It’s a classic rivalry showdown as Navy Men’s and Women’s Basketball face off against Army in a doubleheader packed with school spirit and competitive energy.
Jan 21-27
From cozy community gatherings to big laughs, live music, creative workshops, and even a little donkey love, this week’s lineup has something for every mood. Whether you’re looking to network, shop local, catch a show, cheer on a rivalry game, or try something totally new, these events are perfect excuses to get out, connect, and enjoy what winter has to offer around the region. Grab your calendar, make a plan, and let the week unfold with good vibes, great company, and plenty of memorable moments.
Chamber Monthly Mingle at The Social
January 21st: The Social, Severna Park 4:00pm – 6:00pm
Kick off the new year with a relaxed, social evening designed for connection and conversation at the Chamber Monthly Mingle. Enjoy delicious appetizers, take advantage of a dining discount, and unwind alongside fellow professionals in a welcoming, upbeat atmosphere. It’s the perfect chance to strengthen relationships, make new connections, and ease into the year ahead with great company and good food. Whether you’re a longtime member or attending for the first time, this mingle makes networking feel easy and enjoyable.
Kent Island Farmers' Market at Cult Classic
January 22nd; Cult Classic Brewing Company, Stevensville 3:00pm – 5:00pm
The Kent Island Farmers’ Market brings fresh flavor and local goodness together year-round with a lively mix of vendors and community vibes. Shoppers can browse a wide array of offerings, from farm-fresh produce and grass-fed meats to eggs, sourdough breads, cheeses, olive bar favorites, and eco-friendly home and body care refills. It’s an easy, feel-good stop for stocking up on high-quality essentials, supporting local makers, and enjoying a welcoming neighborhood atmosphere. Whether you’re grabbing ingredients for the week or just popping in to see what’s new, this market is all about fresh finds and friendly faces.
Brampton 1860 Grape Expectations: A Playful Plates Party
January 22nd; Brampton Inn, Chestertown 6:00pm – 8:00pm
Shake off the winter blues with “Winter Escape: Med Edition,” a cozy, playful evening inspired by the warmth and comfort of Mediterranean gatherings. This special dinner invites guests to linger over beautifully crafted small plates, each thoughtfully paired with exceptional wines that enhance every bite. Guided by Monica Conners of DMV Distributing, the experience blends rich flavors, tradition, and great conversation into one unforgettable night. Come ready to sip, savor, and enjoy an atmosphere that feels like a mini escape—perfect for sharing good food, fine wine, and even better company.
Church Hill Theatre Presents Cabaret
January 23rd; Church Hill Theatre, Church Hill 6:30pm
Gather friends and family for a lively, feel-good cabaret evening that celebrates music, theater, and community. This family-friendly cabaret brings together familiar faces and fresh talent for an entertaining mix of songs, storytelling, and stage charm in a relaxed, welcoming setting. Expect a variety of musical moments, playful performances, and plenty of personality as performers share favorites that span styles and generations. Whether you’re a longtime theater lover or just looking for a fun night out, this cabaret offers an easygoing way to enjoy live performance, connect with others, and soak up the joy of being in the audience together.
Andrew Santino Live at The HALL at Live! Casino & Hotel Maryland
January 23rd; Live! Casino & Hotel, Columbia 9:00pm
Get ready for a night of nonstop laughs as comedian Andrew Santino takes the stage with his signature razor-sharp wit and fearless storytelling. Known for his unfiltered humor and quick-fire delivery, Santino brings the kind of comedy that feels smart, bold, and effortlessly hilarious. Fans of his hit podcasts Bad Friends with Bobby Lee and Whiskey Ginger will recognize his candid style and perfectly timed punchlines, but seeing it live is a whole different experience. Expect big laughs, honest observations, and the kind of energy that keeps the room buzzing long after the show ends. This is a must-see for comedy lovers looking for a night that doesn’t hold back.
