TUESDAY, SEPTEMBER 29, 2026
ST. MARY’S INSIDER
THE LOCAL GUIDE TO WHAT’S ACTUALLY HAPPENING
Good morning, St. Mary’s. 👋
October arrives Thursday. Time to find the sweatshirt you put somewhere sensible in April.
Let’s get into it.
🎉 Introducing the Insider Circle
Something kind of cool has happened with this newsletter. What started as a Tuesday email to a handful of people has turned into a real community. Thousands of you reading every week, forwarding issues to friends, arguing about the best crab cake in the group chat. I don't take that for granted.
Here's the thing. There are still so many people in this county who have never heard of the Insider. It's growing fast, but I can't reach them without you.
So let's grow it together.
Every subscriber now has a personal referral link at the bottom of this email. Share it with that friend who always texts "anything going on this weekend?", your coworkers, your neighbors. Every friend who subscribes makes this community a little stronger, and honestly, you're the reason any of this works.
And because good neighbors deserve a thank you:
🎟️ 3 referrals in a month → you're entered in that month's drawing for a $25 gift card good at 15 local spots. (6 referrals = two entries, you get the idea.)
🎁 10 referrals, all-time → a $50 gift card good at 15 local spots, on me.
🍽️ 25 referrals, all-time → dinner for two at a local spot, on me.
One winner drawn every month, announced right here. Your personal link is below. Let's keep building this thing.
🏡 Around the County
🥞 First Watch Opens in California: First Watch opened Monday at South Plaza, in the former Panera space at 45250 Worth Avenue. It’s a new breakfast-and-brunch option for St. Mary’s.
🍳 Abell’s Diner Closed a Week Early: The Clements diner had announced an October 1 closing, but September 23 became its last day after it ran out of food. The family thanked the community after 43 years.
🥯 Boone’s Bagels Gets Beer-and-Wine License Approval: The Alcohol Beverage Board approved a new license for the Leonardtown shop at its September 10 meeting. Sounds like extended hours are coming Friday and Saturday evenings.
🚗 Talk Transportation Tonight: State transportation officials visit the Chesapeake Building in Leonardtown today, September 29, at 6:30 PM to discuss Maryland’s draft six-year transportation plan. The meeting is open to the public and covers local priorities within a proposed $21.9 billion statewide program. If you have thoughts about our roads, this is a useful place to bring them.
🎨 Another Step for the Carver Arts Space: Commissioners also approved the Carver Recreation Center sublease with the St. Mary’s County Arts Council and PaxSpace. It is another concrete step behind the community arts and makerspace project in Lexington Park.
📝 Your Legislative Idea Has a Friday Deadline: Residents and organizations can send proposals for the county commissioners to consider for their 2027 state legislative agenda through October 2. The county has a proposal form online; you can also send ideas directly to the St. Mary’s legislative delegation.
📊 Quick Poll
Where’s your go-to breakfast in St. Mary’s now?
⭐ The Top Pick
Saturday, October 3 | Noon–8:30 PM
Leonardtown Wharf | Leonardtown
If you want one event that can fill most of your Saturday, head to the Wharf. The 58th annual Blessing of the Fleet celebrates the county’s watermen with a boat blessing and Waterman of the Year award.
There’s plenty around it, too: food, kids’ activities, boat rides, local crafters, dance troupes, and three live bands. It’s free, family-friendly, and built for wandering until you find your people, a snack, or a spot to watch the boats.
Stay for the fireworks at 8 PM, or make an earlier visit and call it a win. Either way, Leonardtown Wharf has a great way to spend the Saturday.
🌟 Insider Spotlight
Sponsored by Read & Rally Studio.
Meet Jess and Her Bookstore on Wheels
You may not know this about me yet, but I’m a huge bookworm. I love reading, and I put real effort into getting my kids to pick up books, too. So a bookstore on wheels rolling through Southern Maryland was always going to get my attention.
Jess Ausem, a Navy veteran, started Read & Rally as an online shop. Now she brings Scout, her mobile bookstore, to pop-ups around the region.
The shelves lean adult fiction: romance, romantasy, thrillers, and new releases, with a smaller section for younger readers. She stocks books by independent authors, signed and special editions, and blind date books, and makes some of the bookish gifts herself.
Read & Rally is also becoming a way to get people together. Jess hosts monthly book clubs, brings Scout to private events, and partners with local businesses on gatherings that don’t always revolve around books. Booked & Buzzed meets at Juice Buzz in Solomons. But you don’t have to show up with a book report, or even call yourself a big reader. Jess says you’re welcome to come hang out either way.
