Photography by Steve Ruark
A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of January. Event dates may be subject to change.
Photography by Steve Ruark
Polar Bear Plunge
One of the most-anticipated Maryland traditions closes out January. Plunge into the icy waters of the Chesapeake Bay to raise money for Special Olympics Maryland. There are plenty of special plunges leading up to the official plunge on February 1st at Sandy Point State Park. The Cool Schools plunges will take place on January 29th and 30th, the Police Plunge will be on January 31st, Corporate Plunge on January 31st, and, of course, the Super Plunge (can you handle plunging 24 times in 24 hours?). Push yourself to the limit while raising money for Special Olympics Maryland. Sign up at plungemd.com.
Chesapeake Bay Boat Show
Over 30 Maryland boat dealers with new boats, marine equipment, sportfishing boats, performance boats, ski boats, cruisers, and more will be at the 4th Annual Chesapeake Bay Boat Show on January 10th through 12th at the Maryland State Fairgrounds. Enjoy entertainment, food, beverages, educational seminars, and plenty of vendors throughout the weekend. Find more information at thechesapeakebayboatshow.com.
Dr. Martin Luther King, Jr. Awards Dinner
On January 15th, the 37th Annual Dr. Martin Luther King, Jr. Awards Dinner will be at Maryland Live in Hanover, hosted by The Martin Luther King, Jr. Committee of Maryland. Radio host, renown journalist, author, and political commentator Clay Cane will be the keynote speaker for the event. This is the largest celebration of Dr. King’s birthday in Anne Arundel County, be sure to get your tickets at mlkjrmd.org.
Photo credit Joe Haupt
AMFM Tribute to Carole King Benefit Concert
Annapolis Musicians Fund for Musicians, Inc. (AMFM) will present A Tribute to Carole King on January 26th at Rams Head On Stage. In collaboration with the Songbird Collective, the show will feature local artists performing the time-honored works of the legendary Carole King. Proceeds directly benefit the organization, created in 2006 to provide temporary financial relief to professional Annapolis musicians who cannot work due to sickness, injury, or any other circumstance leaving them unable to perform. Learn more at am-fm.org.
Maryland Yule Ball Celebration
The 2025 Maryland Yule Ball is the perfect time to celebrate the end of the holiday season in your finest 16th to 19th century garb. Eat, dance, and be merry in your Tudor-to-Victorian era dress on January 4th at the DoubleTree in Annapolis. Get your tickets at mdyuleball.com.
Monster Jam
The Monster Jam tour is back in Baltimore January 17th through 19th. Get your adrenaline pumping with the most action-packed motorsports event on four wheels. Witness world-class driver athletes and the most recognizable trucks tear up the dirt and compete in intense competitions of speed and skill. The performances will be at 7 p.m. on January 17th and 18th and 1 p.m. on January 19th all at CFG Bank Arena in Baltimore. Get tickets at cfgbankarena.com.
Photo by Chris Parypa Photography
Penguin Swim
Atlantic General Hospital’s 31st Annual Penguin Swim is back to kick off the new year! On January 1st, plunge into the ocean in front of Princess Royale Oceanfront Resort in Ocean City to support our community’s healthcare heroes. This event supports Atlantic General Hospital, a not-for-profit community hospital that provides care to the Eastern Shore. Find more information at aghpenguinswim.org.
Music is Healing Disaster Relief Show
Kick off the new year in a special way. Music is healing, and there are many who need to be healed after Hurricanes Helene and Milton. A special benefit concert with Burnsie, Heather Britt, Madisun Bailey, and Joe Esham will be held on January 4th from 12 to 4 p.m. at Cult Classic Brewing Company in Stevensville. The goal is to raise money to benefit those affected in North Carolina and Florida. Music is healing! Learn more and get tickets at cultclassicbrewing.com/events.
Photo courtesy of Academy Art Museum
Bugatti
The Academy Art Museum in Easton opened its most ambitious exhibition to date, Bugatti: Reaching for Perfection, in December. The exhibition continues through April and will feature rare automobiles, sculpture, and furniture by the Bugatti family, along with other objects and ephemera related to the renowned marque. Highlights include two grand prix race cars, two Type 57 touring cars, and a miniature “Baby.” Learn more at academyartmuseum.org.
Cambridge Ice & Oyster Festival
Since a snowstorm in 2022, a weekend in January has been dedicated to ice and oysters in Cambridge. The 4th Annual Cambridge Ice & Oyster Festival will take over Downtown Cambridge January 17th and 18th with over 50 ice sculptures and an expected 8,000 visitors. Bring the whole family for golf, thrones, and an ice slide made of ice, sculptures showcasing Eastern Shore culture, ice bars with craft beer and local oysters, a s’mores fire pit, and, new this year, an ice rink at the Hyatt. There will be a shuttle between the Hyatt, Downtown, and the Packing House (where you can enjoy the Friday night kick-off event). Find more information at iceoysterfest.com.
