Happy St. Patrick’s Day, St. Mary’s. 👋
Somewhere in the county, someone is debating a drive to Waldorf and then remembering they don’t actually need that thing after all. Not when we have enough going on to keep the whole weekend local. We’ve got plenty right here.
In today’s Insider:
Historic St. Mary’s City reopens its outdoor exhibits today.
$5 gets you into the Fishing & Outdoor Adventure Fair.
The Vintage Source returns for its monthly opening in Compton.
A 3.5-hour drop-off event for the kids in California.
Let’s get into it.
🏡 Around the County
Historic St. Mary’s City officially reopens its outdoor exhibits today, March 17. That means the Godiah Spray Tobacco Plantation and the Maryland Dove are back open Tuesday through Saturday from 10:00 AM to 4:00 PM. If you’ve been waiting for spring to feel real, this helps.
The Vintage Source returns this weekend in Compton, open Saturday and Sunday from 8:00 AM to 4:00 PM. It only opens one weekend a month, so most plan around it. Expect furniture, accessories, architectural salvage, and the usual “maybe we should get this” conversations.
Construction at Pegg Road and Westbury Boulevard is officially underway as of today, and it is expected to last about three months. If that is part of your normal route, now is a good time to start taking the long way around before rush hour makes the decision for you.
⭐ Top Pick: SoMD Fishing & Outdoor Adventure Fair
Sat, March 21 (8 AM to 3 PM) & Sun, March 22 (9 AM to 2 PM) | St. Mary’s County Fairgrounds – This is the big one this weekend. If you fish, hunt, boat, camp, or just like wandering around outdoor gear you absolutely do not need, the $5 admission is easy to justify. Expect rods, reels, tackle vendors, a kids’ casting contest, and an America’s Boating Club safety course.
☕ The Insider’s Pick: Port of Leonardtown Winery
Leonardtown, MD
If you haven’t been to the winery lately, it’s still one of the easiest ways to spend a weekend afternoon in the county. It skips the stiff winery energy and feels more like a local backyard that happens to serve good wine.
The Vibe: Bright tasting room, easy patio, no pressure to make it a whole production. Good spot when you want to ease into the afternoon and stay a while.
Why It’s Good: This place consistently gets the balance right. It feels social without being loud, relaxed without being boring, and local in a way that does not feel forced.
The Play: Go with a tasting flight instead of a single glass. If you are there Saturday, Napa Grill will be on-site and there is live music on the patio, which is about as easy as a St. Mary’s weekend plan gets.
👨👩👧 Family & Kid Friendly
Cherry Blossom Festival: Sat, March 21, 12:00 PM to 4:00 PM | Lexington Manor Passive Park – Food trucks, disc golf, live music, and origami under the blossoms. It’s a good family pick if you want something outdoors without committing the whole day. Expect a steadier crowd once the afternoon gets going. 🌸
Kids Night Out: Sham-ROCK Party: Sat, March 21, 6:00 PM to 9:30 PM | My Gym St. Mary’s, California – This is the secret weapon for parents. It’s a 3.5-hour drop-off night with tumbling, leprechaun traps, and pizza, which means the kids get a party and you get an actual evening back, even if all you do with it is go to Target.
Spring Scavenger Hunt: Sat, March 21, 10:00 AM | Historic St. Mary’s City – This is an easy one for families. Kids get to roam the grounds looking for clues, and the space out there usually keeps it from feeling too crowded. The hunt runs throughout the day, so you do not have to time it perfectly.
🍷 Date Night
Wines Across America Tasting: Sat, March 21, 2:00 PM to 4:00 PM | The Inn at Leonardtown – This is the polished option for the weekend. You get six American wines plus hors d’oeuvres, and it’s a good fit if you want something that feels a little more put together than the usual bar stop. 21+ only.
Calligraphy & Watercolor Workshop: Fri, March 20, 6:15 PM | Port of Leonardtown Winery – A watercolor and calligraphy class with a glass of wine included. The $60 ticket covers supplies, and it is a nice pick if dinner alone feels a little too predictable. 🎨
Easter Dog Treat Hunt: Sat, March 21, 12:30 PM | Port of Leonardtown Winery – If your dog is somehow part of your date-night planning, here you go. The $35 ticket includes an egg hunt, bandana, treats from Happy Hounds Bakery, and a drink voucher for you. Proceeds support local animal rescue, and pre-registration is required. 🐶
🎶 Night Out
Reggie Rice: Adult Daycare | Sat, March 21, 7:00 PM | The Rex Theatre – Stand-up, magic, and general chaos in a one-night-only show at The Rex. He is back after two years at sea, and this feels like the kind of Saturday ticket that disappears faster than people expect.
No Go Romeo!!: Sat, March 21, 9:00 PM | The Rex Theatre – By 9:00 PM, the Square should be fully awake. If you want the louder, more social version of a Saturday night in Leonardtown, this is probably your move.
Jazz & Soul with Latrice Carr: Sat, March 21, 7:00 PM to 10:00 PM | Pier450, Ridge – This is a good pick if you want live music and a waterfront view without the busier Leonardtown energy. Latrice Carr is a strong local draw, and Pier450 is about as easy as a Saturday night plan gets.
Mechanicsville, MD
A lot of people in the county have no idea this place is home to the only Clydesdale team in Southern Maryland.
The Experience: Private 90-minute guided tours where you meet the horses up close and walk the property with the owners.
The Catch: Tours are by appointment only and cost $15 per person. Kids 6 and under are free, and it is about as far from the usual weekend routine as you can get.
🙌 Community Wins
St. Mary’s Stuffed Ham Historic Marker: St. Mary’s County has been named the official birthplace of stuffed ham, and now it is getting a national “Hungry for History” marker to make it official. The unveiling is set for Sunday, March 29 at 2:00 PM at St. Clement’s Island Museum, followed by a reception with samples from local stuffed ham makers.
📌 Quick Local Tip
If you have kids and Miedzinski Park isn’t in your normal rotation yet, it should be. The kids can climb all the way to the top, the upper section is enclosed so it feels a little less stressful, and there is enough there to make it feel like more than a quick park stop.
That is your Insider for this week.
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See you next Tuesday. ✌️