December 7th through 10th; Annapolis Market House, Downtown Annapolis
This year we look forward to welcoming you back to the newest holiday market in the region that is quickly becoming a holiday tradition. Annapolis, Maryland annually makes the list of top Christmas towns to visit in the USA and this new event will reaffirm why this town is a special place to list during the holidays. The market is located on the historic waterfront City of Annapolis. The downtown area is known for its Charles Dickens holiday spirit. The town is decorated for the season with holiday greens, wreaths on the lamp posts, and beautiful storefront windows.The market will be filled with a wide range of art, crafts, food, and handmade gift items from local and regional art, craft, and food vendors. This type of holiday market is also known as a Kris Kringle market or Christmas market.
December 7th, 4 to 11 p.m.; Downtown Annapolis
Downtown Annapolis Partnership proudly presents Midnight Madness—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, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland and free on the street entertainment.
Live Arts Maryland Celebration of Christmas
December 8th; Maryland Hall, Annapolis
One night only! It’s the most wonderful time of the year – especially for this community favorite and family tradition! Many Annapolitans kick off the season with this concert, which features a sleigh full of holiday cheer provided by the Annapolis Chorale, Chamber Orchestra, and Artistic Director J. Ernest Green, along with special musical guests like audience favorite Mark Berman at the piano!
37th Annual Christmas in St. Michaels
December 8th through 10th; Downtown St. Michaels
Christmas in St. Michaels is celebrating its 37th year of fundraising festivities with the return and expansion of its weekend of holiday events taking place on the water and in the heart of historic St. Michaels, Md. this Dec 8-10. This year’s events include a Lighted Boat Parade and festive Talbot Street Parade; a Tour of Homes; Breakfast with Santa; Holiday Music and Meals; a Santa Dash; a Marketplace and Sweet Shoppe, and a charming, historic, waterfront and businesses all decked out for your holiday enjoyment. Don’t miss your limited edition Christmas in St. Michaels collectible ornament while you’re in town or be sure to order online.
Lighted Drive by the House Tour
December 8th through 10th; St Michaels
Everyone loves to see all the houses decorated for the holidays. If you live in the local Bay Hundred area we hope you will add to the festivities by decorating the outside of your homes for everyone to enjoy.
December 8th and 9th; Ocean City Boardwalk
We hope that you will join Santa this year to spread holiday cheer on our favorite island of misfit toys and support our charities. HOHOHOHOHOHOHOHOHOHOHO!
December 8th, 6 p.m.; Martin Sutton Park, Ridgely
The 9th Annual Santa Chase is a magical evening, dog-friendly, run or walk the 2-mile loop through the town of Ridgely and their Rail Trail light display. Candle luminaries and course monitors provided by the local Lion’s Club volunteers. Registration opens at 6:00 p.m. on December 8th and the race starts at 7 p.m. at Martin Sutton Park in Ridgely. $15 per person or $54 for a group of 4 if registered by December 1st. $20 per person and $72 for a group of 4 after December 1st. Add $5 if running with your dog/reindeer and we’ll have special prizes for our four-legged finishers. Flyers are posted on our website www.carolinerecreation.org. Produced in partnership with Lions International Clubs and the Ridgley Lions Club.
December 9th, 3 p.m.; Gillette Stadium, Foxborough Massachusetts
Though the game is not in our town, you don't have to miss out on the biggest game of the season. On Dec. 9, 2023, America’s Game will come to New England for the first time in the 124-year series history. The 2023 installment of Army-Navy will mark only the third time the historic matchup has taken place outside of the mid-Atlantic region (Chicago, Ill. In 1926 and Pasadena, Calif. In 1983). Tune in on CBS
December 9th through 17th; Maryland Hall
Discover the wonder of this timeless holiday tradition and allow yourself to be magically 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. Travel with Clara through the whirling Kingdoms of Snow and Sweets to the place where the possibility of dreams, the magic of Christmas, and the wonder of the child merge to reveal her destiny. Experience the power and beauty anew as the mysterious Drosselmeier transports you and Clara back in time to capture the spirit of the holiday season through the language of dance and theatre.
