SOUTHERN MARYLAND — Fall has officially arrived, and Southern Maryland is full of opportunities to enjoy the season. Cooler days provide the perfect backdrop for outdoor festivals, historic parades, local hikes and family-friendly activities. This week’s lineup highlights the best of the region — from festivals, markets and pumpkin patches to the One Maryland, One Book: “KIN” author event and Walktober activities that encourage the community to get outside and stay active. There’s something for everyone, whether you’re looking for cozy indoor fun or crisp outdoor adventures.
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THINGS TO DO IN CALVERT COUNTY
Parents’ Night Out on Oct. 3 (6 to 9:30 p.m.), located at Mt. Hope Community Center, 104 Pushaw Station Rd., Sunderland, MD – An evening for kids ages 4–12 to enjoy games, crafts, snacks and outdoor play (weather permitting) while parents take a break. Free admission; children must be potty-trained.
Friends of the Poor 5K Walk/Run & Kiddy-K on Oct. 4 (9 a.m. start; in-person registration 8:30 a.m.), located at Jesus the Good Shepherd Athletic Field, 1601 W Mount Harmony Rd., Owings, MD – Timed 5K on a fast, mostly flat wooded trail with awards for top male/female finishers overall and by age group, plus a Kiddy-K fun run for kids 10 and under, games, fire-department visit, door prizes, 50/50 raffle, silent-auction items and more.
Walk n’ Talk: Murder, Mystery and Mayhem on Oct. 4 (11 a.m. to noon), at Jefferson Patterson Park & Museum Visitor Center, 10515 Mackall Rd., St. Leonard, MD – Step into the spookier side of Southern Maryland history on a guided walk highlighting local tales of intrigue and true crime. A second walk will be offered at 1 p.m. Free, drop-in event; no registration required.
Experience Calvert Festival on Oct. 4 (noon to 5 p.m.), located at North Beach, MD – A family-friendly celebration of all things Calvert County with food trucks, local vendors, live music, beer and wine, children’s activities, a Touch-A-Truck zone, and oysters available for purchase. Free admission.
Monster Market on Oct. 4 (9 a.m. to 2 p.m.), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd., Solomons, MD – A Halloween-themed outdoor market with more than 50 booths of handmade, homemade and homegrown seasonal products, plus food trucks including Mouth of the Bay, Judy’s Food Express and Sip & Klatsch. Pet-friendly (leashed), rain or shine. Free admission.
AmericanK9’s Annual Paws & Pumpkins Fall Fest on Oct. 4 (10 a.m. to 4 p.m.), located at 3869 Birdsville Rd., Davidsonville, MD – A family- and dog-friendly festival featuring a pumpkin patch, 30+ vendors and food trucks, petting zoo, face painting, fall photo booth, live music, costume contest with cash prizes, wooded walking trails, 50/50 raffles and more. Tickets required: $10 per person online or $15 at the gate (cash only); free parking.
Bat Night Hike on Oct. 4 (7 to 8 p.m.), located at Wetlands Overlook Park, 4030 11th St., North Beach, MD – A family-friendly guided evening hike to explore local bat habitats; participants are encouraged to dress for the weather and bring water, bug spray and sunscreen. Free admission; registration may be required
Beyond the Displays: Artifact Stories on Oct. 5 (1:30 to 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.
Hunter’s Full Moon Hike on Oct. 6 (7:30 to 9 p.m.), at Battle Creek Cypress Swamp Sanctuary, 2880 Gray’s Rd., Prince Frederick, MD – Experience the glow of the full Hunter’s Moon on a guided moonlit hike through the swamp’s serene trails. This nocturnal walk highlights the natural world’s seasonal changes and invites hikers of all levels to enjoy the sights and sounds of the evening. Not stroller-friendly, but infants and toddlers in backpacks are welcome. $5 per person; registration required.
Walktober: Farmers Market Walk on Oct. 7 (12 p.m. at Solomons Health Center or 5 p.m. at Calvert Hospital), located at various Calvert County walking sites – Join this themed Walktober stroll and snap a picture of your Farmers Market finds while enjoying a healthy, community walk. Free admission; no preregistration required.
For more Calvert County events, visit the Calvert County Maryland website.
