From live music and comedy to community gatherings, family fun, arts, sports, and hands-on experiences, the coming week is packed with ways to get out and enjoy winter in the Chesapeake region. Whether you’re cheering on Navy teams, exploring creative classes, dancing the night away, browsing vintage finds, or giving back through meaningful fundraisers, there’s something for every interest and every age. It’s the perfect mix of high-energy entertainment and feel-good local events—so bundle up, make a plan, and get ready to support the people and places that make our community shine all season long.
Weather Advisory:
Please note that event details are subject to change due to weather or other unforeseen conditions. We recommend checking with event organizers or venues before heading out, especially during winter weather. Stay safe and warm!
Naval Academy Women’s Basketball vs. Lafayette
February 4th; Annapolis 7:00pm
Cheer on Navy Women’s Basketball as they take on Lafayette in an exciting home matchup filled with fast-paced play and competitive energy. Expect strong defense, sharp shooting, and plenty of Navy pride as the Midshipmen battle it out on the court. It’s a great opportunity to support collegiate athletics and enjoy an evening of high-level basketball action.
Beginner Line Dancing
February 4th; Brooklyn Park Community Library, Baltimore 6:00pm
Kick up your heels and learn the basics at this beginner-friendly line dancing class designed for first-timers and those looking to brush up on the fundamentals. The session focuses on simple steps, rhythm, and coordination in a relaxed, welcoming environment. Come ready to move, laugh, and enjoy a fun way to stay active while learning something new.
Fairytales on Stage
February 4th; Compass Rose Theater, Annapolis 5:30pm
Step into an imaginative world where students bring original fairytales to life through movement, dance, song, and storytelling. This immersive ensemble theater program encourages creativity, collaboration, and self-expression while teaching foundational performance skills. The journey culminates in a magical presentation for family and friends, showcasing the young performers’ hard work and imagination.
G. Love & Special Sauce – Lemonade 20th Anniversary Tour
February 4th; Rams Head On Stage, Annapolis 8:00pm
Celebrate the 20th anniversary of Lemonade as G. Love & Special Sauce return to the stage with their signature blend of hip-hop, blues, funk, and soul. Known for laid-back grooves and energetic live performances, the band delivers a night full of nostalgia and feel-good vibes. Joined by special guest Makua, this show promises genre-bending sound, great storytelling, and an electric atmosphere.
Open Mic Night at Pherm Brewing
February 4th; Pherm Brewing Company, Gambrills 7:00pm
Take the stage or grab a seat for a night that celebrates local creativity and talent. Open Mic Night welcomes musicians, poets, comedians, and performers of all kinds to share their work in a supportive, laid-back setting. Whether you’re performing or cheering from the crowd, it’s a great way to discover new voices and enjoy an evening of community-driven entertainment.
Paws to Read
February 4th; Discoveries: The Library at the Mall, Annapolis 6:00pm
Help young readers build confidence and fluency by reading aloud to Sunny, a certified Pets on Wheels therapy dog. This calm, encouraging program provides a comfortable space for children to practice reading without pressure or judgment. It’s a heartwarming way to strengthen literacy skills while fostering a love of reading.
First Thursdays Karaoke at Cult
February 5th; Cult Classic Brewing Company, Stevensville 6:30pm
Step into the spotlight at First Thursdays Karaoke, where big voices and bold performances take center stage. Whether you’re a seasoned singer or a first-time performer, this lively night is all about having fun and cheering each other on. With an energetic crowd and a welcoming vibe, it’s the perfect excuse to sing your heart out.
The 2026 Chesapeake Bay Boat Show
February 5th–8th; Maryland State Fairgrounds, Timonium
Explore one of the region’s largest boating events, featuring hundreds of boats and marine exhibitors under one roof. From fishing vessels to cruisers and the latest boating gear, the Chesapeake Bay Boat Show offers hands-on exhibits, seminars, and family-friendly attractions. It’s a must-visit for seasoned boaters and curious newcomers alike.
