Charles County Community Events | October 15–18, 2026

Charles County MD events this weekend bring an exciting mix of fall festivals, family-friendly entertainment, community celebrations, and outdoor adventures to Southern Maryland from October 15–18, 2026.

Whether you're searching for things to do near Waldorf, planning a Saturday outing in La Plata, exploring the history of Hughesville, or looking for activities around Indian Head, there's plenty to discover.

This week's highlights include the Humane Society of Charles County Fall Fest, Monster Truck Wars, a free Colonial Faire at historic Maxwell Hall, seasonal craft activities, live music, and more.

Living in Charles County means having access to a wonderful variety of community experiences throughout the year. October is an especially enjoyable time to explore local parks, historic landmarks, seasonal festivals, and events hosted by community organizations.

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

Featured Charles County MD Events This Weekend

1. Humane Society of Charles County Fall Fest

📅 Date: Saturday, October 17, 2026

📍 Location: Humane Society of Charles County, 71 Industrial Park Drive, Waldorf, MD 20602

🕒 Time: 12:00 PM–6:00 PM

Celebrate autumn with an afternoon of pumpkin painting, trunk-or-treating, games, food, local vendors, and a car meet. Visitors can also meet adoptable animals through the Humane Society.

General admission is $5 per person. This is a fun way to enjoy the fall season while supporting a local animal welfare organization.

👉 Event Link: https://humanesocietycc.org/news-events/event-calendar.html/event/2026/10/17/fall-fest/579812

2. La Plata Monster Truck Wars

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

📍 Location: Charles County Fairgrounds, 8440 Fairgrounds Road, La Plata, MD 20646

🕒 Time: Saturday at 12:00 PM and 6:00 PM; Sunday at 1:00 PM

Get ready for a high-energy weekend as Monster Truck Wars brings oversized trucks, exciting stunts, and motorsports entertainment to La Plata.

The event also advertises optional experiences such as a pre-show Pit Party, subject to ticket eligibility. Check the official ticketing information for admission, arrival recommendations, and add-on availability.

👉 Event Link: https://charlescountyfair.com/event/monster-truck-wars-2/

3. Colonial Faire and Fall Festival at Maxwell Hall

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

📍 Location: Maxwell Hall, 17388 Teagues Point Road, Hughesville, MD

🕒 Time: 10:00 AM–3:00 PM each day

Step into the history of Charles County at the Colonial Faire and Fall Festival hosted at historic Maxwell Hall.

This free community event includes seasonal activities, food, photo opportunities, and tours of the historic property. It's an opportunity to enjoy the autumn atmosphere while learning about the county's past.

For visitors looking for free fall festivals in Southern Maryland, Maxwell Hall deserves a place on the weekend calendar.

👉 Event Link: https://www.facebook.com/groups/1580628378848993/posts/4652005348377932/

4. Fall Baby Bazaar

📅 Date: Saturday, October 17, 2026

📍 Location: Somers Community Center, La Plata, MD — venue details should be reconfirmed

🕒 Time: 10:00 AM–2:00 PM

Browse a community shopping event featuring baby-related items and vendor offerings.

The Fall Baby Bazaar is an opportunity to explore local vendors and find practical items while participating in a Charles County community event. Check with Recreation, Parks & Tourism for visitor information and any admission or vendor requirements.

👉 Event Link: https://charlescountymd.myrec.com/info/activities/program_details.aspx?ProgramID=29916

5. Scarecrow Making & Pumpkin Carving

📅 Date: Saturday, October 17, 2026

📍 Location: Charles County, MD — exact venue requires confirmation

🕒 Time: 10:30 AM–12:00 PM

Bring some creativity to your weekend with a hands-on fall activity centered on scarecrow making and pumpkin carving.

This seasonal program offers a different way to celebrate October. Before attending, check the county recreation listing for the activity location, materials, age guidance, and registration details.

👉 Event Link: https://www.charlescountyparks.com/i-want-to/find-an-event/-curm-10/-cury-2026

Don't Miss This Week in Charles County

October is a great time to explore Charles County and experience everything that makes Southern Maryland's community calendar so varied.

From Waldorf's seasonal celebrations to La Plata's entertainment and shopping events, Hughesville's historic attractions, and outdoor activities near Indian Head, there are options for different interests and schedules.

Looking for family-friendly events, free fall festivals, live entertainment, or simply something new to try this weekend? Start with the featured events above and explore the additional activities below.

For more ideas throughout the year, visit Southside Happenings: Southern Maryland Community Events & Local Activities.

This community resource brings together events and activities across Charles, Calvert, and St. Mary's counties, making it easier to discover what's happening around Southern Maryland.

A helpful weekend planning tip: check whether events require advance registration, arrive early for popular activities, and confirm outdoor schedules when weather conditions are uncertain.

More Charles County Events This Week: October 15–18

Want even more things to do in Charles County, MD? These additional listings offer opportunities to enjoy books, music, outdoor recreation, learning, and community involvement.

Please note: Some listings have incomplete schedule or venue details. Check the linked calendar or organizer before traveling.

1. Citizens for CCPL Fall Book Bazaar

📅 Date: Friday–Sunday, October 16–18, 2026, within a longer October 16–24 sale

📍 Location: La Plata Branch, Charles County Public Library

🕒 Time: Saturday, October 17, 9:00 AM–4:30 PM; verify Friday and Sunday access and hours

Browse books, audiobooks, movies, CDs, and other finds while supporting the library community. Friday, October 16 is advertised as a members' early-access day.

