St. Mary's County Events This Weekend | November 12–15, 2026

St. Mary's County events this weekend bring together an exciting mix of local history, live entertainment, outdoor adventures, creative workshops, and community celebrations from Thursday, November 12, through Sunday, November 15, 2026!

Looking for fun things to do near you in Southern Maryland? Whether you're planning an afternoon in Leonardtown, exploring Historic St. Mary's City, enjoying the outdoors in Hollywood, or finding activities around Lexington Park and Charlotte Hall, there's plenty happening across the county.

This weekend's highlights include the free public opening of Historic St. Mary's City's new Visitor Center, live music at Port of Leonardtown Winery, a pop-rock musical at St. Mary's College of Maryland, and a variety of local festivals and library programs.

Grab your calendar, invite a friend, and discover what's happening around St. Mary's County!

Featured St. Mary's County Events This Weekend

Here are three featured experiences worth adding to your weekend plans.

Historic St. Mary's City New Visitor Center Public Opening

📅 Date: Saturday, November 14, 2026

📍 Location: Historic St. Mary's City New Visitor Center, 47373 Old State House Road, St. Mary's City, MD 20686

🕒 Time: 10:00 AM – 4:00 PM

🎟️ Admission: Free on November 14

Step into a new chapter of Maryland history as Historic St. Mary's City welcomes visitors to its newly completed Visitor Center! Explore engaging exhibits, interactive displays, and historical stories highlighting Maryland's beginnings, Indigenous perspectives, and the communities that shaped the region.

This special public opening is a wonderful opportunity to experience one of Southern Maryland's most significant historical destinations. Free admission on November 14 is made possible by the Southern Maryland National Heritage Area.

👉 Event Link: https://www.hsmcdigshistory.org/events/new-visitor-center-opens/

Music with The Wanderers at Port of Leonardtown Winery

📅 Date: Saturday, November 14, 2026

📍 Location: Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD 20650

🕒 Time: 2:00 PM – 5:00 PM

Spend your Saturday afternoon enjoying live music by The Wanderers at Port of Leonardtown Winery!

Relax with local wines, enjoy the music, and check out food offerings from Heidi's Eats & Sages Treats. The winery provides a welcoming setting for an afternoon of conversation, music, and a little weekend relaxation.

If you've been searching for live music in Leonardtown, Maryland, this is one to keep on your radar. 

👉 Event Link: https://www.polwinery.com/event/music-w-the-wanderers/

BKLYN: The Musical at St. Mary's College of Maryland

📅 Date: 

• Nov. 12, 2026 8 p.m. - 10:30 p.m.

• Nov. 13, 2026 8 p.m. - 10:30 p.m.

• Nov. 14, 2026 8 p.m. - 10:30 p.m.

• Nov. 14, 2026 2 p.m. - 4:30 p.m.

• Nov. 15, 2026 2 p.m. - 4:30 p.m.

📍 Location: Bruce Davis Theater, Montgomery Hall Fine Arts Center, St. Mary's College of Maryland, 47645 College Drive, St. Mary's City, MD 20686

🕒 Time: Multiple evening and matinee performances; consult the performance schedule

Get ready for a powerful theatrical experience as the Performing Arts Department at St. Mary's College of Maryland presents BKLYN: The Musical.

Featuring pop-rock music and storytelling, this production follows a group of street performers sharing a moving tale of identity, family, ambition, and belonging.

Whether you're a longtime theater enthusiast or simply looking for a different kind of weekend activity, this production offers an opportunity to experience live performing arts in St. Mary's County.

👉 Event Link: https://inside.smcm.edu/events/performing-arts-department-presents-bklyn-musical?utm_source=vsm&utm_medium=calendar&utm_term=&utm_content=26-27-bklyn

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

There's something special about spending a weekend exploring the communities of St. Mary's County.

From Leonardtown's local gathering places to the historic surroundings of St. Mary's City, the parks of Hollywood, and the creative programs offered by community organizations, Southern Maryland provides plenty of ways to get out and enjoy the area.

Living in St. Mary's County means having access to a distinctive combination of waterfront landscapes, historical landmarks, arts and cultural experiences, outdoor recreation, and community traditions throughout the year.

This November weekend is a great example of that variety.

You can spend Saturday learning about Maryland's early history, catch live music in Leonardtown, attend a local harvest celebration, or explore new creative skills at the library.

And the best part? You don't have to travel far to discover something interesting.

For more local activities, upcoming events, and community discoveries throughout Calvert, Charles, and St. Mary's counties, explore Southside Happenings: Southern Maryland Community Events & Local Activities.

It's your community-focused destination for discovering what's happening around Southern Maryland.

