St. Mary's County Events This Weekend | October 29 – November 1, 2026

St. Mary's County events this weekend bring together Halloween celebrations, live music, corn mazes, creative activities, and community gatherings across Southern Maryland! Whether you're searching for family-friendly fun near Lexington Park, a night of music in Leonardtown, or seasonal adventures around Mechanicsville and Coltons Point, there's plenty to explore from Thursday, October 29, through Sunday, November 1, 2026.

Welcome to another edition of Southside Happenings, your weekly guide to discovering local events, interesting places, and community activities throughout Southern Maryland.

Halloween weekend is an especially fun time to explore St. Mary's County. Local libraries are hosting themed activities, farms are welcoming fall visitors, and entertainment venues are preparing for festive performances.

Planning tip: All event times are Eastern Time. Check the linked organizer pages before traveling. Events identified as awaiting confirmation should not be treated as finalized schedules.

Featured St. Mary's County Events This Weekend

From country music and Halloween parties to pumpkin patches and community celebrations, these five highlights offer different ways to enjoy the final days of October.

Whey Jennings Live in Concert at The Potomac Gardens

📅 Date: Friday, October 30, 2026
📍 Location: The Potomac Gardens, 20254 Colton Point Road, Coltons Point, MD 20626
🕒 Time: 6:00–10:00 PM; concert schedule: gates 5:30 PM, show 7:00 PM

Enjoy an evening of traditional outlaw country music as Whey Jennings brings his distinctive sound to the Potomac waterfront. The grandson of Waylon Jennings and Jessi Colter continues his family's musical tradition while developing his own country style.

It's an appealing option for music enthusiasts looking for live entertainment in St. Mary's County. The tourism listing confirms the October 30 event, but attendees should verify the gate and performance times with the venue.

👉 Event Link: https://www.thepotomacgardens.com/event-details/whey-jennings-full-band

Hit or Miss Halloween Bash at The Rex Theatre 

📅 Date: Saturday, October 31, 2026
📍 Location: The Rex Theatre, 22695 Washington Street, Leonardtown, MD 20650
🕒 Time: 8:00 PM to 11:00 PM

Spend Halloween night in downtown Leonardtown with a live performance by Hit or Miss. The submitted event description also advertises a costume contest, refreshments, and dancing.

The county tourism calendar lists the event for October 31. Check the ticket page for admission information, age restrictions, costume-contest rules, and confirmed doors and performance times.

👉 Event Link: https://www.visitstmarysmd.com/events/halloween-bash-the-rex-2026/

Forrest Hall Farm America 250 Corn Maze  

📅 Date: Thursday, October 29 – Sunday, November 8, 2026
📍 Location: Forrest Hall Farm & Orchard, 39136 Avie Lane, Mechanicsville, MD 20659
🕒 Time: 9:00 AM–5:00 PM

Fall in Southern Maryland wouldn't feel complete without a visit to a local farm! Forrest Hall Farm offers a seasonal setting for exploring corn maze activities, pumpkins, and orchard traditions.

The submitted listing describes an America 250-themed maze, a petting farm, and a pumpkin admission offer. Confirm the exact operating dates, included activities, and pumpkin availability before planning your visit.

👉 Event Link: https://forresthallfarm.com/america-250-corn-maze-forrest-hall-farm-orchard/

Patuxent River Naval Air Museum: Trunk or Treat on the Flight Line

📅 Date: Saturday, October 31, 2026
📍 Location: Patuxent River Naval Air Museum, 22156 Three Notch Road, Lexington Park, MD 20653
🕒 Time: 1:00–3:00 PM

Imagine celebrating Halloween surrounded by aviation history! The submitted event details describe a trunk-or-treat gathering featuring decorated vehicles, candy, and activities near historic aircraft.

This would be a distinctive Halloween outing for aviation enthusiasts and families. However, the supplied 2026 schedule has not been independently established, so please check the organizer's event announcement before visiting.

👉 Event Link: https://www.facebook.com/events/1546383543848282

Bay District VFD Station 3 Safe Candy Giveaway!