Army Navy Double Header
January 24th; Navy Alumni Hall, Annapolis 11:00am – 4:00pm
It’s a classic rivalry showdown as Navy Men’s and Women’s Basketball face off against Army in a doubleheader packed with school spirit and competitive energy. The women tip things off at 11:00 AM, followed by the men’s game at 1:30 PM, making it a perfect day to catch back-to-back action on the court. Expect high-intensity play, plenty of pride on the line, and an electric atmosphere as these longtime rivals go head-to-head. Parking on the Yard is available for those with a DOD license, and a free shuttle will be running to make getting there easy for everyone else. Whether you’re cheering on the women, the men, or staying for both, it’s a great way to spend the day supporting Navy and soaking up the excitement.
Busch Annapolis Library Winter Film Series: Borrowed From The Bard - Shakespeare in Cinema
January 24th; Michael E. Busch Annapolis Library, Annapolis 2:00pm – 4:00pm
Shakespeare takes center stage on the silver screen with this winter film series exploring how his timeless characters and plots continue to inspire cinema. Each screening highlights a different interpretation of the Bard’s influence, from bold musicals to imaginative reimaginings, all introduced by local cinephile Ann Glenn with behind-the-scenes insights and followed by an engaging Q&A. One featured film, Kiss Me Kate (1953), screens Saturday, January 24 at 2:00 pm and brings Cole Porter’s Broadway hit to life in classic MGM Technicolor style. With dazzling choreography, a clever show-within-a-show storyline inspired by The Taming of the Shrew, and standout moments from a young Bob Fosse, this lively musical is a joyful blend of Shakespeare, song, and old-Hollywood charm.
BIGKID DANCE: If I Die Before the Revolution
January 24th; Maryland Hall, Annapolis 7:30pm – 9:00pm
BIGKID DANCE brings bold, expressive contemporary movement to the stage, led by acclaimed artistic director Mark Caserta. This Philadelphia-based queer dance community creates collaborative works that explore love, grief, curiosity, fear, and identity through a powerful and deeply human lens. Their performances blend athleticism with vulnerability, inviting audiences into moments that feel both intimate and expansive. Thought-provoking and emotionally rich, BIGKID DANCE offers an experience that resonates long after the final movement, celebrating connection, authenticity, and the beauty of shared storytelling through dance.
Winter Donkey Cuddling
January 25th; Campbells Lane Farm, Easton 11:00am – 2:00pm
Start the year on a gentle, joy-filled note with a donkey cuddling experience that’s equal parts heartwarming and grounding. Guests are invited to slow down, unplug, and spend meaningful time with a lovable herd—petting, brushing, hugging, or simply sitting together and enjoying their calm, curious presence. Each session offers a relaxed, welcoming atmosphere where the donkeys set the pace, creating natural moments of connection that melt stress away. Afterward, warm up with hot chocolate or tea by the fire pit and soak in the peaceful, cozy vibe. It’s a unique, feel-good experience that brings smiles, mindfulness, and a whole lot of donkey love.
DoArt Collage Workshop - Coasters and Boxes
January 25th; Davidsonville Family Recreational Center, Davidsonville 1:00pm – 3:30pm
Get creative with the Muddy Creek Artists Guild at this hands-on DoART workshop led by artist Martha Mihaly Black. Participants will explore collage-making in a fun, approachable way, creating a unique design on either a small box or a set of coasters. The process begins with building a larger collage, then “harvesting” smaller compositions to transform into finished pieces, complete with added color and a protective finish. No prior art experience is needed—this workshop is designed to spark creativity for beginners and seasoned artists alike. Come on your own or bring a friend and enjoy an art-filled experience that’s equal parts playful, relaxing, and inspiring.
Cult’s Open Mic
January 27th; Cult Classic Brewing Company, Stevensville 7:30pm – 9:00pm
Step into the spotlight at Cult’s Open Mic, where hidden talents and seasoned performers alike get their chance to shine. This welcoming, high-energy night invites musicians, comedians, poets, and creatives of all kinds to take the stage and share their work with an enthusiastic crowd. Performers enjoy a generous set, full stage production with lights and sound, and even a bit of that “real show” backstage feel. Whether you’re testing out new material, chasing an encore, or just soaking in the creativity from the audience, it’s a fun, supportive space that celebrates originality and bold expression. Come ready to perform, cheer, or discover your next favorite local act.
