things to do near me southern maryland

SOUTHERN MARYLAND — Fall is officially here, bringing cooler days and plenty of seasonal activities — from live music and theater to outdoor adventures, festivals, historic reenactments, and family-friendly fun. This week’s calendar wraps up September with the Calvert County Fair, birdwatching walks, riverfront celebrations, and even a few Oktoberfest events. Get ready for pumpkin-filled farm festivals and more.

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THINGS TO DO IN CALVERT COUNTY

Homeschool Day: Maryland, Naturally Amazing! on Sept. 26 (9:30 a.m. to 12:30 p.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD – Designed for homeschool families, this program explores the natural wonders of Maryland. Registration required.

Calvert County Fair on Sept. 26–28 (all day), located at Calvert County Fairgrounds, 140 Calvert Fair Drive, Prince Frederick, MD – Enjoy a Southern Maryland tradition with carnival rides, food, games, livestock shows, educational exhibits, contests, and live entertainment for all ages. Check the fair’s website or social pages for daily schedules and special admission details.

Maze Craze in the Moonlight on Sept. 26 (7 to 10 p.m.), located at Rolling Acres Farm, 3305 St. Leonard Road, Port Republic, MD – Tackle the corn maze after dark with a flashlight for a night of family-friendly adventure under the moonlight. $10 presale / $12 at the gate.

Migration on the Point on Sept. 27 (8 a.m. to noon), located at Point Lookout State Park, 11175 Point Lookout Road, Scotland, MD – Join the Southern Maryland Audubon Society for a guided birdwatching morning to observe fall migratory species along the park’s scenic shoreline. Free with park entry fee.

Halloween Costume & Décor Swap on Sept. 27 ( 2 to 4 p.m.), located at Calvert Library Prince Frederick, 850 Costley Way, Prince Frederick, MD – Bring gently used costumes and décor to exchange for something new-to-you and get ready for a spooky, sustainable Halloween. All ages welcome; registration requested. Free admission.

Music by the Marsh: Jug Bay 40th Anniversary on Sept. 27 (2 to 7 p.m.), located at Jug Bay Wetlands Sanctuary, 1361 Wrighton Rd., Lothian, MD – Enjoy live music, art and archaeology exhibits, lawn games, food trucks, meadow walks, and kids’ activities like “touch a truck” and haystack climbs. Bring chairs or blankets for lawn seating. $5 per person; free for kids 5 and under. Registration required.

FREE Bingo at The Dock on Sept. 27 (3 p.m.), located at The Dock at Rod ‘N’ Reel Resort, 4160 Mears Ave., Chesapeake Beach, MD – Spend a relaxed afternoon by the waterfront with fun, free bingo games, gift card prizes, and a laid-back vibe. Enjoy coastal bites like fish tacos, hummus boards, and boardwalk fries, plus refreshing cocktails, chilled beer, and drinks from the full bar. Free admission.

Moth Mania on Sept. 27 (7 to 9 p.m.), located at North Beach Nature Center, 9404 Dayton Ave, North Beach, MD – Discover the diverse moths of Maryland with naturalist-led moth identification, nature trivia, and s’mores around the fire. Free admission.

Astronomy Night on Sept. 30 (7:30 to 8:30 p.m.), located at Fairview Branch Library Field, 21237 Three Notch Road, Fairview, MD – Explore the night sky with guidance from the Astronomy Club of Southern Maryland and learn about the equipment used for stargazing. All ages welcome; outdoor event, weather permitting. Free admission.

Homeschool Day in Solomons: Autumn – Exploring the Wonders of Day and Night in Nature! on Oct. 1 (10 a.m. to 3 p.m.), located at Calvert Marine Museum & Annmarie Sculpture Garden, Solomons, MD – Families can pick up a Homeschool BINGO card at CMM, complete nature-themed activities at both sites to earn BINGO, and turn it in at Annmarie Garden for a chance to win a prize. Ideal for grades K–5, but all ages welcome. Regular admission applies; CMM members free at CMM.

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

THING TO DO IN CHARLES COUNTY

Charles County’s Largest Indoor Snowball Battle on Sept. 26 (6:30 to 8 p.m.), located at Somers Community Center, 300 Willow Lane, La Plata, MD – Kids ages 4–10 can join over 1,000 soft indoor snowballs for a night of winter-themed fun and friendly competition, no slush or mess required. $20 residents / $25 non-residents. Registration required at CharlesCountyParks.com.

Heart & Sole 5K Walk/Run on Sept. 27 (Sat, registration 7:30 a.m., race start 8 a.m.), located at Indian Head Rail Trail, 10390 Theodore Green Blvd, White Plains, MD – Lace up to run or walk in support of heart disease awareness at this family-friendly fundraiser hosted by The Respect Yourself Project. Proceeds benefit heart health initiatives.

The Great RPT Race on Sept. 27 (10 a.m. to 1 p.m.), located at various Charles County Recreation, Parks & Tourism sites – Compete by exploring parks and facilities across the county and completing your Great RPT Race Passport for a chance to win a Recreation, Parks, and Tourism prize pack. Enjoy demonstrations, giveaways, and fun for all ages. Free admission.

