SOUTHERN MARYLAND — The final days before Christmas bring a full weekend of seasonal events across Southern Maryland, with festive traditions, parades, and last-minute shopping opportunities filling the calendar. Explore decorated exhibits and history during Holidays at Piney Point Lighthouse, enjoy a holiday weekend at A Casual Christmas at Mount Chance Farm, or catch Santa and the Grinch popping up at events in every county. From breakfasts with Santa to markets and live music, this week offers plenty of ways to celebrate, reflect, and make memories close to home.
Check out this week’s regional guides for Santa & Grinch Sightings, Holiday Bazaars, and more holiday happenings through Dec. 25.
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THINGS TO DO IN CALVERT COUNTY
Santa & Grinch Sightings in Calvert County – From firetruck parades to surprise store visits, you never know where Santa or the Grinch might pop up across the county this final holiday weekend. See full list here.
Holiday Bazaars in Calvert County– Finish your shopping with festive markets, ornament pop-ups, and local vendor events happening throughout the region in the days leading up to Christmas. See full list here.
Dramatic Reading of The Polar Express on Dec. 19 (5:30 and 7 p.m.), located at Chesapeake Beach Railway Museum, 4155 Mears Avenue, Chesapeake Beach, MD – A special reading of the classic book inside a historic railcar, followed by hot chocolate and cookies at the Rod ‘N’ Reel Hotel. Ticket required.
Kids Night Out on Dec. 19 (5:30 to 8:30 p.m.), located at Southern Community Center, 20 Appeal Lane, Lusby, MD – Evening drop-off program with fun games and activities for kids while parents enjoy a night off. Ticket required.
Parents’ Night Out on Dec. 19 (6:30 to 9 p.m.), located at Mt. Hope Community Center, 104 Pushaw Station Road, Sunderland, MD – Adults can enjoy a relaxing night out while children are entertained with supervised games and activities. Ticket required.
Breakfast With Santa on Dec. 20 (8 a.m. to noon), located at Prince Frederick Volunteer Rescue Squad Company 4, 755 Solomons Island Road South, Prince Frederick, MD – Enjoy a festive breakfast with Santa, photos, and holiday fun hosted by the local rescue squad. Ticket required.
Breakfast with Santa and Sheriff Ricky Cox on Dec. 20 (8 to 10:30 a.m.), located at Bulrushes Cafe, 135 Central Square Drive, Prince Frederick, MD – Families can enjoy breakfast and take photos with Santa during a festive morning community event. Ticket required.
Snowman Making Workshop on Dec. 20 (9 a.m. to noon), located at University of Maryland Extension Calvert County 4-H, 30 Duke Street, Room 103, Prince Frederick, MD – Participants can create sock snowmen and felt ornaments while enjoying snacks and music during a hands-on holiday craft workshop. Free admission; registration required.
Santa Claus Is Cruisin’ the Town on Dec. 20 (1 to 4 p.m.), located throughout North Beach, MD – Santa makes neighborhood rounds by firetruck for an afternoon of cheerful visits and small-town holiday spirit. Free admission.
Holiday Parade on Dec. 20 (4 p.m.), located along St. Leonard Road, beginning at Mattapany Road and ending at Calvert Beach Road, St. Leonard, MD – The St. Leonard Volunteer Fire Department invites the community to line the streets for their annual holiday parade. Free admission.
Jingle All The Hay: A Festive & Magical Holiday Experience on the Farm on Dec. 20–21 (5 to 9 p.m.), located at Mrs. Moo’s Corner at Spider Hall Farm, 3915 Hallowing Point Road, Prince Frederick, MD – A festive holiday farm experience featuring synchronized light displays, hayrides, animal encounters, Santa visits, crafts, and seasonal activities for all ages. Ticket required.
Beyond the Displays: Artifact Stories on Dec. 21 (1:30 to 2:30 p.m.), located at Calvert Marine Museum, 14200 Solomons Island Road South, Solomons, MD – Take a guided tour exploring the hidden stories behind the museum’s artifacts and how World War II shaped the Solomons region. Included with admission.
For more Calvert County events, visit the Calvert County Maryland website.
THING TO DO IN CHARLES COUNTY
Santa & Grinch Sightings in Charles County – From firetruck parades to surprise store visits, you never know where Santa or the Grinch might pop up across the county this final holiday weekend. See full list here.
