St. Mary's County Community Events | October 15–18, 2026

St. Mary's County events this weekend are bringing together the best of Southern Maryland's fall season, with oyster festivals, pumpkin patches, farm adventures, live music, theater performances, vintage shopping, and community celebrations happening October 15–18, 2026!

Whether you're searching for family-friendly activities near me, planning a weekend outing, or looking for something new to experience around town, there's plenty to explore.

From the Chesapeake Bay traditions of Leonardtown to the autumn farm activities of Mechanicsville and Clements, this weekend offers opportunities to enjoy local food, entertainment, history, and seasonal fun.

You'll also find indoor experiences in Lexington Park, vintage shopping in Charlotte Hall, and additional activities in California, Compton, and Drayden.

Here's your Southside Happenings weekly guide to things to do in St. Mary's County, Maryland.

Event information is based on published listings and organizer information available before the weekend. Check the linked event pages for final schedules, admission details, weather updates, and availability.

Featured St. Mary's County Events This Weekend

1. 60th Annual U.S. Oyster Festival

📅 Date: Saturday–Sunday, October 17–18, 2026

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

🕒 Time: Saturday, 10:00 AM–6:00 PM; Sunday, 11:00 AM–6:00 PM

Celebrate one of Southern Maryland's signature seafood traditions at the 60th Annual U.S. Oyster Festival!

This beloved community event highlights the region's Chesapeake Bay heritage with delicious oyster dishes, oyster-shucking competitions, live entertainment, artisan vendors, and activities for a variety of ages.

Visitors can watch talented competitors demonstrate their oyster-shucking skills while enjoying the lively atmosphere of the fairgrounds.

It's an excellent opportunity to experience local traditions, sample regional flavors, and spend time exploring one of St. Mary's County's best-known annual celebrations.

Weekend tip: Plan extra time for parking, vendor browsing, and the festival's entertainment schedule.

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

2. Fall Friday Night on the Farm & Tractor Treat

📅 Date: Friday, October 16, 2026 

📍 Location: Lyon Family Farms, 39010 Lyon Lane, Mechanicsville, MD

🕒 Time: 4:00–7:30 PM

Looking for a fun way to kick off the weekend?

Fall Friday Night on the Farm & Tractor Treat offers an autumn evening filled with seasonal farm activities.

Enjoy hayrides, a petting zoo, pumpkin-themed fun, games, and tractor displays in a relaxed countryside setting.

This event is a wonderful choice for anyone who enjoys spending time outdoors and experiencing the sights and sounds of fall in Southern Maryland.

Weekend tip: Wear comfortable shoes and bring an extra layer for the cooler evening temperatures.

👉 Event Link: https://www.facebook.com/events/1831500198218078

3. Corn Maze & Pumpkin Patch at Bowles Farms  

📅 Date: Saturday–Sunday, October 17–18, 2026

📍 Location: Bowles Farms, 22880 Budds Creek Road, Clements, MD

🕒 Time: Saturday, 10:00 AM–6:00 PM; Sunday, 10:00 AM–5:00 PM

Nothing says October quite like exploring a corn maze and picking out the perfect pumpkin!

Bowles Farms welcomes visitors to enjoy seasonal farm activities and experience the beauty of autumn in St. Mary's County.

Wander through the corn maze, explore the pumpkin patch, and make time for seasonal photographs.

Whether you're planning an afternoon with friends or a family outing, this local farm offers a classic fall experience.

Weekend tip: Allow enough time to enjoy the maze without rushing, and check the farm's website for admission and activity details.

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

4. The Addams Family at The Newtowne Players Theater

📅 Date: Thursday–Sunday, October 15–18, 2026

📍 Location: The Newtowne Players Theater, 21744 South Coral Drive, Lexington Park, MD

🕒 Time: Thursday–Saturday, 7:00 PM; Sunday, 3:00 PM

Get into the Halloween spirit with a theatrical performance of The Addams Family!

The Newtowne Players bring the famously unusual Addams Family characters to the stage for a spooky-season production filled with humor, music, and memorable personalities.

This indoor event is a great option for theater enthusiasts and anyone looking for an evening of entertainment in Lexington Park.

Supporting community theater is also a meaningful way to enjoy the creative talents of Southern Maryland performers.

Weekend tip: Check ticket availability and any age guidance before attending.

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

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

October is a wonderful time to explore everything St. Mary's County has to offer!

From the waterfront traditions of Leonardtown and the countryside of Mechanicsville to seasonal attractions in Clements, performances in Lexington Park, and shopping in Charlotte Hall, there are plenty of ways to make the most of the weekend.

Living in St. Mary's County means having access to a variety of community experiences throughout the year, including festivals, historic sites, arts programming, farmers markets, and outdoor recreation.

Whether you're a longtime resident, a newcomer, or visiting Southern Maryland for the weekend, local events offer a chance to discover something different and connect with the places that make this region distinctive.

Want even more ideas?

Visit Southside Happenings: Southern Maryland Community Events & Local Activities for community happenings, local guides, and upcoming activities throughout St. Mary's, Calvert, and Charles counties.

More St. Mary's County Events This Week

There's even more happening beyond the featured attractions! Here are eight additional community events to consider for October 15–18.