THING TO DO IN CHARLES COUNTY
Jazzy Nights at El’s Place on Oct. 3 (7 p.m.), located at The Space by LBI, 2901 Festival Way, Waldorf, MD – Experience live jazz, soulful rhythms, and inspired eats by Cravin’ Flavas in an evening where music meets legacy. Advance tickets required.
CAP’s Adult Prom Night Fundraiser on Oct. 3 (7 to 11 p.m.), located at Waldorf Jaycees, 3090 Crain Hwy, Waldorf, MD – Back by popular demand, enjoy a night of dinner, live music by Voice 24/7, raffles, dancing, and plenty of laughter while supporting a great cause. All proceeds benefit survivors and children in crisis in Charles County. Tickets Needed.
Charles County Summer Fest – Free Outdoor Concert on Oct. 3 (6 to 9 p.m.), located at Lamont’s Entertainment Complex, 4400 Livingston Rd., Indian Head, MD – End the season with live outdoor music, food and vendors at this free family-friendly concert. Free admission; bring your own chairs.
Friday Teen Hangouts on Oct. 3 (6 to 9 p.m.), located at multiple Charles County Recreation centers – Enjoy free interactive activities promoting positive youth development. Open to ages 13–17. Free admission with Friday Hangout RecCard required.
Pop Pop’s Fall Festival 2025 on Oct. 4 (10 a.m. to 6 p.m.), located at Pop Pop’s Greenhouse, 13340 Rock Point Road, Newburg, MD – Celebrate the season with a haunted trail, 150-foot super slide, pedal cart track, pumpkin bowling, corn bin, sunflower field, photo props, gem and shark tooth mining, pumpkin slingshots, and more. Admission: $12 per person; free for ages 3 and under.
Hook-tober Fishing Tournament on Oct. 4 (7 a.m. to 3 p.m.), located at Port Tobacco Marina & Ship Store, 7610 Shirley Blvd., Port Tobacco, MD – An all-day fishing tournament with prizes, local vendors, seasonal food and snacks, plus live music and good vibes along the waterfront. Registration required for tournament entries; spectators welcome.
Pinot on the Potomac on Oct. 4 (3 to 7 p.m.), located at Alice Ferguson Foundation, 2001 Bryan Point Rd., Accokeek, MD – Celebrate Maryland vineyards with unlimited wine tastings from the Maryland Wineries Association, preorder cuisine from Blue Wind Gourmet, plus wine by the glass/bottle from Port of Leonardtown Winery and beer from Mully’s Brewery, along with live music, silent auction, photo ops, and sunset views over the Potomac River. Ages 21+ only; rain or shine; pets not permitted. Proceeds benefit children’s outdoor education programs.
La Plata Fall Festival on Oct. 5 (noon to 3 p.m.), located at La Plata Town Hall, 305 Queen Anne St., La Plata, MD – A family-friendly afternoon featuring live music, kids’ activities, craft and food vendors, plus the town’s seasonal Scarecrow Festival. Free admission.
Neighborhood Walk & Talk on Oct. 5 (4 to 5 p.m.), located at Smallwood Village Center, 146 Smallwood Village Center, Waldorf, MD – A one-hour community walk hosted by Strong Towns Charles County to assess sidewalks and street design, starting and ending near the directory sign by WestHouse Studio Salon; approx. 1.5-mile walk on asphalt and concrete. Free admission.
Prime Paint Night on Oct. 8 (6 to 7:30 p.m.), located at La Plata Branch Library, 2 Garrett Avenue, La Plata, MD – Unwind with an adult-centric painting program featuring a new theme every other month. Registration is required. Free admission.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
Oktoberfest First Friday Weekend on Oct. 3 to 5, located throughout Leonardtown Square, Leonardtown, MD – A festive weekend packed with fall fun, including the 7th Annual Scarecrow Stroll opening Friday, live music in the Square, the Friends of the Poor Walk and the 57th Annual Blessing of the Fleet on Saturday, and the beloved Antique Tractor & Truck Parade on Sunday. Free admission to most activities; trolley service available for Saturday’s Blessing of the Fleet.
