December 8th, 4 p.m. to Midnight; 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, 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.
1st Annual Midnight Madness Holiday Artisan Market
December 8th, 5 p.m.; Downtown Annapolis
Discover local artisan vendors at the Maryland Inn while you shop for holiday gifts during Midnight Madness! Our Holiday Artisan Market will start at 5 pm on December 1, 8, and 15 at the Maryland Inn.
December 8th, 5:30 p.m.; Maryland Hall, Annapolis
Maryland Hall and Annapolis Green partner to celebrate the fun side of eco-awareness while making serious connections. Green Drinks, sponsored by Chesapeake Crossroads Heritage Area, will host a flow of conversation, collaboration, and cocktails as the Maryland Hall Community Room takes center stage in its debut as a new zero-waste location for small community events!
Easton Choral Arts Society's Christmas Around the World
December 8th, 7:30 p.m.; Christ Church, Easton
Under the baton of our new Artistic Director Alexis Ward, ECAS will provide Christmas with both new and familiar songs to warm your heart and begin your Christmas season. The magic of Christmas from around the world will be captured in exciting Christmas music from Europe and America. Included are long-time favorites like “We Need a Little Christmas,” “The Most Wonderful Time of the Year,” and a choral telling of “The Night Before Christmas” poem by Clement Moore, complete with illustrations on two large TV screens. A portion of the concert will remind guests that Christmas is celebrated in many places and many languages around the world. This includes the earliest versions of "Stille Nacht" (Silent Night), the Austrian carol that turned from obscurity to a major classic, along with "Twas in the Moon of Wintertime" – one of the oldest Christmas songs of Canada which tells the Christmas story through the eyes of the indigenous Huron people. Also included will be a traditional carol from Catalonia in Spain, “Fum, Fum, Fum,” and the haunting Catalonian work, “El Cant dels Ocells” (Carol of the Birds) by Chris de Silva. “Brightest and Best,” in the American Shaker tradition, will feature a lively bluegrass-style fiddle solo, and “Hurry Now to Bethlehem” presents a new spiritual for guests. Pianist Becky Zinser will be joined by diverse instrumentalists playing strings, oboe, and flute. The choristers will close the program with “Christmas Day,” the rousing medley of Christmas songs by Gustav Holst.
Holiday by the Bay Concert at the Naval Academy Chapel
December 8th, 8-9 p.m.; U.S. Naval Academy, Annapolis
The eclectic concert will feature multiple Naval Academy Band ensembles performing a variety of multicultural holiday favorites, from traditional to modern. The concert will also feature USNA Chapel Organist Monte Maxwell. Santa Claus will pay a special visit to delight children of all ages with holiday cheer and a sweet treat.
December 9th through 11th; St Michaels
Christmas in St. Michaels is celebrating its 36th 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. 9 - 11. 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 Light up the Night drive-by house and harbor tour. The goal for this year’s Christmas in St. Michaels events is to raise funds to distribute grants to local beneficiaries. More than 25 family services, education and child development, and community enhancement organizations depend on Christmas in St. Michaels funds to support their programs and activities.
Live Professional Theatre: Classic Theatre of Maryland Presents "White Christmas"
December 9th, 8-10 p.m.; Classic Theatre of Maryland, Annapolis
This reimagined tribute to Bob Wallace and Phil Davis, two iconic song-and-dance men, follow a sister act to Vermont, only to discover that the nearly-bankrupt lodge they were to perform at is owned by their former commanding general. Buy tickets today!
December 10th; 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. Leading off the parade will be the always fun one mile Santa Dash, see details here. 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, your dog, and a funny hat. Join the fun!
December 10th and 11th; Downtown Snow Hill
Visit Downtown Snow Hill to be transported to the Victorian Era, as the pages of Charles Dicken's 'A Christmas Carol' is brought to life. Vignettes of the classic Christmas story will be performed by the Ocean Pines Community Players, Horse Drawn Carriage Rides, and Carolers will make you feel you have gone back in time. The Merchants will offer Victorian Era themed specials and activities. Come dressed in period correct clothes for a chance to win a prize!
December 10th and 11th; Downtown Cambridge
This award winning Christmas market has grown exponentially since its inception in 2012 and this year will offer almost 60 local artisans, crafters and makers. The Cambridge Christmas Market is a favorite shopping destination for unique gifts, seasonal food and a great shopping atmosphere.
December 10th, 6 p.m.; Solomons Island
The Annual Lighted Boat Parade, at 6 p.m and end along the Riverwalk at approximately 7:15 p.m. weather permitting. The Lighted Boat Parade, coordinated by Solomons Island Yacht Club, Southern Maryland Sailing Association, Patuxent River Sail and Power Squadron, Solomons Yachting Center, and Sail Solomons will begin at dusk and end along the Riverwalk A Captain’s meeting covering the route, safety issues, and rules for judging will begin at 5:15 p.m. at the Solomons Yachting Center. More information to come.
December 10th; Banneker-Douglass Museum, Annapolis
Join us for our 2022 Kwanzaa celebration! This year’s festivities will focus on the creativity (Kuumba) of the people of the African Diaspora. We will highlight the museum’s current exhibit, The Radical Voice of Blackness Speaks of Resistance and Joy, while presenting live performances, Black-owned businesses, and delicious food from across the state of Maryland.
Ballet Theatre of Maryland's "The Nutcracker"
December 10th; Maryland Hall, Annapolis
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 10th, 8 a.m.; Inner Harbor, Baltimore
Wear your favorite holiday costume and spread good cheer for a great cause. We’re raising awareness and funds to support arthritis research for better treatments and a cure. We’re also helping the Arthritis Foundation develop tools, resources and opportunities to connect with each other. Together, we’re committed to conquering arthritis for good. Please join us!
December 10th, 10:30 a.m.; Talbot Street, St Michaels
Yes Santa Claus is coming to town – or maybe LOTS of Santas are coming!! Continuing in 2022 is the St. Michaels Santa Dash, a one mile run/walk that makes YOU the Grand Marshall of the Christmas in St Michaels parade. Choose a Santa suit or hat with your registration and lead off the parade running right down Talbot Street while all the spectators cheer you on!
40th Anniversary of the Eastport Yacht Club Lights Parade
December 10th, 6 p.m.; Annapolis
The 40th Anniversary of Eastport Yacht Club Lights Parade presented by the Long & Foster Real Estate Eastport Office is an event you won’t want to miss. On Saturday December 10th from 6pm to 8pm, Annapolis will be celebrating a momentous anniversary of one of its signature events, the Eastport Yacht Club Lights Parade. This much imitated statewide award winning event draws people from all over the region to Annapolis city dock, waterfront area restaurants, watering holes, hotels, homes, offices and Eastport’s street end parks.
December 11th, 5 p.m.; Crofton Chamber
Join Us for the 3rd annual Light Up Crofton. On Sunday, December 11 let’s transform our neighborhoods into a beautiful winter community! Come together and join us in celebrating this holiday season by lining our neighborhoods with candle luminaries! #LightUpCrofton
December 12th; Rams Head on Stage, Annapolis
Join us along with the Annapolis Musicians Fund for Musicians at this annual favorite! We’ve got a great lineup of talented local artists that will be performing a mix of original and classic holiday songs. This show was inspired by the release of the popular holiday album, "An Annapolis Christmas" 23 years ago, and is now an annual tradition for many local music lovers. All proceeds from this show support the Annapolis Musicians Fund for Musicians, Inc. (AMFM)
