Isaac Martinez is the Nutcracker Prince and Victoria Sanzotera is the Sugar Plum Fairy in BTM’s The Nutcracker. Photo by Joanne Salyer
If your calendar is feeling very merry and very full, you’re doing the holidays right. This week is packed with all the things that make the season shine—sparkling concerts, festive shopping nights, cozy food-and-drink gatherings, playful family adventures, and traditions that feel even better when shared. Whether you’re chasing live music, hunting for the perfect gift, leaning into ugly sweater season, or squeezing in one more memory before the big day, there’s something here to match every mood. Grab your friends, bring the family, or head out solo—holiday magic is happening all around, and this is your guide to making the most of it.
Ugly Sweater Happy Hour at Captain's Daughter Bar & Lounge
December 17th; Captain’s Daughter Bar & Lounge, Annapolis 5:00pm – 7:00pm
Get ready to sip, snack, and show off your most gloriously over-the-top holiday knit at Captain’s Daughter’s Ugly Sweater Happy Hour. Grab your crew for seasonal drinks and craveable bites, then lean into the fun with a little friendly competition—because the boldest (and ugliest) sweater in the room takes home a Captain’s Daughter gift card. Come for the festive specials, stay for the laughs, and leave with full-on holiday cheer.
BSO Presents Classical Christmas
December 17th; Joseph Meyerhoff Symphony Hall, Baltimore 7:30pm – 10:00pm
Classical Christmas brings the season to life with a bright, festive program that feels like stepping into a musical holiday postcard. Conductor Patrick Quigley leads an uplifting mix of favorites—Charpentier’s triumphant Prelude from Te Deum, Mozart’s sparkling Exsultate, jubilate, Bach’s joyful Orchestral Suite No. 4, and beloved highlights from Handel’s Messiah. With soprano Maya Kherani, tenor James Reese, and the Handel Choir of Baltimore, expect soaring vocals, rich choral sound, and plenty of moments that will have you grinning before the final note. It’s the perfect excuse to dress up a little, settle in, and let the music do the merry-making.
Midnight Madness
December 18th; Downtown Annapolis 6:30pm – 12:00am
Midnight Madness turns downtown into a glowing holiday playground, where twinkling lights, festive décor, and free on-the-street entertainment make every block feel like a Christmas card come to life. Stroll at your own pace, pop into shops and galleries for sweet treats and seasonal specials, and knock out your gift list while soaking up the cozy charm that makes Annapolis shine this time of year. It’s the kind of night that’s better with a group—bring friends, bring family, and make an evening of wandering, browsing, and discovering new local favorites. Best of all, every purchase supports the small businesses that keep downtown vibrant all year long.
Thyme for Cheer
December 19th- 23rd; Harvest Thyme Tavern, Davidsonville
Set the table for a season of great food and even better company with Thyme for Cheer, a festive holiday menu series from Chef Rik and his team. Expect made-from-scratch brunch and dinner favorites crafted with standout local ingredients—perfect for a lively catch-up with friends, a family meal that feels special, or a cozy night that still tastes like a celebration. Whether you’re lingering over brunch or picking up dinner to enjoy at home, this is an easy, delicious way to work a little extra holiday joy into your week.
The Talent Machine Presents "A Merry Mix-Up" Holiday Spectacular!
December 19th – 23rd; Indian Creek School, Crownsville 7:00pm – 9:15 pm
Get ready for a holiday outing that feels like stepping straight into the season’s happiest playlist. The Talent Machine Company’s Holiday Spectacular, A Merry Mix-Up, packs the stage with festive songs, high-energy dances, and a playful storyline that keeps everyone guessing as the holiday hustle leads to a few unexpected surprises. Performed by an impressive cast of young talent ages 5 to 18, this annual musical revue delivers big spirit, big smiles, and that feel-good “family tradition” magic from start to finish. And yes—Rudolph, Frosty, Santa, and a crew of merry elves pop in along the way, turning the whole experience into a full-on Christmas celebration you’ll be talking about on the ride home.