📅 Date: Saturday, October 31, 2026
📍 Location: 46900 S Shangri-La Drive Lexington Park, MD 20653
🕒 Time: 5:00PM–8:00 PM

Bring the family and stop by for some yummy candy and Halloween fun! The goal is to provide a safe, family-friendly place for children to enjoy Halloween while collecting plenty of treats.

👉 Event Link: https://www.facebook.com/photo/?fbid=1529386735886621&set=a.553182273507077

Don't Miss This Week in St. Mary's County

Looking for something exciting to do near you this Halloween weekend? St. Mary's County offers an inviting mix of historic downtown streets, waterfront destinations, rural farms, community libraries, and entertainment venues.

You might spend Friday listening to music in Coltons Point, explore a corn maze in Mechanicsville, enjoy a Halloween performance in St. Mary's City, or visit a seasonal activity in Lexington Park.

One of the enjoyable things about living in St. Mary's County is the opportunity to experience community traditions in different settings. The county's waterfront, historic landmarks, parks, farms, and gathering places all contribute to its local character.

For more inspiration, visit Southside Happenings: Southern Maryland Community Events & Local Activities.

Our weekly guides help readers discover happenings throughout St. Mary's, Calvert, and Charles counties, from seasonal celebrations to concerts and neighborhood gatherings.

More St. Mary's County Events This Week: Halloween Fun, Music & Fall Activities

Looking for even more things to do in St. Mary's County? These ten additional listings include Halloween-themed activities, outdoor recreation, community markets, and library programs.

1. Haunted River Cruise & Picnic at St. Clement's Island Museum

📅 Date: Friday, October 29, 2026 
📍 Location: St. Clement's Island Museum, 38370 Point Breeze Road, Coltons Point, MD 20626
🕒 Time: 4:00–6:30 PM

The submitted listing describes a Potomac River cruise featuring maritime ghost stories and a waterfront picnic. The supplied third-party page has not established that this exact experience is scheduled for the requested Friday, so contact the museum before making plans.

👉 Event Link: https://www.unation.com/event/dinner-and-a-cruise-picnic-style-a-haunted-river-cruise-thursday-69033732/

2. Sensory-Friendly Trunk or Treat

📅 Date: Friday, October 30, 2026 
📍 Location: NAS Patuxent River, Building 2118 area, Patuxent River, MD 20670
🕒 Time: 4:00–6:00 PM

The submitted event details describe trunk-or-treating, inflatable activities, costumes, and music for eligible military-community participants. This event is intended for authorized patrons, and both access requirements and the 2026 schedule should be confirmed directly with MWR.

👉 Event Link: https://www.navymwrpaxriver.com/activity/db16e2c2-7642-4c6d-b313-ca91fab43427

3. SMCM Symphony Orchestra: Halloween Spooktacular II

📅 Date: Friday, October 30, 2026
📍 Location: Nancy R. & Norton T. Dodge Performing Arts Center, 47855 College Drive, St. Mary's City, MD 20686
🕒 Time: 7:00–9:00 PM

Celebrate Halloween with an orchestral performance at St. Mary's College of Maryland. Costumes are welcome, and the official tourism listing identifies the concert as free and open to the public.

👉 Event Link: https://www.visitstmarysmd.com/events/smcm-orchestra-halloween-2026/

4. Corn Maze & Pumpkin Patch at Bowles Farms  

📅 Date: Saturday, October 31, 2026
📍 Location: Bowles Farms, 22880 Budds Creek Road, Clements, MD 20624
🕒 Time: 10:00AM to 6:00PM

Spend part of Halloween enjoying the rural side of Southern Maryland. The county tourism calendar lists Bowles Farms' corn maze and pumpkin patch for October 31. Check the farm's admission and operating details before traveling.

