TUESDAY, OCTOBER 20, 2026
ST. MARY’S INSIDER
THE LOCAL GUIDE TO WHAT’S ACTUALLY HAPPENING
Good morning, St. Mary’s. 👋
Halloween is still 11 days away, but there’s plenty on the calendar before then. Here’s what’s worth making plans for this week.
Let’s get into it.
📊 Welcome to Holiday Alley
The pumpkins are out, and I saw someone in Target this weekend proudly sporting a Christmas sweater.The holiday season is upon us.
Which holiday are you looking forward to most?
🏡 Around the County
The Y Cuts the Ribbon Today: The St. Mary’s County Family YMCA gets its ribbon cutting today at 4 PM in Lexington Park. It’s been open to the community since October 3.
Early Voting Starts Thursday: You can vote October 22–29, from 7 AM–8 PM daily, at the Hollywood, Bay District (Lexington Park) or Mechanicsville firehouse. Saturday and Sunday count, too. One less thing to squeeze into a workday.
10X Pilates Opens November 2: Mechanicsville’s new studio opens November 2, with early signups on its website. It calls itself Maryland’s first Sculptformer studio, mixing Pilates and strength training on reformer-style machines. Your legs can find out what that means in November.
The Moll Dyer Premiere Is Sold Out: If you were planning to grab a ticket for the October 22 premiere of The Curse of Moll Dyer at R/C Lexington Exchange, it’s sold out.
Free Baby Shower at the Health Hub: Expecting a baby, or welcomed one after June 1? County residents can register for the health department’s free drive-thru baby shower on October 28, 10 AM–noon, in Lexington Park.
Small Art, October 28 Deadline: Got an idea that fits in four inches? The Arts Council’s Tiny ART Show is open to all ages in St. Mary’s, Calvert and Charles, with up to two pieces per artist.
A $50,000 Surprise in Mechanicsville: A Mechanicsville woman thought her scratch-off had won $25,000 until her husband spotted the multiplier: $50,000. She claimed the prize October 16. Callaway USA Fuel sold the winning ticket and gets a $500 bonus.
Ryken Takes the County’s Top STEM Spot: St. Mary’s Ryken ranked first among county high schools for STEM in Niche’s rankings. The rating considers coursework, math proficiency, student and parent feedback, and college STEM participation, among other factors.
🎃 Keep the Halloween Guide Handy
Trunk-or-treats, haunted nights and places to get another outing out of the costume. The Halloween Guide puts the month’s plans in one place.
⭐ The Top Pick
Saturday, October 24 | 5–8 PM | Historic St. Mary’s City
Trick-or-treat through Maryland’s first capital, past pirates, fortune tellers and costumed interpreters. Your school field trips probably didn’t look like this.
The Town Center has games and candy along the trail, and Read & Rally will be there, too. It’s G-rated, making this a good choice for kids who want the costumes without the haunted-house scares.
Last entry is 7:30 PM.
Thursday–Sunday, October 22–25 | Thu.–Sat. 7 PM; Sun. 3 PM | Three Notch Theatre, Lexington Park
Wednesday Addams brings her boyfriend’s parents home for dinner, and Gomez has a secret to keep from Morticia. This is the final weekend of Newtowne Players’ musical, rated PG and running about 2½ hours with intermission.
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🗓️ Your Weekly Calendar
This week’s calendar is sponsored by the St. Mary’s County Museum Division.
🟢 Wednesday, October 21
Mothman Rises: Teen & Tween Escape Room | 3–7 PM @ Leonardtown Library, Leonardtown. Teens and tweens work together to solve a Mothman mystery in a 20-minute escape room; registration is required.
🟢 Thursday, October 22
GKES Trunk or Treat | 5:30 PM @ Greenview Knolls Elementary, Great Mills. Collect treats from decorated trunks at Greenview Knolls Elementary’s family Halloween evening.
Trivia Fright Night | 6–7:30 PM @ Lexington Park Library, Lexington Park. Test your horror-movie knowledge with friends, with bonus points for showing up in costume; registration is required.
The Addams Family | 7 PM @ Three Notch Theatre, Lexington Park. Wednesday brings her boyfriend home for dinner in Newtowne Players’ musical about the Addams family.
🟢 Friday, October 23
Autumn Harvest at Lyon Family Farms | 10 AM–5 PM @ Lyon Family Farms, Mechanicsville. Wander the milo maze, dig into the corn pit and meet the farm animals.
Sass & Spells | 4–9 PM @ St. Inigoes. Browse books from Read & Rally and other local vendors at this Halloween-themed ladies’ night; see the event link for the venue details.
Mana & Merlot | 5 PM @ Xella Winery, Mechanicsville. Learn Magic: The Gathering or bring your Commander deck for a women’s game night at the winery.
SMCM Jazz Combo Concert | 7–9 PM @ Dodge Performing Arts Center Recital Hall, St. Mary’s College. Student musicians trade solos in St. Mary’s College’s jazz combo.
Greg Barrick & Friends | 8 PM @ Toot’s Bar, Hollywood. HydraFX’s Greg Barrick and friends play at Toot’s.
🟢 Saturday, October 24
Trunk or Treat, Cars & Coffee & Vendor Show | Vendors from 9 AM; trunk-or-treat from noon @ Town Market at the Bell Building, Leonardtown. Browse local makers and classic cars while the kids make their candy rounds.
Bowles Farms Corn Maze & Pumpkin Patch | 10 AM–6 PM @ Bowles Farms, Clements. Find your way through the corn maze, visit the barnyard animals and pick out a pumpkin.
Halloween in the Garden | 10 AM–4 PM @ Annmarie Sculpture Garden, Solomons. Trick-or-treat through the garden’s community booths, with crafts, games and a DJ dance party along the way.
Dixon Family Farm Pumpkin Festival | 11 AM–5 PM @ Dixon Family Farm, Mechanicsville. Follow the trick-or-treat trail, catch some bluegrass and watch juggling and magic around the farm.
Monster Mash Bash | 1–4 PM @ Leonardtown Wharf. Head to the Wharf for a costume contest, trick-or-treat trail and Halloween crafts.
Lost City Trick-or-Treating | 5–8 PM @ Historic St. Mary’s City. Follow the candy trail through Maryland’s first capital, past games and costumed interpreters.
Dead Eye Stare | 8 PM @ Toot’s Bar, Hollywood. The Maryland band plays alternative rock and grunge covers.
🟢 Sunday, October 25
Autumn Harvest at Lyon Family Farms | 10 AM–3 PM @ Lyon Family Farms, Mechanicsville. Take the kids through the milo maze, corn pit and petting zoo.
Howl-Oween Pawty | 11 AM–2 PM @ Ribshot Tattoos, Leonardtown. Meet adoptable pets and snap a Halloween photo with the family at this pet-themed party.
Harvest Festival & Seed Swap | 1–4 PM @ Lexington Manor Passive Park Community Garden, Lexington Park. Swap seeds and native plants with fellow gardeners while enjoying music, crafts and seed-saving demonstrations.
The Addams Family Matinee | 3 PM @ Three Notch Theatre, Lexington Park. Catch the final performance of Newtowne Players’ musical about Wednesday Addams and her very unusual family.
🗓️ Plan Past This Weekend
The Insider’s Local Calendar lets you browse by date and filter by what you’re into. I’m still adding events, so if I’ve missed something, reply and send it over.
That’s your Insider for this week.
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See you next Tuesday. ✌️
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