St. Mary’s County Events This Weekend | September 24–27, 2026

St. Mary’s County events this weekend bring four packed days of county-fair traditions, motorsports, art, live music, outdoor activities, fall fun, and community gatherings to Southern Maryland from September 24–27, 2026.

If you’re searching for things to do near me in St. Mary’s County, there are plenty of options to explore. From Leonardtown and Mechanicsville to St. Mary’s City, Clements, Chaptico, and Coltons Point, events are happening throughout the county.

Living in St. Mary’s County means having access to a unique mix of historic destinations, waterfront recreation, local arts, agriculture, motorsports, festivals, and long-running community traditions. This weekend is a great example, with the St. Mary’s County Fair returning alongside racing, RiverFest, live music, fall activities, and more.

Here’s your Southside Happenings guide to what’s happening around St. Mary’s County September 24–27.

⭐ Featured St. Mary’s County Events This Weekend

⭐ 79th Annual St. Mary’s County Fair

📅 Date: Thursday, September 24–Sunday, September 27, 2026
📍 Location: St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD
🕒 Time: Gates open at 4:00 PM Thursday; 9:00 AM Friday–Sunday

One of St. Mary’s County’s signature annual traditions returns to Leonardtown for four days of fair fun.

Visitors can enjoy the classic county-fair experience with carnival rides, livestock judging, agricultural exhibits, the Queen of Tolerance coronation, 4-H activities and auctions, an antique tractor pull, entertainment, competitions, food, and more throughout the weekend.

If you’re looking for family-friendly events in St. Mary’s County this weekend, the fair is one of the biggest happenings on the calendar.

👉 Event Link: https://smcfair.somd.com/

⭐ XDA Fall Nationals

📅 Date: Friday, September 25–Sunday, September 27, 2026
📍 Location: Maryland International Raceway, 27861 Budds Creek Road, Mechanicsville, MD
🕒 Time: All-day events beginning around 8:00 AM; check the current race schedule

Get ready for a high-energy weekend at Maryland International Raceway as the XDA Fall Nationals comes to Mechanicsville.

Motorcycle drag racers compete throughout the weekend in class championships, Sportsman competition, Grudge racing, and other events. Fans can also explore vendor displays and experience the action trackside.

For motorsports fans searching for things to do in Mechanicsville, MD this weekend, this is one to have on the calendar.

👉 Event Link: https://www.goracemir.com/

⭐ St. Mary’s County Fair Parade

📅 Date: Saturday, September 26, 2026
📍 Location: Leonardtown — beginning near Leonardtown High School/Middle School and continuing toward the St. Mary’s County Fairgrounds
🕒 Time: 10:30 AM

Make fair weekend even more memorable with the annual St. Mary’s County Fair Parade.

Local marching bands, floats, antique vehicles, community organizations, and other participants will make their way through Leonardtown on Saturday morning.

The 2026 parade theme is “Celebrate 250 Years of the United States of America.”

Consider catching the parade in the morning before continuing the day at the county fair.

👉 Event Link: https://thebaynet.com/st-marys-county-fair-2026/

⭐ Fall Doormat Stencil Paint Night

📅 Date: Friday, September 25, 2026
📍 Location: Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD
🕒 Time: 6:00 PM–8:00 PM

Get creative Friday evening with a hands-on Fall Doormat Stencil Paint Night at Port of Leonardtown Winery.

Participants can design a personalized doormat using a variety of stencil choices. Whether you want a festive fall welcome mat or an everyday design, you’ll leave with a custom piece for your front door.

👉 Event Link: https://www.polwinery.com/event/fall-doormat-stencil-paint-night/

🎉 Don’t Miss This Week in St. Mary’s County

There’s a lot happening around Leonardtown, Mechanicsville, St. Mary’s City, Clements, Chaptico, Coltons Point, and surrounding St. Mary’s County communities this week.

Whether you’re looking for a county tradition, a free outdoor event, local art, live music, racing, or seasonal fall activities, make Southside Happenings: Southern Maryland Community Events & Local Activities your starting point for discovering what’s happening across St. Mary’s, Calvert, and Charles counties.

Explore Southside Happenings here:

https://marylandlistings.com/the-southside-happenings

With several events happening at the same time this weekend, always check the organizer’s latest schedule, admission details, parking information, weather policies, and event updates before heading out.

📅 More St. Mary’s County Events This Week

🎟 RiverFest 2026

📅 Date: Saturday, September 26, 2026
📍 Location: Historic St. Mary’s City, 47418 Old State House Road, St. Mary’s City, MD
🕒 Time: 10:00 AM–3:00 PM

Celebrate the St. Mary’s River with a community event focused on the outdoors and the local environment.

Activities include opportunities such as kayaking, live animals, music, face painting, environmental education, and more.

RiverFest is an especially useful addition to your weekend plans if you’re searching for free and family-friendly things to do in St. Mary’s County.

👉 Event Link: https://www.smcart.org/events/river-fest-2026

🎟 Bowles Farms Corn Maze & Fall Activities

📅 Date: Saturday, September 26, 2026
📍 Location: Bowles Farms, 22880 Budds Creek Road, Clements, MD
🕒 Time: Check the farm’s current schedule before visiting

Fall activities get underway at Bowles Farms with the opening of its 2026 corn maze season.

The farm’s large corn maze celebrates America’s 250th birthday with a Statue of Liberty-themed design, adding a patriotic twist to a favorite Southern Maryland fall tradition.

It’s a great seasonal option for anyone looking for fall events in St. Mary’s County.

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

🎟 ArtWalk in Leonardtown

📅 Date: Available during the weekend; ArtWalk continues through September 30, 2026
📍 Location: Participating businesses throughout downtown Leonardtown
🕒 Time: During participating business hours

Take a self-guided walk through downtown Leonardtown and discover artwork displayed at participating local businesses.

