St. Mary’s County Events This Weekend | October 8–11, 2026

St. Mary’s County events this weekend bring together fall festivals, live music, local history, community celebrations, outdoor activities, and seasonal experiences from Thursday, October 8 through Sunday, October 11, 2026.

If you’re searching for things to do in St. Mary’s County this weekend or wondering what’s happening near you, there are activities taking place in Lexington Park, Historic St. Mary’s City, Clements, Hollywood, Mechanicsville, and surrounding Southern Maryland communities.

Living in St. Mary’s County offers plenty of opportunities to experience waterfront history, local farms, music, community gatherings, and seasonal traditions. This October weekend is a great example, with activities ranging from sailing aboard a historic tall ship to navigating a fall corn maze.

Here are some events to put on your calendar.

⭐ Featured St. Mary’s County Events This Weekend

⭐ SoMD Pride 2026: Pride is Power

📅 Date: Sunday, October 11, 2026
📍 Location: Lexington Manor Passive Park, 21675 S. Coral Dr, Lexington Park, MD
🕒 Time: 10:00 AM–4:00 PM

SoMD Pride 2026 brings a vibrant community festival to Lexington Park with local artisans, live performances, resource tables, food trucks, and activities celebrating LGBTQ+ culture, equity, and inclusion.

👉 Event Link:
https://www.eventbrite.com/e/somd-pride-2026-pride-is-power-tickets-1999418359135

⭐ Maryland Dove Sail Experience

📅 Date: Saturday, October 10, 2026
📍 Location: Historic St. Mary’s City Waterfront, 18751 Hogaboom Ln, St. Mary’s City, MD
🕒 Time: 10:00 AM–12:00 PM

Step aboard the Maryland Dove for a seasonal sailing experience at Historic St. Mary’s City. The experience combines time on the water with an interactive look at Maryland’s 17th-century maritime history.

It’s a distinctive option for anyone searching for historical attractions or outdoor things to do in St. Mary’s County this weekend.

👉 Event Link:
https://www.hsmcdigshistory.org/events/maryland-dove-sail/

⭐ Bowles Farms 2026 Corn Maze & Fall Festival

📅 Date: Saturday, October 10–Sunday, October 11, 2026
📍 Location: Bowles Farms, 22880 Bugeye Barn Ln, Clements, MD
🕒 Time: 10:00 AM–6:00 PM

Looking for classic fall activities in St. Mary’s County? Bowles Farms features a massive 15-acre corn maze themed around America’s 250th anniversary, along with wagon rides, farm animals, pumpkin picking, and other seasonal farm activities.

This is one of the weekend’s options for visitors searching for fall festivals and family-friendly things to do in Southern Maryland.

👉 Event Link:
https://www.facebook.com/BowlesFarmsCornMaze/

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

From Lexington Park and Hollywood to Mechanicsville, Clements, and Historic St. Mary’s City, this October weekend offers several ways to get out and experience St. Mary’s County.

Whether you’re searching for a fall festival, local music, history, outdoor activities, or simply things to do near me in St. Mary’s County, this week’s calendar offers a mix of community-focused experiences.

You can also bookmark Southside Happenings: Southern Maryland Community Events & Local Activities to keep discovering upcoming festivals, entertainment, activities, and community happenings throughout Southern Maryland.

Event details can change, so remember to confirm admission requirements, ticket availability, schedules, and weather-related updates directly with the organizer before heading out.

🍂 Fall Festivals & Family-Friendly Things to Do in St. Mary’s County

October is a popular time for St. Mary’s County fall events, with farms, historic destinations, waterfront attractions, and community venues offering different ways to enjoy the season.

Bowles Farms is an obvious destination for traditional fall activities. Its corn maze, wagon rides, farm animals, and pumpkin picking give visitors several seasonal experiences at one location.

History enthusiasts have a very different option at Historic St. Mary’s City.

The Maryland Dove Sail Experience combines outdoor recreation with maritime history, providing a chance to experience the St. Mary’s City waterfront from aboard a re-created 17th-century vessel.

Historic Sotterley also offers an opportunity to explore local history through its Agriculture Over the Centuries themed tours.