Kent Island Farmers’ Market at Cult Classic
February 5th; Cult Classic Brewing Company, Stevensville 3:30pm
This year-round farmers’ market brings together local vendors offering fresh foods, specialty items, and everyday essentials. Browse everything from baked goods and cheeses to meats, eggs, and eco-friendly refills while enjoying a friendly, community-focused atmosphere. It’s an easy and enjoyable way to support local makers and stock up for the week.
Coffee & Wood Chips
February 6th; Chesapeake Bay Maritime Museum, St. Michaels 10:00am
Join CBMM’s Vessel Conservation Manager for a behind-the-scenes look at what’s happening in the shipyard. Over coffee, guests will learn about current restoration projects, traditional boatbuilding techniques, and maritime craftsmanship. This informal gathering offers a fascinating glimpse into preserving Chesapeake Bay heritage.
Summit’s 2026 Purse Bingo
February 6th; The Atrium at Soaring Timbers, Annapolis 5:30pm
Gather your friends for a fun-filled Galentine’s celebration featuring Bingo, designer purses, raffles, and plenty of laughs. This lively evening blends friendly competition with great food and drinks, all while supporting a meaningful cause. It’s a festive night out that combines style, fun, and community spirit.
2026 Summer Camp Fair
February 7th; Severn Run High School, Severn 10:00am
Plan ahead for summer with this family-friendly camp fair showcasing a wide variety of programs. Explore options focused on arts, sports, education, and outdoor adventure while meeting camp representatives and asking questions. It’s a helpful, one-stop opportunity for parents and kids to discover the perfect summer experience.
Naval Academy Men’s Lacrosse vs. Iona
February 7th; Annapolis 12:00pm
Watch Navy Men’s Lacrosse take the field against Iona in an exciting matchup packed with speed, skill, and strategy. Known for high-intensity play, this game promises plenty of action and school spirit. A great way to spend the day supporting Navy athletics.
5th Annual Crofton Cardinal Club Bull Roast
February 7th; Crofton Country Club 6:00pm
Enjoy a classic bull roast evening filled with great food, lively entertainment, and strong community connections. This annual event brings supporters together for a night of fun, conversation, and shared tradition. It’s a local favorite that combines good eats with great company.
Naptown Flea Vintage & Vinyl
February 7th; Maryland Hall, Annapolis 11:00am
Spend the day browsing vintage clothing, vinyl records, and one-of-a-kind finds at this laid-back market. Local DJs set the tone while great food keeps shoppers fueled. Perfect for collectors, music lovers, and anyone who enjoys the thrill of discovering something unique.
Scenic Rivers Winter Walk
February 7th; Philip Merrill Environmental Center, Annapolis 10:00am
Experience the quiet beauty of winter on a guided walk through protected woodland and shoreline trails. Led by a certified forest therapy guide, this contemplative hike encourages participants to slow down, connect with nature, and appreciate the season’s subtle charm. A peaceful, refreshing outdoor experience.
Watermark’s Scandalous Annapolis Walking Tour
February 7th; Market House Park, Annapolis 7:30pm
Discover the city’s more mischievous past on this adults-only, tongue-in-cheek walking tour. Led by a costumed colonial guide, guests hear scandalous stories of intrigue, politics, and nightlife from historic Annapolis. It’s entertaining, humorous, and full of surprising tales.
20th Annual SOUPer Bowl Lunch for the Light House
February 8th; Heritage Baptist Church, Annapolis 11:30am
Warm up with a donation-only community lunch featuring homemade soups, salad, fresh rolls, and dessert. This long-running event supports the Light House Homeless Prevention Center while bringing neighbors together for a meaningful meal. A simple, heartfelt way to give back.
Books & Beers 2026
February 10th; Cult Classic Brewing Company, Stevensville 6:00pm
Books & Beers returns with lively conversation and a new lineup of engaging reads. The evening begins with guided discussion before opening the floor to audience insights and opinions. Free and open to all, it’s a relaxed, social way to connect over books and ideas.
