Saturday, October 3 | 12:00 PM - 7:00 PM 📍 100 Walter Thomas Lane, Indian Head 💵 See link for pricing

🔗 Get event details

This is the one to build your Saturday around. Indian Head turns its waterfront into a full day of live jazz, local wine vendors, and food for the Jazz & Wine Festival, running noon to 7pm right on the water. It's the kind of event that makes you remember why you live somewhere with a river view instead of a parking lot.

Bring a lawn chair or blanket, because you'll want to settle in rather than stand around. Pricing isn't posted publicly yet, so check the link below before you head out, but expect it to run like most SMECO-hosted festivals: reasonable and family-friendly.

Heads up if you've got other Saturday plans in Indian Head or along Route 210, this one will pull a crowd and parking near the waterfront will fill up fast. Get there early if you want a good spot for the music.

🔗 Full details and schedule here

Your county is doing the absolute most this week, mostly on one single Saturday.

Saturday, October 3 | 9:00 AM 📍 10430 Audie Lane, La Plata 💵 Free

🔗 Get details

Finally, an official excuse to clean out the garage. Charles County residents can drop off paint, chemicals, batteries, and other stuff you're definitely not supposed to put in the regular trash, completely free. Load up the car and make a morning of it before your other Saturday plans kick in.

Saturday, October 3 | 10:00 AM 📍 Regency Furniture Stadium, 11765 Saint Linus Drive, Waldorf 💵 See link

🔗 Get tickets

Classic cars, motorcycles, and trucks fill the Regency Furniture Stadium lot for a fundraiser supporting domestic violence survivors and awareness work in the community. Five years running now, and it's grown into a legitimately good car show with a cause behind it worth showing up for.

Saturday, October 3 | 10:00 AM 📍 3235 Leonardtown Road, Waldorf 💵 $23.00

🔗 Event details

A low-key neighborhood fall festival with games, food, and seasonal fun. Nothing flashy, just a nice community gathering to kick off October if you want something easy and close to home before the bigger Saturday events pull you elsewhere.

Friday, October 2 | 7:00 PM - 11:00 PM 📍 Waldorf Jaycees, 3090 Crain Highway, Waldorf 💵 See link

🔗 Get tickets

Relive your high school glory days, minus the awkward chaperones. This grown-up prom night at the Waldorf Jaycees has a full dance floor, dressed-up crowd, and all the nostalgia you can handle. Dust off whatever's fanciest in your closet.

Saturday, October 3 | 7:00 PM 📍 Waldorf Jaycees, 3090 Crain Highway, Waldorf 💵 $103

🔗 Get tickets

An elegant masked evening honoring cancer survivors, with proceeds going to local cancer organizations and community outreach. Six years in and it's become one of those events that quietly does a lot of good for people right here in the county.

Saturday, October 3 | 12:00 PM 📍 The Space by LBI Collective, 2901 Festival Way, Waldorf 💵 Free

🔗 Event details

A town hall aimed at getting young Charles County residents plugged into local civic life and the voting process. Community conversation, resources, and a good reminder that local government is more reachable than people think.

Friday, October 2 | 8:00 AM 📍 Swan Point Yacht & Country Club, 11550 Swan Point Blvd, Issue 💵 See link

🔗 Register here

A benefit tournament supporting the Maryland Veterans Museum at Patriot Park, now in its 12th year. If you golf and you're looking for a Friday that actually does some good, grab a foursome and head to Swan Point.

Saturday, October 3 | 11:30 AM - 3:00 PM 📍 4375 Port Tobacco Road, Nanjemoy 💵 Free

🔗 Event details

This is the quiet gem of the weekend. A free, family-friendly day out in Nanjemoy with a parade, a car show, local art and heritage displays, games, and food. Twenty-four years running and still one of the most genuinely community-built events on the county calendar. Worth the drive out.

Sunday, October 4 | 10:00 AM - 2:00 PM 📍 Charles County Fairgrounds and Event Center, 8440 Fairground Road, La Plata 💵 See link

🔗 Event details

Southern Maryland's first rockabilly-style car, truck, and bike show rolls into the fairgrounds with live music, vendors, a pinup competition, and trophies for the top 20. No pre-registration needed, just show up. A fun, retro way to close out the weekend.

