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SOUTHERN MARYLAND — Halloween may be over, but the fun continues across Southern Maryland. From spooky adventures and community trunk-or-treats to historical celebrations, there’s plenty to enjoy as October rolls into November. This weekend brings Viking warriors, creative crafts, live entertainment and family fun — plus Celebrating Maryland’s Emancipation Day, a free family program in Lexington Park honoring the 1864 abolition of slavery in Maryland with storytelling, art and interactive history activities for all ages. However you celebrate, this week offers the perfect mix of adventure, learning and seasonal fun across Calvert, Charles and St. Mary’s counties.

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THINGS TO DO IN CALVERT COUNTY

Creepy Creatures on Oct. 31 (11 a.m. to noon), at North Beach Nature Center, 9404 Dayton Ave., North Beach, MD – Meet local critters with “bad reputations,” play Halloween bingo, and make spooky crafts at this family-friendly Halloween program. Free admission.

Southern Calvert Baptist Church Trunk-or-Treat on Oct. 31 (6 to 8 p.m.), at 12140 H.G. Trueman Rd., Lusby, MD – Family-friendly evening with games, hot dogs, and candy. Free admission; no scary costumes, please.

Retro Halloween Party by Dusk + Willow on Nov. 1 (6 to 10 p.m.), at The Bakist, 9124 Bay Ave., North Beach, MD – Enjoy a night of spooky glamour, live music by LoveFools and a DJ set by Metronix, plus specialty cocktails and retro vibes. Tickets required.

American Indian Heritage Day on Nov. 1 (11 a.m. to 4 p.m.), at Jefferson Patterson Park and Museum, 10515 Mackall Road, St. Leonard, MD – Celebrate 10,000 years of Native history and culture with dancers, educational demonstrations, and family-friendly activities. Free admission.

Free Community Swim Day on Nov. 2 (noon to 4 p.m.), at Edward T. Hall Aquatic Center, 130 Auto Drive, Prince Frederick, MD – The Calvert County Department of Parks & Recreation invites residents to enjoy free access to the pool with swim clinics, water fitness classes, games, and family-friendly activities. Free admission for all ages. 

Care Net SoMD – Calvert County Location Grand Opening on Nov. 3–5 (9 a.m.), at Care Net SoMD Lusby Center, 12865 HG Trueman Rd., Ste. 102, Lusby, MD – Celebrate the grand opening of Care Net’s new Calvert County location with tours, treats, and giveaways. Supporters and clients are invited to stop by; free packs of diapers available while supplies last. Free admission.

CCPS Agriculture Career Fair on Nov. 4 (9 a.m. to 3 p.m.), at Mrs. Moo’s Corner at Spider Hall Farm, 3915 Hallowing Point Rd., Prince Frederick, MD – A hands-on learning experience for 6th and 9th graders featuring live demonstrations and activities from local farms and agri-businesses. The event aims to spark student interest in agriculture careers and showcase Calvert County’s farming innovation. Free admission.

Team Trivia: Office Space on Nov. 5 (6:30 to 8 p.m.), at Mully’s Taproom, 141 Schooner Ln., Prince Frederick, MD – Gather your crew for themed trivia night inspired by Office Space! Teams of up to six can compete to test their workplace knowledge and win prizes. Free to play.

Sea Squirts: Maryland Symbols – Sports on Nov. 6 & 13 (10:15 & 11:15 a.m.), at Calvert Marine Museum, 14200 Solomons Island Road S., Solomons, MD – Preschoolers (ages 18 months to 3 years) and their caregivers enjoy story time, crafts, and interactive learning about Maryland’s state sports symbols. Free with museum admission.

Resumes & Interviewing Skills Workshop on Nov. 6 (10 a.m. to 12 p.m.), at Calvert Library Prince Frederick, Meeting Room 3, 850 Costley Way, Prince Frederick, MD – Hosted by the Maryland Department of Labor and American Job Center, this free interactive workshop helps attendees strengthen resume writing and interview techniques. Registration closes three days before the event. Free admission.

STEM Competition on Nov. 6 (1:30 to 2:15 p.m.), at Southern Community Center, 20 Appeal Lane, Lusby, MD – In celebration of National STEM Day, Calvert County Parks & Recreation partners with Calvert Library for a friendly challenge testing science, technology, engineering, and math skills. Open to teams of four, ages 7–12. Free admission; preregistration encouraged.

For more Calvert County events, visit the Calvert County Maryland website. 

