SOUTHERN MARYLAND — Halloween is just a week away, and Southern Maryland is packed with spooky fun for all ages. From haunted houses and costume parades to fall festivals and trunk-or-treats, there’s something happening in every corner of the region. Families can enjoy pumpkin patches, trick-or-treat trails, and community fairs, while adults dive into haunted tours, live music, and festive nightlife. Whether you’re after jump scares, family adventures, or pumpkin spice everything, this week offers plenty of ways to celebrate the season across Calvert, Charles, and St. Mary’s counties.
To have your upcoming event featured, please enter your event information on our Events Calendar.
THINGS TO DO IN CALVERT COUNTY
Trunk-or-Treats in Calvert County on Oct. 24–30 – Celebrate Halloween safely at community favorites including Frightfully Fun Halloween Celebration, Halloween in the Garden, Unity in the Lot: Trunk, Treat & Eat, and Halloween at Hallowing Point Park. More fun continues with North Beach Boo Bash, Chesapeake Beach Family Fun Night, Mrs. Moo’s Tract-or-Treat, and the Calvert Nursery School Trunk-or-Treat.
Bad Art Night at Annmarie on Oct. 24 (4:30 to 6:30 p.m.), at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons, MD – Enjoy an outrageous evening of unconventional art-making just for adults! Create your own “bad art” with provided supplies, then vote for “The Best of the Worst.” The night includes prizes, lively music, and a cash bar featuring Annmarie Wine Bar, Mully’s Brewery, and Bowl 29. $7 per person (21+); members free.
Halloween Fun Day in North Beach on Oct. 25 (noon–evening), at North Beach Boardwalk and Waterfront, 9023 Bay Avenue, North Beach, MD – Enjoy a full day of festivities with the Hound of the Town dog parade, the 16th Annual Boo Bash costume contest, trick-or-treating, and a dusk showing of Beetlejuice Beetlejuice on the beach. Free admission; $10 dog parade entry.
Art in the Garden: Autumn Leaves on Oct. 25 (9 a.m. to 2 p.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD – Celebrate the beauty of fall with art activities inspired by the season. Free with registration.
Fall Birding at Jefferson Patterson Park and Museum on Oct. 25 (9 to 11:30 a.m.), located at 10515 Mackall Road, St. Leonard, MD – Led by Phin Rouland, this trip explores wooded trails, open fields, and waterfront views for diverse bird sightings. Free admission. Join the Audubon Society to support bird conservation in our region.
Halloween BinGLOW! on Oct. 25 (8 p.m.), at Rod ‘N’ Reel Resort: The Overlook, 4150 Mears Avenue, Chesapeake Beach, MD – Enjoy a spooktacular glow-in-the-dark Halloween bingo night with exciting prizes, costumes, and mini-game challenges for extra wins. $40 plus fee; limited to 100 tickets.
Festival in the Park on Oct. 26 (11 a.m. to 3 p.m.), at Kings Landing Park, 3255 Kings Landing Road, Huntingtown, MD – Enjoy a day of live music from local artists and bands, guest speakers on mental health and family life, kids’ activities, and a resource fair featuring more than 90 free community services, plus horses and animals. Free admission.
Beyond the Displays: Artifact Stories on Oct. 26 (1:30–2:30 p.m.), located at Calvert Marine Museum, 14200 Solomons Island Rd. S., Solomons, MD – Join a guided exploration uncovering the stories behind the museum’s historic artifacts, from paddle wheel boat emblems and blacksmith tools to WWII-era exhibits and hidden mural details. Included with museum admission.
Witch Hats, Moons and Jack-O-Lanterns on Oct. 27 (1 to 3 p.m.), at Kocen Arts Center, 22 Duke Street, Prince Frederick, MD – Create your own whimsical watercolor art featuring witch hats, moons, and pumpkins in this guided class led by Tara Tokarski. All supplies provided; open to ages 12 and up. $35 per person.
Astronomy Night on Oct. 28 (7 to 8 p.m.), at Fairview Branch Library – Field Behind Library, 8120 Southern Maryland Boulevard, Owings, MD – Explore the wonders of the night sky with the Astronomy Club of Southern Maryland. Learn about stargazing equipment and celestial sights during this all-ages outdoor event (weather permitting). Free admission.
Halloween Pup Parade on Oct. 30 (10:30 to 11 a.m.), at Dunkirk District Park, 10750 Southern Maryland Boulevard, Dunkirk, MD – Dress your pup in costume and parade through the park for a chance to win prizes. All dogs must be leashed and friendly.