Holiday Bazaars in Charles County – Finish your shopping with festive markets, ornament pop-ups, and local vendor events happening throughout the region in the days leading up to Christmas. See full list here.
Reindeer Games on Dec. 19 (2 to 4 p.m.), located at Chick-fil-A La Plata, 107 Drury Drive, La Plata, MD – Kids and families can kick off holiday break with festive games, food, and clowning-around fun featuring Bunkey & Blondi during an after-school celebration. Free admission.
Christmas on the Farm at Pop Pop’s Greenhouse on Dec.(5 to 9 p.m.), located at Pop Pop’s Greenhouse, 13340 Rock Point Rd., Newburg, MD – Enjoy a festive evening with a lighted music trail, 150-foot lighted slide, outdoor movies, bonfires, arts and crafts, Santa and Grinch appearances, a huge playground, and sweet treats from Emma’s Place Bakery and The Sip Society, with admission covering all activities. Ticket required.
Lowe’s Kids Workshop: Sleigh Ride on Dec. 20 (10 a.m.–1 p.m.), at Lowe’s Home Improvement, 2525 Crain Hwy, Waldorf, MD – Free, in-store kids workshop where children can build a festive sleigh ride–themed project with hands-on guidance; supplies included while they last. Free; registration required.
Bedtime Tales with the Grinch & My Gym Elves on Dec. 19 (times vary), located at My Gym Waldorf, 1148 Smallwood Drive, Waldorf, MD – Holiday fun for children ages 0 to 11 featuring Grinch storytime, STEM activities, an obstacle course, dance party, and photos with the Grinch and My Gym Elves. Ticket required.
Pastries with Pinch! on Dec. 20 (8 to 11 a.m.), located at Regency Furniture Stadium, 11765 Saint Linus Drive, Waldorf, MD – Family-friendly morning of holiday crafts, pastries, and photos with Santa and Pinch. Free admission.
Breakfast with Santa on Dec. 20 (10 a.m.), located at Bad Axe Waldorf, 1140A Smallwood Drive, Waldorf, MD – Enjoy breakfast, crafts, and photo opportunities with Santa in a festive axe-throwing venue. Ticket required.
Mr. Grinch Brings Whoville to Waldorf on Dec. 20 and 21 (noon to 5 p.m.), located at The Shops at Waldorf, 3070 Festival Way, Waldorf, MD – The plaza transforms into Whoville with Grinch photos, snacks for sale, and a free cupcake for the first 25 visitors each day. Ticket required.
James E. Richmond Science Center Holiday Dome Shows on Dec. 20 (evening showtimes between 5 and 7:30 p.m.), located at James E. Richmond Science Center, 5305 Piney Church Road, Waldorf, MD – Enjoy the festive “Let It Snow” dome movie alongside James Hood’s immersive “Beautifica: A Celebration of Life,” with full-dome visuals, music, and access to interactive science exhibits for all ages. Ticket required.
125th Anniversary of Radio’s First Voice on Dec. 23 (10 a.m. to 2 p.m.), located at Fisherman’s Field, Cobb Island Road and Neale Sound Drive, Cobb Island, MD – Celebrate the first successful radio voice broadcast with a commemorative station and half-hourly reenactments hosted by the Charles County Amateur Radio Club. Free admission.
St. Charles Towne Center Santa Photo Experience through Dec. 24 (times vary), located at St. Charles Towne Center, 11110 Mall Circle, Waldorf, MD – Visit Santa daily at the mall with walk-up photo opportunities and flexible scheduling throughout the day. Ticket required.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
Santa & Grinch Sightings in St. Mary’s County– From firetruck parades to surprise store visits, you never know where Santa or the Grinch might pop up across the county this final holiday weekend. See full list here.
Holiday Bazaars in St. Mary’s County– Finish your shopping with festive markets, ornament pop-ups, and local vendor events happening throughout the region in the days leading up to Christmas. See full list here.
Holidays at Piney Point through December (10 a.m. to 5 p.m.), located at Piney Point Lighthouse Museum and Historic Park, 44720 Lighthouse Road, Piney Point, MD – Explore the decorated lighthouse, Keeper’s Quarters, and museum with festive seasonal exhibits and guided tours for all ages. (closed Christmas Eve and Christmas Day). Ticket required.
