St. Mary's County Events This Weekend | October 22–25, 2026

St. Mary's County events this weekend are bringing Halloween excitement, historic adventures, creative workshops, and seasonal community gatherings to Southern Maryland from October 22–25, 2026!

Looking for fun things to do near you? From haunted attractions in Avenue and waterfront festivities in Leonardtown to trick-or-treating at Historic St. Mary's City, this weekend offers plenty of opportunities to celebrate fall.

Whether you're interested in family-friendly Halloween activities, local entertainment, educational experiences, or seasonal crafts, there's something to explore across St. Mary's County.

Here's your guide to what's happening this weekend!

Please check individual event pages before attending. Times, admission requirements, and registration availability may change.

Featured Halloween Events in St. Mary's County This Weekend

These four featured events highlight some of the seasonal activities happening around the county.

1. Barefoot Farm of Screams

📅 Date: Thursday–Saturday, October 22–24, 2026
📍 Location: Barefoot Farms, 21851 Oakley Road, Avenue, MD
🕒 Time: 6:30 PM – 9:30 PM

Ready for a spooky adventure? Barefoot Farm of Screams invites Halloween enthusiasts to explore haunted outdoor trails and scare zones set on a working farm.

This seasonal attraction is best suited for adults and older children who enjoy a good fright. Comfortable shoes and weather-appropriate clothing are recommended for the outdoor experience.

👉 Event Link: https://www.facebook.com/share/1CABkkXJVF/

2. Town Market Trunk-or-Treat & Vendor Show

📅 Date: Saturday, October 24, 2026
📍 Location: Town Market, 22675 Washington Street, Leonardtown, MD
🕒 Time: Vendors begin at 9:00 AM | Trunk-or-Treat: 12:00 PM – 4:00 PM (submitted schedule)

Celebrate Halloween with local vendors, decorated vehicles, seasonal merchandise, and plenty of community spirit!

Visitors can browse artisan gifts, fall decorations, and local offerings before enjoying the trunk-or-treat festivities. The submitted event description also includes food vendors, live entertainment, and costume contests.

It's a festive way to spend part of your Saturday in Leonardtown.

👉 Event Link: https://www.facebook.com/events/town-market-llc/trunk-or-treat-vendor-show/855721156861724/

3. Waterfront Monster Mash Bash

📅 Date: Saturday, October 24, 2026
📍 Location: Leonardtown Wharf Park, 22510 Washington Street, Leonardtown, MD
🕒 Time: 1:00 PM – 4:00 PM

Enjoy Halloween fun along the Leonardtown waterfront!

The Waterfront Monster Mash Bash brings seasonal music, lawn games, costumes, and family activities to one of Leonardtown's scenic gathering places.

With beautiful waterfront views and a lively fall atmosphere, this event offers a relaxed way to enjoy the Halloween season in Southern Maryland.

👉 Event Link: https://www.visitstmarysmd.com/events/monster-mash-2026/

5. "Lost City" Trick-or-Treat at Historic St. Mary's City

📅 Date: Saturday, October 24, 2026
📍 Location: Historic Town Center, Historic St. Mary's City, MD
🕒 Time: 5:00 PM – 8:00 PM

Step back in time for a Halloween experience unlike any other!

Historic St. Mary's City transforms its historic town center into a festive trick-or-treat destination featuring seasonal activities and an atmosphere inspired by Maryland's colonial past.

Visitors can explore the historic setting while enjoying a family-friendly evening of Halloween fun. Costumes are encouraged, and the organizer notes that entry closes at 7:30 PM.

👉 Event Link: https://www.visitstmarysmd.com/events/lost-city-2026/

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

There's something special about fall in St. Mary's County.

From the waterfront streets of Leonardtown to the historic grounds of St. Mary's City and the countryside around Avenue, October brings opportunities to enjoy seasonal traditions and connect with local organizations.

This week's events offer a little bit of everything: haunted adventures, Halloween celebrations, hands-on workshops, educational experiences, and community activities.

If you're looking for things to do near you this weekend, these gatherings are a great place to start.

For more community events, local activities, and seasonal inspiration, visit Southside Happenings: Southern Maryland Community Events & Local Activities.

Discover what's happening throughout St. Mary's, Calvert, and Charles counties, and bookmark the page for future weekend plans!

More St. Mary's County Events This Week

Still looking for things to do in St. Mary's County this weekend? Here are additional events and activities happening October 22–25, 2026.

1. Members Twilight Tour of the Plantation

📅 Date: Thursday, October 22, 2026
📍 Location: Godiah Spray Tobacco Plantation, Historic St. Mary's City
🕒 Time: 6:00 PM (submitted schedule)

Discover Maryland's colonial history during an evening guided tour of the reconstructed tobacco plantation.

As the sun sets near the St. Mary's River, participants can explore the setting and learn about life in 17th-century Maryland. Check the organizer's membership and reservation requirements before attending.

👉 Event Link: https://www.somdnews.com/local-events/?_evDiscoveryPath=/event/3872300-members-twilight-tour-of-the-plantation

2. Trivia Fright Night: Horror Movie Trivia

📅 Date: Thursday, October 22, 2026
📍 Location: Lexington Park Library, Meeting Room B
🕒 Time: 6:00 PM – 7:30 PM

Calling all horror movie fans!

