A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of January. Event dates may be subject to change.
Photo by Steve Ruark
2026 Polar Bear Plunge
Dive into one of Maryland’s most iconic winter traditions on January 23rd to January 31st. The Polar Bear Plunge, celebrating 30 years of bold bravery and big-hearted community spirit in 2026. Each year, thousands take the icy leap into the Chesapeake Bay to support the 25,000 athletes and Unified® teammates of Special Olympics Maryland. Every dollar raised goes directly toward year-round sports and leadership programs, all provided at no cost to athletes and their families. By registering for the 2026 Plunge, you’re not just jumping into freezing water—you’re fueling inclusion, empowerment, and joy across the state. Help reach this year’s $4.75 million fundraising goal and make a splash that truly makes a difference. More info: www.plungemd.com
BSO Presents Distant Worlds: music from FINAL FANTASY: Celebrating FINAL FANTASY XVI and XIV
Legendary conductor Arnie Roth brings the world of Final Fantasy to life as he leads a full orchestra and chorus in a spectacular multimedia concert at the Joseph Meyerhoff Symphony Hall in Baltimore. On January 2–3, 2026, fans will be swept into the iconic soundscapes of the series—including music from Final Fantasy XVI and XIV—enhanced by stunning HD visuals from Square Enix. Featuring the unforgettable work of composers like Nobuo Uematsu, Masashi Hamauzu, and Yoko Shimomura, this immersive performance promises an evening of soaring themes, emotional depth, and pure nostalgia. Tickets range from $49 to $75. More info: www.bsomusic.org
Maryland Yuletide Celebrations
Celebrate an entire weekend of winter whimsy at the Maryland Yule Ball festivities, beginning with the Friday Night Winter Fantasy Ball on January 9, 2026, followed by the 7th Annual Yule Ball on Saturday, January 10, both held at the Delta Hotels Baltimore Hunt Valley. Each evening begins with a 6 p.m. cocktail hour before guests sit down to dinner and dance the night away starting at 7 p.m., surrounded by enchanting décor and a magical atmosphere worthy of a storybook celebration. Saturday also features a lively Renfaire Marketplace sponsored by Regal Threads, offering artisan wares, costuming, accessories, and whimsical goods to complete your Yule Ball experience. It’s a full weekend of fantasy, revelry, and immersive holiday fun—tickets are expected to sell quickly, so secure yours early. More info: www.mdyuleball.com
Fireside Revelry: A Colonial Twelfth Night Celebration of Music and Mischief
Fireside Revelry returns to the Hammond-Harwood House on January 10 for an enchanting candlelit concert inspired by the seasonal music, dance, and poetry once shared in 18th-century Annapolis parlors. Anchored in the festive spirit of the Twelve Days of Christmas, the evening blends elegance and mischief with English catches, Scottish airs, and American parlor songs that reflect both refined and rustic winter traditions of the early Republic. Performed inside one of Annapolis’s most storied homes, the concert features soprano Elissa Edwards, artist-in-residence, joined by guest musicians who bring colonial salon culture to life. It’s a warm, spirited way to open the semi-quincentennial year with history, harmony, and a touch of old-world revelry. More info: hammondharwoodhouse.org/event
Candlelight: Tribute to Fleetwood Mac
Candlelight Concerts return to Annapolis on January 3rd with a stunning tribute to the music of Fleetwood Mac, transforming Maryland Hall into a glowing, multi-sensory experience illuminated by hundreds of candles. Across select dates this season, guests will be treated to a 60-minute performance that reimagines the band’s iconic hits in an intimate, atmospheric setting where every note feels close and alive. Doors open 45 minutes before each show, and seating is first-come, first-served within each zone, ensuring a relaxed and welcoming evening for music lovers ages 8 and up. It’s a beautiful way to rediscover the songs you love in a whole new light. More info: marylandhall.org/events
BIGKID DANCE: If I Die Before the Revolution
Led by visionary artistic director Mark Caserta, BIGKID DANCE brings its powerful, queer-centered contemporary works to the stage at Maryland Hall on January 24th with a performance that examines love, identity, grief, curiosity, and the complexities of navigating today’s world. Based in Philadelphia, this movement community is known for its collaborative spirit and emotionally charged choreography that invites audiences to feel, reflect, and connect. With bold storytelling and intimate physicality, BIGKID DANCE creates an experience that resonates long after the final moment. Special student and group rates are available for this performance. More info: marylandhall.org
Keyshia Cole: The Way It Is 20th Anniversary Tour
Keyshia Cole brings her unmistakable voice and heartfelt storytelling to The HALL at Live! on January 18 as she celebrates the 20th anniversary of her iconic debut album, The Way It Is. Fans can relive the emotion, passion, and soulful power that made the record an instant classic, all in a high-energy performance that honors two decades of chart-topping hits and R&B legacy. Doors open at 5:30 p.m., and free parking makes the evening even easier to enjoy. More info: www.livech.com/Maryland
Army Navy Double Header
