Charles County Events This Weekend | October 29 – November 1, 2026

Charles County events this weekend are bringing Halloween excitement, spooky adventures, community celebrations, and plenty of opportunities to enjoy Southern Maryland!

Whether you're searching for Halloween events near Waldorf, free trunk-or-treat activities, or something fun to do in La Plata and Indian Head, this week's Southside Happenings roundup has you covered.

From the thrills of Cornstalkers Trail of Terror to family-friendly festivities and unique library activities, October 29 through November 1 offers a great mix of seasonal experiences.

Living in Charles County means having access to a variety of community gatherings, parks, cultural programs, and seasonal traditions throughout the year. Halloween weekend is a wonderful opportunity to explore what local organizers have planned.

Grab your calendar, check the event details, and get ready for a memorable weekend!

Featured Halloween Events in Charles County This Weekend

Cornstalkers Trail of Terror  

📅 Date: Friday, October 30 – Sunday, November 1, 2026

📍 Location: 11765 St. Linus Drive, Waldorf, MD 20602

🕒 Time: October 30 tickets begin at 7:30 PM

Looking for a serious Halloween scare? Cornstalkers Trail of Terror returns for its 11th season with four themed haunted attractions, including Resurrection 666, Graves Coven Farmhouse, The Barnyard, and Carnies of the Corn.

Visitors can also explore midway entertainment, photo opportunities, and refreshments, with some activities available only on select nights. November 1 features a special Lights Out experience where guests can bring flashlights.

👉 Event Link: https://app.hauntpay.com/events/cornstalkers-11

Waldorf Ford Community Trunk-or-Treat  

📅 Date: Saturday, October 31, 2026

📍 Location: Waldorf Ford, 2440 Crain Highway, Waldorf, MD 20601

🕒 Time: 5:00 PM – 7:00 PM

Celebrate Halloween with decorated vehicles, costumes, candy, games, a moonbounce, and a food truck at Waldorf Ford!

This community celebration is a fun option for visitors seeking a festive Halloween atmosphere without the scares of a haunted attraction. Admission is listed as free, but organizers requested RSVPs by October 26, so check availability before attending.

👉 Event Link: https://www.eventbrite.com/e/waldorf-ford-trunk-or-treat-tickets-2002646421356

Trinity Memorial Gardens Free Trunk-or-Treat

📅 Date: Saturday, October 31, 2026

📍 Location: 3221 Mattawoman Beantown Road, Waldorf, MD 20601

🕒 Time: 3:00 PM – 5:00 PM

Trinity Memorial Gardens is hosting a free Halloween trunk-or-treat with decorated vehicles and candy.

Sponsored by American Legion Auxiliary Edwin Adams Post 293, the event also provides an opportunity to support the Children's Health Fund through voluntary donations. Organizers specify that activities will take place on the grassy center median of the property.

👉 Event Link: https://business.charlescountychamber.org/events/details/free-trunk-or-treat-7742?calendarMonth=2026-10-01

Library After Hours: Paranormal Night

📅 Date: Friday, October 30, 2026

📍 Location: Waldorf West Library, Waldorf, MD

🕒 Time: 6:00 PM – 8:00 PM

The Charles County Public Library is getting spooky with an after-hours evening of paranormal-themed entertainment.

Expect ghost-hunting activities, horror trivia, Jackbox games, and classic scary movies. This event is intended for teens and adults, making it an appealing alternative to traditional Halloween celebrations. Check the registration page for available spaces.

👉 Event Link: https://ccplonline.libnet.info/event/17195972

Don't Miss This Week in Charles County

Halloween weekend is a fantastic time to discover the many experiences happening throughout Charles County!

Whether you're exploring Waldorf's haunted attractions, attending a seasonal event in La Plata, or visiting a community celebration in Indian Head, there are opportunities to enjoy the holiday in different ways.

Not every great local experience needs to be a major festival. Sometimes an afternoon at a neighborhood gathering, a library program, or a community food truck event becomes the highlight of the weekend.

That's why we created Southside Happenings: Southern Maryland Community Events & Local Activities — a place to discover upcoming events, activities, and community happenings throughout Charles, Calvert, and St. Mary's counties.

Bookmark the page and check back for new weekly roundups, seasonal celebrations, and community discoveries.

More Charles County Events This Week

Looking for additional things to do in Charles County this weekend? Here are more activities to consider, including free gatherings, creative programs, and outdoor experiences.

Spooky Story Trail Walk

📅 Date: Thursday, October 29, 2026

📍 Location: Pisgah Park, 6645 Mason Springs Road, La Plata, MD 20646

🕒 Time: 5:30 PM – 6:30 PM

Enjoy a candlelit story trail featuring a delightfully spooky tale and a complimentary warm beverage. The library describes this all-ages activity as festive rather than frightening; it may be canceled for inclement weather.

👉 Event Link: https://ccplonline.libnet.info/event/17063404

Food Truck Friday at Village Green

📅 Date: Friday, October 30, 2026 

📍 Location: Village Green Park, 100 Walter Thomas Road, Indian Head, MD 20640

🕒 Time: 3:00 PM – 7:00 PM

Stop by Indian Head's Village Green for Food Truck Friday! Admission is free, making this a convenient opportunity to enjoy local food vendors and a casual community outing. Food purchases are separate.

👉 Event Link: https://voiceofindianhead.org/event/food-truck-friday-at-village-green/

Charles County Food Truck Week

📅 Date: Thursday, October 29 – Friday, October 30, 2026

📍 Location: La Plata and participating Charles County locations

🕒 Time: 3:00 PM – 7:00 PM

Food Truck Week brings another option for discovering mobile food vendors around Charles County. Visit Maryland lists the celebration through October 30; check the event calendar and participating vendors for specific locations and service hours.