Ugly Sweater Party
December 19th; Live! Casino & Hotel, Columbia 7:00pm – 12:00am
Ugly Sweater Party is your excuse to go all-in on holiday chaos—in the best way. Pull on your most ridiculous sweater and jump into a night of trivia, music, and friendly competition, with a DJ keeping the energy up between rounds. Expect festive contests, plenty of laughs, and the kind of awesome prizes that make showing up in full sparkle-and-tinsel mode totally worth it. With happy hour extended until 9 PM, you’ve got extra time to toast the season, rally your team, and claim bragging rights before the night is over.
ASO’S Annual Holiday Pops concert
December 19th, 20th, 21st; Maryland Hall, Annapolis 3:00pm – 5:00pm
Get ready to experience one of Annapolis’s most cherished holiday traditions with the Annapolis Symphony Orchestra’s Annual Holiday Pops concert, returning with three festive performances across the region. This joyful celebration features the ASO’s 70 world-class musicians performing a sparkling mix of classic carols and heartwarming seasonal favorites that capture the warmth and wonder of the holidays. The Bowie State University Concert Choir joins the orchestra for select performances, adding powerful voices and extra magic to the program.
Catch the Holiday Pops on Friday, December 19, 2025 at 7:30 pm at Maryland Hall with the Bowie State University Choir; Saturday, December 20, 2025 at 3:00 pm at Severna Park High School; and Sunday, December 21, 2025 at 3:00 pm at the Dionne Warwick Theater at Bowie State University, again featuring the Bowie State University Choir. With multiple dates, times, and locations, it’s easy to fit this beloved concert into even the busiest holiday schedule—and impossible to leave without feeling the spirit of the season.
Magic Elf Hunt at Belair Mansion
December 20th; Belair Mansion, Bowie 12:00pm – 4:00pm
Attention elf hunters of all ages—Santa needs backup! The Magic Elf Hunt invites kids and families to step into a festive mystery as Santa’s mischievous elves hide throughout Belair Mansion, just waiting to be found. Young detectives will search room to room, follow clues, and put their sleuthing skills to the test in a playful holiday adventure filled with surprises. Successful hunters earn an official elf-hunting badge and the pride of helping save the season. With free admission and no reservations required, it’s an easy, joy-filled outing that blends holiday magic, imagination, and just the right amount of mischief.
The Nutcracker
December 20th; Maryland Hall, Annapolis 7:00pm – 9:00pm
Be part of a brand-new Annapolis holiday tradition as Ballet Theatre of Maryland debuts Annapolis’s own Nutcracker, a fresh take on the classic that feels right at home. Expect the familiar magic—Clara, the mysterious Drosselmeier, and the brave Nutcracker Prince—reimagined with local flair, from historic costumes to festive sets that nod to the city’s past. As the story unfolds, vibrant dancing and hometown details weave 19th-century Annapolis into every scene, making it feel both timeless and wonderfully new. It’s the perfect way to soak up the season, support local arts, and experience a Nutcracker that belongs to Annapolis.
Gents’ Last Call: Sliders & Spirits at Zachary’s Jewelers
December 22nd; Zachary’s Jewelers, Annapolis 10:00am – 8:00pm
Gents’ Last Call at Zachary’s Jewelers is the ultimate last-minute holiday shopping tradition—equal parts festive pit stop and confidence-boost for gift giving. The Breitling Lounge turns into a cozy holiday hangout with handcrafted sliders, premium spirits, and the kind of expert help that makes picking “the one” feel easy (and actually fun). Expect a relaxed, cheerful atmosphere, gifts-with-purchase, and plenty of inspiration—plus complimentary gift wrapping in Zachary’s signature white paper and red ribbon, so you can walk out looking like you planned ahead. It’s a great excuse to finish your list in style…and maybe add one more item for yourself.
