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Editor's note: This story has been updated with additional events.
Looking for something to do in The Woodlands this fall? These are some of the events coming up in September and October. This list is not comprehensive, and details are subject to change.
September
‘Annie’
Class Act Productions is presenting "Annie," the musical story of a young orphan in 1930s New York City.
Sept. 17-27, times vary
$20-$30
25275 Budde Road, Ste. 27, The Woodlands
The Chamber’s 48th Annual Meeting & Awards Luncheon
The Woodlands Area Chamber of Commerce will recognize member anniversaries, team leaders and retiring board members.
Sept. 25, 11 a.m.-1:30 p.m.
$100 (members), $125 (nonmembers)
Kevin Brady Community Center, 2250 Buckthorne Place, The Woodlands
Dragon Boat Team Challenge
The Woodlands Family YMCA is holding its annual Dragon Boat Team Challenge. Teams consist of 20-30 members in a variety of categories, and the public is invited to watch the event.
Sept. 26, 8 a.m.-noon
Free (attendance)
2505 Lake Woodlands Drive, The Woodlands
Out of the Darkness Walk
The American Foundation for Suicide Prevention's Southeast Texas Chapter will host the Greater Houston Area Out of the Darkness Community Walk at Town Green Park.
Sept. 26, 9 a.m. (check-in), 10 a.m. (event begins)
Donation levels vary
2099 Lake Robbins Drive, The Woodlands
Shakespeare in the Park
Points North Theatre Company is presenting "The Merry Wives of Windsor," a comedy by William Shakespeare.
Sept. 26, 5-8 p.m.
Free
6055 Creekside Forest Drive, The Woodlands
The Woodlands Fine Craft, Art & Design Show
Now in its third year, this event brings in local and national artisans to share their creations.
Sept. 26-27, times vary
$17 (one-day pass), $22 (weekend pass)
1601 Lake Robbins Drive, The Woodlands
Boots vs. Badges Softball Game
The Woodlands Township Neighborhood Services invites the community to the Boots vs. Badges softball game. The Montgomery County Sheriff’s Office will face off against The Woodlands Fire Department. The event will also feature a car show with The Woodlands Car Club Community Car Showcase.
Sept. 27, 4-7 p.m.
Free
Alden Bridge Sports Park, 4751 College Park Drive, The Woodlands
October
In the Pink of Health Luncheon
Memorial Hermann’s In the Pink of Health annual luncheon raises money for breast and ovarian cancer prevention, education and community outreach and to support cancer survivors through the Canopy Cancer Survivorship Center.
Oct. 2, 10 a.m.-1:30 p.m.
$2,500 (Table)
The Woodlands Waterway Marriott, 1601 Lake Robbins Drive, The Woodlands
Run for Hope
Love Fosters Hope will hold the fundraising Run for Hope at Town Green Park.
Oct. 3, 7-10 a.m.
Free
2099 Lake Robbins Drive, The Woodlands
The Woodlands Cars & Coffee for a Cause
Car enthusiasts and The Woodlands Car Club meet on the first Sunday of every month to put on the event, which features an opportunity to raise money for local charities.
Oct. 4, 6-10 a.m.
Free
9595 Six Pines Drive, The Woodlands
National Night Out
The Woodlands Township Neighborhood Services invites the community to an annual night out to promote police-community partnerships, crime prevention awareness and community camaraderie.
Oct. 4, 3-6 p.m.
Free (admission)
Locations throughout The Woodlands
Community Helper Day
The Woodlands Township Neighborhood Services is holding an event where attendees can meet local first responders and learn how to help their community.
Oct. 9, 10 a.m.-noon
Free
George and Cynthia Woods Mitchell Library, 8125 Ashlane Way, The Woodlands
Movie Madness 'Scream'
The community is invited to an outdoor screening of the popular horror movie Scream (1996). Chairs and blankets are encouraged; the event is for ages 13 and up.
Oct. 9, 8:30 p.m.
$5 (admission)
Rob Fleming Recreation Center Amphitheater, 6464 Creekside Forest Drive, The Woodlands
Memorial Hermann 10 for Texas
Runners can participate in the annual 10 for Texas 10-mile race, 3.1 Armadillo Run 5K and the One 4 Texas Kids’ Fun Run through The Woodlands.
Oct. 10, 7 a.m.
$35-$70 (registration)
Northshore Park, 2505 Lake Woodlands Drive, The Woodlands
The Halloween Bash
Attendees can enjoy putt-putt, carnival games, a costume dance contest and craft and food vendors in a family-friendly setting.
Oct. 16, 6:30-9 p.m.
Free (children), $25 (resident), $35 (non-resident)
6464 Creekside Forest Drive, The Woodlands
The Woodlands Wildflower Festival
Attendees can enjoy food trucks, live music, flower seed giveaways, bluebonnet planting, face painting and an annual art contest.
Oct. 17, 10 a.m.-2 p.m.
Free
Rob Fleming Park, 6055 Creekside Forest Drive, The Woodlands
Blood Drive
Donors can sign up to donate blood at The Woodlands Township municipal building.
Oct. 22, 10 a.m.-2:30 p.m.
Free
The Woodlands Township, 2801 Technology Forest Blvd., The Woodlands
Flourish & Nourish Ladies Luncheon
The Montgomery County Food Bank announced its inaugural Flourish & Nourish Ladies Luncheon, a signature event for women in Montgomery County to help fight hunger. Cat Cora, the first female Iron Chef on "Iron Chef America” and founder of the nonprofit Chefs for Humanity, will participate in a fireside chat and Q&A moderated by KPRC 2 news anchor Lisa Hernandez as part of the event.
Oct. 22, 11 a.m.
$250 (individual ticket)
The Blue Magnolia, 1 Whispering Pines St., Magnolia
H-E-B Wine Walk
Attendees can sample food and beverages from local restaurants during a night of live music, craft beers and fine wine.
Oct. 24, 6-9 p.m.
$79 (general admission), $135 (VIP admission)
2301 N. Millbend Drive, The Woodlands
Trick or Treat Trail
Participants can enjoy carnival games and trick-or-treating from local vendors and food trucks.
Oct. 25, 1-5 p.m.
Free (admission)
The Recreation Center at Rob Fleming Park, 6464 Creekside Forest Drive, The Woodlands
The Woodlands Pride Festival 2026
Attendees can enjoy live entertainment, vendors and food trucks in a family-friendly celebration of pride, inclusion and Halloween.
Oct. 31, 10 a.m.-4 p.m.
Free (admission)
Town Green Park, 2099 Lake Robbins Drive, The Woodlands
