A list of our favorite local events for the month of December. Event dates may be subject to change due to COVID restrictions.
Lights on the Bay
Unleash your excitement for the holidays by driving through the 26th Annual Lights on the Bay with the SPCA at Sandy Point Park. The drive-through is two miles along the Chesapeake Bay waterfront and features over 70 animated and stationary light displays. This year’s show will be influenced and by our very own Historic Annapolis. The drive-through experience will be open from 5 to 10 p.m. through January 2nd; 2022 and 3D glasses are available on site. Visit lightsonthebay.org for more information.
Photo by Joanne Marie Photography
The Nutcracker
The Ballet Theatre of Maryland is performing The Nutcracker for two weeks in December. Follow Clara in this perfect holiday tradition as she breaks the Rat Queen’s evil spell. The performances will take place on December 11th and December 18th at 7 p.m. and on December 12th and December 19th at 1 p.m. and 4:30 p.m. All performances will take place at Maryland Hall in Annapolis and tickets are available at balletmaryland.org.
Midnight Madness
Shop local from 4 p.m. to midnight on December 2nd and 9th and then again until the Eleventh hour on December 16th at 90 stores and 80 restaurants in Downtown Annapolis. West Street, Maryland Avenue, Main Street, and the City Dock area will be filled with traditional holiday decorations including beautiful storefront windows, garland, wreaths, holiday lights, a snowflake alley, and so much more. This year, the event will start two hours earlier (4 p.m.) so that people are able to spread out arrival times and reduce crowding. Find more information at midnightmadnessannapolis.com.
Hanging of the Greens
The Jaycees are ready to decorate Downtown Annapolis for the Holiday season. It is an annual tradition for them to decorate storefronts of local downtown businesses with lighted garland and wreaths. They plan to meet at Market House in Downtown Annapolis on December 4th at 7:30 a.m. and divide into teams to work together and conquer the city, hanging greens that will light up Annapolis at night. For more information, or to join in the celebration, visit the Hanging of the Greens Facebook page.
Annapolis Chocolate Binge Festival
Chocolate Lovers are coming together on December 5th to enjoy a day of celebrating the Art of Chocolate. There is something for everyone including about 35 Chocolate vendors, shopping from dozens of local artists, drinks, food, and live music, and plenty of chocolate. There will be live music and entertainment for everyone in Annapolis. Get your camera ready for 5 p.m. as the Holiday Light Canopy over West Street in the Annapolis Arts District is illuminated. Find more information at annapolischocolatebingefestival.com.
2021 Eastport Yacht Club Lights Parade
The Eastport Yacht Club Lights Parade is back for 2021! This is one of Annapolis’ signature events for nearly 40 years and is back to celebrate another holiday season with us. The parade is on Annapolis’ waterfront featuring 40 boats of all shapes and sizes, power, and sail, which are brightly decorated with thousands of lights and crewed by jolly revelers. Skippers who are participating circle the waterfront in two fleets: one circling in front of Eastport, Ego Alley/City Dock, and the Naval Academy Seawall, while the other fleet circles the length of Spa Creek inside the bridge. The parade will be held on December 11th from 6 to 8 p.m. Find more information at eastportyc.org.
Holiday Pops: Sultans of String
The sounds of Annapolis Symphony Orchestra will fill Maryland Hall on December 17th at 8 p.m. The Holiday Pops with the Sultans of String are finally coming, after their original performance was cancelled before the pandemic. Join a joyful and joyous world tour through music in a delightful Christmas Caravan. Find more information about the show at annapolissymphony.org.
A Celebration of Christmas
For one night only, on December 10th from 8 to 10 p.m., Live Arts Maryland will be performing A Celebration of Christmas. Everyone needs a little extra Christmas cheer this year, so join the Annapolis Chorale, Chamber Orchestra, Artistic Director J. Ernest Green, and other special musical guests at Maryland Hall in Annapolis to enjoy the annual holiday concert. This community favorite tradition will kick of the holiday season for Annapolitans. Find more information at Marylandhall.org.
Winter Jam
The fifth annual high school basketball tournament hosted by Severna Park High School will take place on Wednesday, December 29th and Thursday, December 30th. Come see favorite local teams all in one place. This family-friendly event includes JV and Varsity high school athletes from Annapolis Area Christian School, Old Mill, South River, Glen Burnie, Chesapeake, Wilde Lake, St. Mary’s, Northeast, Atholton, and Severna Park. Game times are between 9 a.m. and 6 p.m. For more information visit: severnaparkathletics.org.
Christmas in St. Michaels
Come for a day or stay for the weekend to celebrate the season in historic St. Michaels. December 10th through 12th, children can enjoy breakfast with Santa, the family can tour charming and historic houses, shop collectable ornaments and unique gifts, and enjoy a street parade with a one-mile Santa dash and evening lights boat parade. For more information or to book your stay, visit christmasstmichaels.org.