More St. Mary's County Events This Week: November 12–15, 2026

Looking for even more things to do in St. Mary's County this weekend? Here are ten additional events and activities to explore.

1. Guided Hikes: Forest Bathing & Brunch

📅 Date: November 15, 2026

📍 Location: Greenwell State Park, 25410 Rosedale Manor Lane, Hollywood, MD 20636

🕒 Time: 9:30 AM – 11:30 AM

Enjoy the natural beauty of Southern Maryland with guided outdoor experiences at Greenwell State Park. The Sunday Forest Bathing & Brunch program offers a slower-paced walk focused on connecting with nature, followed by a picnic brunch.

👉 Event Link: https://www.facebook.com/events/25450-rosedale-manor-lane-hollywood-md-united-states-maryland-20636/guided-hike-forest-bathing-brunch/1121067013588148/

2. Special Holiday Opening at Rust and Grain Vintage Market

📅 Date: Friday, November 13, 2026

📍 Location: Rust and Grain Vintage Market, 30155 Three Notch Road, Charlotte Hall, MD 20622

🕒 Time: 4:00 PM – 8:00 PM

Get an early start on seasonal browsing during Rust and Grain's holiday kickoff. Explore vintage finds, distinctive gifts, home décor, and merchandise from local vendors in Charlotte Hall.

👉 Event Link: https://www.facebook.com/events/30155-three-notch-rd-charlotte-hall-md/rust-and-grain-holiday-kick-off/4288912837919180/

3. Paint and Sip Charcuterie Board at Xella Winery

📅 Date: Friday, November 13, 2026

📍 Location: Xella Winery, 26781 Laurel Grove Road, Mechanicsville, MD 20659

🕒 Time: 6:00 PM – 8:00 PM

Enjoy an evening of creativity with a guided painting experience at Xella Winery. Participants can decorate a charcuterie board while enjoying the winery setting. Painting supplies and instruction are included with the listed ticket.

Advance reservations are recommended because space is limited.

👉 Event Link: https://www.facebook.com/events/2245074609395898/

4. St. Michael's Harvest Festival

📅 Date: Saturday, November 14, 2026

📍 Location: St. Michael's Catholic School, 16560 Three Notch Road, Ridge, MD 20680

🕒 Time: 11:00 AM – 5:00 PM

Celebrate the autumn season with games, face painting, hayrides, food trucks, crafts, music, and local vendors. This community harvest festival offers a variety of activities, with proceeds supporting St. Michael's Catholic School.

👉 Event Link: https://www.facebook.com/events/s/st-michaels-harvest-festival/897078932988384/

5. Tots in the Front Yard: Sleepy Seeds in the Front Yard

📅 Date: Saturday, November 14, 2026

📍 Location: Leonardtown Library, Meeting Room 1, Leonardtown, MD

🕒 Time: 10:00 AM – 12:00 PM

Explore the world of seeds, fruits, and plants with Master Gardener volunteers. Designed especially for ages 3–6, this interactive activity includes garden exploration and guided walks, with accompanying adults welcome.

👉 Event Link: https://www.facebook.com/events/1518856043594202/

6. Saturday Storytime at Charlotte Hall Library

📅 Date: Saturday, November 14, 2026

📍 Location: Charlotte Hall Library, Meeting Room, Charlotte Hall, MD

🕒 Time: 10:00 AM – 10:30 AM

Start your Saturday with stories, rhymes, songs, and engaging activities at Charlotte Hall Library. This program is designed for toddlers and preschoolers with their grownups.

Space is limited and available on a first-come, first-served basis.

👉 Event Link: https://stmalib.libnet.info/event/16558982

7. Fall Leaf Suncatchers at Lexington Park Library 

📅 Date: Saturday, November 14, 2026

📍 Location: Lexington Park Library, Makerspace, Lexington Park, MD

🕒 Time: 10:00 AM – 11:30 AM

Celebrate the colors of autumn with a creative workshop making decorative leaf-inspired suncatchers. Participants can use colorful materials and prepared frames to create seasonal artwork.

The library lists this program for upper elementary ages through adults. 

👉 Event Link: https://stmalib.libnet.info/event/17057806?registration=true

8. Canning: Grow It, Eat It, Preserve It!

📅 Date: Saturday, November 14, 2026

📍 Location: Lexington Park Library, Makerspace, Lexington Park, MD

🕒 Time: 1:00 PM – 4:00 PM

Learn practical food-preservation skills during this hands-on workshop presented with expertise from University of Maryland Extension. Participants will explore canning fundamentals and practice preserving food.

This adult program is particularly useful for anyone interested in gardening, home projects, or making the most of seasonal produce. 

