Good Morning St. Mary’s 👋.

The Devil Wears Prada 2 is officially out, which means everybody has suddenly become a fashion expert while wearing the same hoodie three days in a row. No judgment here. My personal fashion system is basically “does this shirt have wrinkles?”

Either way, Memorial Day weekend is here, and St. Mary’s has a packed few days ahead.

Let’s get into it.

In today's Insider:

  • RenFest takes over Leonardtown

  • A local pottery artist is building a fantasy-inspired following

  • Locals get a chance to tell County Leaders what this area needs

  • Memorial Day weekend is packed with festivals, concerts, and markets

🎤 Come Pitch Your Vision for St. Mary’s

What is Southern Maryland missing? A better local sports scene? More entertainment options? A bowling alley? This is your chance to say it out loud. On Saturday, May 23 from 6 PM to 8 PM, Be Better Local is hosting a community forum at the Bay District Volunteer Fire Department.Think Shark Tank meets local talk show energy. County decision-makers (including Commissioner Scott Ostrow) will be there to hear directly from you. Yours truly (Michael from St. Mary’s Insider) will be there as a guest speaker. Come out, share your fresh ideas, and tell the county exactly what you want to see built here.

📰 The Local Scoop

  • One:Eleven Pottery @ RenFest: If you are getting your attire ready for this weekend's Renaissance Festival in Leonardtown, you should know about local maker Raechel Platt. She is the ceramic artist behind One:Eleven Pottery. Raechel channels that focus into throwing custom pottery inspired by wilderness, earth elements, and folklore. Handcrafting everything from functional mugs to alternative-fired sculptures. If you’d like to score one of these unique creations, she’ll be at the St. Mary’s RenFest on Saturday, so go pay her a visit.

  • Chesapeake Focus Frames Our Local Favorites: There is a new way to enjoy local visual storytelling while grabbing a drink this week. The Chesapeake Focus, a group of photographers capturing the scenery and spirit of St. Mary's County, has installed their latest photography collections directly on the walls of two community hubs. You can now browse their prints while ordering an espresso at Social Coffeehouse or down at Taphouse 1637 in California. It’s a good excuse to support local artists and see our county through a fresh set of eyes.

🥪The Great St. Mary’s Sandwich Poll

With Panera Bread permanently closing its doors, weekday lunch routines are officially up in the air. It’s time to crown a new champion.

Who makes the absolute best sandwich in St. Mary's County?

Login or Subscribe to participate

💸 Insider Intel: Win $100 for Shopping Local

We are giving away $100 to spend at any locally owned business of your choice, and all you have to do is head over to THIS Facebook post and comment "already subscribed" to enter. The odds are still pretty friendly, and the money has to go to a true local shop or restaurant, not a national chain. Ends May 22.

🏡 Around the County

New Business Alert: DeSco Beauty arrives this Saturday, May 23 hosting its grand opening from 2 PM to 5 PM in Leonardtown. Located right across from Leonardtown High School, the boutique specializes in brand-name cosmetics, skincare, and haircare.

Free Hurricane Prep: The County Commissioners announced a free, resident-facing sandbag distribution day scheduled for May 30 to help prepare properties ahead of the hurricane season.

School Calendar Alert: SMCPS has a two-hour early dismissal this Friday, May 22, for Professional Responsibilities, and schools are closed on Monday, May 25, for Memorial Day.

⭐ The Top Pick

RenFest Southern Maryland | Sat, May 23 & Sun, May 24 | Brüdergarten, Leonardtown: The festival of the season is here. This year’s medieval gathering features a "Sherwood Forest" theme complete with four active stages, over 50 craft vendors, food, and craft beverages. Voted "Best Event in Southern Maryland" in 2025, it draws a crowd. Sunday’s lineup features a special "Outlawed & Outrageous" Mayor segment alongside aerialists, fire acts, and belly-dance performers.

🚙 Worth a Stop

🍩 Sonny Boy Donut Co.

If you’ve been to the California Farmers Market on a Saturday morning, you’ve probably seen the spot with the long line.

That’s usually the giveaway that Sonny Boy Donut Co. is there.

The local donut and coffee pop-up has quietly built a serious following around handcrafted coffee drinks and some of the best donuts in the county. There are tons of flavors, but the maple bacon donut deserves its own paragraph. Sweet maple glaze, salty bacon, and somehow this perfect little crunch that rounds it all out. There’s no stops at Dunkin on Saturday for this guy.

Honestly, I’m hoping they eventually land a permanent brick-and-mortar spot somewhere in the county. With donuts like these, they deserve it.

Know a local business or hidden gem that deserves a spotlight? Give them some love and let me know.

📅 Your Memorial Day Weekend Calendar

🟢 Thursday, May 21

🟢 Friday, May 22

🟢 Saturday, May 23

  • Library Book Tasting Brunch | 10:00 AM to 12:00 PM | Lexington Park Library: Adult book-sampling and genre browsing with snacks.

  • Touch-A-Truck | 10:00 AM to 2:00 PM | Golden Beach Park & Ride (Charlotte Hall): Kids can explore big trucks and emergency vehicles up close.

  • Sail on Maryland Dove (Morning Voyage) | 10:00 AM to 12:00 PM | Historic St. Mary's City Waterfront: Two-hour public river sail aboard the tall ship.

  • Breakfast with the Animals | 10:30 AM to 11:30 AM | Godiah Spray Plantation (St. Mary's City): Feed livestock and learn about 17th-century farming.

  • Blueberry Festival at Barefoot Farms | 11:00 AM to 6:00 PM | Barefoot Farms (Avenue): Blueberry season kickoff with lots of music, vendors, and delicious food.

  • McFadden Glass Blowing Event #4 | 11:29 AM | Wine & Design (Leonardtown): Personal torch sessions making custom glass pieces. Ages 18+.

  • Memorial Day Vendor Event | 12:00 PM to 5:00 PM | Hooked Gifts & Boutique (Solomons): Pop-up boutique event with custom apparel, boba, crafts, and baked goods.

  • Gloria's Imagination Band Live | 2:00 PM to 5:00 PM | Port of Leonardtown Winery: Live music on the patio with a wood-fired pizza truck.

  • Fight Cancer Fest 2026 | 2:00 PM to 10:00 PM | Twisted B&G (Hollywood): Eight-hour benefit rock concert supporting David Levine.

  • Overnight Equestrian Camp | Starts Saturday 3:00 PM (Runs through Monday 3:00 PM) | Free Rein Equine: Youth bunkhouse camp with riding lessons, bonfires, and meals.

  • Be Better Local Community Pitch Night | 6:00 PM to 8:00 PM | Bay District VFD: Community forum to pitch local ideas to county leaders. Guest speakers include (myself).

  • Winston | Live Show | 6:00 PM to 9:00 PM | Taphouse 1637: Live music set paired with rotating craft taps. Free entry.

  • Whiskey Tango Foxtrot Comedy Night | 8:00 PM to 10:00 PM | Elks Lodge #2092 (California): Stand-up comedy show featuring regional DMV comics.

🟢 Sunday, May 24

🤝Trusted Local Partners

Mary’s Hope on Church Cove

Vandermere Farm

Does your business need a boost? Reply to this email to become a Trusted Local Sponsor.

That’s your Insider for this week.

Know someone who always texts "anything going on this weekend?" Send this to them.

If this was forwarded to you, you can get the Insider delivered every Tuesday morning by subscribing right here.

See you next Tuesday. ✌️

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