THING TO DO IN CHARLES COUNTY

Charles County Trunk-or-Treats on Oct. 31 – Celebrate Halloween across Charles County with family-friendly trunk-or-treats including Mall-O-Ween at St. Charles Towne Center, Family Fall FunFest & Spooktacular at Melwood Recreation Center, Town of Indian Head Trunk-or-Treat, and A Complete Care Event in La Plata. Enjoy candy, games, food trucks, and Halloween fun for all ages. 

Spooky Kiddie Car-nival on Oct. 31 (6 to 9 p.m.), at 11055 Mall Circle, Waldorf, MD – Enjoy a safe trunk-or-treat adventure featuring interactive car displays, games, local vendors, a costume contest, and live music. Tickets required.

A Festival of Bones on Oct. 31–Nov. 2, at Lions Camp Merrick, 3650 Rick Hamilton Place, Nanjemoy, MD – Hosted by the Barony of Dun Carraig (Society for Creative Anachronism), this immersive medieval-themed weekend features armored and rapier combat, arts and sciences competitions, archery, bardic performances, dance, trick-or-treating, and feasts. Activities include the Runway of the Macabre fashion show, fiber arts demos, storytelling contests, youth workshops, and canine costume parade. Tickets required.

Farmers Feeding Charles County on Nov. 1 (11 a.m. to 1 p.m.), at Newburg Elks Lodge, 12445 Rock Point Rd, Newburg, MD – Join Commissioner Gilbert “B.J.” Bowling, the Elks Lodge, and Shiloh Community United Methodist Church for a free community food giveaway. Fresh food items available while supplies last. Free event.

Cirque Italia – Water Circus on Nov. 1–2 (various showtimes), at St. Charles Towne Center, 11110 Mall Circle, Waldorf, MD – Experience breathtaking water-based acrobatics, lights, and international performers in this traveling circus spectacular. Tickets required.

Charles County Fall Oyster Festival on Nov. 1 (1 to 6 p.m.), at Lamont’s Entertainment Complex, 4400 Livingston Road, Indian Head, MD – Celebrate with fresh oysters, food trucks, live music, vendors, and family fun. Advance tickets $55; $65 at the door.

All American Harley-Davidson Halloween Costume Contest & Chili Cook-Off on Nov. 1 (11 a.m. to 2:30 p.m.), located at All American Harley-Davidson, 8126 Old Leonardtown Road, Hughesville, MD – Join the 17th annual Chili Cook-Off and Halloween Costume Contest featuring prizes for adults, kids, pets, and employees. Chili entries open at 11 a.m. with tasting and voting until 2 p.m.; awards announced at 2:30 p.m. Free to attend; limited cook-off entries.

Newburg Volunteer Rescue Squad & Fire Department Trunk or Treat on Nov. 1 (5:30 to 8 p.m.), at 12245 Rock Point Rd., Newburg, MD – A community Halloween celebration featuring trunk-or-treating, contests, and candy donations for the station.

Lackey High School – Fairycakes on Nov. 1 (2 p.m.), at Lackey High School, 3000 Chickamuxen Road, Indian Head, MD – A whimsical blend of A Midsummer Night’s Dream and fairy-tale magic.Tickets required.

VikingsCon on Nov. 1–2, at the Charles County Fairgrounds, 8440 Fairground Road, La Plata, MD – A fully immersive Viking-themed convention celebrating Norse culture, history, and fantasy. Enjoy reenactments, live combat demos, artisans, workshops, and vendors offering themed goods. Tickets required.

For more Charles County events, visit the Charles County Maryland website.

THINGS TO DO IN ST. MARY’S COUNTY

St. Mary’s County Trunk-or-Treats on Oct. 31 – Families can enjoy safe Halloween fun at Wildewood Center’s Trick or Treat, Ridge Volunteer Fire Department Trunk-or-Treat, and Tom Hodges Mitsubishi Trunk or Treat in Hollywood. Expect candy, costumes, balloon twisting, and festive activities for all ages

SuperHero NOT Halloween Party on Oct. 31 (9 p.m.), at Twisted Bar & Grill, 23955 Mervell Dean Rd., Hollywood, MD – Suit up for a superhero-themed night with a costume contest, DJ entertainment, games, and signature cocktails. $10 cover (includes one drink); free for firefighters, EMTs, police, nurses, and teachers.

Loffler’s Haunted Family Farm on Oct. 31 (1 to 4 p.m.), at Loffler Senior Activity Center, 21905 Chancellors Run Rd., Great Mills, MD – Experience a spooky family adventure with costume contests, monster mash dancing, and eerie farm-themed fun. Free admission; advance registration required.