👉 Event Link: https://stmalib.libnet.info/event/16819111

9. Mario Kart Tournament at Charlotte Hall Library

📅 Date: Saturday, November 14, 2026

📍 Location: Charlotte Hall Library, Meeting Room, Charlotte Hall, MD

🕒 Time: 2:00 PM – 4:30 PM

Ready to race? Join other gaming enthusiasts for a Mario Kart tournament at Charlotte Hall Library. Participants can enjoy friendly competition, and the winner will receive a gift card.

This event is intended for ages 16 and older. 

👉 Event Link: https://stmalib.libnet.info/event/16799011

10. Seed-Saving Smarts: Hands-on Native Plant Workshop

📅 Date: Sunday, November 15, 2026

📍 Location: Lexington Park Library, Meeting Rooms A & B, Lexington Park, MD

🕒 Time: 2:00 PM – 3:30 PM

Wrap up the weekend with an educational gardening workshop led by Master Gardeners Molly Moore and Darcy White.

Learn how to collect, clean, identify, and store native plant seeds for future gardening projects. The workshop welcomes beginners and experienced gardeners alike, with hands-on practice using seed samples.

👉 Event Link: https://stmalib.libnet.info/event/16172769

Weekend planning tip: Event schedules, registration availability, admission policies, and weather-related arrangements can change. Always check the linked organizer page before heading out.

Want Your St. Mary's County Event Featured?

Are you organizing a community festival, fundraiser, workshop, concert, neighborhood gathering, or seasonal celebration in St. Mary's County?

We'd love to help more people discover what's happening throughout Southern Maryland!

Southside Happenings welcomes community event submissions and spotlight opportunities from local organizations, nonprofits, businesses, artists, and event organizers.

Whether you're planning something in Leonardtown, Lexington Park, Hollywood, Mechanicsville, Charlotte Hall, Ridge, or another St. Mary's County community, sharing your event helps local residents and visitors stay informed.

Have an upcoming event worth sharing?

👉 Submit Your Event or Request a Community Spotlight Feature

You can also share upcoming activities in Calvert and Charles counties to help connect communities across Southern Maryland.

Stay Connected with Local Events in Southern Maryland

The fun doesn't end after this weekend!

Southern Maryland offers activities throughout the year, from outdoor adventures and local performances to community celebrations and seasonal traditions.

Follow Southside Happenings for updates about:

✔ Local festivals — Community celebrations, cultural events, craft markets, and seasonal festivals.

✔ Family-friendly activities — Storytimes, educational programs, outdoor experiences, and interactive workshops.

✔ Live music & entertainment — Concerts, theater productions, performances, and local musicians.

✔ Community gatherings — Fundraisers, nonprofit events, public programs, and neighborhood activities.

✔ Seasonal events across Southern Maryland — Holiday markets, autumn festivals, spring celebrations, and summer activities.

Whether you've lived in St. Mary's County for years or are exploring the area for the first time, staying connected to local happenings is a great way to discover new places and experiences.

Looking for free events near you? Start with public library calendars, historical attractions offering special admission days, parks, and community organization announcements.

Interested in music and the arts? Explore local theaters, college performances, and community venues.

Prefer the outdoors? Southern Maryland's parks, trails, and waterfront settings provide opportunities to enjoy the changing seasons.

Whatever your interests, there's always another local experience worth discovering.

Discover More Things to Do in Southern Maryland

Looking for more activities beyond November 12–15?

Southside Happenings makes it easier to explore community events, local attractions, entertainment, and seasonal activities throughout St. Mary's, Calvert, and Charles counties.

Explore these helpful community resources:

🎉 Southside Happenings: Southern Maryland Community Events & Local Activities

Discover the main community events hub, find upcoming activities, and learn how to share your own event.

🔎 Discover More Things to Do in Southern Maryland

Browse additional articles featuring local activities, attractions, entertainment, and places to explore throughout the region.

🏡 Explore Home Tips, Home Hacks, Decorating & Maintenance Guides

Looking for helpful ideas for everyday living? Explore practical tips for home organization, decorating, seasonal maintenance, and creative projects.

📣 Get Featured in Our Community Spotlight

Have a local event, organization, or business you'd like the community to know about? Share your story and connect with Southern Maryland readers.

Make the Most of Your Weekend!

From discovering history at St. Mary's City to enjoying live music in Leonardtown, exploring local parks, attending workshops, and supporting community celebrations, November 12–15, 2026, offers plenty of opportunities to enjoy St. Mary's County.

Save this guide, share it with someone planning their weekend, and check back for more Southside Happenings updates.

Know about an event we should include next week? Submit it to Community Spotlight and help us keep Southern Maryland connected, one local event at a time!