TUESDAY, OCTOBER 6, 2026
ST. MARY’S INSIDER
THE LOCAL GUIDE TO WHAT’S ACTUALLY HAPPENING
Good morning, St. Mary’s. 👋
October has officially taken over. Pumpkins are showing up on every porch and the sun is clocking out early. Its time to pick out a new costume, or dust off the old mask you’ve worn for the last 5 years like me.
This issue is packed with goodness, so buckle up.
Let’s get into it.
🎃 The Insider’s Halloween Guide Is Here
For Halloween this year, I wanted to build something I had never seen done here: one interactive guide to the entire month.
It has 78 events across St. Mary’s County, plus the good ones worth crossing the bridge for. Trunk-or-treats, fall festivals, haunted nights, library crafts, firehouse candy stops and trick-or-treating among actual aircraft. If it involves a costume or candy, it’s probably in there.
Everything is sorted by category and easy to search, so you can stop hunting through Facebook events and work on getting one more night out of the costume.
Free and ready to share.
🎉 The Insider Circle
This is week two of the Insider Circle, and I’m a little overwhelmed by how many of you have already referred friends. Thank you. Seriously.
The $50 gift cards are still available at 10 verified referrals, so get yours while the budget still has a pulse. At the rate you’re sharing this thing, I may have to transition future rewards to a very respectable sticker.
🏡 Around the County
🏊 Southern Maryland Has Its First YMCA: The St. Mary’s County Family YMCA opened to the community Saturday on Great Mills Road. The first YMCA built in St. Mary’s includes fitness areas, group classes, youth programming, and space intended to grow with the community after a decade-long local effort.
☕ 7 Brew Wants the Old Applebee’s Site: A concept plan proposes demolishing the former Applebee’s on 235 and replacing it with a drive-thru coffee stand. The project still needs approvals, so don’t start lining up yet.
🏘️ The Wildewood Preserve Request Is Off the 2050 Plan: Stanley Martin Homes withdrew its request to change the property’s land-use designation. The request won’t be considered at tonight’s St. Mary’s 2050 public hearing at 6:30 PM in the Chesapeake Building.
⛴️ Last Call for the St. Clement’s Island Water Taxi: The season’s final trips run October 13 from 10 AM to 2 PM. Service returns in March 2027 after the vessel completes required upgrades and certifications.
🎬 Moll Dyer Is Headed to the Big Screen: Filmmaker Paul Awad turned Leonardtown’s best-known legend into a feature-length folk-horror movie, filmed around Southern Maryland and featuring cameos from St. Mary’s residents. The Curse of Moll Dyer premieres October 22 at R/C Lexington Exchange.
🦪 A New Short Film Follows St. Mary’s Oyster Businesses: Visit St. Mary’s released Waterman’s Heritage: Oysters in St. Mary’s County, following Bay River Fishing, Wild Willy’s Seafood, Loose Stones Oyster Company, and Double T Oyster Ranch from harvest and restoration work to the dinner table. Convenient timing with the U.S. Oyster Festival coming October 17–18.
👩🍳 Behind the Business
Kneaded Baking Co.
It’s time for round two of Behind the Business. This week, we’re stepping inside Kneaded Baking Co.
Kneaded Baking Co.’s croissant dough takes three days. Owner Kelly Davin spent eight years perfecting the scone recipe. Neither fact fully explains how years of pastry work led from hotel kitchens and wedding cakes to a bakery of her own in downtown Leonardtown.
Behind that pastry case is a story about skill, patience, and refusing to take shortcuts.
⭐ The Top Pick
Saturday, October 10 | 10 AM to 4 PM
Patuxent River Appreciation Day has been celebrating the river since 1978, and the Calvert Marine Museum grounds turn into a waterside festival.
Free rides head out on the Wm. B. Tennison, Witch of the Wave, Draketail, and Poe Skiff. There are row and pedal boats, remote-control sailboats, and dockside tours aboard the Dee of St. Mary’s.
Back on land, expect live music, arts and crafts, environmental exhibits, children’s activities, a petting zoo, and makers selling home-spun goods. Kids can also build a toy boat for a $3 cash donation.
Admission and parking are free. A food court will have food, beer, and wine available for purchase.
