Charles County events this weekend offer plenty of ways to get out and explore Southern Maryland from September 24–27, 2026, with live entertainment, local shopping, family activities, creative workshops, community recreation, and more.
If you’re searching for things to do near me in Charles County, start with this weekend guide. Waldorf has several activities on the calendar, while La Plata and other communities around the county add even more possibilities for your weekend plans.
Living in Charles County means having access to a mix of community events, parks and recreation, arts and entertainment, locally owned businesses, historic destinations, and seasonal activities. Whether you want a night out, an activity with the family, or somewhere new to explore, there’s something happening this weekend.
Here’s your Southside Happenings guide to Charles County for September 24–27.
⭐ Featured Charles County Events This Weekend
⭐ Dueling Through the Decades
📅 Date: Friday, September 25, 2026
📍 Location: Waldorf Town Center, Waldorf, MD
🕒 Time: 7:00 PM–11:00 PM
Travel through decades of music during this interactive live entertainment experience in Waldorf.
Skilled dueling performers take on crowd-favorite hits from different eras, creating an audience-driven evening where familiar songs and live performance come together.
If you’re searching for live entertainment or things to do in Waldorf this weekend, add this Friday-night event to your list.
👉 Event Link: https://www.explorecharlescounty.com/events?imgoing-event=dueling-through-the-decades-6a4eb3c8fb71de33c8748ca1
⭐ Pop-Up & Grow Vendor Market
📅 Date: Saturday, September 26 & Sunday, September 27, 2026
📍 Location: Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD
🕒 Time: 12:00 PM–6:00 PM
Spend part of the weekend browsing a variety of local vendors at the Pop-Up & Grow Vendor Market.
The market brings together artisans and small businesses offering items such as hand-poured soaps, baked goods, custom clothing, unique gifts, and other locally produced finds.
With two days to visit, it’s an easy activity to work into your weekend schedule.
👉 Event Link: https://www.explorecharlescounty.com/events?imgoing-event=pop-up-grow-vendor-market-698ad325fa4fd54b8cd7750e
⭐ Karaoke & Korean Fried Chicken Night
📅 Date: Thursday, September 24, 2026
📍 Location: Bonchon Waldorf, 3059 Waldorf Market Place, Waldorf, MD
🕒 Time: 7:00 PM–10:00 PM
Kick off the weekend a little early with karaoke and Korean fried chicken in Waldorf.
Kennections Entertainment hosts the karaoke while guests can enjoy Bonchon favorites and wing specials. Whether you plan to take the microphone or listen from your table, it offers a casual Thursday-night option.
👉 Event Link: https://www.facebook.com/share/19PJFpQN1e/
🎉 Don’t Miss This Week in Charles County
There’s plenty happening around Waldorf, La Plata, Indian Head, Hughesville, Port Tobacco, and surrounding Charles County communities.
Whether you’re looking for live entertainment, family activities, shopping, recreation, creative workshops, or community gatherings, Southside Happenings: Southern Maryland Community Events & Local Activities can help you discover more happening across Charles, St. Mary’s, and Calvert counties.
With event schedules and details subject to change, always check directly with the organizer for the latest information on registration, tickets, parking, age requirements, and weather-related updates before leaving home.
📅 More Charles County Events This Week
🎟 RPT Exploration Day
📅 Date: Saturday, September 26, 2026
📍 Location: Participating Charles County Recreation, Parks & Tourism facilities
🕒 Time: Activities scheduled throughout the day; times vary by location
Charles County Recreation, Parks & Tourism is hosting a countywide day of hands-on activities designed to introduce residents and visitors to local recreational opportunities.
Activities are scheduled at multiple locations and include everything from creative projects and demonstrations to aquatic activities, music, giveaways, and other opportunities to get moving and explore.
Because activities and times vary by facility, check the county schedule when planning your day.
👉 Event Link: https://www.charlescountyparks.com/Home/Components/Calendar/Event/17994/568
🎟 Fall Toddler Cookie + Mini Pumpkin Decorating Workshop
📅 Date: Saturday, September 26, 2026
📍 Location: The Baker’s Lab at 5-12 Dessert, 11850 Park Waldorf Lane, Suite 109, Waldorf, MD
🕒 Time: 11:00 AM–12:15 PM
Little bakers ages 2–4 and their grown-ups can enjoy a hands-on fall activity featuring cookie baking and mini pumpkin decorating.
The workshop gives young participants a chance to roll and cut cookie dough, decorate their creations, and enjoy a seasonal activity together.
Advance registration and admission fees apply.
🎟 Page Turners Virtual Book Discussion
📅 Date: Saturday, September 26, 2026
📍 Location: Virtual program presented through Charles County Public Library
🕒 Time: 10:00 AM–12:00 PM
Prefer something you can join from home? Page Turners hosts a virtual discussion of No Sense in Wishing by Lawrence Burney as part of One Maryland One Book.
Participants can share reactions, insights, and favorite parts of the book during the online discussion. Registration is required.
