Charles County Community Events | September 18–20, 2026

Charles County events are filling the calendar September 18–20, 2026, with the county fair, local markets, community celebrations, family activities, food, entertainment, and plenty of reasons to get out and explore Southern Maryland.

If you’re searching for things to do in Charles County this weekend, this roundup makes it easier to see what’s happening around La Plata, Waldorf, Port Tobacco, and nearby communities.

Living in Charles County offers plenty of opportunities to enjoy both established community traditions and smaller local events. This weekend’s centerpiece is the 102nd Charles County Fair, but you’ll also find markets, youth activities, community celebrations, food events, and more.

Event schedules can change, so always check the organizer’s event page before heading out, particularly for tickets, registration requirements, weather updates, and last-minute schedule changes.

⭐ Featured Charles County Events This Weekend

⭐ 102nd Annual Charles County Fair

📅 Date: Friday–Sunday, September 18–20, 2026
📍 Location: Charles County Fairgrounds, 8440 Fairgrounds Rd, La Plata, MD 20646
🕒 Time: Hours vary by day

One of Charles County’s biggest annual traditions is back. The 102nd Annual Charles County Fair actually begins Thursday, September 17, and continues through Sunday, September 20, so it will be in full swing throughout this weekend roundup.

The fair celebrates the county’s agricultural heritage with livestock and agricultural exhibits, 4-H activities, demonstrations, entertainment, food, games, and carnival rides. The fair also advertises four stages featuring shows, music, games, and performers.

Friday and Saturday gates open at 8:00 AM, while Sunday gates open at 9:00 AM. The midway runs from 10:00 AM–10:00 PM Friday and Saturday and 11:00 AM–7:00 PM Sunday.

Friday is also School Children’s Day, with school children admitted free from 9:00 AM–5:00 PM.

👉 102nd Annual Charles County Fair Details

⭐ Pop-Up & Grow Vendor Market

📅 Date: Saturday, September 19, 2026
📍 Location: Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD 20601
🕒 Time: 10:00 AM–4:00 PM

Spend part of Saturday browsing a local vendor market in Waldorf. The Pop-Up & Grow Vendor Market brings together small businesses and creators, offering another way to spend the weekend while discovering locally available products, handmade goods, fashion, food, and more.

It’s an easy option to pair with other Waldorf activities on this weekend’s calendar.

👉 Pop-Up & Grow Vendor Market Details

🎉 Don’t Miss This Week in Charles County

From the fairgrounds in La Plata to community activities in Waldorf, Charles County events this weekend offer several different ways to experience the area.

You can spend a full day at the county fair, browse a local market, attend a community gala, take the kids to a pirate-themed pool party, or build your own itinerary around activities in different parts of the county.

For even more ideas, bookmark Southside Happenings: Southern Maryland Community Events & Local Activities. It’s your hub for community happenings and local activities across Charles, Calvert, and St. Mary’s counties.

📅 More Charles County Events This Weekend

🎟 Divine By Design Mentoring Annual Royal Gala

📅 Date: Friday, September 18, 2026
📍 Location: Old Waldorf School, 3074 Crain Hwy, Waldorf, MD 20601
🕒 Time: 6:30 PM–10:00 PM

Dress up for an evening celebrating community impact and youth mentorship. Divine By Design Mentoring’s annual event brings supporters together for an evening centered on the organization and its work.

👉 Divine By Design Royal Ball Details

🎟 Captain Ethan’s Pirate Party

📅 Date: Saturday, September 19, 2026
📍 Location: North Point High School Indoor Pool, 2500 Davis Rd, Waldorf, MD 20601
🕒 Time: 1:00 PM–3:00 PM

Ahoy, Waldorf! Captain Ethan’s Pirate Party offers a pirate-themed afternoon at North Point Pool with a treasure hunt, crafts, games, and opportunities for photos with pirate characters.

Charles County Recreation’s current calendar confirms the September 19 event from 1:00–3:00 PM, so note that updated time when planning your Saturday.