2025 Monarchs & Milkweed Festival on Sept. 27 (10 a.m. to 2 p.m.), located at Merkle Natural Resources Management Area, 11704 Fenno Rd., Upper Marlboro, MD – Celebrate the migration season with butterfly tagging and release, guest speakers, food trucks, kids’ crafts and games, garden tours, hikes, and the popular costume contest. Free, family-friendly event. 

2nd Annual Soldiering Through the Ages on Sept. 27–28 (Saturday, 9 a.m. to 5 p.m.; Sunday, 9 a.m. to 3 p.m.), located at Maryland Veterans Museum at Patriot Park, 11000 Crain Highway, Newburg, MD – Experience military history brought to life with reenactors and living historians from Roman, Viking, Napoleonic, Revolutionary War, Civil War, and World War II eras, plus static displays, black powder and cannon demonstrations. Free family-friendly event.

Community Bike Ride on Sept. 28 (11 a.m.), located at 3200 Leonardtown Rd., Waldorf –  Meet at Urban Cycling & Road Safety Workshop with Trek staff (light refreshments), then join a casual 7-mile group ride at noon around Waldorf. Helmets required; suitable for most ages and abilities.

Goosebay Marina 2nd Annual Car Show on Sept. 28 (10 a.m. to 4 p.m., rain date Oct. 5), at Goosebay Marina, 9355 Goosebay Lane, Welcome, MD – Benefit for Tenth District Volunteer Fire Dept. with classic cars, live bands, food trucks, door prizes, 50/50 raffle, and trophies for Best in Show and more. $25 entry; $10 spectator (kids 12 & under free).

Walk Maryland Day with the Town of La Plata on Oct. 1 (6 to 7 p.m.), starting and ending at Bird City Pocket Park, corner of St. Mary’s Avenue and Centennial Street, La Plata, MD – Join the Town of La Plata and Strong Towns Charles County for a community “Neighborhood Walk & Talk” in honor of Walk Maryland Day. Residents are invited to stroll downtown together to celebrate the state’s official exercise and discuss ways to make local streets more walkable. Free, public event; registration encouraged.

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

THINGS TO DO IN ST. MARY’S COUNTY

SMTMD Fall Concert: IONA on Sept. 26 (7 p.m.), located at Christ Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – Enjoy an evening of live Celtic music and dance as IONA brings the sounds of the seven Celtic Nations to Southern Maryland. The group has entertained audiences since 1986 with lively tunes, storytelling, and cultural commentary, offering a rich celebration of traditional and contemporary Celtic heritage.

Free Garage Sale on Sept. 27 (9 a.m.), located at 22747 Old Rolling Road, Lexington Park, MD – Browse through a variety of items at this community garage and yard sale. Everything is free, and monetary donations will not be accepted. Free admission.

RiverFest 2025 on Sept. 27 (10 a.m. to 3 p.m.), located at Historic St. Mary’s City, St. Mary’s City, MD – Celebrate the St. Mary’s River with live music from the Eastport Oyster Boys, Indian Summer, and Chesapeake Public Charter School students, plus kayaking, oyster tonging, and the ceremonial river wade-in at 2 p.m. Enjoy wildlife encounters, Chesapeake Bay Retriever demos, face painting, balloon animals, food vendors, and crafts. Free admission, rain or shine. Free, public event.

Autumn Harvest on the Farm at Lyon Family Farms on Sept. 26–28 (Friday & Saturday, 10 a.m. to 5 p.m.; Sunday, 10 a.m. to 2 p.m.), located at Lyon Family Farms, 39010 Lyon Lane, Mechanicsville, MD –  Enjoy hayrides, a petting zoo, yard games, pumpkin bowling, a hay maze, a playset, and picnic areas, plus food trucks, seasonal produce, meats, and fall porch décor for sale. $12 admission includes one pumpkin; kids 3 & under free.

Taste of St. Mary’s at the Airport on Sept. 27 (noon to 4 p.m.), located at 44200 Airport Road, California, MD – Savor food and drinks from local vendors while enjoying aircraft displays, model plane demos, a classic car show, axe lane, games, kids’ make-and-take crafts, a dollhouse raffle, and more. Rain or shine, free admission.

Fall Craft & Vendor Sale and Community Yard Sale on Sept. 27 (7 a.m. to 1 p.m.), located at St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD – Enjoy a morning of treasure hunting with local vendors, handmade crafts, and yard sale bargains, plus coffee, breakfast, or lunch from Dan D’s Food Truck. Proceeds from table rentals benefit the SDVFD&RS Auxiliary. Free admission.

Skit: Grandma’s Bible on Sept. 27 (3 p.m.), located at First Missionary Baptist Church, 46370 Pegg Lane, Lexington Park, MD – Join the Drama Ministry for a heartfelt performance of Grandma’s Bible. Temperature checks will be taken at the door for everyone’s health and safety, and hand sanitizer will be available. Free admission.