1. Monthly Indoor Vintage Market

📅 Date: Saturday–Sunday, October 17–18, 2026

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

🕒 Time: Saturday, 9:00 AM–4:00 PM; Sunday, 10:00 AM–3:00 PM

Browse antiques, vintage treasures, collectibles, and unique home décor while exploring finds from local vendors. This indoor market is ideal for anyone who enjoys discovering distinctive pieces and creative decorating inspiration.

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

2. Floral Pumpkin Workshop at Xella Winery

📅 Date: Saturday, October 17, 2026

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

🕒 Time: 10:00 AM–12:00 PM

Celebrate the season with a hands-on floral pumpkin workshop! Create an autumn-inspired arrangement while learning creative techniques for combining pumpkins and seasonal flowers.

Check the organizer's page for registration requirements and availability.

👉 Event Link: https://sunnysideflorals.com/products/2026-xella-floral-pumpkin-workshop

3. Jackson Perkins Live at The Rex Theatre

📅 Date: Saturday, October 17, 2026

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

🕒 Time: 8:00 PM

Spend your Saturday evening enjoying live music with Jackson Perkins at The Rex Theatre in downtown Leonardtown. Consider pairing the performance with a stroll around town for a relaxed weekend outing.

👉 Event Link: https://allevents.in/leonardtown/jackson-perkins-live-at-the-rex-theatre/200030384348455

4. Hispanic Heritage Fiesta Latin Dance Night at La Vida

📅 Date: Thursday, October 15, 2026

📍 Location: La Vida Mexican Bar & Grill, 22767 Three Notch Road, California, MD

🕒 Time: 7:00–10:00 PM

Celebrate Hispanic Heritage Month with music, dancing, and community at La Vida. The evening features dance instruction, social dancing, and performances in a welcoming atmosphere.

Admission is listed as free, making it an appealing option for an evening out.

👉 Event Link: https://www.visitstmarysmd.com/events/hispanic-heritage-night-la-vida-2026/

5. Analog Pop-Up Market at Slice House

📅 Date: Sunday, October 18, 2026

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

🕒 Time: 12:00 PM to 5:00 PM

Add a local pop-up market to your Sunday plans in downtown Leonardtown. Stop by to explore the event and see what participating vendors have to offer.

Check the event listing for vendor details and the confirmed schedule before heading out.

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

Family-Friendly Fall Activities Near Me in St. Mary's County

If you've been searching for family-friendly fall activities near me, St. Mary's County has several great options this October weekend.

For classic autumn experiences, start with Bowles Farms in Clements or Lyon Family Farms in Mechanicsville. These locations offer opportunities to enjoy the harvest season and spend time outdoors.

For a larger community celebration, the U.S. Oyster Festival in Leonardtown combines Chesapeake Bay food traditions with live entertainment and activities.

If you prefer indoor experiences, consider a local theater performance, a vintage market, or a seasonal workshop.

A few tips for planning your weekend:

• Check admission details: Some festivals, workshops, and performances require paid tickets or advance registration.

• Review the weather: Outdoor farm activities may be affected by rain or changing conditions.

• Plan your travel: Events take place across several towns, so allow time between destinations.

• Confirm event hours: Schedules can change, particularly for pop-up markets and seasonal attractions.

• Explore nearby stops: A weekend outing can also be a chance to visit local shops, restaurants, and historic destinations.

With so many activities spread throughout the county, it's easy to create a weekend itinerary based on your interests, schedule, and preferred travel distance.

Want Your St. Mary's County Event Featured?

Are you organizing a festival, fundraiser, community gathering, workshop, concert, or seasonal celebration in Southern Maryland?

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

Southside Happenings highlights local activities and community events throughout St. Mary's, Calvert, and Charles counties.

If you represent a local organization, community group, venue, or business with an upcoming event, consider submitting your information for a future feature.

Include your event name, date, time, location, description, and an official event link so readers can easily find the details.

👉 Submit Your Event or Apply for a Community Spotlight

Help us keep Southern Maryland connected, one community event at a time!

Stay Connected with Local Events in Southern Maryland

There's always something new to discover across St. Mary's County and the surrounding Southern Maryland region.

Follow Southside Happenings for regular updates featuring:

• ✔ Local festivals and annual celebrations

• ✔ Family-friendly activities and weekend adventures

• ✔ Live music, theater, and entertainment

• ✔ Community gatherings, markets, and workshops

• ✔ Seasonal events across Southern Maryland

Whether you're looking for things to do this weekend or planning ahead for an upcoming holiday, keeping up with local event listings can help you make the most of your free time.

From small community gatherings to well-known regional festivals, each event offers another opportunity to explore the area.

Discover More Things to Do in Southern Maryland

Your weekend adventures don't have to end on Sunday!

Explore more community events, seasonal activities, and local guides through Southside Happenings.

🎉 Explore More Things to Do in Southern Maryland

Discover more local happenings, entertainment ideas, and activities across St. Mary's, Calvert, and Charles counties.

📅 Visit the Southside Happenings Community Events Hub

Stay connected with upcoming events, featured community experiences, and seasonal happenings.

🏡 Explore Home Tips, Decorating Ideas & Maintenance Guides

Looking for inspiration between weekend outings? Explore practical home hacks, seasonal decorating ideas, and maintenance tips.

📣 Get Featured in the Community Spotlight

Have an upcoming event or a local business you'd like the community to discover? Submit your information for consideration.

Make the most of October 15–18, 2026! Pick an event, explore a new corner of St. Mary's County, and share Southside Happenings with someone looking for their next Southern Maryland adventure.

See you around the county!