SOUTHERN MARYLAND — Fall fun is in full swing as Southern Maryland gears up for the 59th U.S. Oyster Festival in Leonardtown this weekend. Celebrate the Bay’s favorite tradition with oysters, live music, and the U.S. National Oyster Shucking Championship at the St. Mary’s County Fairgrounds. Families can hit this week’s Trunk-or-Treats across all three counties, while thrill seekers head to haunted houses and ghost tours lighting up the region. However you celebrate, it’s the perfect week to explore, taste, and enjoy the best of SoMD.
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THINGS TO DO IN CALVERT COUNTY
Trunk-or-Treats in Calvert County from Oct. 17–23 – Enjoy Halloween fun with family favorites including Halloween in the Garden, St. Paul UMC Trunk-or-Treat, Unity in the Lot: Trunk, Treat & Eat, and Halloween at Hallowing Point Park. More celebrations continue through the week with the Spooktacular Candy Crawl, North Beach Boo Bash, and Chesapeake Beach Family Fun Night. See the list of events here.
CalvertHealth Breast Cancer 5K Run/Walk on Oct. 18 (7 a.m.), located at Solomons Medical Offices, 14090 H.G. Trueman Road, Solomons, MD – Take part in the annual 5K and one-mile fun walk supporting the Sheldon E. Goldberg Center for Breast Care. Enjoy scenic views of Solomons Island, team fundraising, prizes, and a chance to win a Viking Cruise valued up to $10,000. Registration required.
Village Days on Oct. 18 (10 a.m. to 3 p.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD – Experience early Maryland life through crafts, trades, and costumed interpreters. Free admission.
Lower Marlboro Freedom Day on Oct. 18 (11 a.m.–4 p.m.), located at Lower Marlboro United Methodist Church, 6519 Lower Marlboro Lane, and Lower Marlboro Hall, 3911 Lower Marlboro Road, Owings, MD – Celebrate Calvert County history with a day of walking tours, speakers, entertainment, food, and exhibits commemorating those who gained freedom with the help of the British during the War of 1812. Free community event.
Calvert County Bluegrass and Acoustic Music Festival on Oct. 18 (noon–5 p.m.), located at Waters Memorial United Methodist Church, 5400 Mackall Road, St. Leonard, MD – Enjoy live performances by Jay Armsworthy and Cuzin’s Harmony, Justus 2, The Port Tobacco Pickers, 15 Strings, and The Unclouded Day. Food trucks include Hance Funnel Cakes, K’s Lunchbox, and Cutty’s Rock and Ribs. Free admission; donations to Calvert Hospice appreciated.
Enchanted Woodland Fairy Festival on Oct. 18 (10 a.m.), located at Patuxent River 4-H Center, 18405 Queen Anne Road, Upper Marlboro, MD – Step into a magical day featuring fairies, woodland creatures, a fairy trail, unicorn rides, petting zoo, axe throwing, performances, and food. Costumes encouraged—bring your wings, wands, and imagination for a day full of wonder. Tickets required.
ACLT Guided Canoe Trip on Oct. 18 (1–4 p.m.), at Warrior’s Rest Nature Sanctuary in Port Republic – Paddle through the scenic Parkers Creek with expert guides from the American Chestnut Land Trust. This three-hour trip offers a mix of adventure and education through one of Calvert’s most pristine waterways. Advance registration required; open to ACLT members first.
First Responders & Military Appreciation Day at Rolling Acres Farm on Oct. 19 (10 a.m.–2 p.m.), at Rolling Acres Farm in Port Republic – A free community day celebrating local heroes with St. Leonard Volunteer Fire Department and Calvert County Sheriff’s Office rigs on site for a touch-a-truck experience. Free admission for all first responders and military personnel with badge or ID.
Meet an Astronaut at Calvert Library on Oct. 21 (6:30 p.m.), located at Calvert Library Twin Beaches Branch, 3819 Harbor Road, North Beach, MD – Meet astronaut Col. Frederick D. Gregory, the first African American to command a space shuttle, for an evening of stories about exploration, leadership, and breaking barriers. Registration required.
