St. Mary's County Events This Weekend | November 5–8, 2026

St. Mary's County events this weekend bring together exciting motorsports, live music, art exhibitions, seasonal shopping, and community celebrations from Thursday, November 5, through Sunday, November 8, 2026!

If you're searching for things to do near Leonardtown, Lexington Park, Mechanicsville, or St. Mary's City, you've come to the right place.

This week's Southside Happenings guide highlights 15 events and activities throughout St. Mary's County, including five featured experiences and ten additional happenings worth exploring.

Whether you're planning a relaxing afternoon, looking for a local concert, browsing handmade gifts, or enjoying the crisp November weather, Southern Maryland offers plenty of ways to spend the weekend.

Planning tip: Event schedules, admission requirements, and availability can change. Check the linked organizer or event page before leaving home, especially for ticketed activities.

Featured St. Mary's County Events This Weekend

Haltech World Cup Finals: Import vs. Domestic

📅 Date: November 4–8, 2026 

📍 Location: Maryland International Raceway, 27861 Budds Creek Road, Mechanicsville, MD 20659

🕒 Time: Daily racing schedule varies. Depends on tickets.

Get ready for one of the region's most exciting motorsports experiences! The Haltech World Cup Finals brings import vehicles and American muscle cars together for high-performance drag racing at Maryland International Raceway.

The event draws racing enthusiasts to Mechanicsville for competitive action and an energetic trackside atmosphere.

Important: The official tourism calendar currently lists this event as SOLD OUT. Do not travel expecting tickets at the gate without confirming availability.

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

Color & Light Society Opening Reception

📅 Date: Friday, November 6, 2026

📍 Location: St. Mary's County Arts Council Gallery & Gift Shop, 22660 Washington Street, Leonardtown, MD 20650

🕒 Time: 5:00 PM–8:00 PM

Spend your Friday evening celebrating local creativity in downtown Leonardtown!

The St. Mary's County Arts Council welcomes visitors to the opening reception of the Color & Light Society exhibition. Explore original artwork and meet members of the Southern Maryland arts community.

It's a wonderful opportunity to discover local talent while enjoying Leonardtown's First Friday atmosphere.

👉 Event Link: https://www.facebook.com/photo/?fbid=1773746971423407&set=a.484738480324269

The Reagan Years Live at the Dodge Performing Arts Center

📅 Date: Saturday, November 7, 2026

📍 Location: Nancy R. & Norton T. Dodge Performing Arts Center, 47855 College Drive, St. Mary's City, MD 20686

🕒 Time: 7:00 PM–9:00 PM

Ready for a musical trip back to the 1980s?

The Reagan Years return to St. Mary's College of Maryland with a lively tribute to the decade's unforgettable pop and rock hits.

This performance is a great choice for anyone who enjoys retro music, energetic live entertainment, and an evening at one of the county's performing arts venues.

Tickets are required; check availability before attending.

👉 Event Link: https://inside.smcm.edu/events/reagan-years-0?utm_source=vsm&utm_medium=calendar&utm_term=&utm_content=26-27-reagan

Coastal Arts Market at Leonardtown Wharf

📅 Date: Saturday, November 7, 2026 

📍 Location: Leonardtown Wharf Park, Leonardtown, MD 20650

🕒 Time: 9:00 AM–3:00 PM

Enjoy a fall outing along Breton Bay while discovering handmade goods and creative work from regional vendors.

The proposed Coastal Arts Market features artisan shopping in a scenic waterfront setting, with opportunities to browse gifts, crafts, and other locally made products.

Pair your visit with a walk around Leonardtown Wharf and time to enjoy the waterfront views.

👉 Event Link: https://www.facebook.com/events/1467047535489069/

Fall Artisan Market at Summerseat Farm

📅 Date: Saturday, November 7, 2026

📍 Location: Summerseat Farm, 27205 Summerseat Lane, Mechanicsville, MD 20659

🕒 Time: 09:00 AM–3:00 PM 

Celebrate the season with a visit to historic Summerseat Farm in Mechanicsville.

The proposed fall artisan market offers a chance to explore handmade crafts, seasonal goods, and the character of this historic Southern Maryland property.

It's an appealing option for readers who enjoy historic places, creative vendors, and relaxed autumn outings.

👉 Event Link: https://summerseat.org/fall-artisan-market-3/

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

There's something special about a November weekend in Southern Maryland.

From Leonardtown's galleries and independent shops to the open spaces of Mechanicsville and the cultural attractions around St. Mary's City, the county offers a wide range of experiences.

Living in St. Mary's County means having access to historic destinations, waterfront scenery, community traditions, and a growing calendar of local activities.