👉 Event Link: https://www.mdhumanities.org/event/page-turners-virtual-book-discussion/
🎟 Indoor Yard Sale
📅 Date: Saturday, September 26, 2026
📍 Location: Richard R. Clark Senior Center, 1210 Charles Street, La Plata, MD
🕒 Time: 8:00 AM–1:00 PM
Start Saturday with a little bargain hunting in La Plata.
The indoor sale is scheduled to feature multiple tables with items ranging from handmade crafts and clothing to vintage comic books and other finds. Proceeds from table rentals support the Senior Council and its activities.
👉 Event Link: https://somd.com/calendar/?day=26&month=9&view_day=on&year=2026
🎟 Ride for Vocations
📅 Date: Saturday, September 26, 2026
📍 Location: Sacred Heart Catholic Church, 205 St. Mary’s Avenue, La Plata, MD
🕒 Time: Check the organizer’s rider schedule for departure details
Cyclists can participate in the 11th Annual Ride for Vocations, beginning in La Plata and traveling through Southern Maryland.
Several distances are available, including approximately 21-, 50-, 70-, and 100-mile routes, making the ride accessible to cyclists looking for different levels of challenge.
Registration is required, and the event supports vocation-related programs.
👉 Event Link: https://dcpriest.org/event/2026-ride-for-vocations/
🎟 Fall Into Edible Artistry at The Baker’s Lab
📅 Date: Saturday, September 26, 2026
📍 Location: The Baker’s Lab at 5-12 Dessert, 11850 Park Waldorf Lane, Suite 109, Waldorf, MD
🕒 Time: 7:00 PM–9:30 PM
Turn dessert into a canvas during this creative Saturday-night workshop in Waldorf.
Participants will work with a prepared cake and cookies, using buttercream and royal icing to create their own edible designs while enjoying seasonal refreshments.
Advance tickets are required.
🎟 Quarter Auction Benefit
📅 Date: Saturday, September 26, 2026
📍 Location: Archbishop Neale School Gym, 104 Port Tobacco Road, La Plata, MD
🕒 Time: Doors open at 4:00 PM; auction begins at 5:00 PM
Spend Saturday evening at a community quarter auction benefiting the Catholic Daughters of the Americas.
Participants will have numerous opportunities to bid on prizes while supporting the organization. Both regular and all-in paddles are expected to be available.
👉 Event Link: https://somd.com/calendar/?day=26&month=9&view_day=on&year=2026
🎶 Family-Friendly, Local & Weekend Events in Charles County
Searching for family-friendly events in Charles County MD or activities to do near you this weekend?
RPT Exploration Day stands out for families because activities are planned at multiple county recreation facilities, including hands-on experiences and demonstrations.
For younger children, the Fall Toddler Cookie + Mini Pumpkin Decorating Workshop offers a structured seasonal activity in Waldorf.
If shopping local is more your style, the Pop-Up & Grow Vendor Market runs Saturday and Sunday, giving you two opportunities to browse local makers and vendors.
Adults looking for an evening activity have several choices too, including Dueling Through the Decades, karaoke in Waldorf, and the Fall Into Edible Artistry workshop.
And for readers looking for something in La Plata, Saturday includes the Indoor Yard Sale, Ride for Vocations, and Quarter Auction Benefit.
Always confirm the latest schedule, availability, registration requirements, and admission information directly with the event organizer before attending.
📣 Want Your Charles County Event Featured?
Hosting a festival, fundraiser, workshop, concert, market, community gathering, nonprofit activity, or other event in Charles County?
Submit it through the Southside Happenings Community Spotlight so your event can be considered for an upcoming weekly feature.
Local businesses and community organizations can also submit information for consideration in a future Community Spotlight.
📅 Stay Connected with Local Events
Check Southside Happenings each week to discover:
✔ Local festivals
✔ Family-friendly activities
✔ Live music & entertainment
✔ Community gatherings
✔ Seasonal events across Southern Maryland
Our weekly event guides make it easier to explore activities happening across Charles County, St. Mary’s County, and Calvert County.
Check back each week for another roundup of things to do around Southern Maryland.
🔎 Discover More Things to Do in Southern Maryland
Looking for even more things to do in Southern Maryland?
Explore our Things to Do in Southern Maryland collection for local guides, activities, attractions, seasonal ideas, and community happenings.
You can also visit Southside Happenings: Southern Maryland Community Events & Local Activities for our main community-events hub covering Charles County, St. Mary’s County, Calvert County, and the surrounding Southern Maryland region.
Looking for useful ideas for around the house? Browse Tips, Home Hacks, Home Decoration & Maintenance Tips for seasonal projects, decorating inspiration, maintenance ideas, and helpful household guides.
And if you know about an upcoming event, local business, nonprofit, or community organization that deserves some attention, submit it through our Community Spotlight for consideration in an upcoming feature.
📅 Follow Southside Happenings for weekly updates, explore more Southern Maryland guides, and submit your event so we can keep the community calendar growing.
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