Trivia Night at CBQ on Oct. 22 (6:30 p.m.), located at CBQ, 4150 Mears Avenue, Chesapeake Beach, MD – Gather your team for a night of laughter, competition, and great food with quirky, survey-style trivia questions. Enjoy pulled pork sandwiches, loaded quesadillas, rum runners, and bourbon smashes while testing your wits for the top answers. Free to play; food and drinks available for purchase.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
Trunk-or-Treats in Charles County from Oct. 17–23 – This week includes Fall Fest at Westlake High School, Spooky Fall Fest at Shops at Waldorf Center, Dr. Higdon Elementary Trunk-or-Treat, Connect Church Trunk-or-Treat, and La Plata’s Trick-or-Treat Trail. More family events include B.Funk Dance Studio Trunk-or-Treat, Westlake Volunteer Fire Department’s “Get Spooky,” and the Charles County Sheriff’s Office Trunk-or-Treat. See the list of events here.
Lowe’s Kids Workshop: Play Firehouse on Oct. 18 (10 a.m.), located at Lowe’s Home Improvement, 2525 Crain Highway, Waldorf, MD – Celebrate Fire Safety Month with a hands-on mini–firehouse workshop by Lowe’s and First Alert. Kids can build their own miniature firehouse complete with a working pole while learning about fire safety. Free with registration.
Colonial Faire and Fall Festival on Oct. 18–19 (10 a.m.–3 p.m.), at Historic Maxwell Hall in Hughesville – Celebrate fall with a weekend of colonial history, live entertainment, cannon firings, and hands-on fun. The event includes food, craft vendors, and tastings of local wine, rum, and beer. Hosted by Friends of Maxwell Hall. Free admission.
Spooky Fall Festival on October 18 (12 to 4 pm), located at The Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – Celebrate the season with a fun-filled day of music, trick-or-treating, crafts, face painting, photo ops, and more fall fun for the whole family. Free admission. Rain date: October 25.
Veterans Service Dog Meet & Greet at All American Harley-Davidson on Oct. 18 (11 a.m.–1:50 p.m.), located at All American Harley-Davidson, 8126 Old Leonardtown Road, Hughesville, MD – Meet Chewy the veteran service dog, learn about the Veterans Service Dog Memorial, and pick up merchandise or a brick order form. Enjoy food, patch sewing, test rides, and a special sidecar setup for dogs. Free community event.
Fall Book Bazaar from Oct. 18–25, located at the Charles County Public Library – La Plata Branch, 2 Garrett Avenue, La Plata, MD – Browse thousands of books, movies, and music at bargain prices while supporting local library programs. Hours are Monday–Thursday 10 a.m.–6 p.m. and Friday–Saturday 9 a.m.–4:30 p.m. Member’s Day is Oct. 17, and Bag Days are Oct. 24–25 ($3 per grocery-sized bag). Free admission.
Glowpocalypse at Southern Maryland Paintball on Oct. 18 (7–11 p.m.), at Southern Maryland Paintball in Newburg – Step under the black lights for a glowing night of paintball fun at “Glowpocalypse.” Bring a first-timer and get BOGO admission! Open to ages 8 and up, featuring rental gear, glow paintballs, and prizes. Tickets required.
Maryland Diaper Bank Giveaway in Waldorf on Oct. 19 (11 a.m.–12:30 p.m.), located at Pop Up & Grow, 3035 Festival Way, Waldorf, MD – Families in need can pick up free diapers and wipes during this community distribution hosted by the Maryland Diaper Bank. Supplies are available on a first-come, first-served basis. Free event.
Dinosaurs & I Heart Cookies in La Plata on Oct. 21 (2–7 p.m.), located at Lowe’s Home Improvement, 300 Rosewick Road, La Plata, MD – Experience a dino-sized day with animatronic dinosaurs, cookie giveaways, and family fun as I Heart Cookies food truck makes its first visit to La Plata. Enjoy free cookies, meet life-sized T-Rex and Raptor displays, and explore interactive exhibits. Free admission.
Malala Yousafzai Virtual Author Talk on Oct. 22 (7 p.m.), hosted by Charles County Public Library, online – Hear Nobel Peace Prize winner Malala Yousafzai discuss her new memoir “Finding My Way” and reflect on her journey as an activist for girls’ education and equality. Attendees can submit questions in advance for this free live-streamed event. Free with registration.