Whether your ideal fall weekend involves pumpkins, historic sites, waterfront scenery, or community festivals, there are several things to do in St. Mary’s County this weekend without having to travel far from Southern Maryland.

🎶 Live Music & Community Events Near Lexington Park and Mechanicsville

Music and entertainment are also part of this weekend’s St. Mary’s County event calendar.

Roots & Rhythmfest at Thomas Family Farm brings regional music and community activities to Lexington Park on Saturday. The festival includes musical acts, local craft beer, fresh oysters, and activity areas.

Meanwhile, Corteau Vineyards in Mechanicsville is hosting an afternoon of live acoustic music alongside the release of its seasonal Sweet Barbara wine.

These events add more choices for anyone searching for Lexington Park events this weekend, Mechanicsville MD events, or live entertainment in St. Mary’s County.

Check individual venue policies, ticket information, admission requirements, and age restrictions before attending.

📅 More St. Mary’s County Events This Week

🎟 Historic Sotterley: Agriculture Over the Centuries Tour

📅 Date: Friday, October 9–Sunday, October 11, 2026
📍 Location: Historic Sotterley, 44300 Sotterley Ln, Hollywood, MD
🕒 Time: 10:00 AM–4:00 PM

Explore more than 300 years of agricultural history through special seasonal guided tours at Historic Sotterley. The experience connects farming history, historic architecture, the surrounding landscape, and autumn riverfront scenery.

For anyone interested in history and seasonal activities, it’s another way to experience fall in St. Mary’s County.

👉 Event Link:
https://sotterley.org/event/agriculture-over-the-centuries-themed-tours/

🎟 Roots & Rhythmfest at Thomas Family Farm

📅 Date: Saturday, October 10, 2026
📍 Location: Thomas Family Farm, Lexington Park, MD
🕒 Time: 11:00 AM–6:00 PM

Spend Saturday enjoying a fall music and community festival featuring regional performers, local craft beer, fresh oysters, and activity zones.

Roots & Rhythmfest provides another option for those looking for live music and community events near Lexington Park this weekend.

👉 Event Link:
https://www.visitstmarysmd.com/events/roots-rhythmfest-thomas-family-farm-2026/

🎟 Corteau Vineyards Sweet Barbara Wine Release & Live Music

📅 Date: Saturday, October 10, 2026
📍 Location: Corteau Vineyards, 22000 Busy Corner Rd, Mechanicsville, MD
🕒 Time: 12:00 PM–6:00 PM

Corteau Vineyards welcomes visitors for the seasonal release of Sweet Barbara along with live acoustic music from CPR Trio.

If you’re looking for Saturday afternoon entertainment around Mechanicsville, this event combines local wine and live music in a vineyard setting.

Check directly with the venue for current tasting, admission, reservation, and age-related details.

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

📣 Want Your Event Featured?

Hosting an upcoming festival, community gathering, fundraiser, performance, workshop, market, or other local event?

Local organizations, businesses, and event organizers can use the Community Spotlight / Submit an Event opportunity to share their information for consideration.

When submitting an event, include the event name, date, time, location, a brief description, and an official event or registration link whenever possible.

Providing complete information helps Southern Maryland residents discover upcoming community activities and plan their weekends.

📅 Stay Connected with Local Events

Check back regularly for:

• ✔ Local festivals

• ✔ Family-friendly activities

• ✔ Live music & entertainment

• ✔ Community gatherings

• ✔ Seasonal events across Southern Maryland

Schedules, ticket availability, admission requirements, and weather policies can change, so always confirm the latest information directly with the event organizer or venue before attending.

🔎 Discover More Things to Do in Southern Maryland

The weekend doesn’t end with this list.

Explore Things to Do in Southern Maryland for more local activities, seasonal guides, destinations, and ideas for exploring the region.

For weekly community calendars and upcoming activities, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities.

Have a community event or local business you’d like considered for a future feature? Visit the Community Spotlight / Submit an Event page.

You can also explore Tips, Home Hacks, Home Decoration & Maintenance for practical ideas, seasonal inspiration, and helpful guides.

Save this guide, follow Southside Happenings for weekly updates, and submit your event so more Southern Maryland residents can discover what’s happening around St. Mary’s County.