Gospel, jazz, hand dancing, and a Jersey club night, this week has range.

Friday, October 2 | 7:00 PM - 8:00 PM 📍 Potomac Branch Library, 3225 Rose Hill Road, Waldorf 💵 Free

🔗 Event details

The library turns into a music venue for the evening as the Carly Harvey Trio takes over Potomac Branch after hours. Free, relaxed, and honestly one of the more surprising date-night options on this list.

Tuesday, September 29 | 6:00 PM 📍 The Square at St. Charles Towne Center, 11110 Mall Circle #Level 2, Waldorf 💵 See link

🔗 Get tickets

An evening of gospel music and worship at The Square, the community event space tucked inside St. Charles Towne Center. A good midweek reset if you need one.

Friday, October 2 | 6:00 PM 📍 Graces Event Center, 4045 Renner Road, Waldorf 💵 $12

🔗 Get tickets

Two different promoters have this same night listed separately, but it's one event: good food and hand dancing at Graces Event Center to kick off the weekend. Come hungry and ready to move.

Saturday, October 3 | 8:00 PM 📍 Shark Bar and Seafood House, 2056 Crain Highway, Waldorf 💵 28

🔗 Get tickets

Old-school visuals meet next-level sound at this late-night showcase at Shark Bar. If you want your Saturday to end on a high note, this is it.

Sunday, October 4 | 3:00 PM 📍 Graces Event Center, 4045 Renner Road, Waldorf 💵 $23

🔗 Get tickets

A monthly gospel karaoke night paired with a full buffet. Come for the food, stay to belt out a hymn or two with the room. A sweet, low-key way to close the week.

Make something, try something, or catch the last weekend of something great.

Through Sunday, October 4 | Times vary, check ptplayers.com 📍 Port Tobacco Players Theatre, 508 Charles Street, La Plata 💵 $16

🔗 Get tickets

Last call. Port Tobacco Players closes out this Southern comedy-drama about six women and their friendship inside a small-town beauty salon this weekend. If it's been on your list all month, this is the final chance to catch it before it's gone.

Saturday, October 3 | 10:30 AM - 12:30 PM 📍 AR Workshop, La Plata 💵 See link

🔗 Book here

Build your own chunky-knit pumpkin to take home, no knitting experience required. A cozy, hands-on way to start your fall decorating without lifting a needle more than once.

Thursday, October 1 | 6:00 PM 📍 Paint N Sip, 11110 Mall Circle, Waldorf 💵 See link

🔗 Get tickets

Exactly what it sounds like, dancing optional and painting guaranteed. A high-energy way to spend a Thursday night at Paint N Sip in St. Charles Towne Center.

Saturday, October 3 | 2:00 PM 📍 Paint N Sip, 11110 Mall Circle, Waldorf 💵 $25

🔗 Get tickets

A "build your own crown" painting event made for young girls to feel a little celebrated. Sweet, simple, and a nice one to bring the kids to on a Saturday.

Friday, October 2 | 5:00 PM 📍 Joyful Studio, 115A La Grange Avenue Suite 103, La Plata 💵 See link

🔗 Get tickets

Bring a little one for a cozy fall-themed ceramic painting session together at Joyful Studio. A nice one-on-one activity before the weekend gets busy.

Tuesday, September 29 | 5:00 PM 📍 Idlewilde Farm, 8710 Idlewilde Farm Place, La Plata 💵 $50

🔗 Get tickets

A cozy introduction to knitting and crochet at a working farm. Learn the basics and start your fiber-arts journey somewhere prettier than your living room.

Monday, September 28 | 6:00 PM - 7:00 PM 📍 P.D. Brown Memorial Branch Library, 5 Garrett Avenue, La Plata 💵 Free, wait list

🔗 Join the wait list

Make a cute ghost decoration for your home just in time for spooky season. Teens and adults welcome, though the event was showing full at last check, so the wait list is your best bet.

