December 1st, 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 1st, 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.
Mid-Atlantic Symphony Orchestra Season of Celebration
December 1st, 7 p.m.; Chesapeake College, Wye Mills
Enjoy Mid-Atlantic Symphony Orchestra's Holiday Joy performance on December 1st at 7 p.m. They will also be back December 4th at the Performing Arts Center in Ocean City.
December 2nd through 4th; Homestead Gardens, Davidsonville
The Rotary Club of South Anne Arundel County is delighted to announce the 9th Annual Lights of Kindness charity event, a Christmas tree decorating contest, December 2–4 at Homestead Gardens in Davidsonville, Maryland. This event has been important to our community over the past years as, with the help of business and private event sponsors, these unique and magical events raised $162,980 over eight years for local charities, including the Rotary Club's commitment to the Bountiful Backpack Program, providing food every week for disadvantaged South County children and their families.
Muddy Creek Artists Guild Holiday Show "Gifts from the Arts"
December 2nd; Main Street at the Villages of South River Colony, Edgewater
Muddy Creek Artists Guild presents unique creations by over 40 South AA County artists in a wide variety of media, including jewelry, photography, painting, stained glass, mixed media, sculpture and wood, ceramics, pottery, fiber and more. Get holiday gifts and stock up on greeting cards! Show times: Fridays and Saturdays Dec. 2, 3, 9, 10: 10 am- 7 pm, Sundays Dec. 4 and 11: 11 am - 5 pm. Meet the Artists Reception with free beverages and snacks: Dec 3, 5 - 7 pm. FREE Art making workshops Saturdays Dec. 3 and 10: 1-4 pm, Sunday Dec. 4: 1-4 pm. All materials provided.
December 2nd through 3rd; Chestertown Town Hall
The 5th Annual Dickens of a Christmas is back on December 2-3, 2022! Join us for even more Victorian events and fun as popular favorites return after a Covid hiatus and new events debut. Dickens of a Christmas is hosted by Main Street Chestertown and all proceeds further Main Street’s work to make downtown Chestertown a vibrant community.
Holiday Village with Frosty the Snowman
December 2nd, 5 p.m.; Talbot County Courthouse, Easton
For All Seasons invites you to an evening with Frosty! Stroll through our holiday village and enjoy FREE activities, including professional photos with Frosty, complimentary cocoa, cider, and donuts, and a continuous showing of “Frosty’s Winter Wonderland” on the big screen. This is an outdoor event so grab your coat and hat, and don’t forget to bring some holiday CHEER!
Annual Tree Lighting at the Chamber
December 2nd, 5-6 p.m.; Greater Severna Park and Arnold Chamber of Commerce, Annapolis
We are so excited to hold our Annual Open House and Tree Lighting at the Chamber! Free and fun! Fun for the entire family to enjoy singing, dancing, music, cookies and warm cider, and more!! Elves provided by the Toast of Severna Park Toastmasters Club. Enjoy performances, music and more! Get your family pictures taken with Santa AND the Grinch. Sponsorships are available for $250 and you will be promoted on Social Media, printed materials, visible signage at the event, and website. Please provide us with your promotional materials to distribute at the event.
December 2nd, 7 p.m.; Maryland Hall, Annapolis
You are invited to Annapolis Opera’s Golden Gala, an unforgettable, one-night-only celebration of five glorious decades of opera in Annapolis, which honors our past and looks forward to the next fifty years! Limited VIP Tickets include reserved parking, early entrance, VIP seating, and a signed 50th anniversary poster!
December 3rd; Downtown St Michaels
Celebrating the holidays in St. Michaels is a tradition for many, and this year is no different. Maryland’s Eastern Shore is home to many picturesque towns, but none embody an old-fashioned holiday feel quite like St. Michaels. With our quaint shops, world-class dining and jolly spirit, St. Michaels is transformed during the holidays into a Christmas Village. The holiday spirit is felt throughout town, which makes coming to St Michaels during the holiday season a special experience, year after year, and provides a wonderful backdrop to shop for the holidays.
Queen Annes County Watermen's Basket Tree Lighting
December 3rd; Kent Narrows
Last year’s watermen’s basket tree display at Kent Narrows was so popular, the project will return to Kent Narrows this year with more trees! A ceremonial tree lighting, hosted by the Queen Anne’s County Watermen’s Association, is scheduled for the evening of December 3, 2022. The trees are made from painted crab baskets, will remain in place through the last week in January.
December 3rd; Downtown Annapolis
Join us as we decorate downtown Annapolis for the Holiday season! It is an annual tradition for the Jaycees of Annapolis to decorate storefronts of local downtown businesses with lighted garland and wreaths. We separate into teams and work together to hang greens that will light up Annapolis at night. Our plan is to use Stan & Joe's Saloon's Parking Lot (37 West Street, Annapolis MD) as the location to launch our event.
December 3rd, 8:30 a.m. - 11:30 a.m.; Slayton House Studio, Columbia
The Wilde Lake Community Association invites you to delight in classic Christmas cartoons, enjoy a delicious continental breakfast, and meet Santa on our beautifully decorated stage. Spread the holiday cheer and teach your little ones the joy of giving at our Kids Only Holiday Shop (cash only).