Folk Salad Luncheon on Dec. 19 (11:30 a.m. to 1:30 p.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Lane, Leonardtown, MD – Enjoy live acoustic music from Folk Salad with lunch served at noon and performances beginning at 12:30 p.m.; advanced registration encouraged. Ticket required.
A Casual Christmas @ Mount Chance Farm on Dec. 19–21 (times vary), located at Mount Chance Farm, 23713 Mount Chance Farm Lane, Clements, MD – A laid-back, family-friendly holiday weekend featuring pony rides, hayrides, train rides, Santa visits, games, cocoa, s’mores, local vendors, and festive activities across the decorated barn and farm. Ticket required.
SMTMD HomeSpun CoffeeHouse Holiday Open Mic & Potluck on Dec. 19 (6:30 to 9 p.m.), located at Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – All are welcome to enjoy local music, bring a dish for the potluck, and participate in a holiday-themed open mic night. Ticket required.
Toots Christmas Party on Fri., Dec. 19 (7 to 11 p.m.), at Toots, 23971 Mervell Dean Road, Hollywood, MD – Holiday carol karaoke contest with festive drinks and singing, plus a stop on the Christmas Crawl benefiting A Message of Hope, organized by Brandy Sutor in memory of Rob Sutor, with the crawl portion starting at 9:15 p.m. Free; open to the public.
Lowe’s Kids Workshop: Sleigh Ride on Dec. 20 (10 a.m. to 1 p.m.), at Lowe’s Home Improvement, 45075 Worth Ave, California, MD– Free, in-store kids workshop where children can build a festive sleigh ride–themed project with hands-on guidance; supplies included while they last. Free; registration required.
Pictures with Santa on Dec. 20 (9 a.m. to 5 p.m.), located at Town Market LLC, Leonardtown, MD – Full-day holiday photo event with Santa and local vendor shopping. Free admission.
Santa Claus Is Coming to CMA’s Hyundai of Lexington Park on Dec. 20 (9 to 11 a.m.), located at CMA’s Hyundai of Lexington Park, 22515 Three Notch Road, Lexington Park, MD – Stop by the showroom for festive photos with Santa and a morning of family-friendly holiday cheer. Free admission.
Last Chance Christmas Market on Dec. 20 (noon to 5 p.m.), located at Dixon Family Farm, Mechanicsville, MD – Shop final holiday gifts and seasonal décor at this end-of-season outdoor vendor market. Free admission.
Grinch Garbage Grab on Dec. 20 (1 to 3 p.m.), located at Greenwell State Park, Hollywood, MD – Join a community beach trail cleanup with environmental groups; trash bags provided, Grinch costumes encouraged. Free admission.
Breakfast with Santa on Dec. 21 (9 to 11 a.m.), located at Botanic Café, 22720 Duke Street, Leonardtown, MD – Celebrate the season with a festive breakfast, cocoa bar, and Santa photos in a cozy café setting. Ticket required.
Sunday Fun Day on Dec. 21 (noon to 10 p.m.), located at Action Lounge & Billiards, 25470 Point Lookout Road, Leonardtown, MD – A full day of casual holiday fun with free pool, free cornhole, free darts, kids’ junior league play in the afternoon, and discounted axe throwing in a festive, family-friendly atmosphere. Free admission.
Meet the Grinch at Annmarie Garden In Lights on Dec. 21 (5 to 8 p.m.), located at Annmarie Sculpture Garden & Arts Center, 13480 Dowell Road, Solomons, MD – Meet the Grinch and snap photos during your Garden In Lights visit; appearance location varies by weather. Ticket required.
