TUESDAY, SEPTEMBER 22, 2026
ST. MARY’S INSIDER
THE LOCAL GUIDE TO WHAT’S ACTUALLY HAPPENING
Good morning, St. Mary’s. 👋
Fall officially starts today. Somewhere a pumpkin spice executive is popping champagne, and my wife, who hates the cold, is crying.
The fair opens Thursday, the corn maze opens Saturday, and RiverFest has free kayaking.
Pro Tip: Do the corn maze before the drinks. It’s already hard enough to find your way out.
Let’s get into it.
🧐 The County Quiz
Where were the first two St. Mary’s County Fairs held, in 1947 and 1948?
🏡 Around the County
🥤 Juice Buzz Is Coming to Leonardtown: Juice Buzz is joining SOF Market with cold-pressed juices and fresh eats. We don’t have a date yet, so for now, the Leonardtown location is listed as “coming soon.”
✂️ The Babe Cave Has a Temporary Home: After a vehicle struck the salon in Helen on September 16, the team is working out of The Hair Company in Leonardtown Square. That is community kindness at its finest. A fundraiser is also helping the salon recover.
🏫 No School for SMCPS Students Friday: September 25 is a professional day for staff. Put it on the family calendar now…you know the kids will be asking to go to the fair.
🏡 Have a Say in County Growth: The St. Mary’s 2050 comprehensive-plan hearing is October 6 at 6:30 PM at the Chesapeake Building in Leonardtown; doors open at 5:30. If you plan on making your voice hear, you can read the draft plan HERE first.
🏗️ Bradley Brook Gets Another Hearing: The Board of Appeals voted 3–2 to reconsider the previously denied subdivision near Lexington Park. Emergency access remains part of the dispute (kind of important).
📚 Your Library Card Comes With More Than Books: The library offers free New York Times access, including Cooking, Games, The Athletic, and Wirecutter. The one-day pass is renewable with a free NYT account. Worth checking before another subscription renews.
🛹 Chaptico’s New Skatepark Is Open: Chaptico Park now has more than 6,600 square feet for skateboards, scooters, inline skates, and BMX bikes. Bring your helmet, or your mom will worry. Anyone else remember Rocket Power? Just me?
⭐ The Top Pick
Thursday–Sunday, September 24–27
St. Mary’s County Fairgrounds | Leonardtown
In a poll few weeks back, you all showed how the County Fair is the favorite event of the year for many Insider readers, so it’s finally go-time. If you’ve driven by the fair grounds lately, you can get an idea of how much work goes into getting it all prepped for us (high five for the fair workers).
This is the weekend for livestock barns, exhibit ribbons, rides, plenty of fried food and running into your co-workers outside of work, which is always fun.
The gates open Thursday, 4–9 PM; Friday and Saturday, 9 AM–9 PM; and Sunday, 9 AM–6 PM. Friday is School and 4-H Day, Saturday is the big Parade, and Sunday is a great family day.
🗓️ Your Weekly Calendar
This week’s calendar is presented in partnership with the St. Mary’s County Museum Division.
🟢 Thursday, September 24
Little Minnows | 10:15–10:45 AM @ Calvert Marine Museum, Solomons. Preschoolers ages 3–5 can join story time and make a take-home craft.
St. Mary’s County Fair Opens | 4–9 PM @ the fairgrounds, Leonardtown. Opening night brings exhibits, rides, and the first of three evening horse pulls.
Team Trivia at The Bay | 6–8 PM @ Breton Bay Golf & Country Club, Leonardtown. Bring a team for the club’s every-other-Thursday trivia night.
🟢 Friday, September 25
The Market at MedStar | 10 AM–2 PM @ MedStar St. Mary’s Hospital, Leonardtown. Browse local vendors in the front-side parking lot; admission is free.
Fall Doormat Paint Night | 6–8 PM @ Port of Leonardtown Winery. Paint a fall doormat with supplies and a glass of wine, slushy, or sangria included.
🟢 Saturday, September 26
XDA Fall Nationals | Gates at 8 AM @ Maryland International Raceway, Mechanicsville. Drag Motorcycles going 200+ mph. Qualifying starts at 9 AM, with Afterdark Underground racing from 4–11 PM.
LEXBA Market Days | 9 AM–noon @ the Aaron’s parking lot, 21703 Great Mills Road, Lexington Park. Shop local vendors at the free community market.
DIG! St. Mary’s Fort Excavation Experience | 9 AM–4 PM @ Historic St. Mary’s City. Dig and screen alongside professional archaeologists; ages 18+, with lunch included.
Bowles Farms Opening Weekend | 10 AM–6 PM @ Bowles Farms, Clements. The Statue of Liberty corn maze, farm animals, wagon rides, and pumpkin patch return
RiverFest | 10 AM–3 PM @ Historic St. Mary’s City. Free kayaking, family activities, and live music from the Eastport Oyster Boys, plus the 2 PM wade-in.
Militia Muster | 10 AM–4 PM @ Historic St. Mary’s City. Watch musket demonstrations, military drills, and historical fencing.
Chesapeake Biological Laboratory Open House | Noon–4 PM @ Chesapeake Biological Laboratory, 146 Williams Street, Solomons. Get a behind-the-scenes look at local research through hands-on science activities, demonstrations, and exhibits for all ages.
Cork for Cuties | Sign-ups at noon; play starts at 1 PM @ Action Lounge & Billiards, Leonardtown. Darts competitions support Clements Cuties and local families facing childhood cancer, with events through the evening.
Jazz/Wine Series Finale | 6–8 PM @ Corteau Vineyards, Mechanicsville. Close out the six-month concert series with an evening of jazz and a glass of wine or sangria.
🟢 Sunday, September 27
Smiles for Miles Sunday Run Club | 8–10 AM @ The Beanery/Juice Buzz parking lot, Solomons. Meet for a beginner-friendly loop of roughly 3–4 miles, with a planned pace of about 14–15 minutes per mile.
SOMD Cars & Coffee | 8–11 AM @ Laurel Glen Shopping Center, California. Start Sunday with cars and coffee before heading to the fair.
Levi Stephens at the Winery | 2–5 PM @ Port of Leonardtown Winery. Live music with food available from Farm.Fork.Soul.
🎟️ Before Today’s Fairgrounds
The quiz answer is Camp Calvert. The Fair Association was established in 1947, and its first two fairs were held on rented grounds there, with exhibits housed in tents.
The permanent home as we know it today came in 1949, when the county leased the Fair Association a parcel known as the Alms Property on Route 5, two miles south of Leonardtown. That’s the site we’re heading back to this weekend.
🤝 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.
Know someone who says there’s nothing to do around here? Send this to them. This weekend should settle that.
If this was forwarded to you, get the Insider delivered every Tuesday morning by subscribing right here.
See you next Tuesday. ✌️
St. Mary’s Insider is supported by local businesses and trusted partners. Sponsored sections are clearly identified. Reply to this email to learn more about partnership opportunities.