Free admission; pre-registration encouraged.
For more Calvert County events, visit the Calvert County Maryland website.
THING TO DO IN CHARLES COUNTY
Trunk-or-Treats in Charles County on Oct. 24–30 – Family favorites include Fall Fest at Westlake High School, Spooky Fall Fest at the Shops at Waldorf Center, Connect Church Trunk-or-Treat, and Dr. Higdon Elementary’s event, plus Charles County Sheriff’s Office Trunk-or-Treat, Westlake Volunteer Fire Department’s “Get Spooky,” and La Plata’s Trick-or-Treat Trail.
Halloween Drive Thru on Oct. 24 (7 to 9 p.m.), at Hughesville Volunteer Firehouse, 15245 Prince Frederick Road, Hughesville, MD – Cruise through a festive Halloween display hosted by the Ladies Auxiliary to the HVFD & EMS, featuring spooky scenes and sweet treats for the whole family. Free admission.
Fall Book Bazaar Bag Days on Oct. 24–25 (10 a.m. to 4 p.m.), at La Plata Branch Library, 2 Garrett Avenue, La Plata, MD – Shop thousands of gently used books, movies, and more, with “Bag Day” discounts on Saturday where you can fill a grocery-sized bag for just $3. All proceeds benefit Charles County Public Library programs.
Vampire Manor on Oct. 24–25 (7 to 11 p.m.), at Bel Alton Volunteer Fire Department, 9765 Bel Alton–Newtown Road, Bel Alton, MD – Begin your fright-filled adventure at the firehouse before being guided to the chilling two-story Vampire Manor, where ghostly apparitions and spine-tingling scares await. This annual Halloween tradition supports the Charles County Dive Rescue Team and the Bel Alton Volunteer Fire Department. $15 adults; $10 children (12 & under).
La Plata High School – Murder on the Orient Express on Oct. 24–25 (6:30 p.m.), at La Plata High School, 6035 Radio Station Road, La Plata, MD – A thrilling mystery unfolds aboard a snowbound train where every passenger hides a secret. Tickets available through CCPS school sites.
SMCPS 10th Annual STEAM Festival on Oct. 25 (10 a.m. to 2 p.m.), at St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD – Celebrate science, technology, engineering, arts, and math at this family-friendly festival featuring interactive exhibits, hands-on activities, food, and fun for all ages. Free admission.
Halloween Blaster Battle on Oct. 25 (check-in 11:30 a.m., games noon to 4 p.m.), at Charles County Fairgrounds, 8400 Fairground Road, La Plata, MD – Join Southern Maryland House of Nerf for a high-energy Halloween showdown featuring stock, modded, and competitive blaster rounds. Open to ages 7 and up (under 16 with adult). Eye protection required; players must sign an online waiver before participating. Tickets available.
Saturday with Stone Plessure and DJ Bubb on Oct. 25 (7 p.m. to midnight), at Martinis of White Plains, 10553 Theodore Green Boulevard, White Plains, MD – Enjoy a night of live R&B and soul with Stone Plessure, plus mixes by DJ Bubb. Doors open at 6 p.m.; food available for purchase. $20 admission.
Assault Wrestling Alliance Presents Brutality Reigns 2 on Oct. 25 (doors 6 p.m., bell time 7 p.m.), at Unique Sports Academy, 109 Post Office Road, Waldorf, MD – Southern Maryland’s Assault Wrestling Alliance returns for a Halloween-weekend showdown featuring top AWA champions and rising stars. Tickets available.
Rec Xpress Fall Festival on Oct. 26 (1 to 4 p.m.), at Bensville Park, 6980 Bensville Rd., Waldorf, MD – Spend an afternoon of free family fun featuring community vendors, a DJ, food trucks, face painting, costume contests, safe trick-or-treating and more. Free admission.
TNA Fest 2025 on Oct. 26 (11 a.m. to 2 p.m.), at Truck’n America, 2130 Old Washington Road, Waldorf, MD – Enjoy a Halloween-themed truck, car, and bike show featuring classic rides, live music, food, raffles, and fun for the whole family. Prizes awarded for Best Decorated Vehicle and Kids’ Best Halloween Costume, with proceeds benefiting the Charlotte Hall Veterans Home. Vehicle registration $25; trunk-or-treat entry $10.