This weekend is a great reminder that discovering something new doesn't always require traveling far from home.

Maybe you'll find a favorite artist, enjoy a concert, explore a seasonal market, or spend an afternoon supporting a local organization.

Looking for more inspiration beyond November 8?

Visit Southside Happenings: Southern Maryland Community Events & Local Activities for additional happenings across St. Mary's, Calvert, and Charles counties.

Bookmark the hub to make planning your next Southern Maryland weekend easier!

More St. Mary's County Events This Week: November 5–8

Still looking for more things to do? Here are ten additional events and activities to consider.

1. Southern Maryland Pride: Pride is Power Festival

📅 Date: Sunday, November 8, 2026

📍 Location: Lexington Manor Passive Park, 21675 Coral Drive South, Lexington Park, MD 20653

🕒 Time: 11:00 AM–4:00 PM

Celebrate community and creativity at this free festival featuring music, performers, food vendors, activities, and community connections.

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

2. Passport to the Holidays — Leonardtown First Friday Weekend

📅 Date: Friday, November 6 – Sunday, November 8, 2026

📍 Location: Participating downtown Leonardtown businesses, Leonardtown, MD

🕒 Time: November 6 - 10:00AM; November 8 - 5:00AM

Kick off seasonal shopping with a downtown shop-and-stroll experience featuring participating local retailers.

Explore shops, discover gifts, and enjoy a festive reason to spend time in Leonardtown.

👉 Event Link: https://www.facebook.com/events/4456624811238510

3. The Sacred Journey at St. Mary's College of Maryland

📅 Date: Friday, November 6, 2026

📍 Location: St. Mary's College of Maryland, 47777 Mattapany Road, St. Mary's City, MD 20686

🕒 Time: 4:45 PM–6:15 PM

This free commemorative gathering honors the legacy of enslaved people in Southern Maryland through reflection, a procession, and a waterfront ceremony.

It offers a meaningful opportunity to engage with the region's history and community.

👉 Event Link: https://inside.smcm.edu/events/sacred-journey-beloved-community-nov-6?utm_source=vsm&utm_medium=calendar&utm_term=&utm_content=26-27-sacred

4. Wannabe: Spice Girls Tribute

📅 Date: Friday, November 6, 2026

📍 Location: The Rex Theatre, 22695 Washington Street, Leonardtown, MD 20650

🕒 Time: Doors @7 PM | Show @ 8 PM

Bring some pop nostalgia to your Friday night with a Spice Girls tribute performance at The Rex Theatre.

This is a 21-and-over show, so review the venue's admission and ticket requirements before attending.

👉 Event Link: https://www.facebook.com/therexleonardtown/posts/spice-up-your-life-your-friday-night-next-friday-november-6th-%F0%9D%99%92%F0%9D%98%BC%F0%9D%99%89%F0%9D%99%89%F0%9D%98%BC%F0%9D%98%BD%F0%9D%99%80-1-spice-gi/1707969174666066/

5. Harry Potter Mystic Market

📅 Date: Saturday, November 7, 2026

📍 Location: Town Market, 22675 Washington Street, Leonardtown, MD 20650

🕒 Time: 9:00 AM–4:00 PM

Step into a magical market atmosphere with themed shopping, handmade goods, treats, and a costume contest.

Admission is free, making it an appealing option for anyone who enjoys creative markets and fantasy-inspired fun.

👉 Event Link: https://www.facebook.com/events/3395300243964329

6. Friends of the Library Fall Book Sale

📅 Date: Saturday, November 7, 2026

📍 Location: St. Mary's County Fairgrounds Auditorium, 42455 Fairgrounds Road, Leonardtown, MD

🕒 Time: 12:00 PM – 5:00 PM public sale; 10:00 AM – noon members only.

Book lovers, this one's for you!

Browse a wide selection of gently used books while supporting the Friends of the St. Mary's County Library. Public admission is free, and purchases help support library services.

👉 Event Link: https://www.facebook.com/events/1398980905130462

7. Boots & BBQ Hoedown

📅 Date: Saturday, November 7, 2026

📍 Location: Greenwell State Park, 25420 Rosedale Manor Lane, Hollywood, MD 20636

🕒 Time: 4:00 PM–8:00 PM

Enjoy an evening of barbecue, music, dancing, and community fundraising at the Greenwell Foundation's signature event.

This ticketed event is for adults ages 21 and older and supports the foundation's work with veterans and first responders.

