SOUTHERN MARYLAND — The final week of 2025 brings plenty of opportunities to relax, recharge, and celebrate across Calvert, Charles, and St. Mary’s counties. From family-friendly winter break activities to end-of-year live music, light displays, and community fun, there’s something for everyone looking to make the most of the days between Christmas and New Year’s.
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THINGS TO DO IN CALVERT COUNTY
New Year’s Eve Events in Calvert County – Whether you’re looking for a dance party or a cozy dinner celebration, Calvert County has several ways to ring in 2026. From masquerade balls to waterfront toasts, there’s something festive for every vibe. See the full list here.
Lighthouse Keeper for a Day at Calvert Marine Museum on Dec. 26 (10 a.m.–3 p.m.), at Calvert Marine Museum, 14200 Solomons Island Road S, Solomons, MD – Kids ages 5–10 can play-act the duties of a lighthouse keeper and complete a scavenger hunt at the Drum Point Lighthouse. Ticket required.
Bring the Family to Mully’s on Dec. 27 (1–9 p.m.), at Mully’s Taproom, 141 Schooner Lane, Prince Frederick, MD – Tired of the house? Escape to Mully’s for a family-friendly taproom day with card games, coloring pages, snacks, and hot chocolate for the kids, plus local brews for the adults. Free admission.
Meet the Snow Princess on Dec. 28 (5–8 p.m.), at Annmarie Sculpture Garden, 13480 Dowell Road, Solomons, MD – Step into a winter wonderland and snap photos with the magical Snow Princess as part of the Garden in Lights celebration. Appearance included with event admission; first come, first served. Advance light show tickets required.
Teen Birding: Winter Raptor Survey on Mon. Dec. 30 (9 a.m.–1 p.m.), at Battle Creek Cypress Swamp, 2880 Grays Road, Prince Frederick, MD – Teens (ages 12–16) can join naturalist Gene Groshon for roadside raptor banding surveys to help collect local wildlife data. Travel includes van transport to sites throughout Calvert. Advanced registration required.
Hike into the New Year at Calvert Cliffs State Park on Dec. 31 (10:30 p.m.–12:30 a.m.), at Calvert Cliffs State Park, 10540 H.G. Truman Rd., Lusby, MD – Join rangers for a 3.6-mile round-trip night hike on the Red Trail to the beach, complete with a group countdown to midnight and a peaceful New Year’s start in nature. Bring a flashlight and dress for the weather. Ticket required.
WHBG 5th Annual Onesie Polar Plunge Party on Jan. 1 (10 a.m.–7 p.m.), at Wheel House Beer Garden, 4109 7th Street, North Beach, MD – Live music, food trucks, giveaways, DJ sets, and the plunge itself at 1 p.m., plus raffle and auctions to support a local family. Ticket required.
Guided First Day Hike on Jan. 1 (10 a.m.–noon), at Flag Ponds Nature Park, 1525 Flag Ponds Parkway, Lusby, MD – Start the new year with a 2-mile guided hike through nature. A park naturalist will lead the way and share insights about the site. Not stroller-friendly; advance registration required.
North Beach Polar Plunge on Jan. 1 (1 p.m. plunge time), at North Beach Boardwalk, 8916 Chesapeake Ave, North Beach, MD – Take the annual icy dip to support Ladies of Charity Calvert County. Stick around for hot chocolate, food trucks, live music, and giveaways. Registration required.
THING TO DO IN CHARLES COUNTY
New Year’s Eve Events in Charles County – Local bars and restaurants are closing out 2025 with live music, drink specials, and midnight cheers. Plan your night out or a low-key celebration close to home. See the full list here.
Meowing at the Moon Late Night Event on Dec. 26 (7–8:30 p.m.), at Feline Felons Cat Cafe, 24 Industrial Park Drive, Waldorf, MD – Monthly late-night creative craft event offering a relaxed, guided experience alongside the café’s resident cats, designed for adults looking to unwind, get creative, and connect in a cozy, welcoming atmosphere. Ticket required.
Winter Wellness Mini-Market on Dec. 27 (9–11 a.m.), at Raw Juice Market, 4455 Crain Hwy., White Plains, MD – Enjoy a relaxed Saturday morning with local vendors offering fresh greens, raw milk, cold-pressed juices, farm eggs, and more. Hosted by Simpson’s Market Garden, The Farm at Thorne Gut, and Raw Juice Market. Free admission.