December 3rd, 10 a.m.; College Park Aviation Museum, College Park
Watch Santa fly into the College Park Airport and Aviation Museum! All guests will have the opportunity to take two pictures with Santa and create several in-person crafts. Santa will arrive between 10:00 am-10:15 am. We encourage guests to start arriving at 9:30 am. Museum members are free, while non-members are $5. Everyone over the age of 2 must have a ticket.
December 3rd, 11 a.m.-4 p.m.; Kent Narrows
The Queen Anne’s Railroad Society will once again be hosting a Festival of Trains indoors the first two weekends in December. There is no admission fee, but donations are welcome. We have already begun setup for the Festival at the same venue as years prior: the old Kent Narrows Outlets (56 Piney Narrows Rd) in Chester, MD. There will be 10,000 square feet of exhibits in G, Standard, O, S, HO, N and Z scales.
December 3rd, 2 p.m.; William Paca House and Garden, Annapolis
You are cordially invited to celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead. It’s the year 1772, and you'll experience the holiday traditions, music, and stories of Christmases past.
16th Annual Holiday Clothing & Toy Drive - Santa Under the Stars
December 3rd, 4-7 p.m.; Fence & Deck Connection, Annapolis
Bring a Donation & Enjoy FREE Family Fun! Free Photo with Santa for Your Little Ones!Enjoy Our Large Outdoor Ice Skating Rink!Cookie Decorating Kits!Holiday Crafts & Fun!Hot Chocolate & Sweet Treats from T&J Waffles!This event directly benefits THE BLUE RIBBON PROJECT & their programs that support victims of child abuse & local youth in foster care. DONATION NEEDS: New (with tags) Children's Clothing and Toys This includes children's clothing & outfits, pajamas, socks, underwear, and backpack
December 3rd, 4-10 p.m.; Kent Island
SantaCon Kent Island is celebrating our 6th annual event on Saturday December 3rd, 2022 from 4pm - 10pm. Attendees dress in anything Christmas, start at any of the participating venues and move throughout the evening to the other venues by way of the free SantaCon buses. Each venue supports a different local charities raising awareness and generating fund for the charity in house. This year's charities include Not My Child QAC, The Kinera Foundation, The Jacob Sloan Foundation and The Julianne Rosela Foundation. All of charities participating in SantaCon Kent Island support local children and families in Queen Anne County. There is a free event for admission, you only pay for the food and beverage you consume and hopefully support the charities of SantaCon Kent Island.
73rd Annual Parade "Crabby Christmas"
December 3rd, 5 p.m.; Cambridge Race and Gay Streets, Cambridge
The Cambridge ~ Dorchester County Christmas Parade is held annually on the first Saturday in December each year. Once hailed as the 'largest nighttime parade', the parade continues each year as a timeless tradition throughout the decades. The parade is hosted and brought to the community by a small group of community volunteers for their love of community and the Holiday Season. The parade is 100% donor funded by local businesses, charities, and the community at large. Each year brings something new and exciting, but always present are the glittering lights, sounds of music, Holiday cheer, and laughter. This year's parade will not disappoint.
December 3rd, 6 p.m.; Easton
Hope you’re ready for some holiday cheer! Easton’s holiday parade will take place December 3rd, 2022. The event will kick off with a tree Lighting at 6 p.m. followed by a parade that will begin at 6:30 p.m. With a myriad of vehicles, novelties, and floats this parade is sure to showcase the very best of Easton during the Christmas season. Join in the festivities!
December 3rd, 6 p.m.; Church at Severn Run, Severn
Life of Joy Foundation's signature faith-based outreach program and benefit concert supporting all those affected by suicide, depression or other mental health challenges. Set in the healing elements of song, prayer and testimony, it's about bringing HOPE and resources to those struggling, those in recovery, those healing from loss, and all who support them!
Annapolis Chocolate Binge Festival
December 4th; West Street, Annapolis
Another vendor at the Annapolis Chocolate Binge Festival is Annapolis Chocolate Bar’s Cheryl Starr. When she is not at the Annapolis Chocolate Binge Festival, Cheryl Starr splits her time between her store at Maryland Avenue, corporate events, weddings, and other events. Her signature offering at the Annapolis Chocolate Binge Festival is sea salt caramels which come wrapped in holiday boxes. Other vendors at the Annapolis Chocolate Binge Festival offer a broad range of chocolate temptations such as bonbons, candies, cookies, fudge, truffles, cakes, and chocolate caramels. Other events that you can find at the Annapolis Chocolate Binge Festival include gluten-free, organic, Non-GMO, kosher, and vegan selections.
December 4th, 9 a.m.; Childrens Theatre of Annapolis
Join us for a special Breakfast with Santa on Sunday, December 4! Santa’s elves will be on hand to provide your little ones with plenty of merriment, including games, Christmas carols, breakfast and a special visit from Santa (including a photo opportunity)!