Monday, September 28 | 6:00 PM - 7:30 PM 📍 Potomac Branch Library (also virtual), Indian Head 💵 Free

🔗 Register here

An evening of crocheting, knitting, and socializing for beginners and pros alike, in person or online. Bring your project or just come learn something new.

Saturday, October 3 | 11:00 AM - 12:00 PM 📍 Waldorf West Branch Library, 10405 O'Donnell Place, Waldorf 💵 Free

🔗 Register here

In honor of LGBTQ+ History Month, learn to make a pride flag bracelet while exploring the history behind the symbols. Registration required, and it's a nice one to bring a teen to.

Two pumpkin patches, a monster-movie night, and a library full of bats and dogs.

Sat-Sun, Sept 29-30 & Oct 3-4 | 10:00 AM - 5:00 PM 📍 Shlagel Farms, 12850 Shlagel Road, Waldorf 💵 Admission fee, pumpkins by the pound

🔗 Plan your visit

A classic Southern Maryland fall tradition: petting zoo, straw maze, corn box, and a hayride out to the pumpkin patch. Open both weekends in this window, so there's no excuse to miss it this year.

Saturday, October 3 | 10:00 AM - 4:00 PM 📍 Zekiah Farms, 5235 Bryantown Road, Waldorf 💵 $40-50

🔗 Get tickets

The other big pumpkin-patch option this weekend: local artisans, food, crafts, and Zekiah's popular pumpkin-picking experience. Pricier than Shlagel's but a different vibe, more of a festival marketplace than a farm visit.

Saturday, October 3 | Evening, check link for exact time 📍 My Gym Waldorf, 1148 Smallwood Drive W, Waldorf 💵$35-$44.99 depending on package

🔗 Register Here

Drop the kids off for a Halloween-themed night of monster-movie fun, crafts, games, and refreshments while you get an actual night off. Ages 3.5-9.

Thursday, October 1 | 10:45 AM - 11:45 AM 📍 La Plata Branch Library, 2 Garrett Avenue, La Plata 💵 Free

🔗 Event details

Friendly, well-trained dogs visit the library for a feel-good meet-and-greet. A guaranteed hit with kids of every age, and honestly with most of the adults too.

Saturday, October 3 | 2:00 PM - 3:00 PM 📍 La Plata Branch Library, 2 Garrett Avenue, La Plata 💵 Free

🔗 Event details

A kid-friendly, myth-busting look at bats just in time for spooky season, led by Farmer Sharon. Perfect timing with everything else going on that Saturday if you need a mid-afternoon break.

Thursday, October 1 | 6:00 PM - 7:00 PM 📍 Waldorf West Branch Library, 10405 O'Donnell Place, Waldorf 💵 Free

🔗 Register here

Tweens and teens get hands-on with 3D printing in this bi-monthly STEM club session. Free, and a great after-school option for the science-curious kid in your house.

Your library is doing more than you think this week. A lot more.

Tuesday, September 29 | 6:00 PM 📍 Waldorf West Branch Library, 10405 O'Donnell Place, Waldorf 💵 Free

🔗 Reserve your spot

A free workshop on protecting your assets, avoiding common legal pitfalls in probate, and putting a real plan in place for your family's future. Not the most exciting Tuesday night out, but genuinely useful, and free.

Thursday, October 1 | 7:00 PM - 8:00 PM 📍 Virtual, CCPL Author Speaker Series 💵 Free, registration required

🔗 Register here

The dystopian-fiction icon behind Divergent joins CCPL's virtual author series to talk courage, choice, and what comes next. Join from home, free with registration.

Tuesday, September 29 | 6:00 PM - 7:00 PM 📍 Potomac Branch Library, Indian Head 💵 Free

🔗 Event details

Teens learn how to get better results from AI tools, spot weak or misleading answers, and fact-check what they get back against trusted sources. A genuinely useful skill for 2026.