I’ll be looking for Scout the next time it rolls through St. Mary’s.
🗓️ Your Weekly Calendar
🟢 Friday, October 2
Old Jail Museum Open Late | 10 AM–7 PM @ Old Jail Museum, Leonardtown. Visit the historic jail and official town visitor center during extended First Friday hours. Admission is free.
First Friday Drum Circle | 5–5:30 PM @ St. Mary’s County Arts Council, Leonardtown. Bring a percussion instrument or borrow one for this free, all-ages gathering; a drumline performance follows from 5:30–6 PM.
A Harvest of Haunts | 5–8 PM @ St. Mary’s County Arts Council Gallery & Gift Shop, Leonardtown. Meet the artists at the opening reception for October’s spooky-themed exhibition.
Boone’s Bagels Evening Launch Party | 5–8 PM @ 41654 Fenwick Street, Leonardtown. Daniel Murray brings live jazz for the shop’s first evening launch party, with a dinner menu and locally crafted beer, wine, and champagne.
Sam Grow at First Friday | 6–8 PM @ Leonardtown Square. The Backyards & Bonfires Tour performance is free and open to everyone.
The Addams Family Opens | 7 PM @ Three Notch Theatre, Lexington Park. Newtowne Players opens its October run of the musical. Catch another performance Saturday at 7 PM or Sunday at 3 PM.
🟢 Saturday, October 3
Scarecrow Stroll Begins | Self-guided @ locations throughout Leonardtown. Look for handmade scarecrows around town while you shop or stop for dinner. The displays continue through October 31, with voting open October 6–26.
Fall Craft & Vendor Fair | 7 AM–1 PM @ St. Mary’s County Fairgrounds, Leonardtown. Shop handmade goods and local vendors at this fundraiser for the Second District volunteer fire and rescue squad.
First Saturday Market | 9 AM–4 PM @ Town Market, Leonardtown. Shop local produce, baked goods, crafts, and more at the Bell Building on Washington Street.
Little Flower Community Fall Festival | Begins at 10 AM @ Little Flower School, Great Mills. The fourth annual festival brings carnival games, a petting zoo, face painting, a cake walk, craft vendors, and a silent auction to the school grounds.
Bowles Farms Corn Maze & Pumpkin Patch | 10 AM–6 PM @ Bowles Farms, Clements. Explore the corn maze, visit the animals, and make your pumpkin selection. The farm also opens Sunday from 10 AM–5 PM.
Drayden Schoolhouse Open House | 11 AM–2 PM @ Drayden African American Schoolhouse, Drayden. Step inside the restored one-room schoolhouse and hear its history from volunteers. All ages are welcome, and admission is free.
Blessing of the Fleet | Noon–8:30 PM @ Leonardtown Wharf. Celebrate St. Mary’s watermen with a boat blessing, live music, food, and family activities. Fireworks begin at 8 PM; admission is free.
Film on the Flight Line: Apollo 13 | 7 PM @ Patuxent River Naval Air Museum, Lexington Park. Bring chairs or blankets for the outdoor movie. Tickets are required; see this week’s Top Pick.
Comedy Showcase | 8 PM @ Elks Lodge #2092, California. Outlaw Comedy brings local comics and a guest from Atlanta. Ages 18 and up; doors open at 7 PM.
🟢 Sunday, October 4
Flutter Fest 5K | 8:30 AM start; packet pickup 7:30–8:15 AM @ Baggett Park, Mechanicsville. Choose the timed race or fun run/walk supporting access to mental health and wellness services in Southern Maryland. Register by 6 PM Saturday, October 3; there is no race-day registration.
Read & Rally at the LB Boudoir Autumn Open House | 11 AM–4 PM @ LB Boudoir, Leonardtown. Browse Scout’s mobile-bookstore shelves during Read & Rally’s local pop-up.
Pages in the Park | 1–3 PM @ Port of Leonardtown Park, Leonardtown. Spend the afternoon reading and crafting with the Mobile Library. Pack a picnic, and bring a book to exchange if you want; registration is requested.
250th Under the Oaks at Tudor Hall | 3–5 PM @ Tudor Hall, 41680 Tudor Place, Leonardtown. David and Joe Norris perform songs inspired by St. Mary’s County and Southern Maryland at this free family gathering. Bring a lawn chair or blanket.
🤝 Trusted Local Partners
St. Mary’s Insider is supported by local businesses and organizations that help keep this thing going.
* Contest details are at the bottom of this email.
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.
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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.
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.