St. Mary’s County Community Events | October 1–4, 2026

St. Mary’s County events this weekend are bringing fall fun to Leonardtown, Mechanicsville, and communities throughout Southern Maryland from October 1–4, 2026.

If you’ve been searching for things to do in St. Mary’s County this weekend, this is a busy start to October. The calendar includes Leonardtown First Friday activities, arts and crafts, fall markets, corn mazes, community gatherings, and seasonal activities.

Event details can change, so check the event link before heading out.

⭐ Featured St. Mary’s County Events This Weekend

⭐ Leonardtown First Friday & “A Harvest of Haunts” Opening

📅 Date: Friday, October 2, 2026
📍 Location: Downtown Square & St. Mary’s County Arts Council Gallery, 22660 Washington St., Leonardtown
🕒 Time: 5:00 PM–8:00 PM

Downtown Leonardtown kicks off October with spooky-themed art exhibits, live street music, a public drum circle, art workshops, and evening dining specials.

👉 Event Link: https://www.facebook.com/events/22660-washington-st-leonardtown-md-united-states-maryland-20650/a-harvest-of-haunts-first-friday-opening-reception/1046208288167681/

👉 Leonardtown Events Calendar: https://www.visitleonardtownmd.com/eventscalendar

⭐ First Friday Drumline & Pop-Up Watercolor Activity

📅 Date: Friday, October 2, 2026
📍 Location: St. Mary’s County Arts Council Gallery, Leonardtown
🕒 Time: 5:00 PM–7:30 PM

Enjoy a free, family-friendly watercolor activity alongside live outdoor drumline performances during Leonardtown First Friday.

👉 Event Link: https://www.facebook.com/share/1K2kTtAteX/

👉 St. Mary’s County Arts Council Events: https://www.smcart.org/events

⭐ Forrest Hall Farm Corn Maze & Farm Market

📅 Date: Saturday, October 3 & Sunday, October 4, 2026
📍 Location: Forrest Hall Farm, 39130 Woodburn Rd., Mechanicsville
🕒 Time: 9:00 AM–5:00 PM

Enjoy scenic hayrides, farm animals, fresh apple cider doughnuts, and a custom corn maze designed for all ages.

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

⭐ Blessing of the Fleet at Leonardtown Wharf

📅 Date: Saturday, October 3, 2026
📍 Location: Leonardtown Wharf, 22510 Washington St., Leonardtown
🕒 Time: 12:00 PM–8:30 PM

Celebrate St. Mary’s County’s maritime heritage at the annual Blessing of the Fleet. The community event includes the blessing of the boats, live entertainment, local vendors, food, activities, and waterfront festivities.

👉 Event Link: https://www.visitstmarysmd.com/events/blessing-of-the-fleet-2026/

⭐ Corn Maze & Pumpkin Patch at Bowles Farms

📅 Date: Saturday, October 3 & Sunday, October 4, 2026
📍 Location: Bowles Farms, 22880 Budds Creek Rd., Clements
🕒 Time: Saturday 10:00 AM–6:00 PM | Sunday 10:00 AM–5:00 PM

Spend part of the weekend exploring the farm’s corn maze, pumpkin patch, play areas, barnyard animals, and other seasonal activities.

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

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

There’s plenty happening around Leonardtown, Mechanicsville, Clements, and other St. Mary’s County communities as October begins.

From First Friday festivities and creative activities to fall markets, corn mazes, and outdoor community events, there are plenty of ways to build your weekend itinerary.

For even more local activities, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities:

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

Whether you’re searching for St. Mary’s County events near me, looking for something to do this weekend, or planning ahead for another Southern Maryland outing, Southside Happenings brings local activities together in one place.

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

October is a great month to explore seasonal activities throughout St. Mary’s County.

Corn mazes are opening, pumpkin patches are welcoming visitors, and community calendars are filling with outdoor events, markets, arts activities, and fall gatherings.

For a traditional fall farm experience, Forrest Hall Farm in Mechanicsville and Bowles Farms in Clements both offer seasonal activities this weekend.