SoMD Savor the Flavor on Oct. 26 (4 to 8 p.m.), located at The Pavilion at Weatherly, 14145 Banks Odee Road, Newburg, MD – Enjoy an evening of food tastings, cocktails, casino games, a live band, and more at this signature Charles County Chamber of Commerce event presented with K&I Healthcare Services. VIP guests will enjoy a culinary experience with celebrity chef Anthony Thomas. Tickets available.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
Trunk-or-Treats in St. Mary’s County on Oct. 24–30 – Enjoy family fun at Lyon Family Farms’ Fall Friday Night on the Farm, Historic St. Mary’s City’s “Lost City” Trick-or-Treat, Leonardtown Baptist Church Fall Festival, and the Leonardtown Town Market Trunk-or-Treat. More fun continues with Real Life Church, Ridge Volunteer Fire Department, and Tom Hodges Mitsubishi Trunk-or-Treat events.
Murder, Magic, and Mayhem: An Adults-Only Tour on Oct. 24–25 (5, 5:30 & 6 p.m.), at Historic St. Mary’s City – Farthing’s Picnic Area, 47418 Old State House Road, St. Mary’s City, MD – Step into the 17th century on a chilling one-hour walking tour exploring Maryland’s darker colonial past. Hear tales of witchcraft, crime, and superstition led by a costumed guide through the shadows of history. Ages 18+. $20 per person; $15 for members. Advance registration required.
Underground Railroad Network to Freedom Tour on Oct. 25 (10 to 11 a.m. & 2 to 3 p.m.), at Point Lookout State Park, 11175 Point Lookout Road, Scotland, MD – Explore four historic sites connected to the National Park Service’s Underground Railroad Network to Freedom during this guided tour led by Susan Youhn. Meet at the park’s Pay Shelter/Headquarters. Free tour; park entry fee required.
Dixon Family Farm Pumpkin Festival on Oct. 25 (noon to 5 p.m.), at Dixon Family Farm, South Sandgates Road, Mechanicsville, MD – Enjoy a day of family fun with a pumpkin patch, trick-or-treat trail, bounce house, cookie decorating, face painting, axe throwing, and live music. Entertainment includes juggling and magic by Crickett and vintage American tunes from The Knuckle Dusters. Tickets required.
Legends & Lore Specialty Tour on Oct. 25 (6, 6:45, 7:30 & 8:15 p.m.), located at Historic Sotterley, 44300 Sotterley Lane, Hollywood, MD – Step into a world of mystery, forbidden love, and intrigue as historian Sam Baldwin joins actors Michael Blackwell and Shannon Spalding to bring Sotterley’s haunting legends to life through live scenes and storytelling inside the historic manor. Advance reservations required; ages 16+.
A Haunted Halloween Spooktacular on Oct. 25 (4:30 to 7 p.m.), at Brinsfield Funeral Home, 22955 Hollywood Road, Leonardtown, MD – Come in costume and enjoy an evening of family fun with games, face painting, a petting zoo, and festive activities. Meet members of the Maryland State Police, Leonardtown Volunteer Fire Department, Rescue Squad, and Sheriff’s Office as they join in the Halloween celebration. Free admission.
Fall Festival at Swords and Spoons on Oct. 25–26, at Swords and Spoons, 22599 MacArthur Boulevard, Suite 126, California, MD – Celebrate a weekend of spooky fun with youth and adult D&D sessions, a kids’ costume contest, pumpkin painting, and Halloween-themed crafts. Sunday features Pokémon and Lorcana tournaments with treats and prizes. Free admission.
Family Costume Run 5K on Oct. 26 (9 to 11 a.m.), at Lexington Manor Passive Park, Lexington Park, MD – Lace up for a fun, family-friendly 5K where runners are encouraged to wear their best costumes for a spooky seasonal dash through the park. Registration required.
Halloween Flash Tattoo Event + Spooky Vendors on Oct. 26 (11 a.m. to 4 p.m.), at Hunny Bee Tattoo, 25580 Three Notch Road, Hollywood, MD – Celebrate spooky season with first-come, first-served flash tattoos by Bridgett and guest artist Isabela, plus local vendors offering art, jewelry, tarot readings, and more. Free admission; tattoos priced per design.