Junior Billiard League on Dec. 27 (noon–3 p.m.), at World Class Billiard Room, 2720 Crain Highway, Waldorf, MD – Young players ages 12 & under and 13–17 can join the weekly league to develop skills, compete, and work toward scholarship opportunities. Adult supervision required. Ticket required.
Crank Vol.1 Holiday Jam on Dec. 27 (9 p.m.–2 a.m.), at Lamont’s Nightclub, 4400 Livingston Rd., Indian Head, MD – Grown & Sexy takes over Lamont’s with live performances from Black Print Experience and Rock Steady Project, featuring DJ Supa Dan. Ticket required.
Family Night at Chick-fil-A La Plata on Dec. 30 (5:30–7:30 p.m.), at Chick-fil-A, 107 Drury Dr., La Plata, MD – Enjoy family time with fun activities, crafts, and a free Kids’ Meal with purchase of an adult meal. Hosted the last Tuesday of each month. Free admission.
First Day Hike at Smallwood State Park on Jan. 1 (7 a.m.–sunset), at Smallwood State Park, 2750 Sweden Point Rd., Marbury, MD – Enjoy a self-guided walk along the General’s Walk Trail (~2 miles) past historic sites and wooded landscapes. Look for waterfowl and bald eagles as you explore at your own pace. Leashed pets welcome. Not stroller/wheelchair accessible. Admission required.
First Day Hike at Chapman State Park on Jan. 1 (sunrise–sunset), at Chapman State Park, 3452 Ferry Pl., Indian Head, MD – Explore the River Access and Potomac River Trails (~2.75 miles) on a self-guided walk featuring woodlands, river views, and historic landmarks near the manor house. Leashed pets welcome. Not stroller/wheelchair accessible. Free admission.
Free New Year Paintball Day on Thurs. Jan. 1 (10 a.m.–4 p.m.), at Southern Maryland Paintball, [location not specified] – Kick off 2026 with free admission, free rental marker and mask, and a full day of action-packed fun. Just bring friends and buy your paint.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
New Year’s Eve Events in St. Mary’s County – From glamorous theater bashes to champagne countdowns and DJ-fueled dance floors, St. Mary’s has plenty of ways to welcome the new year in style. See the full list here.
Holidays at Piney Point Lighthouse Museum on select dates (10 a.m.–5 p.m., closed Dec. 24–25), at Piney Point Lighthouse Museum, 44720 Lighthouse Road, Piney Point, MD – Enjoy decorated museum exhibits, holiday-themed tours, and unique gifts in the store. Special programs include candlelit evenings, a building brick challenge, and storytime with Santa & Mrs. Claus in Lexington Park. Ticket required.
All Sinners Night at The Rex on Dec. 26 (8 p.m.), at The Rex, 22695 MD-326, Leonardtown, MD – Post-Christmas dance party featuring live music from Smoke Signals and DJ PAPERS, with a festive “naughty or sinner” theme encouraging creative holiday and dark-themed costumes. Free admission.
Kids Barn Day on Dec. 27 (10 a.m.–2 p.m.), at Free Rein Equine LLC, Hollywood, MD – Hands-on barn experience for kids featuring riding activities, arts and crafts, horse care workshops, games, and stable time, with lunch and snacks included; designed for children ages 4–12, with limited spots available. Ticket required.
Pilates and Pints on Dec. 27 (10 a.m.), at Taphouse 1637, 23418 Three Notch Road, California, MD – Join instructor Emma Fowler for a fun and energizing full-body pilates session followed by a well-earned pint. Hosted by Taphouse 1637. Ticket required.
Family Roller Skating at Leonard Hall on Dec. 28 (2–5 p.m.), at Leonard Hall Recreation Center, 23145 Leonard Hall Drive, Leonardtown, MD – Weekly family skate session hosted by St. Mary’s County Recreation & Parks with open skating for all ages. Skate rentals available on site. Ticket required.
Little Mania Wrestling: All Out Mayhem on Dec. 28 (doors 4 p.m., show 5 p.m.), at The Rex Theatre, 22695 Washington St., Leonardtown, MD – A high-energy, 21+ wrestling event featuring top stars from the Little Mania World Tour. Standing room and VIP table options available. Ticket required.