Friday, October 2 | 2:00 PM - 3:00 PM 📍 Waldorf West Branch Library, 10405 O'Donnell Place, Waldorf 💵 Free

🔗 Event details

Games, prizes, and good company at the library's monthly bingo social. All ages welcome, free, and a nice easy way to spend a Friday afternoon.

Your county is making decisions this week. Here's where to show up.

Monday, September 28 | 6:00 PM 📍 Charles County Government Building, 200 Baltimore Street, La Plata 💵 Free

🔗 Meeting details

The county's Ethics Commission holds its regular monthly meeting. Open to the public as always.

Tuesday, September 29 | Time not posted, recent meetings have started at 9:00 AM, confirm before heading out 📍 Charles County Government Building, 200 Baltimore Street, La Plata 💵 Free

🔗 Meeting details

The Commissioners hold their regular biweekly public session, with time built in for public comment. Worth checking the county calendar closer to the date since the start time wasn't posted this week.

Tuesday, September 29 | Time and topic not posted, see county calendar 📍 Charles County Government Building, 200 Baltimore Street, La Plata 💵 Free

🔗 Meeting details

A public hearing is scheduled alongside Tuesday's Commissioners meeting. The county hadn't posted the specific topic as of this newsletter going out, so check the calendar closer to the date if this affects you directly.

Thursday, October 1 | 6:15 PM 📍 Virtual meeting 💵 Free

🔗 Meeting details

The county board that hears HOA-related disputes meets virtually this week. Relevant if you've got a dispute in the pipeline or just want to see how it works.

How to Watch: Can't make it in person? Charles County Government TV (CCGTV) streams most public meetings live and archives them afterward. Check charlescountymd.gov for the viewing schedule.

Support the people who make this place feel like home.

Saturday, October 3 | 10:00 AM - 6:00 PM 📍 The Shops at Waldorf Center, 2925 Festival Way, Waldorf 💵 Free

🔗 Event details

Dozens of local small-business vendors set up shop for the weekend at The Shops at Waldorf Center. Handmade goods, local makers, and a genuinely good excuse to skip the big-box store this Saturday.

Saturday, October 3 | 9:00 AM - 2:00 PM 📍 209 Washington Avenue, La Plata 💵 Free

🔗 Market details

The town's farmers market runs every Saturday through November 28, produce, meats, eggs, honey, and everything else Southern Maryland growers bring in. Get there early for the best pick.

Saturday, October 3 | 10:00 AM - 2:00 PM, confirm still running before you go 📍 The Shops at Waldorf Center, 2935 Crain Highway, Waldorf 💵 Free

🔗 Facebook page, see link for updates

A Saturday staple at The Shops at Waldorf Center. Quick note: a few posts this season mentioned a "last market of the season" without a specific date, so it's worth a glance at their Facebook page before you head over.

Thursday, October 1 | 11:00 AM 📍 40 Drury Drive, La Plata 💵 Free

🔗 Event details

Come celebrate the ribbon-cutting for this new salon and spa in La Plata. Always worth showing up for a new local business's opening day.

Saturday, October 3 | 1:00 PM 📍 11637 Terrace Drive, Waldorf 💵 Free

🔗 Event details

A new wellness and aesthetics business opens its doors in Waldorf. Stop by and give the new neighbors a proper welcome.

Sunday, October 4 | 1:00 PM 📍 GD Event Space (Glam Dolls), 1302 Smallwood Drive West, Waldorf 💵 See link

🔗 Get tickets

A community closet-cleanout and swap-slash-pop-up-shop at Glam Dolls. Clear out what you're not wearing and find someone else's treasure while you're at it.

Got a favorite spot that deserves more love? A new restaurant, boutique, artist, or service that your neighbors should know about?

You can nominate one for a future issue → Here

Forward this to a neighbor, a coworker, or anyone who calls Charles County home. It only takes a second and it means a lot.

Before you go,

If you make it out to the Jazz & Wine Festival, a pumpkin patch, or Nanjemoy Heritage Day this weekend, reply and tell me where you ended up, I want to hear about it. And if there's something happening next week I should know about, send it my way.

That's the week.

From one local to another

— Candace