Dancing for Neuroplasticity: Halloween Vibes on Oct. 27 (1 to 2:30 p.m.), at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Experience a scientifically backed dance session that blends movement, memory, and Halloween-themed fun to boost brain health and coordination. $20 per person.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – October 24th
5:00pm – Chris Dean – Greene Turtle Sports Bar – California MD
5:00pm – Mike Mead – Greene Turtle Sports Bar – La Plata MD
5:00pm – Dust on the Bottle – Running Hare Winery – Prince Frederick MD
5:00pm – Joseph Norris – Snellman’s Shuck Shack – Hollywood MD
5:30pm – Joey Tippett & Highway Ramblers – Blue Fish Pub – Solomons MD
5:30pm – Lissie Deere – Pier 450 Restaurant – Ridge MD
6:00pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Ro Cube & Tom Crosby – PTR Waterfront – Port Tobacco MD
6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – John Luskey – Dockside Tiki Bar – Colonial Beach VA
7:00pm – Mike Trujillo – The Taphouse 1637 – California MD
7:00pm – Carla Simpson – O’Gannigan’s Irish Pub – Prince Frederick MD
8:00pm – Southbound 4 – Hill’s Store, Bar & Grill – Helen MD
8:00pm – Wesley Spangler – Twisted Bar & Grill – Hollywood MD
8:00pm – HydraFX – Toots Bar – Hollywood MD
8:30pm – My Chemical Bromance – Ollie’s Bar & Grill – La Plata MD
9:00pm – Swamp Weasels – Betty Russell’s Store & Bar – Valley Lee MD
Saturday – October 25th
2:00pm – GrooveSpan – Perigeaux Vineyards & Winery – Saint Leonard MD
2:00pm – Levi Stephens – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Eddie Pasa – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Mike Mead – Corteau Vineyards – Mechanicsville MD
2:00pm – Rocktober Fest – VFW Post #2632 – California MD
————– Vivid Vertigo, Redgate, Stereo Purple, Karosha,
————— Citizen X, Assembly 6 & Censored Image –
3:00pm – Jason Bishop – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Noel Duke & Friends – The Scuttlebutt – Cobb Island MD
4:00pm – Monkey Business – PTR Waterfront – Port Tobacco MD
5:00pm – Hyland Brothers – Running Hare Winery – Prince Frederick MD
5:00pm – Taboo – Wilderness Run Vineyards – Spotsylvania VA
5:00pm – Vertigo Red – Blue Fish Pub – Solomons MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:30pm – HydraFX – Southern Trail Distillery – Mechanicsville MD
6:00pm – John Luskey – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Shaun Gomban – The Local – Hollywood MD
6:00pm – Byron Ciotter – Pax River Ale House – Lexington Park MD
7:00pm – Josh Airhart – The Brass Tap – California MD
7:00pm – Billy Breslin – Neptune’s Seafood Pub – North Beach MD
7:00pm – Nightcap – 6 Bears & A Goat Brewery – Fredericksburg VA
7:00pm – shallowDeep Album Release – Twisted Bar & Grill – Hollywood MD
———w/ Others May Fall, Buffalo Velcro, One of the Living, Jebus & Bryce –
8:00pm – Talib Kweli – The Rex Theatre – Leonardtown MD
8:00pm – Hot Ice – The Remedy 20601 – Waldorf MD
8:00pm – Steel Toe Flip Flop – Dockside Tiki Bar – Colonial Beach VA
8:00pm – 4th Wall Break – Toots Bar – Hollywood MD
8:00pm – Never 2 Late – The Tavern – Saint Leonard MD
8:00pm – Smoke Signals – The Taphouse 1637 – California MD
8:00pm – Wes Ryce – Cryer’s Back Road Inn – Leonardtown MD
9:00pm – Framing the Tin Man – Huntt’s Tavern – Pomfret MD
9:00pm – Social – Apehangers Bar & Grill – Bel Alton MD
Sunday – October 26th
11:00am – SOMD Jazz Duo Aldous & Emma – Pier 450 – Ridge MD
2:00pm – Folk Salad – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – John Luskey – Wharf 38 – Deale MD
2:00pm – Gabriel Heisey – Port of Leonardtown Winery – Leonardtown MD
3:00pm – Billy Yeager – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Park’s Edge – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Steve Potter Band – PTR Waterfront – Port Tobacco MD
Monday – October 27th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – October 28th
5:00pm – Hyland Brothers – Heritage 485 – Prince Frederick MD
6:00pm – Justin Crenshaw – Apehangers Bar & Grill – Bel Alton MD
6:00pm – Greg Barrick – The Tavern – Saint Leonard MD
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – October 29th
5:00pm – Loose Change – The Boathouse @ Anchored Inn – Deale MD
5:00pm – Elena Barrett – Ketch 22 Restaurant – North Beach MD
6:00pm – Levi Stephens – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
Got a tip or photo? Text us at 888-871-NEWS (6397) or email news@thebaynet.com.
Join The BayNet Membership for exclusive perks and zero ads.
Don’t miss a story—sign up for our newsletter!
