Top Things to Do This Week in The Woodlands – September 21 - 27, 2026

THE WOODLANDS, TX – Quote of the week: “There are only two seasons - winter and Baseball.” – Bill Veeck

This week could be the turning point in our weather where the humidity will catch up with the falling temperatures. Though our “natural” highs have been in the 90s lately, the wetness in the air has pushed the “feels-like” temperatures into the 100s. As this week progresses, it looks like both temperatures and heat indices will steadily decline as we officially commence autumn. Help us celebrate by hitting some of these events!

Monday, September 21
Get the guys together for Dude Bingo on Monday, September 21 at 6:00 p.m. at Sawyer Park Icehouse. Presented by Keep It Location Foundation, this isn’t your typical bingo night. The prizes are made for the fellas, with BBQ pits, hunting gear, whiskey, power tools, golf items, watches, and more up for grabs. Bring your buddies, grab a drink, and get ready for a night of bingo, prizes and plenty of fun. Tickets are on sale now — get yours before they’re gone.
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Monday, September 21
Join us in celebrating 40 years of Shadowbend YMCA and four decades of strengthening our community. Reconnect with old friends, meet community members, and visit with the people who helped shape our Y over the years. Together, you’ll celebrate the memories, relationships, and lasting impact that have made Shadowbend such a special part of our community. They want to highlight the people, memories, and moments that have made our Y so special. If you have a favorite story, old photo, or meaningful memory from your time at Shadowbend, please share it.
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Tuesday, September 22
Join The Woodlands Area Chamber of Commerce for a complimentary, monthly meet and greet reception where they will introduce up to 10 new members to the general membership. New members will provide a one-time only introductory commercial on the microphone (not to exceed 90 seconds). The event provides opportunities for members to meet other members and learn how we can all do business together. This month’s meeting is hosted by WorkLodge.
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Wednesday, September 23
The 2026 Wise Conference will be taking place today from 9:00 a.m. - 3:00 p.m. at Church Project, 602 Pruitt Rd. Don’t miss this year's targeted networking opportunity. WISE is honored to continue its tradition of supporting local non-profits in the Montgomery County area. It is their goal to enable smaller organizations to reach more of the community they support. Each year, The WISE Conference gathers women from the greater Houston area for a day of empowerment, connection, and recognition. The event includes a time of networking, a market featuring local small businesses, educational segments by community leaders, and Breakout Speakers that best exemplify the theme of the event.
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Thursday, September 24
In Precision Camera’s Panasonic Lumix Camera class, you will focus on the basic functions as well as all of the great creative modes, shooting techniques, and features of the Panasonic Camera system. This three-hour class will cover a variety of topics. So, no matter your skill level, come join the crew. Learn about all the great things your camera has to offer to enrich your photographic experience.
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Thursday, September 24
Shadow Puppet Theatre today at The Woodlands Children’s Museum at 11:00 a.m. presents “What Can You Do with a Paleta?” by Carmen Tafolla. In honor of Hispanic Heritage Month (September 15 - October 15), this story takes us on a walk through a young girl’s barrio, introducing children to the frozen fruity treat and showing all the creative things that can be done with a paleta. Included in the price of admission, which is $10 for adults and children 1 year and older.
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Thursday - Saturday, September 24 - 26
The YMCA Dragon Boat Team Challenge is an event designed to build community spirit among corporations, civic groups and community organizations. The activities are designed to bring individuals together to achieve a single goal – to have fun. They achieve this by becoming a team and working together as a synchronized unit. It’s much more than ‘beating the other team.’ It’s the camaraderie, visiting and playing with old friends, meeting new friends, working hard, and feeling good about it. At the YMCA, everybody plays and everybody wins.
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Friday, September 25