ArtWalk showcases work from area artists across a variety of media and styles while giving visitors another way to explore the Leonardtown Arts & Entertainment District.

This is also a flexible option because you can fit the walk around other weekend activities.

👉 Event Link: https://www.visitstmarysmd.com/events/artwalk-september-2026/

🎟 The Market @ MedStar Health in Leonardtown

📅 Date: Friday, September 25, 2026
📍 Location: MedStar St. Mary’s Hospital, 25500 Point Lookout Road, Leonardtown, MD
🕒 Time: 10:00 AM–2:00 PM

Stop by this community farmers market for local produce, honey, prepared foods, farm products, and other offerings from participating area vendors.

It’s an easy Friday stop if you’re already spending time around Leonardtown.

👉 Event Link: https://www.visitstmarysmd.com/events/the-market-medstar-health-in-leonardtown-2026/

🎟 John Paycheck at The Potomac Gardens

📅 Date: Thursday, September 24, 2026
📍 Location: The Potomac Gardens, 20254 Colton Point Road, Coltons Point, MD
🕒 Time: 7:00 PM

Start the weekend early with live country music in Coltons Point.

John Paycheck takes the stage at The Potomac Gardens Thursday evening, adding another live entertainment option to this week’s St. Mary’s County calendar.

Check directly with the venue for the latest admission and event information before attending.

👉 Event Link: https://www.thepotomacgardens.com/

🎟 Sam Farthing & The Method Featuring Tom Mitchell

📅 Date: Friday, September 25, 2026
📍 Location: Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD
🕒 Time: 7:30 PM–10:00 PM; doors open at 7:00 PM

Southern Maryland Traditional Music and Dance presents an evening of music featuring Sam Farthing & The Method, with special guest Tom Mitchell.

It’s another option for local music fans looking beyond the larger weekend festivals and attractions.

Check the organizer’s current listing for admission and other attendance details.

👉 Event Link: https://www.smtmd.org/

🎟 Live Music: Neverland Band

📅 Date: Saturday, September 26, 2026
📍 Location: Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD
🕒 Time: 2:00 PM–5:00 PM

Spend part of Saturday afternoon listening to live music from the Neverland Band at Port of Leonardtown Winery.

It’s an easy addition to a Leonardtown weekend itinerary, especially if you’re looking for live entertainment after visiting another nearby event.

Check the winery calendar for the latest event and food-truck information.

👉 Event Link: https://www.polwinery.com/events/

🎟 Live Music: Levi Stephens

📅 Date: Sunday, September 27, 2026
📍 Location: Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD
🕒 Time: 2:00 PM–5:00 PM

Wind down the weekend with an afternoon performance by Levi Stephens at Port of Leonardtown Winery.

The Sunday afternoon event gives visitors another live-music option after a busy weekend of fairs, festivals, racing, and fall activities throughout St. Mary’s County.

👉 Event Link: https://www.polwinery.com/events/

🎟 Paw Crawl in Leonardtown

📅 Date: Sunday, September 27, 2026
📍 Location: Leonardtown, MD
🕒 Time: Check the current Leonardtown event listing for details

Leonardtown’s September calendar includes Paw Crawl on Sunday, September 27.

Check with the Town of Leonardtown before attending for the latest information on times, participating locations, activities, and any attendance requirements.

👉 Event Link: https://www.leonardtown.com/events

🍂 Family-Friendly & Fall Events in St. Mary’s County

Searching for family-friendly events in St. Mary’s County or fall things to do near you?

There are several possibilities this weekend.

RiverFest combines outdoor recreation with environmental education and community activities. Bowles Farms begins its corn-maze season, while the St. Mary’s County Fair brings agricultural exhibits, carnival attractions, competitions, entertainment, and longstanding county traditions together in Leonardtown.

ArtWalk is another flexible activity for visitors who want to spend some time exploring downtown Leonardtown at their own pace.

Because event schedules, admission requirements, age restrictions, and weather policies can change, check directly with each organizer before leaving home.

📣 Want Your Event Featured?

Are you organizing a festival, fundraiser, workshop, performance, community gathering, market, nonprofit activity, or other event in Southern Maryland?

Submit it through the Southside Happenings Community Spotlight so upcoming local activities and organizations can be considered for a future feature.

Businesses and community organizations can also submit themselves for consideration in the Community Spotlight.

👉 Community Spotlight:
https://marylandlistings.com/the-southside-happenings#spotlight

📅 Stay Connected with Local Events

Check Southside Happenings each week to discover:

✔ Local festivals
✔ Family-friendly activities
✔ Live music & entertainment
✔ Community gatherings
✔ Seasonal events across Southern Maryland

Our weekly guides help you discover activities throughout St. Mary’s County, Calvert County, and Charles County without having to search dozens of individual calendars.

Bookmark the community events hub and check back for the next weekly roundup:

https://marylandlistings.com/the-southside-happenings

🔎 Discover More Things to Do in Southern Maryland

Looking for even more things to do in Southern Maryland?

Explore our Things to Do in Southern Maryland collection for local guides, activities, attractions, seasonal ideas, and community happenings.

You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities for our main community-events hub covering St. Mary’s County, Calvert County, Charles County, and the surrounding Southern Maryland region.

Looking for useful ideas for around the house? Browse Tips, Home Hacks, Home Decoration & Maintenance Tips for seasonal projects, decorating inspiration, maintenance ideas, and helpful household guides.

And if you know about an upcoming event, local business, nonprofit, or community organization that deserves some attention, submit it through our Community Spotlight for consideration in an upcoming feature.

📅 Follow Southside Happenings for weekly updates, explore more Southern Maryland guides, and submit your event so we can keep the community calendar growing.