The calendar is stacked and the season isn’t slowing down just yet. From bold New Year’s Eve celebrations and icy plunges for a good cause to glowing candlelit concerts, waterfront fireworks, and the final chances to soak in holiday magic, this week is all about closing out the year in style and jumping into the next one with energy. Whether you’re looking to dance, cruise, plunge, listen, laugh, or simply make one more great memory, these events give you plenty of reasons to get out and celebrate what makes our community so special.
2025 DUMPSTER FIRE
December 31st; Cult Classic Brewing Company, Stevensville 6:00pm – 11:00pm
Get ready to send 2025 out with a little catharsis and a lot of fun. By popular demand, Cult Classic is bringing back the legendary NYE Dumpster Fire — the ultimate way to toss out old resolutions, lingering wishes, and love notes to a year you’re ready to leave behind. Write it down, throw it in, and watch it go up in flames (safely, of course) with help from the real-life heroes at the Kent Island Volunteer Fire Department. Once the fire fades, the night keeps rolling with movies, music, and all the chaotic joy you’ve come to expect from Cult Classic. It’s bold, ridiculous, oddly therapeutic, and the perfect way to close the year in true Cult Classic style.
New Year's Eve Annapolis Yacht Party
December 31st; Watermark Journey, Annapolis 8:00pm – 10:00pm
Ring in the New Year with a front-row view and zero stress at this family-friendly celebration on the water. Step aboard a Watermark yacht for an easygoing evening filled with music from DJ Lampdawg, dancing, and festive vibes for all ages. Adults can toast with a complimentary glass of bubbly while kids stay cozy with hot cocoa, and everyone gets a prime view of Annapolis’s fireworks lighting up the sky. With a full-service bar offering alcoholic and non-alcoholic options, it’s a relaxed, memorable way to celebrate together—whether you head back out on the town afterward or call it an early night with smiles all around. Even if fireworks plans change, the cruise goes on, keeping the celebration afloat no matter what.
Viva La Captain's Daughter NYE Party
December 31st; Captains daughter Bar & Lounge, Annapolis 9:00pm – 1:00am
Ring in 2026 in true Captain’s Daughter style with a lively New Year’s Eve bash packed with great food, music, drinks, and nonstop good vibes. Your ticket includes a tasty appetizer of your choice, a complimentary midnight toast to kick off the new year, and the chance to snag fun prizes as the night unfolds. With an energetic atmosphere and discounted valet parking to keep things easy, it’s the perfect place to celebrate, toast, and start the year on a high note surrounded by festive cheer.
ATLANTIC GENERAL HOSPITAL'S 32nd ANNUAL PENGUIN SWIM
January 1st; Princess Royale, Ocean City 9:00am – 12:00pm
Start the new year with a splash — literally — at the annual Penguin Swim, a beloved winter tradition that blends bold fun with an even bigger heart. Each year, hundreds of brave participants wade into icy ocean waters to raise vital funds for Atlantic General Hospital, helping ensure high-quality, compassionate care for the community. Whether you’re plunging in yourself or cheering from the shore, the energy is contagious and the cause couldn’t be more meaningful. Every dollar raised supports healthcare heroes and keeps essential services strong for patients and families across the region. It’s cold, it’s exhilarating, and it’s all for a great reason — the perfect way to kick off the year feeling accomplished, connected, and proud to be part of something bigger.
BSO Presents Distant Worlds: music from FINAL FANTASY: Celebrating FINAL FANTASY XVI and XIV
January 2nd; Joseph Meyerhoff Symphony Hall, Baltimore 8:00pm – 10:00pm
Step into an epic musical journey as legendary conductor Arnie Roth leads a full orchestra and chorus through the unforgettable soundscapes of the FINAL FANTASY universe. Featuring powerful selections from FINAL FANTASY XVI and XIV, this immersive concert pairs sweeping symphonic performances with stunning HD visuals from SQUARE ENIX, bringing the worlds of the beloved series vividly to life. Fans will recognize and rediscover iconic compositions by Nobuo Uematsu, Masashi Hamauzu, Yoko Shimomura, and more, all performed with cinematic intensity and emotional depth. Whether you’re a longtime gamer or a lover of grand orchestral music, this multimedia experience delivers nostalgia, drama, and pure magic in every note.
Choptank Chill & Cheer!
January 3rd; Hyatt Regency Chesapeake Bay Golf Resort, Cambridge 2:00pm – 4:00pm
Bundle up and dive into something new with the first-ever Choptank Chill & Cheer, a bold and heartwarming plunge that combines winter fun with community impact. Hosted by the Cambridge Rotary Club, this spirited event invites brave participants and cheerful spectators alike to come together for a great cause while learning more about Rotary’s local mission. Expect plenty of energy, camaraderie, and feel-good vibes as the community rallies to support an important organization making a difference close to home. Whether you’re taking the plunge or cheering from the sidelines, it’s a refreshing way to kick off the season with purpose and connection.
Candlelight: Tribute to Fleetwood Mac
January 3rd; Friends of the Annapolis Symphony Orchestra, Annapolis 6:30pm – 7:45pm
Experience the music of Fleetwood Mac like you’ve never heard it before as Candlelight Concerts transform the space into an intimate, glowing escape. Surrounded by the soft flicker of hundreds of candles, this performance reimagines the band’s most iconic songs with rich instrumentation and an atmosphere that feels both nostalgic and refreshingly new. From soaring melodies to quietly emotional moments, every note feels closer, warmer, and more immersive. It’s a relaxed yet unforgettable evening that invites you to slow down, settle in, and rediscover beloved classics in a beautifully unexpected way—perfect for longtime fans and first-time listeners alike.
Lights on the Bay
January 1st; Sandy Point State Park, Annapolis 5:00pm – 9:00pm
This is your last chance to experience the magic of Lights on the Bay before the season comes to a close. The beloved drive-through tradition transforms Sandy Point State Park into a glowing two-mile journey along the Chesapeake Bay, filled with nearly 70 animated and stationary light displays that bring the roadway to life. Families can make it extra fun with the nightly scavenger hunt, encouraging kids to spot hidden details, answer display-themed questions, and enter to win prizes. With sparkling scenes around every turn and that cozy, end-of-the-year holiday feeling in the air, it’s the perfect way to soak up the season one more time before the lights go dark.