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 from Oct. 17–23 – Visit Lyon Family Farms for Fall Friday Night on the Farm, explore Historic St. Mary’s City’s “Lost City” Trick-or-Treat, stop by Animal Services’ Trunk-or-Treat & Adoption Day, or enjoy the R/C Drag Club Halloween Race. More fun continues with Leonardtown Baptist Church Fall Festival and the Leonardtown Town Market Trunk-or-Treat. See the list of events here.
Craft & Vendor Sale – Fall 2025 on Oct. 17 (9 a.m.–2 p.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Browse handmade crafts, holiday décor, and gifts while supporting local vendors and artisans. Open to the public with no registration needed to shop. Free admission.
U.S. Oyster Festival on Oct. 18–19 (10 a.m.–6 p.m. Sat, 11 a.m.–6 p.m. Sun), located at St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD – Enjoy oysters grilled, smoked, raw, and more, artisan vendors, live music, kids’ activities, and the U.S. National Oyster Shucking Championship competition at 2 p.m. daily. Tickets required.
Lowe’s Kids Workshop: Play Firehouse on Oct. 18 (10 a.m.), located at Lowe’s Home Improvement, 45075 Worth Ave., California, MD – Join Lowe’s and First Alert for a fun, educational Fire Safety Month project where kids can create their own firehouse model and learn about fire prevention. Free with registration.
Vampire Manor on Oct.18 (6 p.m.), located at Historic St. Mary’s City, 47418 Old State House Road, St. Mary’s City, MD – Enjoy an elegant, adults-only evening of food, drink, and entertainment at the State House. Costumes encouraged; ages 21+. Tickets required.
Optimus Prime and Friends on Oct. 18–19 (10 a.m.–4 p.m.), located at Patuxent River Naval Air Museum, 22156 Three Notch Road, Lexington Park, MD – Experience an action-packed weekend featuring 24 Transformers vehicles, live robot cosplayers, Ghostbusters and Star Wars displays, the HALO Warthog, and community outreach from local heroes and nonprofits. Enjoy food trucks, vendors, and family-friendly meet-and-greets promoting kindness and anti-bullying. Free community event; donations benefit Ridge Lions Club programs.
Legends & Lore Specialty Tour on Oct. 17 – 18, (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+.
Monster Mash Bash on Oct. 19 (1–4 p.m.), located at Leonardtown Wharf, 22500 Washington Street, Leonardtown, MD – Enjoy a spooktacular afternoon of family fun featuring a costume contest, trick-or-treat trail, art activities, and festive vendors along the decorated waterfront. The Leonardtown Trolley will provide special event transportation. Free community event.
Audition Call: A Night on Broadway – Broadway Backwards on Oct. 22–23 (6–9:30 p.m.), located at Three Notch Theatre, 21744 South Coral Drive, Lexington Park, MD – Three Notch Theatre invites performers to audition for Broadway Backwards, a creative reimagining of iconic stage moments in bold, unexpected ways. Open to performers from high school age through adult.
SMTMD HomeSpun CoffeeHouse Open Mic on October 24 (7 to 9:30 pm), located at Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – Acoustic musicians of all skill levels are welcome to perform their favorite tunes or enjoy a night out listening to some local talent. A keyboard can be made available by prior arrangement. Contact Chris Dudley in advance (ccdudley@rocketmail.com) to sign up as a performer. Admission is $8; children 17 and under (when accompanied by a paying adult) and performers are admitted free of charge.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – October 17th
5:00pm – Chris Dean – Greene Turtle Sports Bar – La Plata MD
5:00pm – Nightcap – Mully’s Brewery – Prince Frederick MD
5:00pm – Hyland Brothers – Running Hare Vineyard – Prince Frederick MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
6:00pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Byron Ciotter – Barefoot Farms – Avenue MD
6:00pm – Joe Parsons – Southern Trail Distillery – Mechanicsvile MD
6:00pm – Rayon Walker – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Marianne Styles – The Local – Hollywood MD
