Eastport Light Parade
December 12th and 19th; 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.
Naval Academy Band Holiday by the Bay Concert
December 12th, 8 p.m.; US Naval Academy Main Chapel, Annapolis
Our annual "Holiday by the Bay" concert will take place on Thursday, December 12th at 8:00 p.m. at the Main Chapel on the grounds of the United States Naval Academy. The eclectic concert will feature multiple Naval Academy Band ensembles performing a variety of multicultural holiday favorites, from traditional to modern. Santa Claus might just pay a special visit to delight children of all ages with holiday cheer and a sweet treat!
December 13th through 15th; Oxford Community Center, Oxford
We are delighted to announce the inaugural Oxford Holiday Market, a festive event taking place from Friday, December 13 to Sunday, December 15, 2024 in the historic town of Oxford, Maryland. This charming event promises to be a highlight of the holiday season, offering a weekend filled with unique artisan gifts, delicious food, and holiday music.
December 13th, 7:30 p.m.; Maryland Hall, Annapolis
December 14th, 3 p.m.; Severna Park High School
Get ready to experience one of the most beloved traditions in Annapolis—the Annual Holiday Pops concert! This festive season, join the Annapolis Symphony Orchestra and 70 world-class musicians as we bring the joy, beauty, and warmth of the holidays to life with a dazzling mix of classical music, carols, and heartwarming holiday tunes.
December 14th through 22nd; 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 14th through 15th; St. Michaels
The houses in town are within walking distance of each other, which gives visitors a great opportunity to stroll through town and soak up the historic atmosphere. Most of the homes, built in the 18th and 19th centuries, had at one time been the residences of watermen and seafarers. Many of these homes have since been restored, expanded, and adapted to today’s life style.
December 14th, 10 a.m.; Downtown Chestertown
Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, at a Pop-Up Gallery. Live music will also be happening throughout town. For information email hester@kentculture.org or call the Kent Cultural Alliance at 410-778-3700
December 14th; Hyatt Regency Chesapeake Bay Resort, Cambridge
Take a dip in the Choptank River on Saturday, Dec. 14, to help the Care and Share Fund, Inc. raise funds for the needy and other worthy projects in Dorchester County. The Santa Swim happens at the Hyatt Regency Chesapeake Bay Resort in Cambridge, MD. Swimmers bring monies from their personal fundraising as the entrance fee for the swim.
December 14th, 10:30 a.m.; Talbot Street, St Michaels
Who doesn’t love a traditional Christmas parade complete with marching bands, antique cars and boats, fire engines, horses, kazoo bands and llamas?! Perhaps you may even see a penny farthing. Santa and Mrs. Claus will arrive to close out the parade. Come early on Saturday morning to get a great spot along the parade route for the largest holiday parade on the Eastern Shore. Bring a lawn chair and a funny hat. Join the fun!
December 14th; Charles Carroll House, Annapolis
Join CoreShark H2O and 250 guests at our winter fundraiser, Bay Bells & Shark Tails. This event at the historic Charles Carroll House on Spa Creek in downtown Annapolis offers a bird’s eye view of the Eastport Yacht Club Lights Parade from a heated tent. At the same time, guests enjoy a full open bar, abundant experiential food stations, shucked-to-order oysters from Madhouse Oyster Company, silent auction, raffle items and dancing to the amazing beat of Radio City!
December 14th, 6-8 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 14th, 6 p.m.; St. Michaels Harbor
Once again we are excited to present the Lighted Boat Parade on Saturday night, December 14 at 6pm, around St. Michaels Harbor. Last year we had 18 entrants that wowed us with their creativity and decorating skills.