Stand-Up Comedy Night at Taphouse 1637 on Sept. 27 (8:30 p.m.), located at 23418 Three Notch Road, California, MD – Enjoy 90 minutes of big laughs with new comics at Taphouse 1637. Tickets are limited—reserve in advance

Karaoke Cake Walk on Sept. 30 (10 to 11:30 a.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Sing your favorite songs, have fun, and join in the center’s beloved Cake Walk tradition—a musical-chairs-style game where baked goods are the prizes. This casual event is open to amateurs and perfect for making memories with friends. Free admission; advance registration required.

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

Friday – September 26th

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

5:00pm – Alex Barnett – Corteau Vineyards – Mechanicsville MD

5:00pm – Jack Allen – The Local – Hollywood MD

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

5:30pm – Out of Order – Running Hare Vineyards – Prince Frederick MD

6:00pm – Chris Dean – Mully’s Brewery – Prince Frederick MD

6:00pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD

6:00pm – Sean Postanowicz – Southern Trail Distillery – Mechanicsville MD

6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD

6:00pm – Ryan Forrester – Happy Harbor Restaurant – Deale MD

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

6:30pm – Last Shot Band – Blue Fish Pub – Solomons MD

7:00pm – Snacks & Company – Swan Point Country Club – Swan Point MD

7:00pm – Greg Barrick – The Taphouse 1637 – California MD

8:00pm – Monkey Business – Toots Bar – Hollywood MD

8:00pm – Jay Shade – Phil’s Place – Hughesville MD

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

9:00pm – Smoke Signals – Apehangers Bar & Grill – Bel Alton MD

Saturday – September 27th

1:00pm – Joseph Norris -Taste of St Marys @ SMC Airport – California MD

2:00pm – Mike Trujillo & Krys Baker – POL Winery – Leonardtown MD

2:00pm – Chris Dean – Robin Hill Farm & Vineyard – Brandywine MD

2:00pm – Greg Floberg – Corteau Vineyards – Mechanicsville MD

2:00pm – Bob Hale – Perigeaux Vineyards & Winery – Saint Leonard MD

2:00pm – Copper Pennies – Potomac Speedway – Budds Creek MD

3:00pm – 3 of a Kind – The Boathouse @ Anchored Inn – Deale MD

3:00pm – Vicki Roberts Band & Friends – Skipper’s Pier – Deale MD

4:00pm – Kevin Lee – Happy Harbor Restaurant – Deale MD

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

5:00pm – Byron Ciotter – Port Oysteria & Brewery – Fredericksburg VA

5:30pm – Blazin’ Keys Dueling Pianos – Vol. Fire Dept. – Hollywood MD

6:00pm – Stealin’ The Deal – Blue Fish Pub – Solomons MD

6:00pm – Troll Tribe – Wheel House Beer Garden – North Beach MD

7:00pm – Ben Connelly – Bugeye Grill – Solomons MD

6:00pm – Pork Donut – Southern Trail Distillery – Mechanicsville MD

6:00pm – Billy Breslin – The Local – Hollywood MD

6:00pm – GrooveSpan Band – Dixon Family Farm – Mechanicsville MD

6:00pm – First Friday – Dockside Restaurant & Sports Bar – Deale MD

7:00pm – Funkzilla Unplugged – Cryer’s Back Road Inn – Leonardtown MD

7:00pm – Joe Parsons – Pax River Ale House – Lexington Park MD

7:00pm – Myles Deep Band – The Scuttlebutt – Cobb Island

8:00pm – Chris Dean – Bushmill Tavern – Abingdon MD

8:00pm – Backstage Pass – The Tavern – Saint Leonard MD

8:00pm – Tommy McKee Band – Toots Bar – Hollywood MD

8:00pm – Never 2 Late – Twisted Bar & Grill – Hollywood MD

8:00pm – Midnight Sunsets – Buckets Bar & Grill – Lusby MD

9:00pm – Steve Potter Band – Huntt’s Tavern – Pomfret MD

Sunday – September 28th

11:00am – Jim Stephanson – Pier 450 Restaurant – Ridge MD

2:00pm – Greg Barrick – Wharf 38 – Deale MD

2:00pm – Sarah Gravelle – Port of Leonardtown Winery – Leonardtown MD

2:00pm – Jack Allen – Brudergarten Beer Garden – Leonardtown MD

2:00pm – Levi Stephens – Robin Hill Farm & Vineyard – Brandywine MD

2:30pm – GrooveSpan – LobsterFest @ Charles Co Fairgrounds – La Plata MD

3:00pm – Fat Whiskey – Happy Harbor Restaurant – Deale MD

3:00pm – Billy Breslin – Coast 2 Coast Seafood Bar – Solomons MD

3:00pm – Nightcap – The Boathouse @ Anchored Inn – Deale MD

3:00pm – Doc Lohn – The Pier – Solomons MD

Monday – September 29th

7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD

Tuesday – September 30th

5:00pm – Mike Mead – Heritage 485 – Prince Frederick MD

6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD

Wednesday – October 1st

6:00pm – Ryan Forrester – Brick Wood Fired Bistro – Prince Frederick MD

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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