December 9th; West Shore Park, Baltimore
Be part of the original festive race for charity and signature Arthritis Foundation holiday event! Wear your favorite holiday attire and together, we’ll jingle all the way to a cure! Register as an individual or bring a team of friends, family and co-workers to run, walk or stroll, and spread the good cheer. Together, we’re raising funds to support research for ARTHRITIS TREATMENTS & A CURE — plus life-changing ARTHRITIS RESOURCES & LOCAL PROGRAMS.
'A Story to Tell' Opening Reception & Kwanzaa Celebration
December 9th, 11 a.m. to 3 p.m.; Banneker-Douglass Museum, Annapolis
Join us for our annual Kwanzaa celebration as we highlight our newest exhibit, 'A Story to Tell', curated by Chanel C. Johnson, featuring the art of Maryland artist Ernest Shaw and a selection of children’s and young adults' books by Baltimore Read Aloud. 'A Story to Tell' is an arts and literacy exhibition celebrating the beauty and importance of Black history, art, & literature. The exhibit features portraits by Maryland artist Ernest Shaw and children and young adult (YA) books presented by Baltimore Read Aloud. Baltimore Read Aloud is a leading bookstore that features socially conscious books by Black authors.
Holiday Spirit Tour: Yuletide Traditions
December 9th, 11 a.m. to Noon; William Paca House and Garden, Annapolis
Celebrate the season with a holiday tour of the William Paca House! Bring family and friends to enjoy the elegant decorations, learn about 18th century Maryland holiday traditions, and stories of Christmases past. This guided, one-hour candlelit tour highlights how the Paca household prepared for their holiday guests. The historic home is ready to greet you with music, garlands, a sweet treat, and a take-home recipe!
December 9th, 6 p.m.; Eastport Yacht Club, Annapolis
It's a beloved Annapolis tradition! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers!
December 9th, 6 p.m.; St. Michaels Harbour
Once again we are excited to present the Lighted Boat Parade on Saturday night, December 9, at 6pm, around St. Michaels Harbor. Last year we had 24 entrants that wowed us with their creativity and decorating skills.
December 10th, 4 to 8 p.m.; Neighborhoods in Annapolis and Broadneck
The Annapolis Santa Run is a all volunteer event that is sponsored by Annapolis Firefighters Local 1926. Each year on the second Sunday in December Santa and his elves set out in search of new toys for needy children in Annapolis and Anne Arundel county. With the help of the community, local businesses, Annapolis Fire Department, Annapolis Police Department, Anne Arundel county Sheriffs Office, and many volunteers we have been able to brighten Christmas morning for almost 5000 children over the past ten years.
December 10th, 4 p.m.; Christ Church, Easton
Easton Choral Arts Society presents its 2023 Holiday Concert, “Home for the Holidays”. Travel through the United States as this program takes the audience through a festive stylistic journey from Southern gospel to Midwestern folk to the Northeastern crooners and West Coast Hollywood flare. Even the islands from both the Atlantic and Pacific (Puerto Rico, Hawaii and more) will share their Christmas spirit. The program also features glorious works celebrating the sacred miracles of Hanukkah, the cultural principles of Kwanzaa, and the traditional sacred melodies of Christmas.
Homestead Gardens Holiday Girls Night Out
December 13th, 6-9 p.m.; Homestead Gardens, Davidsonville
Join us on Wednesday, December 13, from 6:00-9:00 pm at the Davidsonville location for a magical evening of shopping, sipping, and mingling. Bring your friends and loved ones for an enchanting start to the holiday season. In the spirit of giving, a portion of the proceeds will be donated to Charting Careers, a non-profit organization dedicated to inspiring youth to discover their power and reach their goals. Your presence will not only create cherished memories but also make a positive difference in our community.
