Updated July 2026 · Written by James Armel, licensed Maryland Realtor (License #676208) and born-and-raised Southern Maryland local
August in Southern Maryland means late-summer heat, waterfront breezes, and a packed calendar before the back-to-school season kicks in. Whether you are heading to Solomons for a big-name concert, catching a free Friday night show in La Plata, or exploring the Chesapeake Bay’s natural and maritime history with your kids, there is no shortage of things to do in Southern Maryland in August 2026. Here is a county-by-county breakdown of what is happening this month.
What Is the Biggest Event in Southern Maryland This August?
The marquee event is Brothers Osborne at the Calvert Marine Museum’s Waterside Pavilion in Solomons on Saturday, August 22 at 7 p.m. The duo — John and TJ Osborne, raised in nearby Deale, Maryland — have earned 13 GRAMMY nominations and a 2022 GRAMMY Award for “Younger Me.” In 2026 they are celebrating the 10-year anniversary of their breakthrough album Pawn Shop, making this a homecoming worth seeing. Tickets are $70–$110 and available at calvertmarinemuseum.com. The museum closes at 3 p.m. that day for concert preparations.
What Is Happening at the Calvert Marine Museum in August 2026?
The Calvert Marine Museum in Solomons is one of the top things to do in Southern Maryland any time of year, and August is one of its busiest months. Most programming is included with regular admission or free.
- Wm. B. Tennison Public Cruise — Wednesdays through Sundays throughout August at 2 p.m. One-hour cruise on the Patuxent River. $9 adults, $5 children ages 12 and under.
- Cove Point Lighthouse — Open Wednesdays, Saturdays, and Sundays, 1–4 p.m. Free admission, no beach access.
- Family Fun Friday: Freestyle Friday! — Friday, August 7, 9–11 a.m. Crafts and activities for families with children ages 5–12. Included with admission.
- First Fossil Friday — Friday, August 7, 1–4:30 p.m. Bring your Calvert Cliffs fossil finds for free expert identification.
- Toy Boat Building — Saturday, August 15, 1–4 p.m. Build a wooden toy boat under the Corbin Nature Pavilion. Ages 5 and older. $2 donation per boat requested; museum admission applies.
- Artifact Stories — Sundays August 2, 9, 16, 23, and 30 at 1:30–2:30 p.m. Guided exploration of museum artifacts and maritime history murals. Included with admission.
- Lore Oyster House — Open select dates in August, free admission. The 1934 seafood packing house is 0.6 miles south of the main campus. Check calvertmarinemuseum.com for dates.
The museum is open daily 10 a.m.–5 p.m. Admission is $11 adults, $9 seniors/military/veterans, $6 children ages 5–12. Children under 5 and members are free.
What Is Happening in Charles County in August 2026?
Charles County offers some of the best things to do in Southern Maryland in August for families and music fans, anchored by a free concert series running every Friday through the end of the month.
La Plata Summer Concert Series runs every Friday evening through August 28, 7–9 p.m., on the Town Hall Lawn at 305 Queen Anne Street in La Plata. The lineup spans pop rock, R&B, Latin, jazz, reggae, and more. Bring a blanket or lawn chair; food vendors are on-site. Concerts are free. For the August lineup visit townoflaplata.org.
Other August events in Charles County include the Splash into Success Back-to-School Pool Party on Saturday, August 8 at Hampshire Neighborhood Pool in Waldorf, and the 7th Annual Youth Shark Tank Kidpreneur Competition and Fun Festival on Saturday, August 15 at 2952 Festival Way, Waldorf. Note that the Charles County Fair is scheduled for September 17–20, 2026.
What Is Happening in St. Mary’s County in August 2026?
St. Mary’s County shifts into a quieter August rhythm, but live music is easy to find on weekends. Toot’s Bar in Hollywood (23971 Mervell Dean Rd) hosts live bands nearly every weekend, with karaoke, trivia, and themed nights through the month. The venue completed a full renovation in 2025 adding a new outdoor stage. Check their Facebook page for the monthly lineup.
The county’s bigger events move into fall: the St. Mary’s County Fair runs September 24–27, 2026 in Leonardtown, and the End of Summer Bash with Fireworks at the Leonardtown Wharf is September 5. Worth marking your calendar now.
Is August a Good Time to Buy or Sell a Home in Southern Maryland?
It depends on your situation, but August has real advantages for both sides. Sellers often catch buyers motivated by a before-school deadline — particularly military families with PCS orders. That urgency can work in a seller’s favor on price and timeline. Buyers may find slightly less competition than the spring peak, with sellers who have been on the market since May more open to negotiation.
If you are thinking about a move before year-end, August is a practical time to start. The fall market in Southern Maryland moves quickly, and getting properly prepared takes time. I am happy to walk you through what the current market looks like in your county.
Where to Find More Things to Do in Southern Maryland
For a full and current list of things to do in Southern Maryland, thebaynet.com and smnewsnet.com publish regular event roundups covering all three counties. If you are new to the area or considering a move, our guide to buying a home in Southern Maryland covers what life looks like county by county — from commute times and school districts to waterfront neighborhoods and local market data.
Leave a Reply