Test your knowledge through three rounds of spooky movie trivia. Participants can compete individually or in teams of up to four, with prizes and extra points available for costumes.

Registration is requested for each participant.

👉 Event Link: https://stmalib.libnet.info/event/17600237

3. Spooky Sweets & Sips at Port of Leonardtown Winery

📅 Date: Friday, October 23, 2026
📍 Location: Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD
🕒 Time: 6:00 PM – 8:00 PM

Get creative with a Halloween-inspired cookie decorating workshop!

Participants will learn how to assemble and decorate a haunted house cookie scene with guidance from Selina. The workshop offers a fun opportunity to explore seasonal baking and decorating techniques.

Check the registration page for ticket availability and participation requirements.

👉 Event Link: https://www.polwinery.com/event/spooky-sweets-sips-haunted-house-cookie-decorating-w-selina/

4. Animal Services Howl-O-Ween Preview

📅 Date: Friday, October 23, 2026
📍 Location: Leonardtown Library, Lobby
🕒 Time: 9:00 AM – 11:00 AM

Stop by Leonardtown Library to meet representatives from St. Mary's County Animal Services.

Learn about local animal welfare resources, the pet food pantry, and available services. Representatives will also share information about adoptable animals and the upcoming Howl-O-Ween celebration.

👉 Event Link: https://www.stmalib.org/events/adult-events/howl-o-ween/

6. Our Library Neighborhood: Informal Story Hour

📅 Date: Friday, October 23, 2026
📍 Location: Lexington Park Library, Children's Area
🕒 Time: 3:30 PM – 4:30 PM

Enjoy a relaxed afternoon of picture books and storytelling at Lexington Park Library.

Children can choose books from the shelves and listen as library staff read aloud. It's a welcoming indoor activity for young readers and their accompanying adults.

👉 Event Link: https://www.stmalib.org/events/calendar/

8. DIG! St. Mary's Fort Excavation Experience

📅 Date: Saturday, October 24, 2026
📍 Location: Historic St. Mary's City, St. Mary's Fort Archaeological Site
🕒 Time: 9:00 AM – 4:00 PM

Ever wondered what it's like to participate in a real archaeological excavation?

This hands-on experience gives adults the opportunity to learn excavation techniques and work alongside professional archaeologists while discovering more about Maryland's early history.

The program is for ages 18 and older. All scheduled spaces are currently full, but the organizer offers a waitlist inquiry option.

👉 Event Link: https://www.hsmcdigshistory.org/events/dig-st-marys-fort-excavation-experience/

Things to Do in Leonardtown and St. Mary's City This Weekend

Planning a weekend outing is easier when you organize activities by location.

Leonardtown offers several seasonal attractions, including the Town Market Trunk-or-Treat, Waterfront Monster Mash Bash, and library activities. Visitors can enjoy community gatherings while exploring the town's waterfront and downtown surroundings.

Historic St. Mary's City offers opportunities to experience Maryland history through the Lost City celebration, the Members Twilight Tour, and the archaeology experience.

Avenue provides a spookier Halloween option with Barefoot Farm of Screams.

Lexington Park offers indoor activities at the public library, including horror movie trivia and storytime.

One of the enjoyable aspects of living in St. Mary's County is the variety of historic destinations, waterfront spaces, and community traditions available throughout the region.

Before heading out, remember to check the weather, event admission policies, parking information, and registration requirements.

Want Your St. Mary's County Event Featured?

Are you organizing a local festival, community celebration, seasonal market, fundraiser, workshop, or special event?

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

Southside Happenings welcomes submissions from local organizations, community groups, event organizers, and businesses interested in sharing their upcoming activities.

👉 Submit Your Event or Apply for a Community Spotlight

Help spread the word about the people, places, and events that make Southern Maryland special.

Stay Connected with Local Events

Looking for more things to do throughout the year?

Stay connected with Southside Happenings for updates and inspiration featuring:

✔ Local festivals — Seasonal celebrations, markets, and community traditions.

✔ Family-friendly activities — Crafts, outdoor experiences, and educational programs.

✔ Live music & entertainment — Performances, concerts, and special events.

✔ Community gatherings — Workshops, fundraisers, and local celebrations.

✔ Seasonal events across Southern Maryland — Halloween fun, holiday festivities, and year-round activities.

Whether you're planning a weekend adventure or simply exploring what's happening nearby, there's always something new to discover.

Discover More Things to Do in Southern Maryland

Your local adventures don't have to end after Halloween weekend!

Explore additional festivals, community events, historic attractions, and seasonal activities throughout St. Mary's, Calvert, and Charles counties.

👉 Discover More Things to Do in Southern Maryland

👉 Explore Southside Happenings: Southern Maryland Community Events & Local Activities

Looking for more inspiration? Explore practical home organization ideas, seasonal decorating projects, and home maintenance tips.

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

Have an upcoming event you'd like the community to know about?

👉 Submit Your Event for a Community Spotlight

Stay connected, support local happenings, and make the most of every Southern Maryland weekend!