Drive-Thru Children’s Christmas Party on Dec. 21 (5 to 7 p.m.), located at Mechanicsville Volunteer Fire Department, 28165 Hills Club Road, Mechanicsville, MD – Kids can wave to Santa, drop off wish lists, and receive stockings from the comfort of the car. Free admission.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – December 19th
4:00pm – Alex Barnett – Truman Vineyard & Winery – Aquasco MD
5:00pm – Billy Breslin – Green Turtle Sports Bar – California MD
5:00pm – Jack Allen – Mully’s Brewery – Prince Frederick MD
5:00pm – Joseph Norris – Snellman’s Store & Shuck Shack – Hollywood MD
5:30pm – Wes Ryce – The Local – Hollywood MD
6:00pm – WIP Acoustic – Helen’s Cafe – Leonardtown MD
6:00pm – Myles Deep Band – Wheel House Beer Garden – North Beach MD
6:00pm – Doc Lohn – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Davis Norris & Keith Arneson – The Ruddy Duck – Solomons MD
7:00pm – Daniela Bubb – Antoinette’s Garden Wine Bar – Leonardtown MD
7:00pm – Dust on the Bottle – O’Gannigan’s Pub – Prince Frederick MD
7:30pm – Kevin Lee – Pirate’s Cove Dock Bar – Galesville MD
8:00pm – Mistlefoes Comedy Show – Twisted Bar & Grill – Hollywood MD
8:00pm – Shane Graham – Action Lounge & Billiards – Leonardtown MD
8:30pm – HydraFX – Ollie’s Bar & Grill – La Plata MD
Saturday – December 20th
2:00pm – Monkey Busness – Port of Leonardtown Winery – Leonardtown MD
2:00pm – South Co. Musicians Alliance – Robin Hill Farm – Brandywine MD
5:00pm – Hamner & Dean – Southern Trail Distillery – Mechanicsville MD
6:00pm – Nightcap – The Local – Hollywood MD
6:00pm – Ryan Forrester – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – WIP Acoustic – Pax River Ale House – Lexington Park MD
6:00pm – Catey Peters – Baia Coastal Kitchen – Chesapeake Beach MD
6:00pm – Jeremy Robinson – Brick Wood Fired Bistro – Prince Frederick MD
6:00pm – Three of a Kind – Wheel House Beer Garden – North Beach MD
7:00pm – Byron Ciotter – The Brass Tap – California MD
7:00pm – John Luskey – Lord Calvert Bowling Center – Huntingtown MD
7:00pm – Richard Hayward – Neptune’s Seafood Pub – North Beach MD
7:00pm – Chesapeake Sons – The Potomac Gardens – Coltons Point MD
7:00pm – Slam The Xmas Tree – The Tavern – Saint Leonard MD
——— Crow Hunter, Space Lumberjacks, Coast Is Clear,
———- Molldyer & Screaming Mad Dee Calhoun –
7:30pm – Hyland Brothers – Pirate’s Cove Dock Bar – Galesville MD
8:00pm – 5 South – Toots Bar – Hollywood MD
8:00pm – Jason Bishop – Russell’s Store & Bar – Valley Lee MD
8:00pm – Whistlin’ Kitty Chasers – Buckets Bar & Grill – Lusby MD
8:00pm – Mike Damron – Olde Town Pub – Leonardtown MD
8:00pm – Girl Crush – Cryer’s Back Road Inn – Lenardtown MD
8:00pm – Double Duran (Duran Duran tribute) – The Rex – Leonardtown MD
8:00pm – Nice & Naughty Rock Show – O’Gannigan’s – Prince Frederick MD
——— shallowDeep, Buffalo Velcro, Redgate
———- The Young Swains & Red Skies Dawning –
9:00pm – Steve Potter Blues Band – Huntt’s Tavern – Pomfret MD
Sunday – December 21st
9:30am – Lissie Deere – Bugeye Grill – Solomons MD
2:00pm – Shortcut Sunny – Port of Leonardtown Winery – Leonardtown MD
3:00pm – Doug Segree – Pirate’s Cove Dock Bar – Galesville MD
3:00pm – Derek Norris – Toots Bar – Hollywood MD
Monday – December 22nd
4:00pm – Wes Ryce – Rucci’s Italian Kitchen & Grille – Leonardtown MD
6:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – December 23rd
5:00pm – Mike Ferro – Heritage 485 – Prince Frederick MD
6:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
6:00pm – Wes Ryce, Moe Owens & JZ – Apehangers Bar – Bel Alton MD
7:00pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
7:00pm – Multi Artist Christmas Jam – The Tavern – Saint Leonard MD
7:00pm – Justin Myles & The Prophessor – Buckets Bar & Grill – Lusby MD
Wednesday – December 24th – Christmas Eve
4:00pm – Ben Connelly – Bugeye Grill – Solomons MD
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