St. Mary’s County Community Events | September 18–20, 2026

St. Mary’s County events are filling the calendar for September 18–20, 2026, with food, live entertainment, historic experiences, outdoor activities, cars, community gatherings, and plenty of reasons to get out and explore Southern Maryland.

If you’re searching for things to do in St. Mary’s County this weekend or simply wondering what’s happening near you, this week’s roundup takes you from California and Lexington Park to Leonardtown, Hollywood, St. Mary’s City, Mechanicsville, and beyond.

Living in St. Mary’s County means having access to an interesting mix of waterfront landscapes, historic destinations, locally owned gathering places, community organizations, and seasonal events. This weekend is a particularly busy one, so check event pages before heading out for the latest information on tickets, registration, weather policies, and schedule changes.

⭐ Featured St. Mary’s County Events This Weekend

⭐ Taste of St. Mary’s 2026

📅 Date: Saturday, September 19, 2026
📍 Location: St. Mary’s County Regional Airport, 44174 Airport Rd, California, MD 20619
🕒 Time: 12:00 PM–4:00 PM

Come hungry for one of the county’s signature annual food events. Taste of St. Mary’s brings local restaurants, food trucks, caterers, entertainment, aircraft displays, children’s activities, and a classic car show together at the airport.

Admission is free, with tasting tickets available for food and drink samples.

👉 Taste of St. Mary’s Event Details

⭐ Sunset at Sotterley

📅 Date: Saturday, September 19, 2026
📍 Location: Historic Sotterley, 44300 Sotterley Ln, Hollywood, MD 20636
🕒 Time: 6:00 PM–9:00 PM

Spend Saturday evening at Historic Sotterley for its annual Sunset at Sotterley gala. The evening includes sunset views, entertainment, auction experiences, and dinner in the Barns of Sotterley event space.

This is a ticketed fundraiser supporting Historic Sotterley and its educational programming.

👉 Sunset at Sotterley Event Details

⭐ Wheels and Wings Car Show

📅 Date: Saturday, September 19, 2026
📍 Location: Patuxent River Naval Air Museum, 22156 Three Notch Rd, Lexington Park, MD 20653
🕒 Time: 10:00 AM–3:00 PM

Cars meet aviation history at this Lexington Park event. Visitors can check out classic vehicles and custom rides alongside the aircraft and exhibits that make the Patuxent River Naval Air Museum a distinctive Southern Maryland destination.

The St. Mary’s County tourism calendar confirms Wheels and Wings for September 19 at the museum.

👉 Wheels & Wings Event Information

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

Whether you’re looking for a festival in California, an evening event in Hollywood, something to do in Leonardtown, or an activity near Lexington Park, September 18–21 offers plenty of ways to explore St. Mary’s County.

Bookmark Southside Happenings: Southern Maryland Community Events & Local Activities for ongoing local event ideas across St. Mary’s, Calvert, and Charles counties.

From community celebrations and live entertainment to local history and outdoor activities, Southside Happenings makes it easier to see what’s coming up around Southern Maryland.

📅 More St. Mary’s County Events This Week

🎟 Maryland Dove Passenger Sail

📅 Date: Saturday, September 19, 2026
📍 Location: Historic St. Mary’s City Waterfront, 47414 Old State House Rd, St. Mary’s City, MD 20686
🕒 Time: Sailings at 10:00 AM and 1:00 PM

Step aboard the Maryland Dove for a two-hour public sail on the St. Mary’s River. The wooden vessel is inspired by the original Dove of 1634, offering a hands-on connection with Maryland’s maritime past. Registration is required and the program is for ages 5 and older.

👉 Maryland Dove Passenger Sail Details

🎟 Outdoor Art & Movie Night at Town Market

📅 Date: Saturday, September 19, 2026
📍 Location: Town Market / The Bell Building, 22675 Washington St, Leonardtown, MD 20650
🕒 Time: 6:00 PM–9:00 PM

Head into downtown Leonardtown for an evening combining art, local vendors, food, and an outdoor movie. It’s an easy addition to the list for anyone searching for things to do around Leonardtown on Saturday night. The county tourism calendar lists the event for September 19.

👉 Visit Leonardtown Events Calendar

🎟 Star Party with Southern Maryland Astronomical Society

📅 Date: Friday, September 18, 2026
📍 Location: Lexington Park Library, Lexington Park, MD
🕒 Time: 7:30 PM–9:00 PM

Start the weekend looking up. The St. Mary’s County Library and Southern Maryland Astronomical Society are hosting an evening of telescope observing following a short introduction to safe observing and what visitors can expect to see in the night sky.

The event is weather-dependent, so registered participants should check for updates before leaving home.