6:00pm – Mike Mead Band – PTR Waterfront – Port Tobacco MD
6:30pm – Unfinished Business – Brudergarten – Leonardtown MD
7:00pm – Shaun Gomban – The Brass Tap – California MD
7:00pm – Billy Breslin – The Heist – Bowling Green VA
7:00pm – Sam Lowe – Blue Fish Pub – Solomons MD
7:00pm – Justin Myles & The Prophessor – The Ruddy Duck – Solomons MD
8:00pm – All Funked Up Experience – The Remedy 20601 – Waldorf MD
8:00pm – WildGood Band – Water View Inn – Bushwood MD
8:00pm – Social – Toots Bar – Hollywood MD
8:30pm – Girl Crush – Ollie’s Bar & Grill – La Plata MD
9:30pm – Greg Barick & David Hamner – C & R Pub – Towson MD
10:00pm – Hyland Brothers – Lord Calvert Bowling – Huntington MD
Saturday – October 18th
11:00am – Bootleggers – OysterFest @ Fairgrounds – Leonardtown MD
12:00pm – Bluegrass Fest – Waters Mem Methodist Church – St Leonard MD
————— 15 Strings, Port Tobacco Pickers, Cuzn’s Harmony & more
12:00pm – Doc Lohn – Two Lions Vineyards – Brandywine MD
12:00pm – Whiskers – OysterFest @ Fairgrounds – Leonardtown MD
1:00pm – One Trick Pony – OysterFest @ Fairgrounds – Leonardtown MD
1:00pm – Funkzilla – OysterFest @ Fairgrounds – Leonardtown MD
2:00pm – Chris Dean – Corteau Vineyards – Mechanicsville MD
2:00pm – Folk Salad – Perigeaux Vineyards & Winery – Saint Leonard MD
2:00pm – Nightcap – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Dust on the Bottle – Robin Hill Farm & Vineyard – Brandywine MD
3:00pm – Myles Deep Band – OysterFest @ Fairgrounds – Leonardtown MD
3:00pm – Greg Barrick – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Tunnels End – The Taphouse 1637 – California MD
5:00pm – Swamp Weasels – Running Hare Winery – Prince Frederick MD
5:00pm – Dean Crawford & Dunn’s River – Blue Fish Pub – Solomons MD
6:00pm – Byron Ciotter – The Local – Hollywood MD
6:00pm – 3 of a Kind – The Wheelhouse Beer Garden – North Beach MD
6:00pm – Chandler Finch – Pax River Ale House – Lexington Park MD
6:00pm – Shaun Gomban – Bugeye Grill – Solomons MD
6:00pm – Bradley Turner – Southern Trail Distillery – Mechanicsvile MD
6:00pm – Kevin Lee – Dockside Restaurant & Sports Bar – Deale MD
7:00pm – Voice – PTR Waterfront – Port Tobacco MD
7:00pm – Hyland Brothers – Neptune’s Seafood Pub – North Beach MD
7:00pm – Marianne Styles – The Brass Tap – California MD
8:00pm – Unfinished Business – Buckets Bar & Grill – Lusby MD
8:00pm – South Creek – Cryer’s Back Road Inn – Leonardtown MD
8:00pm – Fake Happy (Paramore tribute) – Rex Theatre – Leonardtown MD
8:30pm – HydraFX – The Tavern – Saint Leonard MD
9:00pm – Steve Potter Band – Huntt’s Tavern – Pomfret MD
9:00pm – Angerbox – Apehangers Bar & Grill – Bel Alton MD
Sunday – October 19th
11:00am – Lissie Deere – Pier 450 – Ridge MD
12:00pm – Blair Ritch Project – OysterFest @ Fairgrounds – Leonardtown MD
1:00pm – Reluctant Jazz – OysterFest @ Fairgrounds – Leonardtown MD
2:00pm – West Mob Band – OysterFest @ Fairgrounds – Leonardtown MD
2:00pm – Just Us – Wharf 38 – Deale MD
2:00pm – Shortcut Sunny – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Greg Floberg – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Jack Allen – Brudergarten Beer Garden – Leonardtown MD
3:00pm – Hyland Brothers – Pirate’s Cove Dock Bar – Galesville MD
3:00pm – Cramer & Ivy – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Shane Graham – The Pier – Solomons MD
3:00pm – Rob Blake & David Hamner – PTR Waterfront – Port Tobacco MD
3:00pm – HydraFX – OysterFest @ Fairgrounds – Leonardtown MD
Monday – October 20th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – October 21st
6:00pm – Greg Barrick – Apehangers Bar & Grill – Bel Alton MD
6:30pm – Brian Grumbine – The Tavern – saint Leonard MD
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – October 22nd
5:00pm – Ryan Forrester – Ketch 22 Restaurant – North Beach MD
5:00pm – Pete Best – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Mike Heuer – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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