Navy men’s and women’s basketball take the court against Army on January 24, 2026, for one of the most spirited doubleheaders of the season, with the women tipping off at 11:00 a.m. and the men following at 1:30 p.m. at Alumni Hall in Annapolis. Fans can enjoy the electric rivalry atmosphere as the Midshipmen battle the Black Knights in back-to-back games that define service-academy competition. Parking is available on the Yard for those with a DOD license, and a free shuttle bus will be running for all other spectators for easy access. It’s a high-energy day of hoops, pride, and tradition you won’t want to miss. More info: navysports.evenue.net
Christmas at Gaylord National
Still holding on to the Christmas spirit? You’ve got a few days left to experience Christmas at the Gaylord, where dazzling displays, festive shows, tempting treats, and holiday activities turn the resort into a winter wonderland. Wander through ICE!, featuring breathtaking scenes from The Polar Express™ carved into towering, colorful ice sculptures, then enjoy all the seasonal magic the Gaylord is known for. Whether you’re visiting for the day or making it an overnight escape, it’s the perfect way to wrap up the holiday season with unforgettable memories. More info: www.christmasatgaylordnational.com
Brampton 1860 Winter Wedding Open House
Experience the charm of Brampton 1860 at its Winter Wedding and Event Open House on Sunday, January 4, 2026, from 12 to 3 p.m., where guests can tour the historic estate, explore ceremony spaces and guest rooms, meet the event team, and enjoy complimentary bubbly and light refreshments. Whether you’re planning an intimate elopement, a full weekend wedding celebration, or a special family gathering, this open house offers an inspiring inside look at what makes Brampton 1860 such a beloved venue. Attendees are entered to win an overnight stay, with exclusive booking discounts available during the event. Limited 2026–2027 dates remain, making this the perfect moment to secure your celebration. More info: www.eventbrite.com/e/brampton-1860-winter-wedding-open-house
Atlantic General Hospital’s 32nd Annual Penguin Swim
Start the new year with a splash at the 32nd Annual Penguin Swim on Thursday, January 1, 2026, as participants gather on the beach at the Princess Royale Oceanfront Hotel (91st Street & the Ocean, Ocean City) for a chilly dive into the Atlantic to support Atlantic General Hospital. This beloved community tradition unites individuals, teams, and local businesses to raise essential funds for the not-for-profit hospital, helping ensure vital health services and quality care across the region. Whether you’re taking the plunge or cheering from the shore, the Penguin Swim is a spirited, feel-good way to welcome the new year while honoring the Healthcare Heroes who serve the community year-round. More info: secure.qgiv.com/event/penguinswim2026
Flowerpot Snack n’ Paint Xperience
Add a splash of color to your spring at the Flowerpot Snack n’ Paint Xperience on Thursday January 1st, 8th, 15th, and 22nd from 2–4 p.m. at 9S Studios (9 South Harrison Street). Guests will unwind, snack, and create their own hand-painted flowerpots inspired by the cheerful glow of sunset daisies, guided by Chroma Pop’s vibrant artistic twist. This upbeat workshop blends creativity and relaxation, offering a welcoming studio atmosphere and all the materials you need to craft a personalized, garden-ready piece bursting with personality. Whether you’re looking to try something new, enjoy a mindful break, or bring home a creative keepsake, this is the perfect weekend escape. More info: eventbrite.com/flowerpot-snack-n-paint-xperience
Choptank Chill & Cheer!
Dive into one of Maryland’s most iconic winter traditions on January 23rd to January 31st. The Polar Bear Plunge, celebrating 30 years of bold bravery and big-hearted community spirit in 2026. Each year, thousands take the icy leap into the Chesapeake Bay to support the 25,000 athletes and Unified® teammates of Special Olympics Maryland. Every dollar raised goes directly toward year-round sports and leadership programs, all provided at no cost to athletes and their families. By registering for the 2026 Plunge, you’re not just jumping into freezing water—you’re fueling inclusion, empowerment, and joy across the state. Help reach this year’s $4.75 million fundraising goal and make a splash that truly makes a difference. More info: cambridgerotary.org
Murder at the Long Branch Saloon
Step into a Wild West parody unlike any other at “Murder at the Long Branch Saloon,” a rowdy murder mystery dinner taking place at Cult Classic Brewery on Friday, January 23, 2026, with doors opening at 6 p.m., dinner at 6:30 p.m., and the show kicking off at 7:30 p.m. Guests are summoned to a town hall meeting called by Miss Kitty West, owner of the Long Branch Saloon, where rumors swirl about MarDelVa’s most notorious outlaw strong-arming locals into giving up their land—raising the question of whether the townsfolk might finally fight back… or consider something far more sinister. The evening includes a full pre-show meal featuring endless soup, salad, and breadsticks, a hearty pasta dinner with your choice of meatballs or sausage with peppers and onions, plus cake and cannoli, along with a drink token good for draft beer or wine. It’s a deliciously chaotic blend of comedy, intrigue, and cowboy-style troublemaking that brings the Old West straight to the Chesapeake. Reserved seating is $54 per person and all sales are final.