👉 Event Link: https://www.facebook.com/ccplonline/posts/want-early-access-to-the-bazaarcitizens-members-get-the-red-carpet-treatment-wit/1543650344459974/

2. Who Done It? A Mystery Dinner Experience

📅 Date: Saturday, October 17, 2026

📍 Location: Venue to be confirmed with Charles County Recreation, Parks & Tourism

🕒 Time: 6:00 PM–8:00 PM

Enjoy an evening built around a mystery dinner experience. This county-listed event offers a change of pace from daytime fall festivals; confirm admission, age guidance, and registration before attending.

👉 Event Link: https://www.charlescountyparks.com/i-want-to/find-an-event/-curm-10/-cury-2026

3. Gentle Yoga at Smallwood State Park

📅 Date: Thursday, October 15, 2026

📍 Location: Smallwood State Park — Discovery Center Deck

🕒 Time: 9:15 am - 10:00 am

Ease into the weekend with a gentle yoga activity in a park setting. The program is free; standard park entry fees apply.

👉 Event Link: https://voiceofindianhead.org/event/gentle-yoga-at-smallwood-state-park-4/

4. Sparks at Smallwood

📅 Date: Friday, October 16, 2026

📍 Location: Smallwood State Park, Marbury, MD

🕒 Time: 3:15 pm - 4:00 pm 

The program is free; standard park entry fees apply. Children must be accompanied by an adult. Registration is recommended but not required. One registration per family or group is sufficient.

👉 Event Link: https://voiceofindianhead.org/event/sparks-at-smallwood-6/

5. Sunset Paddle at Mallows Bay

📅 Date: Friday, October 16, 2026 — listed locally; reconfirm with organizer

📍 Location: Mallows Bay area, Charles County, MD

🕒 Time: 3:30 PM

Enjoy an outdoor experience near the Potomac River and the historic Mallows Bay area. Reserve with Atlantic Kayak Company; confirm price and tour length when booking.

👉 Event Link: https://voiceofindianhead.org/event/sunset-paddle-at-mallows-bay/

6. Oak-tober Fun Day

📅 Date: Saturday, October 17, 2026 

📍 Location: Smallwood State Park, Marbury, MD

🕒 Time: 2:00 PM - 5:00PM

The program is free; standard park entry fees apply. Children must be accompanied by an adult. Registration is required.

👉 Event Link: https://voiceofindianhead.org/event/oak-tober-fun-day-at-smallwood-state-park/

7. Southern Maryland Bluegrass

📅 Date: Sunday, October 18, 2026

📍 Location: Calvert Elks Lodge

🕒 Time: 2:00 pm – 4:30 pm

Enjoy a music-focused Sunday with Southern Maryland Bluegrass, listed on the Charles County Chamber's October events calendar. Check the organizer's listing for performers, tickets, and venue details.

👉 Event Link: https://www.fredericknewspost.com/calendar/performing_arts_and_music/southern-maryland-bluegrass-concert/event_50c3074d-572c-469b-b5da-73ab254ce991.html

Want Your Charles County Event Featured?

Are you organizing a community festival, local performance, charity fundraiser, workshop, cultural celebration, or seasonal activity in Charles County?

Southside Happenings welcomes opportunities to spotlight local organizations, community events, and businesses contributing to Southern Maryland's event calendar.

Whether your event takes place in Waldorf, La Plata, Indian Head, Hughesville, Bryans Road, or another Charles County community, sharing it can help more local residents discover what's happening.

Submit your event or apply for a Community Spotlight feature.

Have an event coming up next month? Submit the details early so there's time to review the information for a future community roundup.

Stay Connected with Local Events in Southern Maryland

There's always something new to discover around Charles County and the surrounding Southern Maryland region.

Follow Southside Happenings for updates and ideas featuring:

• ✔ Local festivals and community celebrations

• ✔ Family-friendly activities and weekend outings

• ✔ Live music and entertainment

• ✔ Community gatherings and nonprofit events

• ✔ Seasonal events across Southern Maryland

Whether you're planning a quick afternoon outing or an entire weekend of activities, checking the local events calendar regularly can help you discover opportunities you might otherwise miss.

Living in Charles County also means being within reach of activities across Calvert and St. Mary's counties, expanding the possibilities for regional day trips and seasonal adventures.

Remember that event schedules, prices, registration requirements, and weather arrangements can change. Always check directly with organizers before traveling.

Discover More Things to Do in Southern Maryland

Looking for more than just this weekend's events?

Explore the Southern Maryland Things to Do & Community Guides for ideas about activities, seasonal outings, and community experiences throughout the region.

You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities to keep up with local happenings across Charles, Calvert, and St. Mary's counties.

For everyday inspiration beyond the events calendar, browse Home Tips, Home Hacks, Decorating & Maintenance Guides.

Make the most of October in Charles County! Explore a fall festival, enjoy live entertainment, discover a local organization, or try an activity you've never experienced before.

And if you're hosting an upcoming event, don't keep it a secret.

📣 Get featured in Southside Happenings through Community Spotlight and help the Southern Maryland community discover what's next.