🌟 Insider Spotlight (Sponsored)
Hollywood’s Living Room Since 1947
If live music is your thing, this is your room. Toot’s on Mervell Dean Road has been putting bands on stage since 1947, and the calendar stays packed. Live music takes over every weekend of the year, Thursday nights belong to the beer-pong crowd, and football season brings specials on Mondays, Thursdays, and Sundays. Murder Mystery Monday Trivia runs throughout October.
October is the month to find your way there. Shake The Room plays Friday night. National recording artists Shallow Side arrive with direct support from Anger Box on October 17, and Halloween weekend brings live music and costume contests both nights.
It’s the kind of room where the walls hold nearly 80 years of stories and first-timers get treated like regulars. Come for a band, stay for cornhole or the free outdoor pool table.
No velvet rope, no attitude. Just walk in.
If live music is your weekend plan, check their Facebook page for whats coming up, or call (240) 948-6044.
🗓️ Your Weekly Calendar
🟢 Thursday, October 8
Faux Pumpkin Decoupage | 6 PM to 8 PM @ Port of Leonardtown Winery, Leonardtown. Advance registration is required for a guided workshop turning a faux pumpkin into reusable fall décor.
The Addams Family | 7 PM @ Three Notch Theatre, Lexington Park. The Newtowne Players bring the famously strange family to the stage; the production continues Friday and Saturday at 7 PM and Sunday at 3 PM.
🟢 Friday, October 9
Farmers Market at MedStar St. Mary’s Hospital | 10 AM to 2 PM @ MedStar St. Mary’s Hospital, Leonardtown. The hospital’s farmers market returns with local vendors.
Annmarie After Hours | 5 PM to 7 PM @ Annmarie Sculpture Garden & Arts Center, Solomons. Adults 21 and older can preview Inked: The Art of the Tattoo with live music, food trucks, and a cash bar.
Shake The Room at Toot’s | 8 PM to midnight @ Toot’s Bar, Hollywood. The Southern Maryland cover band brings rock, pop, and dance-floor material to Friday night on Mervell Dean Road.
🟢 Saturday, October 10
Coastal Arts Market | 9 AM to 3 PM @ Leonardtown Wharf Park, Leonardtown. Shop a lineup of Southern Maryland artisans working in jewelry, pottery, stained glass, woodworking, fiber arts, and more.
Monster Market | 9 AM to 2 PM @ Annmarie Sculpture Garden & Arts Center, Solomons. Browse strange, spooky, and offbeat handmade goods with food and drink trucks on site.
Batty for Bats | 10 AM to 12 PM @ Piney Point Lighthouse Museum & Historic Park, Piney Point. Learn about local bats and decorate a bat box to take home.
Patuxent River Appreciation Day | 10 AM to 4 PM @ Calvert Marine Museum, Solomons. The waterfront festival brings boat rides, live music, artisans, environmental displays, children’s activities, and a petting zoo to the museum grounds.
Leonardtown Fall Oyster Crawl | 12 PM to 11:30 PM @ Participating restaurants and bars throughout Leonardtown. Expect oyster dishes, fall drinks, and seasonal specials at stops around town.
Five Note Theory | 7 PM to 9 PM @ Nancy R. & Norton T. Dodge Performing Arts Center, St. Mary’s City. The five-part vocal jazz ensemble brings tight harmonies and a fresh take on jazz classics to St. Mary’s College of Maryland.
🟢 Sunday, October 11
Southern Maryland Cars & Coffee | 8 AM to 11 AM @ Laurel Glen Shopping Center, California. Classics, imports, customs, and performance cars gather for the Sunday-morning meet.
Unfinished Business | 2 PM to 5 PM @ Port of Leonardtown Winery, Leonardtown. The band handles Sunday-afternoon music while Grizzly Mountain BBQ handles the food.
The British Are Coming | 3 PM @ Nancy R. & Norton T. Dodge Performing Arts Center, St. Mary’s City. COSMIC Symphony opens its season with works by Walton, Elgar, and Vaughan Williams featuring solo tubist Jasmine Pigott.
🤝 Trusted Local Partners
St. Mary’s Insider is supported by local businesses and organizations that help keep this thing going.
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That’s your Insider for this week.
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Drawing details: No purchase or payment required. Every 3 verified referrals earned in a calendar month gives you one entry in that month’s drawing for a $25 gift card usable at 15 local spots. Odds depend on total entries. One winner is drawn on the last day of the month and announced in the next month’s first Tuesday issue.