First Day Hike at St. Mary’s River State Park on Jan. 1 (7 a.m.–sunset), at St. Mary’s River State Park, 21250 Camp Cosoma Rd., Leonardtown, MD – Take a self-guided hike along the White Trail (7.5 miles) through scenic forest. Start at the Camp Cosoma parking lot and follow the white blazes. Leashed pets welcome. Not stroller/wheelchair accessible. Admission required.
First Day Hike at Greenwell State Park on Jan. 1 (1 p.m.), located at Greenwell State Park, 25420 Rosedale Manor Rd., Hollywood, MD – Start the new year with a ranger-led 1.5-mile hike along the Brown Trail. Meet at the pavilion and dress for the weather, as the trail may be muddy and slightly hilly. Leashed pets welcome. Portable restrooms available. Admission required.
Toots Uno Tournament on Jan. 1 (3 p.m.), at Toots Bar, 23971 Mervell Dean Rd, Hollywood, MD – Kick off the year with a competitive Uno showdown. Free entry; RSVP encouraged.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – December 26th
5:00pm – Carla Simpson – Mully’s Brewery – Prince Frederick MD
5:00pm – I & I Riddim – Wheel House Beer Garden – North Beach MD
7:00pm – Shawn & Andy – Neptune’s Seafood Pub – North Beach MD
7:00pm – Mike Mead – O’Gannigan’s Irish Pub – Prince Frederick MD
8:00pm – Smoke Signals – The Rex Theatre – Leonardtown MD
8:00pm – HydraFX – Toots Bar – Hollywood MD
Saturday – December 27th
2:00pm – Bob Pinnola & Rosa Hance- POL Winery – Leonardtown MD
6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Troll Tribe – Wheel House Beer Garden – North Beach MD
6:00pm – Byron Ciotter – Pax River Ale House – Lexington Park MD
7:00pm – Nightcap – The Brass Tap – California MD
7:00pm – Chappel – Neptune’s Seafood Pub – North Beach MD
7:30pm – John Luskey – Killarney House Irish Pub – Davidsonville MD
8:00pm – Pork Donut – Toots Bar – Hollywood MD
8:00pm – Taboo – Buckets Bar & Grill – Lusby MD
8:00pm – HydraFX – The Tavern – Saint Leonard MD
8:30pm – Bangerz Only – Ollie’s Bar & Grill – La Plata MD
9:00pm – Myles Deep Band – 219 Restaurant – Alexandria VA
9:30pm – Joe Cox / Trace Haggard – Huntt’s Tavern – Pomfret MD
Sunday – December 28th
2:00pm – Levi Stephens – Port of Leonardtown Winery – Leonardtown MD
Monday – December 29th
6:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – December 30th
5:00pm – Jason Bishop – Heritage 485 – Prince Frederick MD
7:00pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – December 31st – New Years Eve
6:30pm – Lissie Deere – Bugeye Grill – Solomons MD
8:00pm – HydraFX – The Scuttlebutt – Cobb Island MD
8:00pm – Never 2 Late – Toots Bar – Hollywood MD
9:00pm – South Creek – Seabreeze Restaurant – Mechanicsville MD
9:00pm – River Rock Band – Water View Inn – Bushwood MD
9:00pm – Southland – Wheel House Beer Garden – North Beach MD
New Years Eve – DJ’s & Karaoke
6:00pm – Kids Karaoke – The Taphouse 1637 – California MD
7:00pm – DJ Magic Rick – O”Gannigan’s Irish Pub – Prince Frederick MD
8:00pm – DJ – Russell’s Store & Bar – Valley Lee MD
8:00pm – Duncan Deejay’s Karaoke – OCI Pub/Pizza King – Piney Point MD
8:30pm – DJ Just Jeff – Ollie’s Bar & Grill – La Plata MD
9:00pm – DJ SammySammz & DJ Ernie – The Rex Theatre – Leonardtown MD
9:00pm – DJ Rick – Twisted Bar & Grill – Hollywood MD
9:00pm – DJ Kitty Scratches Karaoke – The Tavern – Saint Leoard MD
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