Leonardtown also has an especially active schedule, making it easy to combine several events into one weekend visit.

📅 More St. Mary’s County Events This Week

🎟 First Saturday Market Series

📅 Date: Saturday, October 3, 2026
📍 Location: Town Market, 22675 Washington St., Leonardtown
🕒 Time: 9:00 AM–4:00 PM

Browse local produce, baked goods, flowers, plants, crafts, apparel, and other market finds during Leonardtown’s First Saturday Market.

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

🎟 Fall Craft & Vendor Fair

📅 Date: Saturday, October 3, 2026
📍 Location: St. Mary’s County Fairgrounds, 42455 Fairgrounds Rd., Leonardtown
🕒 Time: Check event page for current schedule

Browse handmade goods, crafts, artwork, and products from local and regional vendors at the St. Mary’s County Fairgrounds.

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

🎟 Fall Market at Southern Trail Distillery

📅 Date: Saturday, October 3, 2026
📍 Location: 27227 Morganza Turner Rd., Mechanicsville
🕒 Time: 10:00 AM–5:00 PM

The annual Fall Market brings local vendors and food trucks together for a seasonal community market in Mechanicsville.

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

🎟 Drayden African American Schoolhouse Open House

📅 Date: Saturday, October 3, 2026
📍 Location: 18287 Cherryfield Rd., Drayden
🕒 Time: Check event page for current schedule

Explore an important part of St. Mary’s County history during a public open house at the historic Drayden African American Schoolhouse.

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

🎟 Autumn Harvest on the Farm at Lyon Family Farms

📅 Date: October 2–4, 2026
📍 Location: Lyon Family Farms, 39010 Lyon Ln., Mechanicsville
🕒 Time: Check the farm/event page for daily hours

Add another seasonal farm stop to your weekend with Autumn Harvest on the Farm in Mechanicsville.

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

🎟 Pages in the Park

📅 Date: Sunday, October 4, 2026
📍 Location: Port of Leonardtown Park
🕒 Time: 1:00 PM–3:00 PM

Bring a book, blanket, or chair and enjoy a relaxed outdoor reading gathering in Leonardtown.

👉 Event Link: https://www.stmalib.org/about-us/mobile-library-and-outreach-services/mobile-library-community-stops/

🎟 250th Under the Oaks at Tudor Hall

📅 Date: Sunday, October 4, 2026
📍 Location: Historic Tudor Hall, 41680 Tudor Place, Leonardtown
🕒 Time: 3:00 PM–5:00 PM

Spend Sunday afternoon outdoors at historic Tudor Hall with local music and St. Mary’s County history.

👉 Event Link: https://www.stmaryshistory.org/

📣 Want Your Event Featured?

Have an upcoming festival, community gathering, workshop, market, performance, business event, or other Southern Maryland happening?

Submit it for consideration through the Southside Happenings Community Spotlight:

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

📅 Stay Connected with Local Events

Follow Southside Happenings each week for:

• ✔ Local festivals

• ✔ Family-friendly activities

• ✔ Live music & entertainment

• ✔ Community gatherings

• ✔ Seasonal events across Southern Maryland

Event schedules can change because of weather, organizer updates, or other circumstances. Always check the event link before making your trip.

🔎 Discover More Things to Do in Southern Maryland

Looking for more local activities and guides?

Explore Things to Do in Southern Maryland for more activities, attractions, community happenings, and ideas for getting out around the region.

Visit Southside Happenings: Southern Maryland Community Events & Local Activities to keep up with upcoming events throughout St. Mary’s, Charles, and Calvert counties.

Check out Tips, Home Hacks, Home Decoration & Maintenance for helpful seasonal tips, decorating inspiration, maintenance ideas, and practical guides.

Have a local event or business you’d like featured? Visit the Community Spotlight — Submit Your Business or Event to share the details.

Save Southside Happenings, follow the weekly updates, and check back for the next roundup of St. Mary’s County events this weekend and activities throughout Southern Maryland.