👉 Event Link: https://www.visitmaryland.org/things-to-do/events-fairs-festivals?f%5B0%5D=eventregions%3A1536

Illumination Lab

📅 Date: Thursday, October 29, 2026

📍 Location: Potomac Branch, Charles County Public Library

🕒 Time: 6:00 PM – 7:00 PM

Explore two glow-in-the-dark activities at this creative library program for tweens and teens. It's a fun seasonal choice for anyone interested in hands-on science and art.

👉 Event Link: https://ccplonline.libnet.info/events?a=Children%2CTweens&n=3&r=months

Mahjong Lounge

📅 Date: Friday, October 30, 2026

📍 Location: Waldorf West Library, Waldorf, MD

🕒 Time: 2:00 PM – 3:30 PM

Take a break from Halloween festivities and try a game of Mahjong! The library welcomes participants of all ages to learn and play.

👉 Event Link: https://ccplonline.libnet.info/events?n=3&term=Mahjong+Lounge&r=months

Trunk-or-Treat at Smallwood State Park

📅 Date: Friday, October 30, 2026

📍 Location: Smallwood State Park, Charles County, MD

🕒 Time: 5:00 PM – 6:00 PM

Celebrate Halloween outdoors with a trunk-or-treat program at Smallwood State Park. Registration is required; the program is listed as free, although standard park entry fees apply.

👉 Event Link: https://voiceofindianhead.org/event/trunk-or-treat-at-smallwood-state-park/

MCAC 7th Annual Run for the Arts — 5K Fun Run & Walk 

📅 Date: Saturday, October 31, 2026

📍 Location: Smallwood State Park, Charles County, MD

🕒 Time: 10:00 AM – 12:30 PM

Start Halloween with a little movement! This Halloween-themed 5K fun run and walk supports the visual arts in Southern Maryland. The community calendar lists a $35 participation fee.

👉 Event Link: https://voiceofindianhead.org/event/mcac-7th-annual-run-for-the-arts-5k-fun-run-walk/

Indian Head Village Green Trunk-or-Treat 

📅 Date: Saturday, October 31, 2026

📍 Location: Village Green Park, 100 Walter Thomas Road, Indian Head, MD 20640

🕒 Time: 6:00 PM – 8:00 PM

Head to the Village Green for a Halloween celebration featuring candy and music. This is another option for those searching for community trunk-or-treat events outside Waldorf.

👉 Event Link: https://voiceofindianhead.org/event/trunk-or-treat-at-village-green-park/

Family-Friendly Halloween Activities Near Waldorf and La Plata

With so many Charles County Halloween events happening this weekend, choosing the right activity can be part of the fun!

For visitors who prefer a lighter Halloween experience, the trunk-or-treat celebrations at Waldorf Ford, Trinity Memorial Gardens, and Indian Head Village Green offer festive community settings.

The Spooky Story Trail Walk at Pisgah Park is another option, combining outdoor recreation, reading, and seasonal atmosphere.

For those seeking a more intense Halloween adventure, Cornstalkers Trail of Terror offers immersive scares and theatrical haunted attractions. Review the organizer's age guidance and attraction descriptions before purchasing tickets.

A few simple planning tips can help make the weekend more enjoyable:

• Check admission details. Some activities are free, while others require tickets, registration, or park entry fees.

• Confirm event times. Halloween schedules may change because of weather or organizer updates.

• Plan transportation. Popular evening events may attract additional traffic and require extra parking time.

• Dress for the weather. Late-October outdoor activities can become chilly after sunset.

• Bring essentials. Comfortable shoes, a flashlight when appropriate, and a charged phone can be useful.

If you're planning multiple events on Halloween night, allow enough time between destinations. Waldorf, La Plata, and Indian Head each offer different experiences, and a little preparation can help you enjoy them without rushing.

Want Your Charles County Event Featured?

Are you organizing a community festival, charity event, workshop, live performance, holiday celebration, or local business activity?

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

Southside Happenings welcomes event and community spotlight submissions from Charles County and the surrounding region.

Whether you're a local organization, small business, nonprofit, or event coordinator, sharing your event can help residents and visitors learn about upcoming opportunities to connect with the community.

Submit your event or request a Community Spotlight feature:

👉 Get Featured on Southside Happenings

Don't wait until the week of your event. Submit upcoming activities early so there's time for them to be considered for future community roundups.

Stay Connected with Local Events

Halloween may be one of the most exciting weekends of the fall, but Charles County has community activities happening throughout the year.

Southside Happenings helps readers discover:

• ✔ Local festivals

• ✔ Family-friendly activities

• ✔ Live music & entertainment

• ✔ Community gatherings

• ✔ Seasonal events across Southern Maryland

From outdoor recreation and cultural programs to holiday celebrations and creative workshops, there are always new experiences worth exploring.

Follow the weekly updates, share upcoming events with others, and check the organizer's official website before heading out.

Discover More Things to Do in Southern Maryland

Looking for more events beyond Halloween weekend?

Explore our Southern Maryland Things to Do & Community Activities Blog for more inspiration, local happenings, and seasonal guides.

You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities to discover community events across Charles, Calvert, and St. Mary's counties.

And when you're ready for inspiration at home, explore our Home Tips, Decorating Ideas & Maintenance Guides for seasonal decorating, everyday home hacks, and helpful maintenance ideas.

Have an upcoming event that deserves attention? Submit it to our Community Spotlight and help others discover what's happening locally.

Make the most of October 29 – November 1, 2026, and keep exploring Charles County and Southern Maryland — one community event at a time!

Event details were checked against publicly available listings before publication. Dates, availability, fees, and activities may change. Always confirm with the event organizer before attending.