👉 Event Link: https://bowlesfarms.com/

5. Farm of Screams at Barefoot Farms

📅 Date: Thursday, October 29 and Friday, October 30, 2026
📍 Location: Barefoot Farms, 21851 Oakley Road, Avenue, MD 20609
🕒 Time: 6:30–9:30 PM

Looking for something a little scarier? Explore a haunted nature trail with spooky surprises and seasonal vendors. The tourism listing identifies admission as $15 and advises that the experience is not intended for children under ten.

👉 Event Link: https://www.facebook.com/events/2103670663858097/

6. Spooky Stop-In: Halloween Crafts at Charlotte Hall Library

📅 Date: Saturday, October 31, 2026
📍 Location: Charlotte Hall Library, Meeting Room, Charlotte Hall, MD
🕒 Time: 1:30–3:30 PM

Make a Halloween keepsake by decorating a trick-or-treat bag, creating a bookmark, or assembling a spooky sensory bottle. This drop-in library program is intended for tweens, teens, and adults, with no registration required.

👉 Event Link: https://stmalib.libnet.info/event/16825711

Want Your St. Mary's County Event Featured?

Are you organizing a local festival, concert, charity event, market, workshop, or community celebration?

Southside Happenings welcomes opportunities to spotlight activities throughout Southern Maryland.

Whether your event is in Leonardtown, Lexington Park, Mechanicsville, California, or another St. Mary's County community, we'd love to help readers discover what's happening.

Submit your business or event to Community Spotlight and help keep our community calendar filled with local experiences.

Have another event coming up in November? Share it for consideration in an upcoming weekly guide!

Stay Connected with Local Events in Southern Maryland

Halloween weekend is only one part of the Southern Maryland events calendar. Throughout the year, there are opportunities to discover new activities and revisit favorite local traditions.

Follow Southside Happenings for updates about:

• ✔ Local festivals — seasonal celebrations, markets, and community traditions.

• ✔ Family-friendly activities — library programs, farm visits, and educational experiences.

• ✔ Live music & entertainment — concerts, theater performances, and local musicians.

• ✔ Community gatherings — nonprofit events, open houses, and neighborhood celebrations.

• ✔ Seasonal events across Southern Maryland — holiday activities, outdoor recreation, and weekend adventures.

Checking event details before leaving home is always a good idea, especially when outdoor activities depend on the weather.

For busy weekends, consider grouping activities by town. A morning library visit and an afternoon community market might make a convenient Lexington Park outing, while downtown Leonardtown offers another opportunity to explore shops, seasonal displays, and entertainment.

Discover More Things to Do in Southern Maryland

Want to keep exploring after Halloween weekend?

Our Southern Maryland guides highlight local activities, places to visit, and upcoming community happenings throughout St. Mary's, Calvert, and Charles counties.

Explore More Things to Do in Southern Maryland for ideas beyond this week's event calendar.

You can also bookmark Southside Happenings: Southern Maryland Community Events & Local Activities to discover future weekly updates.

If you're planning an upcoming event, don't forget to join our Community Spotlight.

Seasonal Home Tips & Fall Maintenance Ideas in Southern Maryland

While you're enjoying the last days of October, it's also a good time to welcome the changing season at home.

A few simple ideas can make fall feel festive and comfortable:

• Refresh your front entrance. Pumpkins, autumn wreaths, and seasonal planters add a cheerful touch.

• Check outdoor lighting. Clear walkways and working porch lights are especially helpful during Halloween activities.

• Keep paths tidy. Remove fallen leaves and outdoor clutter from steps and walkways.

• Prepare for cooler evenings. Inspect weatherstripping, organize outdoor furniture, and review your seasonal maintenance checklist.

• Reuse fall decorations. Natural colors, baskets, and simple harvest accents can transition from Halloween into November.

For more ideas, visit our Home Tips, Hacks, Decorating & Maintenance Guides.

Where can I find more Southern Maryland events near me?

Visit the Southside Happenings Community Events Hub for community-focused guides, and browse the Southern Maryland activities blog for additional inspiration.

🎉 Keep exploring Southern Maryland! Follow Southside Happenings for weekly updates, share this guide with someone planning their weekend, and submit your upcoming community event through Community Spotlight. There's always something new to discover close to home.