Things to Do in Cypress This Weekend

Looking for something to do in Cypress this weekend? I refresh this guide every week so the best of what’s happening close to home lands in one place — no endless scrolling required. This is the weekend of September 18–20, 2026, and it has a little of everything: a charity 5K out at John Paul Landing that honors first responders, Friday-night football under the lights, live music on the lake, a couple of plant and craft markets, and a pumpkin patch that’s fully open for the season. Here’s what stood out to me.

Weekend of September 18–20, 2026

Friday night: Cy-Fair ISD high school football. Friday-night football is back across the district, and if you’ve never done a Cy-Fair ISD game — the bands, the drill teams, the concession-stand nachos, the whole production — this is a good weekend to start. Check the CFISD football schedule for Friday’s matchups and which stadium, and buy your tickets online through the district before you drive over.

Friday and Saturday: Judy Dierker Holiday Market at The Foundry Church. Don’t let the name fool you — this one runs in September, and it’s right here in Cy-Fair at The Foundry Church on Jones Road, with local vendors, handmade crafts, and gifts if you want to get a jump on the holidays. It’s open Friday from 9 a.m. to 4 p.m. and Saturday from 9 a.m. to 3 p.m., and it’s an easy, free browse close to home. Details are on the Foundry Church holiday market page.

Friday and Saturday nights: live music on the water at The Boardwalk at Towne Lake. The Boardwalk’s live music plays every Friday and Saturday evening from 6:30 to 9:30 p.m., and it’s still the easiest night out in Cypress: no cover to listen, free parking, dinner on a lakefront patio, and room for the kids to work the promenade while you finish your meal. Lineup and details are on the Boardwalk events page.

Friday, 6 to 9 p.m.: Grow with Stacy Plant Social. If you’ve got a green thumb — or want one — Stacy Tran’s plant social brings houseplants, succulents, hanging baskets, rare tropicals, and local vendors together for an evening at Stomping Ground in Garden Oaks (1225 W. 34th Street). It’s a bit of a drive in from Cypress, but it’s a fun, low-key night for plant people and a good way to support small local growers. Details are on the Grow Expo page.

Saturday, 7:30 a.m.: Tunnel to Towers 5K Run & Walk. The Tunnel to Towers Foundation brings its annual 5K out to John Paul Landing Park (9950 Katy Hockley Road) on Saturday morning, raising money to support first responders, military families, and the families of the fallen. You can run it, walk it, or just bring the kids and cheer from the sidelines — it’s the kind of Saturday morning that feels good to be part of. Registration and start details are on the event page.

Saturday and Sunday: Fall Festival at Dewberry Farm. The pumpkin patch is fully open for the season out in Brookshire — Dewberry Farm’s Fall Festival runs weekends with the corn maze, friendly farm animals, hayrides, and dozens of rides and attractions across the property. It’s about a 30- to 40-minute drive west, and mid-September Saturdays run a good bit calmer than the peak-October crowds, so this is a smart weekend to go before things get busy. Hours and tickets are at dewberryfarm.com.

Friday through Sunday: “Clue ON STAGE” at Playhouse 1960. Our neighborhood community theater on Gant Road is running the comedic murder-mystery based on the board game and the cult movie — Friday at 7:30 p.m., Saturday at 7 p.m., and Sunday at 3 p.m. It’s a fun, low-cost night out close to home, and community theater is one of those Cy-Fair things a lot of people don’t realize is right on their doorstep. Tickets are at ph1960.com.

Sunday: Best Friends Pet Adoption opens at Traders Village. Traders Village on North Eldridge kicks off a pet-adoption event with Best Friends, the shelter-rescue organization, running Sundays into mid-October. Admission is free (parking is $6), so you can wander the market, grab a turkey leg, and meet some adoptable animals — and if your family’s ready, maybe bring one home. Details are at tradersvillage.com.

Always a good time in Cypress

When the calendar thins out or the heat wins, a few Cypress regulars are always there. Cypress Top Historic Park preserves 2.6 acres of the original 1850s railroad town — the Juergen home, the general store, the depot, the dance hall — with shade, no admission, and about an hour’s worth of wandering. Telge Park is the low-key neighborhood option: 111 wooded acres on Cypress Creek with a fenced playground, a wetland boardwalk, and enough tree cover to make an evening walk workable. And the same John Paul Landing Park hosting Saturday’s 5K gives you 876 acres of trails and open water any other day of the week.

More ideas for any weekend: browse our Places to Visit directory, including the parks we’ve photographed around Cypress and Houston.

Thinking about calling Cypress home?

Look at what this weekend actually asks of you: a Friday-night football game, a charity 5K, live music on the lake, a couple of markets, community theater, and a pumpkin patch — most of it inside about fifteen minutes of a typical Cypress address, and much of it costing little beyond what you eat. That’s the part people tend to underestimate before they move out here — not the amenity lists in the brochures, but how short the drive is to a Saturday that’s already planned for you. Master-planned communities with their own lakes and trails, a real choice of Cy-Fair schools, and none of it requiring a fight with Houston traffic to get home. If a weekend like this has you picturing your own address out here, I’m glad to walk you through how these neighborhoods actually differ — price, commute, schools, and what you trade off in each one. Start with my Bridgeland neighborhood guide or my guide to living in Cypress, or just reach out. I’m a local broker and glad to help.

Last updated: September 17, 2026 · Refreshed every week with the coming weekend’s events.