Photo by Mary Simmons
A Dickens of a Christmas
This year is Chestertown’s 4th Annual Victorian holiday extravaganza: A Dickens of a Christmas. December 3rd through 4th, stroll through downtown Chestertown for a lively London themed weekend with entertainment, food, shopping, children’s activities, and more. A full schedule of all events, 5K information, petting zoos, and carriage rides can all be found at mainstreetchestertown.org/dickens.
Easton Choral Arts Society: A Merry Rutter Christmas
Composer and Arranger John Rutter and the Easton Choral Arts Society are returning to the stage at Christ Church in Easton on December 2nd and 5th for A Merry Rutter Christmas. The show will feature classic Christmas songs and more. In addition to the live performances, the show will also be live streamed on YouTube. December 2nd’s show will be at 7:30 p.m. and December 5th’s show will begin at 4 p.m. Buy tickets today at eastonchoralarts.com.
Corddry Company Crossing’s Annual Holiday Model Train Garden
Get ready to experience one of the Eastern Shore’s most exciting and kid-friendly train gardens. After their kick-off night on December 3rd from 5 to 8 p.m., the garden will be open from 1 to 4 p.m. on December 4, 5, 11, 12, 18, 19, and 26 on the second floor of Pocomoke River Canoe Company in Snow Hill. The show will feature running water, realistic sounds, running engines, and plenty of interactive features. This train garden has been running and building since 1992. Visit snowhillmodeltrains.com for more information.
Firing of the Guns
Kick off the Christmas season with the St. Michaels tradition: the Firing of the Guns. The event will take place at noon on December 11th at Chesapeake Bay Maritime Museum. Between noon and 12:30 p.m., interpretive volunteers from the Chesapeake Independent Blues and the NPS Fort McHenry Guard will demonstrate the loading and firing of reproduction artillery and muskets used during the War of 1812, recalling the early 19th century traditions of the Christmas season. Find more information at cbmm.org.
Skate with Santa
Santa is taking a couple days off from his busy schedule on December 8th and 9th to visit Talbot County Community Center, ice skate, and make holiday memories with the whole family. Parents will be able to bring their own cameras to take pictures of their kids sitting on Santa’s lap and there will be complimentary hot cocoa and cookies. The event will take place 6 to 8 p.m. Be sure to pre-register at discovereaston.com.
Shrek: The Musical
For three weekends in December, visit Garfield Center for the Arts in Chestertown to see your favorite Ogre. Shrek: The Musical is based on the Dreamworks animated film where a disagreeable ogre, Shrek, must rescue a fairy-tale princess from a fiery dragon to save his swamp alongside his new companion, a talkative, obnoxious Donkey. The production will open December 3rd and run weekends through December 19th with performances at 7 p.m. on Fridays and Saturdays, as well as 2 p.m. on Sundays. Visit garfieldcenter.org to buy tickets.
Deck the Hall, Town Hall
The Town of Galena invites you to share the Christmas Spirit with Santa, Mrs. Claus, and the Galena Volunteer Fire Company on December 4th at 6 p.m. Enjoy holiday cookies and hot chocolate on Main Street and Mayor Carroll will do a Facebook "drive through Galena" to share the lights of the season to find the best displays in town. For more information, call Galena Volunteer Fire Company at 410-648-5050.
Santa Arrives by Boat and Crab Basket Christmas Tree Lighting
Lots of things are going on December 4th at 6 p.m. in Rock Hall this year! Christmas festivities are here and Santa and Mrs. Claus will be showing up for them by a boat parade at the bulkhead on Main Street. Hear live music from The Community Band, see Santa on the boat, and stick around for Santa's firetruck entrance to Main Street to officiate the lighting of Rock Hall's Crab Basket Christmas Tree. This tree features several hundred decorated baskets in memory and in honor of loved ones. The event will be followed by tasty s'mores in a community fire pit and the opportunity for children to visit "Santa's House" (in the Visitor Center). Visit kentcounty.com for details.
Easton Holiday Parade
Kick off the holiday season early in December by watching Easton's Holiday Parade. The night will begin with a tree lighting at 6 p.m. followed by the parade at 6:30 p.m. on December 4th. This parade will include an abundance of vehicles, novelties, parade floats, reindeers, elves, and more. For more information, visit eastondc.com.
Festival of Trees Weekend
Visit Chestertown December 3rd through 5th to see a large display of trees decorated by businesses, organizations, and local families. The trees will be displayed at 1st UM Church during the Winter Festival and is open 5–7 p.m. on Friday, 10 a.m. to 7 p.m. Saturday, and noon to 3 p.m. on Sunday. Bring your camera and see Santa and Mrs. Claus from 12–2 p.m. on Saturday and Sunday. Find more information about this free community event at Townofchestertown.com.