Join Celebree School at their free Grow Big Community Family Festival and enjoy hands-on children’s activities, local vendors, food, bounce house, face painting, and school tours. The event is open to the entire community – bring your friends and family. Families exploring preschool options can also tour the school and learn about their limited September enrollment promotion.
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Friday, September 25
Come celebrate the life, music, and magic of Dolly with a fun Twist Paint Party at Painting With a Twist. You’ll paint a Dolly-inspired masterpiece while listening to her greatest hits, enjoying good company, and celebrating the joy and kindness she’s brought to so many. Ages 16 and up (with a painting adult) are welcome at this class. The studio operates on a BYOB basis, so feel free to bring your favorite snacks and beverages. Please note that you must be at least 21 years old to consume alcohol on the premises.
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Friday, September 25
At the Annual Meeting and Awards Luncheon, The Woodlands Area Chamber of Commerce recognizes loyal members, board members, and team leaders, as well as the recipients of the Community Citizen of the Year, Chamber Volunteer of the Year, Diplomat of the Year, Chamber Emerging Leader, and Chairman’s Award. Members of the Chamber submit nominations for three awards: Community Citizen of the Year and Chamber Emerging Leader. The Chamber also honors a Legacy Award Recipient that has made a significant contribution to the betterment of The Woodlands Area and South Montgomery County. The Legacy award recipient is honored in recognition of their extraordinary personal commitment leaving a long-lasting impact on the community and future generations.
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Saturday, September 26
The 29th annual Woodlands Landscaping Solutions, a free community event celebrating sustainable landscaping, gardening and environmental stewardship, will take place today from 9:00 a.m. to 12 noon at The Recreation Center at Rob Fleming Park, 6464 Creekside Forest Drive.
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Saturday, September 26
Board Pirate and Mermaid Day, The Woodlands Children’s Museum’s version of the Jolly Roger, and keep a close eye out for treasure and mermaids. Navigate your way through the museum with your best peg-legs and fancy tails to find the hidden treasure. Ariel meet-n-greets at 10:30 a.m., 11:30 a.m., 12:30 p.m., and 1:30 p.m. Pirate meet-n-greets at 11:30 a.m., 12:30 p.m., and 1:30 p.m. Coastal Cotton Candy and Pirate Popcorn will be served to visitors in the Atrium. Special Storytime readings by Ms. Jan at 11:00 a.m. and 1:00 p.m. Included in the price of admission, which is $10 for adults and children 1 year and older.
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Saturday, September 26
Join theatre-lovers everywhere for a special evening at Shakespeare in the Park today from 5:00 to 8:00 p.m. at Rob Fleming Park. Enjoy a live outdoor theatre performance of The Merry Wives of Windsor by Points North Theatre Company, with pre-show music by The Woodlands Symphony Brass lead by Darryl Bayer beginning at 5:15 p.m. Bring your lawn chairs, blankets, friends and family for a magical night of theatre. Concessions will be on site for purchase. Performance will begin at 6:00 p.m.
EVENT LINK

Saturday - Sunday, September 26 - 27
More than an event, The Woodlands Fine Craft, Art and Design Show is a celebration of creativity, community, and connection. At the event, artists from across the country come together to elevate and showcase the very best in fine craft. Art enthusiasts welcome the opportunity to experience an extraordinary collection of fine craft right here at home. Dedicated board members and community leaders champion the transformative power of art. Sponsors and media partners play a vital role in bringing an event of this caliber to life. A committed team working year-round to make world-class fine craft accessible to our region. A friendly, welcoming group that ensures artists and guests alike feel supported and valued. Meet the artists, hear their stories, and take home a piece that truly resonates. The Woodlands Fine Craft, Art and Design Show is where artistry meets community – an inspiring experience that connects people and celebrates the beauty of fine craft.
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Sunday, September 27
Join The Woodlands Fire Department and the Montgomery County Sheriff’s Office for HOT RODS & HOMERUNS at the annual Boots vs. Badges Softball Game. Meet and support public safety officials as they square off in this annual competition. Free admission and free hot dogs and hamburgers (while supplies last). There will also be a KidZone and a car show for grownups featuring The Woodlands Car Club Community Car Showcase.
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Visit our Events page for more upcoming events at www.woodlandsonline.com/evps.