Good morning, St. Mary’s 👋
We’ve got a busy stretch ahead. Between new shops opening in Leonardtown and the first wave of St. Patrick’s Day events kicking off, the calendar filled up fast. We sorted through it and pulled the things actually worth your time.
In Today’s Insider:
A major upgrade for downtown Leonardtown’s retail scene.
A charcuterie class at the winery and St. Patty’s day in California.
STEAM Day at the Navy Museum and a community formalwear event.
A homegrown Principal of the Year!
Let’s dive in.
🏡 Around the County
The Vintage Collective is Live
The Vintage Collective just opened up on Washington and it’s a solid upgrade for downtown Leonardtown. This isn't a dusty basement find; it’s a curated mix of mid-century furniture, Victorian jewelry, and Y2K nostalgia that will take you back to the good ole’ days. If your space is looking a little generic, this is the spot to find some actual character.
SMCPS Calendar Adjustment
Superintendent Dr. Scott Smith announced this week that Easter Monday (April 6, 2026) is now a full school day to make up for winter weather closures. Sorry kids.
Summer Camp Season is Here
St. Mary’s County Rec & Parks opened registration for 2026 summer camps as of March 2nd. If you’ve lived here long enough, you know the popular spots fill up fast. Better to handle it now than scramble in May.
⭐ The Top Pick
St. Paddy’s Day Charcuterie Class Saturday, March 14, 6:15 PM | Port of Leonardtown Winery
This is a clear winner for Saturday. For $60, you’re not just eating, you’re learning the craft. You’ll build a 12-inch board with Irish cheeses and seasonal pairings, and they even provide a take-home box for your leftovers. It’s a relaxed, structured way to ease into the holiday without the rowdy crowds.
☕ The Insider's Pick: Smash House MD
If you’re tired of the same thick burger patties that take forever to cook, Smash House in Leonardtown is worth a stop. They recently moved into their new spot on Fenwick Street, and the vibe is completely different from most places on the square. Think comic-book walls, neon lighting, and a high-energy feel that almost seems like a city burger spot dropped into Leonardtown.
The Vibe: Fast, unique, and modern. A good place to kick off a Saturday night before taking a walk around downtown.
Why it’s good: They source their beef locally from Sassafras Farms in Dunkirk, and the smashed patties hit a hot griddle that gives you those crispy edges I just can’t seem to get right at home. 🤤
The Order: The OG Smash 🍔 — one, two, or three patties with American cheese, pickles, Smash Sauce on a potato roll. If you’re hungry, the Smash Fries can easily become a full meal.
👨👩👧 Family & Community
STEAM Day @ The Navy Museum Saturday, March 14, 10:00 AM – 3:00 PM | Patuxent River Naval Air Museum – This is the perfect Saturday plan for families. The museum is hosting a full day of hands-on Science, Technology, Engineering, Art, and Math (STEAM) exhibits. It’s interactive, it’s educational, and it’s a great way to explore local aviation history with the kids. Bonus: the event includes special family-friendly admission offers, so it’s worth checking before you go.
4th Annual Prom Ensemble Event Sat–Sun, March 14–15, 10:00 AM - 4:00 PM | St. Mary’s County Fairgrounds – This is one of the best community lifts in the county. The Cinderella Society is providing free dresses and tuxedos at the Fairgrounds. They’ve also partnered with My Sister’s Closet to offer professional business attire for women. It’s the easiest way to cut prom costs to zero while supporting a local nonprofit.
Shamrock 5K Fun Run Sunday, March 15, 8:00 AM | Wicomico Shores Golf Course –Mechanicsville is hosting the R&P Shamrock 5K at its new home on the golf course. It’s an early start, but the sunrise views over the greens make it worth the wake-up call. The trail is manageable and all paid finishers get a medal (because if there’s no medal, did it even happen?) Best part: If you’re 21+, your registration includes a voucher for a golden lager at the Riverview Restaurant right there on the course to celebrate your finish.
🍷 The Date Night Edit
Mind > Blown Speaker Series Sunday, March 15, 3:00 PM - 5:00PM | Pier450, Ridge – If your ideal Sunday leans more “thoughtful conversation” than “loud bar,” this is a great pick. This week features Ruth Mitchell, Manager of Archaeological Services at Historic St. Mary’s City, sharing insights from the region’s deep colonial past. Followed by a casual reception, making it an easy way to mix local history with a glass of wine.
"The Mad Ones" Musical Friday-Sunday, March 6–15 | Three Notch Theatre, Lexington Park – The Newtowne Players are performing this contemporary musical about a young woman at a crossroads. It’s a story-driven, intimate production which is perfect for a quieter Sunday afternoon.
🎶 Night Out & St. Paddy’s Pre-Gaming
St. Paddy’s Bash @ Taphouse 1637 Saturday, March 14, | California – Taphouse is kicking off St. Patrick’s weekend with live music from Straight Vibin’. The place fills up fast, everyone’s wearing something green, and the patio starts buzzing once the music gets going. Grab a pint, find a spot near the stage, and settle in for a proper St. Paddy’s warm-up.
Get Lucked Up @ The Rex Theatre Friday, March 13, 9:00 PM | Leonardtown – If you want the full "party" vibe, Friday is the night. It’s free entry with a DJ, shot specials, and a prize wheel. It’ll be loud, it'll be busy, and parking on the square will be non-existent.
🙌 Community Wins
Principal of the Year: A big shout-out to Dr. Deborah Dennie of Leonardtown Middle School, who was recently named the 2026 Maryland Middle School Principal of the Year. Not a bad week to be a Jaguar.
📌 Quick Local Tip
Leonardtown is going to be tight this Saturday night. If the Square is full, just head for the lower lot by the wharf. Think of the walk back up the hill as your pre-dinner workout. You’re earning those Pub wings. Your knees might complain, but it beats circling for a spot that isn't there.
That’s your Insider for this week.
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See you next Tuesday. ✌️