👉 Event Link: https://www.facebook.com/events/1362689782612088

8. 80's Rock Power House Trio With Anthony Corder of TORA TORA

📅 Date: Saturday, November 7, 2026

📍 Location: The Potomac Gardens, 20254 Colton Point Road, Coltons Point, MD 20626

🕒 Time: 7:00 PM–10:00 PM

Fans of classic rock can enjoy a live performance featuring Frank Harnell of TNT and Anthony Cordor of Tora Tora.

It's another exciting choice for readers looking for Saturday evening entertainment in Southern Maryland.

👉 Event Link: https://www.facebook.com/events/1609811254266857

9. SOMD Cars & Coffee

📅 Date: Sunday, November 8, 2026 

📍 Location: Laurel Glenn Shopping Center, 46315 Alton Lane, California, MD 20619

🕒 Time: 8:00 AM to 11:00 AM

Car enthusiasts can connect with fellow automotive fans at this community gathering in California, Maryland.

Check the event listing for participation details and the latest schedule before heading out.

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

10. Analog Pop-Up Market

📅 Date: Sunday, November 8, 2026 

📍 Location: Slice House, 22745 Washington Street, Leonardtown, MD 20650

🕒 Time: 12:00 PM to 5:00 PM

Discover independent sellers and a mix of creative goods, artwork, collectibles, and vintage-inspired finds.

The county tourism calendar lists a November 8 market; the precise hours still need verification.

👉 Event Link: https://www.facebook.com/people/Analog-Popup-Market/61586534401568/

Want Your St. Mary's County Event Featured?

Have an upcoming community festival, fundraiser, performance, workshop, or special event?

Southside Happenings is always looking for activities worth sharing throughout Southern Maryland.

If you organize an event in St. Mary's County, Calvert County, or Charles County, we'd love to help community members discover it.

Submit your event or nominate a local business or organization for our Community Spotlight.

👉 Submit Your Event or Apply for Community Spotlight

The more events we share, the easier it becomes for neighbors and visitors to discover what's happening around Southern Maryland.

Stay Connected with Local Events in Southern Maryland

The fun doesn't end when the weekend is over!

St. Mary's County has a rich mix of community activities, from historic-site programs to performing arts, markets, and seasonal celebrations.

Follow Southside Happenings for updates featuring:

✔ Local festivals — Annual celebrations, cultural events, and community traditions.

✔ Family-friendly activities — Markets, outdoor outings, creative workshops, and seasonal fun.

✔ Live music & entertainment — Concerts, performances, and local music venues.

✔ Community gatherings — Fundraisers, nonprofit events, and opportunities to connect.

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

For anyone searching for Southern Maryland events near me, our weekly guides help bring local happenings together in one convenient place.

Be sure to check event pages before attending, since weather, ticket availability, and organizer schedules may affect plans.

Discover More Things to Do in Southern Maryland

Looking for more local inspiration?

Whether you're planning your next weekend, exploring a nearby town, or searching for a new community activity, Southside Happenings makes it easier to discover opportunities throughout the region.

Explore more local resources:

Discover More Things to Do in Southern Maryland

Browse community activities, seasonal inspiration, and ideas for getting out and exploring.

Southside Happenings: Southern Maryland Community Events & Local Activities

Visit the main community events hub for more happenings across St. Mary's, Calvert, and Charles counties.

Home Tips, Décor & Maintenance Guides

Find helpful seasonal home care ideas, decorating inspiration, practical maintenance tips, and everyday home hacks.

Frequently Asked Questions About St. Mary's County Weekend Events

What are the best things to do in St. Mary's County this weekend?

For November 5–8, 2026, highlights include The Reagan Years concert, the Color & Light Society reception, Harry Potter Mystic Market, Southern Maryland Pride, and several other community events. The Haltech World Cup Finals is also scheduled, but is listed as sold out.

Are there free events in Southern Maryland this weekend?

Yes! Free options include The Sacred Journey, Harry Potter Mystic Market, the Friends of the Library Fall Book Sale's public admission, and the Southern Maryland Pride festival. Some activities, shopping, or refreshments may have additional costs.

Where can I find family-friendly activities near Leonardtown and Lexington Park?

Explore Leonardtown's themed markets and book sale, or visit the Southern Maryland Pride festival in Lexington Park. Always check individual event details for age guidance and activities.

How can I submit an event to Southside Happenings?

Visit the Community Spotlight submission page to share an upcoming event or nominate a local organization.

From waterfront views and art galleries to concerts, seasonal markets, and community celebrations, there's always something new to discover in St. Mary's County.

Save this guide, share it with someone planning a weekend outing, and follow Southside Happenings for more weekly community event updates.

Have something happening in your community? Submit your event here and help spread the word!