“The Mousetrap” by Agatha Christie showing Oct. 3–5, located at Three Notch Theatre, 21744 South Coral Dr., Lexington Park, MD – The Newtowne Players present Agatha Christie’s classic murder mystery full of twists and turns as seven strangers snowed in at Monkswell Manor discover a killer is among them. Showtimes this weekend: Friday & Saturday at 8 p.m., Sunday at 3 p.m. Tickets required: Adults $20; Groups $17; Children 6–11 $15; under 5 free (not recommended for young children).
Big Fight Alert! Southern MD Smoke 18 on Oct. 4 (doors open 2 p.m.; first fight 3 p.m.), located at The Rex Theatre, 22695 Washington Street, Leonardtown, MD – Knowledge Boxing Center of Southern Maryland presents 12+ thrilling amateur bouts in an electrifying afternoon of live boxing action. Tickets needed.
PAXCON Scale Model Show & Contest on Oct. 4 (9 a.m. to 3 p.m.), located at Hollywood VFD Rental Hall, 24801 Three Notch Rd., Hollywood, MD – Vendors, hourly raffle drawings, gold/silver/bronze open-award contest, and on-site food from the Ladies Auxiliary. Entry fees: Juniors (17 & under) $10/10 models, Adults $15/10 models (only 5 judged); browsing only $10 individual or $15 family.
13th Annual Cruisin’ Southern Maryland on Oct. 4 (opening ceremony 9:10 a.m.; cruise departs 9:30 a.m.), starting at Golden Beach Park & Ride, 37750 Golden Beach Rd., Charlotte Hall, MD, with a lunch stop at Walmart, 45485 Miramar Ln., California, MD, and finishing at Charlotte Hall Veterans Home, 29449 Charlotte Hall Rd., Charlotte Hall, MD – A classic car cruise traveling through Southern Maryland with hot dogs and refreshments served at the finish. Free admission for spectators; awards ceremony at 3:30 p.m.
6th Annual Fall Market on Oct. 4 (10 a.m. to 5 p.m.), located at Southern Trail Distillery, 27227 Morganza Turner Road, Mechanicsville, MD – A lively fall market with 40 local vendors, three food trucks, handcrafted cocktails from Southern Trail Distillery, and live music by HydraFX from noon to 3 p.m. Free admission.
Children’s Book Signing – Meet the Author & Illustrator on Oct. 5 (10 a.m.–4 p.m.), located at Fenwick Street Used Books & Music, 41665 Fenwick St., Leonardtown, MD – Meet author JoLyn H. and illustrator Ali Brown, hear about their creative process, get your copy of “Mr. Ugly and the Terrible Raid” signed, and enjoy discount offers plus kids’ activities like bookmarks and coloring sheets. Free admission.
Little Explorers: Fall Colors on Oct. 8 (10 to 11 a.m.), located at Historic St. Mary’s City Plantation, 47414 Old State House Rd., St. Mary’s City, MD – Preschoolers discover the beauty of autumn through crafts and play, includes one adult and museum admission. Tickets required: $4 per child / $3 for members. Call 301-994-4370 for details.
Dance for Neuroplasticity: Hippy’s ’60s Theme on Oct. 7 (10 to 11:15 a.m.), located at Loffler Senior Activity Center, 21905 Chancellors Run Rd., Great Mills, MD – A themed dance-and-learning class exploring how dance supports neuroplasticity to boost cognitive function, emotional well-being, and overall brain health; advance registration required. Tickets Needed.