👉 Captain Ethan’s Pirate Party Details

🎟 Butler’s Farm 4th Annual Crab Feast

📅 Date: Saturday, September 19, 2026
📍 Location: Butler’s Farm, 3835 Gardiner Rd, Waldorf, MD 20601
🕒 Time: 1:00 PM–5:00 PM

Maryland crabs and a September weekend are a natural combination. Butler’s Farm’s annual Crab Feast offers an afternoon centered around steamed blue crabs, food, music, and time on the farm.

Check the organizer’s ticket listing for current admission details and availability before attending.

👉 Butler’s Farm 4th Annual Crab Feast

🎟 Magnolia Market at La Plata

📅 Date: Saturday, September 19, 2026
📍 Location: La Plata, MD 20646
🕒 Time: 9:00 AM–2:00 PM

Make time for some local shopping before or after visiting the fair. Magnolia Market offers another Saturday stop in La Plata, with vendors and an outdoor-market atmosphere.

Because both Magnolia Market and the Charles County Fair are in the La Plata area, visitors interested in both can check travel times and event schedules to build a Saturday itinerary.

👉 Magnolia Market Event Listing

👨‍👩‍👧‍👦 Family-Friendly Things to Do in Charles County

Searching for family-friendly things to do in Charles County this weekend? The county fair offers one of the broadest selections.

The fair’s official information describes carnival rides for different ages, including a separate kiddie midway. Saturday’s schedule includes activities such as a baby show, 4-H robotics/STEM demonstration, rabbit jumping, a children’s pie-eating contest, livestock exhibits, and lawnmower races. Sunday includes sheep and goat shows, miniature horse pulls, and other fair activities.

Captain Ethan’s Pirate Party is another Saturday option, particularly for kids who enjoy swimming, crafts, treasure hunts, and pirate-themed activities.

Remember that individual activities can have their own age, registration, admission, or supervision requirements. Checking the official listing before leaving home is the easiest way to avoid surprises.

📍 Things to Do Near La Plata, Waldorf & Port Tobacco

If your weekend search begins with “events near me,” narrowing the calendar by town can make planning easier.

La Plata is the place to be for the 102nd Annual Charles County Fair, with activities continuing Friday, Saturday, and Sunday. The fairgrounds are located about three miles south of La Plata, and the fair provides free general parking as well as satellite parking at the Charles County Courthouse and Government Building with shuttle service.

Waldorf has several Saturday choices, including the Pop-Up & Grow Vendor Market, Captain Ethan’s Pirate Party, and Butler’s Farm Crab Feast. Friday evening also brings the Divine By Design Mentoring event.

If you’re exploring Port Tobacco or another part of Charles County, it’s worth checking the county and tourism calendars before heading out. I have intentionally left the originally supplied Port Tobacco Marina music event out of this edition because the provided link points to an unrelated event, and I don’t want to send readers to an incorrect source.

That approach keeps Southside Happenings useful: when details can’t be adequately verified, it’s better to direct readers toward reliable calendars than publish questionable event information.

📣 Want Your Charles County Event Featured?

Have an upcoming Charles County festival, fundraiser, performance, workshop, market, community gathering, or seasonal event?

Submit it for consideration through the Southside Happenings Community Spotlight.

Businesses, nonprofits, organizations, and event organizers throughout Southern Maryland can use the Community Spotlight to share upcoming happenings that local readers may want to discover.

📅 Stay Connected with Local Events

Southside Happenings makes it easier to keep an eye on what’s happening around Charles County and throughout Southern Maryland, including:

• ✔ Local festivals
• ✔ Family-friendly activities
• ✔ Live music & entertainment
• ✔ Community gatherings
• ✔ Seasonal events across Southern Maryland

Schedules, ticket availability, admission policies, and weather plans can change. Always confirm the latest details with the event organizer before attending.

🔎 Discover More Things to Do in Southern Maryland

The weekend doesn’t have to end with this roundup. Visit Discover More Things to Do in Southern Maryland for additional community guides, destinations, activities, and local ideas.

Bookmark Southside Happenings: Southern Maryland Community Events & Local Activities for weekly happenings across Charles, Calvert, and St. Mary’s counties.

You can also explore Tips, Home Hacks, Home Decoration and Maintenance Tips for helpful ideas beyond the community calendar.

Know about something coming up? Use the Community Spotlight submission section to tell us about your business, organization, or event—and follow Southside Happenings for another roundup of Southern Maryland events next week.