👉 St. Mary’s County Library Events Calendar

🎟 La Vida Turns One! Latin Dance Night

📅 Date: Friday, September 18, 2026
📍 Location: La Vida, 22767 Three Notch Rd, California, MD 20619
🕒 Time: 7:00 PM–11:00 PM

Kick off the weekend with an anniversary celebration featuring Latin music and dancing. The evening includes a cumbia lesson from 7:30–8:30 PM followed by social dancing with a DJ. Admission is free.

👉 Latin Dance Night Event Details

🎟 Monthly Indoor Vintage Market

📅 Date: Saturday, September 19, 2026
📍 Location: Rust and Grain Vintage Market, 30155 Three Notch Rd, Charlotte Hall, MD 20622
🕒 Time: Check event listing for current hours

If vintage finds are more your speed, the county tourism calendar lists Rust and Grain’s Monthly Indoor Vintage Market for Saturday. Browse vintage pieces and make it part of a day exploring northern St. Mary’s County.

👉 St. Mary’s County Events Calendar

🎟 Monthly Opening at The Vintage Source

📅 Date: Saturday, September 19, 2026
📍 Location: The Vintage Source, 22080 Newtowne Neck Rd, Compton, MD 20627
🕒 Time: Check event listing for current hours

The Vintage Source’s limited monthly opening gives visitors a chance to browse vintage furniture, décor, artwork, clothing, and other one-of-a-kind finds.

👉 St. Mary’s County Events Calendar

🎟 Grandparents Day Paddle + Picnic

📅 Date: Saturday, September 19, 2026
📍 Location: Greenwell State Park, 25410 Rosedale Manor Ln, Hollywood, MD 20636
🕒 Time: Check event listing for current schedule

Add some time on the Patuxent River to the weekend. Greenwell State Park’s special paddle-and-picnic event appears on the official county tourism calendar for September 19.

👉 St. Mary’s County Events Calendar

🎟 Free Public Open House at Drayden African American Schoolhouse

📅 Date: Saturday, September 19, 2026
📍 Location: 18287 Cherryfield Rd, Drayden, MD 20630
🕒 Time: Check the event listing before visiting

Explore an important part of St. Mary’s County history at the Drayden African American Schoolhouse. The free public open house is included on the county’s September 19 event calendar.

👉 St. Mary’s County Events Calendar

🎟 Demolition Derby at Potomac Speedway

📅 Date: Saturday, September 19, 2026
📍 Location: Potomac Speedway, 27963 Budds Creek Rd, Mechanicsville, MD 20659
🕒 Time: Check the event listing for current schedule

For a louder Saturday option, Potomac Speedway’s Demolition Derby is also on the county tourism calendar for September 19 in Mechanicsville.

👉 St. Mary’s County Events Calendar

👨‍👩‍👧‍👦 Family-Friendly Things to Do in St. Mary’s County

Families looking for weekend activities have several options to investigate. Taste of St. Mary’s specifically advertises children’s activities alongside food, music, aircraft displays, and the car show, while the Maryland Dove sail welcomes passengers ages five and older.

The library calendar is another useful place to check. On September 18, Lexington Park Library has an informal story hour and a family-friendly crockpot cooking demonstration in addition to that evening’s Star Party. Registration requirements vary by program.

With outdoor events, sails, and stargazing on the schedule, remember to check organizers’ pages for weather updates before heading out.

📍 Things to Do Near Leonardtown, Lexington Park & California MD

One of the advantages of exploring events in St. Mary’s County is the variety within a relatively compact area.

California has Taste of St. Mary’s and Friday evening’s Latin Dance Night. Lexington Park has the Wheels and Wings Car Show plus library activities. Leonardtown adds art, entertainment, and downtown activities, while Hollywood offers both Greenwell State Park and Historic Sotterley.

Farther south, St. Mary’s City offers the chance to get on the water aboard the Maryland Dove, while Drayden provides an opportunity to explore local history.

If you’re searching “events near me,” checking events by town can be especially useful because start times, ticket requirements, and travel times can make it possible to combine more than one activity in a day.

📣 Want Your Event Featured?

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

Submit it for consideration through the Southside Happenings Community Spotlight.

Local businesses and organizations can also use the Community Spotlight to share activities that Southern Maryland residents may want to know about.

📅 Stay Connected with Local Events

Follow Southside Happenings each week for ideas including:

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

Schedules can change, especially for outdoor activities, so always confirm times, ticket availability, age requirements, and weather policies directly with the event organizer before attending.

🔎 Discover More Things to Do in Southern Maryland

Ready to keep exploring? Visit Discover More Things to Do in Southern Maryland for more local guides, activities, destinations, and community ideas.

For weekly event roundups across St. Mary’s, Calvert, and Charles counties, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities.

You can also browse Tips, Home Hacks, Home Decoration and Maintenance Tips for useful ideas beyond the weekend calendar.

And if there’s an event or organization we should know about, submit it to the Community Spotlight so it can be considered for an upcoming Southside Happenings feature.