One Maryland, One Book: “KIN” Author Event on Oct. 8 (exhibits open 6:30 p.m.; author talk 7 p.m.), at Performing Arts Center, 47835 College Dr., St. Mary’s City, MD – Join author Carole Boston Weatherford and artist Jeffrey Boston Weatherford for a discussion on their book Kin: Rooted in Hope, exploring family history, art, and Black heritage across generations, followed by book signing and lobby exhibits by local historical organizations. Free admission for all ages; no tickets required.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – October 3rd
5:00pm – Mike Mead & Eric Wolf – Mully’s Brewery – Prince Frederick MD
5:00pm – Billy Breslin – Greene Turtle Sports Bar – La Plata MD
5:00pm – Joseph Norris – Snellman’s Store & Shuck Shack – Hollywood MD
5:30pm – Jusin Allen – Port of Leonardtown Winery – Leonardtown MD
6:00pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Jayce Gallagher – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Shaun Gomban – The Local – Hollywood MD
6:00pm – Chesapeake Sons – Blue Fish Pub – Solomons MD
6:00pm – Myles Deep Band – Wheel House Beer Garden – North Beach MD
6:00pm – Wes Ryce – Album Release Show @ Town Square – Leonadtown MD
6:30pm – Audra Keeler & Johnny Brown – The Ruddy Duck – Solomons MD
7:00pm – Hometown Band – Swan Point Country Club – Swan Point MD
7:00pm – HydraFX – The Taphouse 1637 – California MD
8:00pm – Drivetrain – Toots Bar – Hollywood MD
8:00pm – 2nd Hand News (Fleetwood Mac) – Running Hare – Pr. Frederick MD
8:30pm – Sister Midnight – Coconut Joe’s – Edgewater MD
8:30pm – Million Proof / Intentionally Blank – Ollie’s Bar – La Plata MD
9:00pm – The Rise Band & Show – Twisted Bar & Grill – Hollywood MD
Saturday – October 4th
9:00am – Joseph Norris – Antiques & General Store – Port Royal VA
12:00pm – HydraFX – Southern Trail Distillery – Mechanicsville MD
12:00pm – Suckerpunch – Wheel House Beer Garden – North Beach MD
2:00pm – Copper Pennies – Potomac Speedway – Budds Creek MD
2:00pm – Mike Mead – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Sax Appeal – Corteau Vineyards – Mechanicsville MD
2:00pm – Monkey Business – Port of Leonardtown Winery – Leonardtown MD
3:00pm – Loose Change – The Boathouse @ Anchored Inn – Deale MD
5:00pm – Johnny Seaton & Bad Behavior – Blue Fish Pub – Solomons MD
5:00pm – Nightcap – Running Hare Vineyard – Prince Frederick MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
6:00pm – James Cornett – The Local – Hollywood MD
6:00pm – Southland – Wheel House Beer Garden – North Beach MD
6:00am – Byron Ciotter – Bugeye Grill – Solomons MD
6:00pm – Brad Turner – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – HydraFX – Brudergarten Beer Garden – Leonardtown MD
6:30pm – The Prophessor – Cryer’s Back Road Inn – Leonardtown MD
7:00pm – The Basement Snakes – Lort Calvert Bowling – Huntingtown MD
7:00pm – Richard Hayward – Neptune’s Seafood Pub – North Beach MD
7:00pm – Mike Trujillo – The Brass Tap – California MD
7:00pm – Chris Dean – Pax River Ale House – Lexington Park MD
8:00pm – Girl Crush – The Taphouse 1637 – California MD
8:00pm – Red Jam – Toots Bar – Hollywood MD
8:00pm – Jack Allen – Olde Town Pub – Leonardtown MD
8:00pm – Taboo – The Tavern – Saint Leonard MD
8:00pm – Sister Midnight – O’Gannigan’s Irish Pub – Prince Frederick MD
8:30pm – UnSung – Ollie’s Bar & Grill – La Plata MD
9:00pm – No Go Romeo – Apehangers Bar & Grill – Bel Alton MD
Sunday – October 5th
1:00pm – Buffalo Velcro – Ruddy Duck Brewery & Grill – Solomons MD
2:00pm – Rob Blake – Wharf 38 – Deale MD
2:00pm – Nightcap – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Patrick Ward – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Seldom Scene – Elks Lodge # 2620 – Prince Frederick MD
2:00pm – Benefit for Peter James – Ketch 22 Restaurant – Deale MD
————– John Luskey, Ryan Forrester, Michael Ferro & Pete Best –
3:00pm – Morgan Tripp Band – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Jack Allen – The Pier – Solomons MD
4:00pm – Justin Jeansonne – Blue Fish Pub – Solomons MD
Monday – October 6th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – October 7th
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – October 8th
5:00pm – John Luskey – The Boathouse @ Anchored Inn – Deale MD
5:00pm – Mike Hauer – Ketch 22 Restaurant – North Beach MD
6:00pm – Hyland Brothers – Brick Wood Fired Bistro – Prince Frederick MD
6:00pm – Ryan Forrester – The Pier – Solomons MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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