TUESDAY, SEPTEMBER 1, 2026
ST. MARY’S INSIDER
THE LOCAL GUIDE TO WHAT’S ACTUALLY HAPPENING
Good morning, St. Mary’s. 👋
Can you believe there are only three more weeks of summer? I don’t know about you, but that went by entirely too fast for my liking…
Let’s get into it.
🏪 Behind the Business
If you missed To the People Betting on St. Mary’s County, start there. That was the letter to the local owners putting their name, money, time, and reputation behind an idea.
I said the Insider was going to spend more time on what happens before the doors open: the mistakes, pivots, close calls, and decisions behind the sign. The first story is Smash House.
I sat down with Jon, one of the owners of Smash House, to talk about how a backyard Blackstone became a full restaurant in downtown Leonardtown. We got into the early struggles, the admin side of starting a business that made “all in” feel very real, and why the beef was the one thing they refuse to compromise on. Read Behind the Business: Smash House.
Jon Kerley, Smash House in Leonardtown.
🗳️ What Should the Insider Bring You Next?
This week’s poll is a useful kind of nosy. I’m trying to make the Insider better at bringing you local deals and recommendations you might actually use. If I could convince one local business to give Insider readers a genuinely useful offer this fall, where should I start?
Which local deal would you actually care about?
🏡 Around the County
Shannon Farm Park Is Moving Forward, Slowly: St. Mary’s County has started work to restore and protect wetlands connected to the planned 212-acre park off Route 235 near Home Grown Market and Forest Park Road. The first phase calls for an 84-space lot and an accessible trail and boardwalk to 3,000 feet of Chesapeake Bay shoreline, but there is still no construction start date while grant funding and shoreline design move forward.
Jersey Mike’s Is Finally Open in Lexington Park: After missing its original July target, the new Pax River Village Center shop opened August 19 near Gate 2. It is open daily from 10 AM to 9 PM, so the “coming soon” phase has officially been replaced by the lunch line.
Planet Fitness Is Coming to Lexington Park: Planet Fitness now lists a new club as “coming soon” near Gate 2. It will join the newly opened Jersey Mike’s and the Starbucks planned for the same center, though we don’t have opening date yet.
The Airport May Become a New Place to Hold Events: The county will hold a September 15 public hearing on proposed rules for renting the airport terminal’s conference room, atrium, and waterfront pergola. Nothing is final yet, but weddings, meetings, and community events at the airport are now a real possibility.
A New Pickleball Ladder Is Starting at Baggett Park: The six-week program runs Monday evenings from September 14 through October 19 and is open to players 16 and older. It costs $30 for county residents and registration closes at noon September 11. Pickleball continues its very polite takeover of local recreation.
St. Mary’s College Students Are Hunting for a Lost 1638 Manor House: County commissioners approved $5,000 to help archaeologists search for the original Cross Manor, built just four years after the Ark and Dove arrived. Its location has never been confirmed, which means part of early Maryland may still be sitting under a field in St. Mary’s. Am I the only one who immediately thinks of the Netflix show Outer Banks when hearing this?
⭐ The Top Pick
Saturday, September 5 | 5–9 PM
Leonardtown Wharf | 22500 Washington Street, Leonardtown
Free
If you want one easy Labor Day weekend plan, this is it. South Creek and HydraFX play from 5 to 8:30 PM, followed by fireworks over the Wharf to close out summer.
There will also be food, drinks, games, and free trolley service up and down Wharf Hill. Bring a chair or blanket, settle in by the water, and let somebody else worry about producing the grand finale.
📅 Your Weekend Calendar
🟢 Thursday, September 3
Free Military, Veteran & First Responder Kayak Paddle | 5:30–7:30 PM at Greenwell State Park, Hollywood. The two-hour guided Patuxent River paddle is free for military members, veterans, and first responders. Advance registration is required.
🟢 Friday, September 4
Old Jail Museum First Friday Extended Hours | 10 AM–7 PM at the Old Jail Museum, Leonardtown. Tour the 1876 jail during free extended hours for First Friday.
Nonprofit Expo | 4–6 PM on Glendening Lawn at St. Mary’s College. Meet local nonprofit groups and learn about volunteer and community-service opportunities. The rain location is the Michael P. O’Brien Athletics & Recreation Center.
Arts & Entertainment Celebration First Friday | 5–8 PM at Leonardtown Square. Galleries, shops, restaurants, and other downtown businesses feature local artists, exhibits, and specials throughout the weekend.
🟢 Saturday, September 5
First Saturday Market | 9 AM–4 PM at Town Market, Leonardtown. Shop local produce, meats, cheeses, breads, desserts, flowers, plants, apparel, and handmade goods. Admission is free.
Southern Maryland Sunflower Festival | 10 AM–4 PM at Serenity Farm in Hughesville. Explore six acres of sunflowers, pick flowers, take a hayride, visit the petting area, and browse art and food vendors. Parking is free, leashed dogs are welcome.
Maryland Dove Passenger Sail | 10 AM–noon or 1–3 PM at Historic St. Mary’s City. Sail aboard the full-scale wooden ship with a choice of two-hour trips. Tickets are $60, or $50 for HSMC members; advance reservations are required. Ages 5 and up.
Free Drayden Schoolhouse Open House | 11 AM–2 PM at the Drayden African American Schoolhouse. Tour one of the nation’s best-preserved one-room African American schoolhouses and hear how local students learned there through the mid-20th century. Admission is free; donations are accepted.
WildGood at Port of Leonardtown Winery | 2–5 PM at Port of Leonardtown Winery. The Southern Maryland party band plays pop and rock across the decades, with food and local wine available.
End of Summer Bash | 5–9 PM at Leonardtown Wharf. Live music, food, drinks, games, trolley rides, and fireworks. Free and family-friendly.
The Wailin’ Jennys | 7–9 PM at the Dodge Performing Arts Center, St. Mary’s City. The award-winning folk and bluegrass trio performs in the Concert Hall.
🟢 Sunday, September 6
Southern Maryland Sunflower Festival | 10 AM–4 PM at Serenity Farm in Hughesville. The Southern Maryland Sunflower Festival continues Sunday.
Cars & Coffee Car Show | 10 AM–2 PM at Town Market, Leonardtown. Check out the cars, plus a 50/50 raffle, door prizes, cornhole, and music. Free to attend.
Live Music on the Beach with Latrice Carr | 5–8 PM at Pier450, Ridge. Spend Sunday evening by the water with jazz, blues, pop, and soul. There is no cover.
🤝 Trusted Local Partners
St. Mary’s Insider is supported by local businesses and organizations that help keep this thing going.
That’s your Insider for this week.
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See you next Tuesday. ✌️
Michael Cole, Publisher | St. Mary’s Insider
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