and uniqueness. The Artisan’s market will be December 1st, from 4 to 9 p.m., December 2nd, from 9 a.m. to 5 p.m. and December 3rd from 10 a.m. to 3 p.m. Find more information at discovereaston.com.
Rescue Fire Company Train Garden
Cambridge Fire Company’s Train Garden is back with the tradition that has taken place each December for almost nine decades. The Train Garden is in “the Old Firehouse” at 307 Gay Street in Cambridge. Starting December 1st, the train garden will be open Monday through Friday from 6 to 9 p.m. and open 1 to 4 p.m. and again, from 6 to 9 p.m. on Saturdays and Sundays. Find more information at rfctraingarden.org.
Tour of Homes
St. Michael’s Tour of Homes is the highlight of Christmas in St. Michaels weekend and is one of the longest running home tours in Maryland. December 9th and 10th will feature historic homes in town and some very special countryside homes. A ticket includes admission to all homes, transportation to the countryside homes, admission to the Chesapeake Bay Maritime Museum on Saturday and Sunday, as well as admission to the Classic Motor Museum on both Saturday and Sunday. Find more information at christmasinstmichaels.org.
Skate With Santa
Santa will be taking a break from his busy schedule at the North Pole to visit the Talbot County Community Center to share holiday memories with the whole family! Kids will have an opportunity to tell Santa their seasonal wishes and receive a special gift! Please bring your own camera to take a memorable photograph with Santa. Complimentary hot chocolate and cookies will be provided. Pre-registration is required as Santa’s helpers need to maintain quantity and quality skates and gifts. Find more information and pre-register at talbotparks.org.
The Merry Market
Dorchester Center for the Art’s new Merry Market is bringing the spirit of the season now through December 23rd. DCA will transform their entire art gallery into a whimsical shopping experience. The inaugural event will feature dozens of artists displaying a wide variety of their hand-crafted, quality items such as traditional arts and crafts, jewelry, candles, and more. Find more information at dorchesterarts.org.
Home for the Holidays
On December 7th at 7:30 p.m. and on December 10th at 4 p.m. at Christ Church in Easton, Easton Choral Arts Society will be performing their 2023 Holiday Concert: Home for the Holidays. Travel through the United States while this program takes the audience through a festive, stylistic journey from Southern gospel to Midwestern folk to the Northeastern crooners, West Coast Hollywood flare, and beyond. Find more information and order tickets at eastonchoralarts.com.
Easton’s Moonlight Madness
Celebrate the holidays at Moonlight Madness in Downtown Easton. On December 1st, from 5 to 9 p.m., downtown shops and restaurants will be open with refreshments, snacks, and holiday gifts. There will be music, entertainment, and fun while we shop for the holidays! Find more information at discovereaston.com.
Breakfast with Santa
Another Christmas in St. Michaels tradition is the family-favorite Breakfast with Santa. Breakfast with Santa is December 9th from 8 to 10 a.m. for children ages 4 to 9. Come together at Foxy’s Harbor Grille for breakfast, pictures, and plenty of holiday spirit. Find more information and order tickets at christmasinstmichaels.org.
Marketplace and Sweet Shoppe
Visit the Granite Lodge on St. Mary’s Square in St. Michaels on December 8th through 10th for the 2023 Christmas in St. Michaels Marketplace and Sweet Shoppe. The marketplace offers one-of-a-kind artisan craft items and culinary delights throughout the weekend. The sweet shoppe will serve hot mulled cider, hot coffee, and a variety of treats baked by the chefs of local inns and restaurants. Find more information at christmasinstmichaels.org.
SantaCon
All of the Santas are coming to town on December 8th and 9th in Ocean City. The Ocean City boardwalk has turned into the North Pole every year since 2011. Since its inaugural year, SantaCon OCMD has hosted more than 600 Santas annually to support Assateague Coastal Trust and Kenille’s Kupboard Pet Pantry & Rescue. Find more information about this year’s SantaCon at santaconocmd.com.
Photograph by Ted Mueller
First Night Talbot
Celebrate the end of the year with the 30th anniversary of First Night Talbot on December 31st in Easton. There will be plenty of free activities for the whole family including face painting, arts and crafts, Carlos the Fire-Juggler, Mike Elzey’s Guitar Studio, and so much more. The night will also include the Giant Crab Drop at both 9 p.m. and midnight. Find more information at discovereaston.com.