Celebrating Maryland’s Emancipation Day: Stories, Art & History for All Ages on Nov. 1 (noon to 2 p.m.), at 21675 S. Coral Drive, Lexington Park, MD – Join the U.S. Colored Troops Interpretive Center and local museums in commemorating the 1864 abolition of slavery in Maryland. This free event features storytelling, art, and historical exhibits honoring the state’s third constitution and those who fought for freedom. Free admission.

Fall Artisan & Vendor Market on Nov. 1 (9 a.m. to 3 p.m., rain or shine), at Summersseat Farm, 26655 Three Notch Road, Mechanicsville, MD – Shop handmade goods, jewelry, baked treats, and crafts from local vendors while enjoying food and drink options at this seasonal market on the farm. Free admission.

Joyful Tea & Mind Connection: Encouraging Memory, Movements & Mood on Nov. 3 (1 to 2:15 p.m.), at Northern Senior Activity Center, 21905 Chancellors Run Rd., Charlotte Hall, MD – Join Paty Massón for a relaxing, therapeutic session combining stretching, coordination tasks, and art activities to support neuroplasticity, confidence, and mood—all while enjoying tea. $10 per person.

Native American Heritage Month with the Piscataway Nation—Stories, Tradition and Powwow-Style Dance on Nov. 4 (7 to 8:30 p.m.), at Nancy R. and Norton T. Dodge Performing Arts Center – Concert Hall, St. Mary’s College of Maryland, 47645 College Drive, St. Mary’s City, MD – Celebrate Native American Heritage Month with Mark Tayac and the Piscataway Nation Singers & Dancers, featuring traditional powwow-style drumming, dance, and storytelling honoring the rich heritage of the Piscataway people. Free tickets; registration required.

live music schedule southern maryland

SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS

Friday – October 31st – Halloween

5:00pm – Brian Grumbine – Greene Turtle Sports Bar – La Plata MD

5:00pm – Tim Guilliams – Mully’s Brewery – Prince Frederick MD

5:00pm – Joseph Norris – Snellman’s Shuck Shack – Hollywood MD

6:00pm – Midnight Sunsets – Wheel House Beer Garden – North Beach MD

6:30pm – Swamp Weasels – Ruddy Duck Brewery & Grill – Solomons MD

8:00pm – 3 of a Kind – Buckets Bar & Grill – Lusby MD

8:00pm – Wesley Spangler – The Tavern – Saint Leonard MD

8:00pm – Backstage Pass – Seabreeze Restaurant – Mechanicsville MD

8:00pm – Roxygen – Dockside Restaurant & Sports Bar – Deale MD

8:00pm – HydraFX – The Taphouse 1637 – California MD

8:30pm – Absinthe – Ollie’s Bar & Grill – La Plata MD

9:00pm – Myles Deep Band – 219 Restaurant – Alexandria VA

9:00pm – Hit or Miss – The Rex Theatre – Leonardtown MD

Saturday – November 1st

2:00pm – Swing Away Jazz – Port of Leonardtown Winery – Leonardtown MD

5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD

5:30pm – Byron Ciotter – Port Oysteria & Brewery – Fredericksburg VA

6:00pm – 4th Wall Break – Pax River Ale House – Lexington Park MD

6:00pm – Mixed Business – Wheel House Beer Garden – North Beach MD

6:00pm – LoveFools – The Bakist Coffee Shop – North Beach MD

7:00pm – Nightcap – The Brass Tap – California MD

8:00pm – HydraFX – Buckets Bar & Grill – Lusby MD

8:00pm – Southbound 4 – Toots Bar – Hollywood MD

8:00pm – Intentionally Blank / Lucky Has Fallen – Twisted – Hollywood MD

9:00pm – Chris Dean & Matt Silkworth – Huntt’s Tavern – Pomfret MD

9:00pm – Girl Crush – Apehangers Bar & Grill – Bel Alton MD

9:00pm – FMsix (Fleetwood Mac) – Ollie’s Bar & Grill – La Plata MD

Sunday – November 2nd

2:00pm – Richard Wagner – Port of Leonardtown Winery – Leonardtown MD

2:00pm – Joey Tippett w/Stu Geisbert – Back Road Inn – Leonardtown MD

Monday – November 3rd

6:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD

Tuesday – November 4th

7:00pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD

Wednesday – November 5th

7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD


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Jessica Jennings, a Tampa, Florida native, brings a rich and diverse perspective shaped by her global experiences as a U.S. Navy veteran and military spouse. After joining the Navy at 19, Jessica’s service...

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