Fall is bringing a full calendar of things to do in The Woodlands. From outdoor concerts and local art shows to community races, family-friendly Halloween events and major performances at The Cynthia Woods Mitchell Pavilion, September and October offer plenty of reasons to get out and explore.
Whether you are looking for a weekend activity, live music or something the whole family can enjoy, here are some of the upcoming events to have on your calendar.
What events are happening in The Woodlands in September and October 2026?
The Woodlands Fine Craft, Art & Design Show
September 26–27, 2026
The Woodlands Waterway Marriott Hotel
The Woodlands Fine Craft, Art & Design Show returns for a weekend dedicated to art, craftsmanship and design. Presented by The Woodlands Arts Council, the indoor show brings together more than 50 juried artists and designers with original jewelry, ceramics, glass, woodwork, leather, fiber arts and other handcrafted pieces.
Visitors can shop directly from participating artists while enjoying live music, artist talks and specialty vendors throughout the weekend.
Dead Symphony: The Music of Grateful Dead and More
September 29, 2026
The Cynthia Woods Mitchell Pavilion
The Woodlands Symphony Orchestra takes the stage for a unique evening combining orchestral music with the improvisational spirit of the Grateful Dead and other jam-band influences.
The performance begins at 7:30 p.m. and is free to attend, with no ticket required.
Market Street Fall Concert Series
Thursdays Beginning September 24, 2026
Central Park at Market Street
Live music returns to Market Street for its Fall Concert Series, bringing local and regional performers to Central Park on Thursday evenings.
The outdoor series offers an easy way to enjoy the cooler fall evenings while exploring the restaurants, shops and gathering spaces around Market Street.
October Events in The Woodlands
Moonlight Paddle & Starlight Swan Rides
Beginning October 2, 2026
Riva Row Boat House
Fall evenings can also be spent on the water. Riva Row Boat House will host Moonlight Paddle on October 2, while Starlight Swan Rides begin the same evening and continue on select dates through November.
These nighttime experiences offer a different way to take in The Woodlands Waterway after sunset.
Cars & Coffee for a Cause
October 4, 2026
Market Street
Cars & Coffee for a Cause returns to Market Street on the first Sunday of October. The monthly gathering brings car enthusiasts together to see an ever-changing collection of vehicles while supporting local charitable organizations.
It has become a familiar Sunday morning tradition in The Woodlands and a relaxed way to spend time at Market Street.
Memorial Hermann 10 for Texas
October 10, 2026
Northshore Park
One of The Woodlands' signature fall sporting events returns to Northshore Park with the Memorial Hermann 10 for Texas.
Runners will take to the streets and pathways of The Woodlands for the annual race, bringing together athletes, families, volunteers and spectators for a morning centered around fitness and community.
Fall Fine Arts Show
October 17, 2026
Central Park at Market Street
Art returns to Market Street with the Fall Fine Arts Show, a free event showcasing work from artists in and around The Woodlands.
Visitors can stroll through Central Park, meet participating artists and browse original artwork while spending the day in one of The Woodlands' most active shopping and dining destinations.
Hocus Pocus Pops
October 23, 2026
The Cynthia Woods Mitchell Pavilion
One of The Woodlands' favorite Halloween traditions returns when the Houston Symphony presents Hocus Pocus Pops.
The family-friendly evening combines Halloween music with costumes, candy, trick-or-treating and pre-show activities around The Pavilion. Guests are encouraged to arrive in costume and enjoy the festivities before the Symphony takes the stage.
The show begins at 7:30 p.m. and is free, with no ticket required.
Live Music at The Cynthia Woods Mitchell Pavilion
The fall calendar at The Pavilion extends well beyond its free performing arts events. October brings a packed lineup of touring artists to The Woodlands.
Upcoming performances include:
October 1: Mumford & Sons with Marcus King Band
October 2: Boz Scaggs with Irma Thomas
October 3: Eagle Fest featuring ZZ Top with Cheap Trick
October 4: TLC & Salt-N-Pepa with En Vogue
October 8: Brad Paisley with Jake Worthington and Mackenzie Carpenter
October 9: Hayley Williams with Magdalena Bay and Rico Nasty
October 10: Breaking Benjamin with Kami Kehoe, Starset and Chevelle
October 15: Bryson Tiller with Majid Jordan, Ty Dolla $ign and Austin Millz
October 16: beabadoobee with Wisp
October 17: Staind with Seether, Hoobastank and Hinder
October 23: Houston Symphony: Hocus Pocus Pops
October 24: Majic Under the Stars featuring Babyface, Keyshia Cole and more
October 25: Three Days Grace with I Prevail and The Funeral Portrait
October 31: MercyMe with Jeremy Camp, Tim Timmons and Sam Wesley
With everything from symphonic performances and classic rock to country, pop and alternative music, The Pavilion remains one of the biggest draws in The Woodlands throughout the fall.
Fall in The Woodlands
What makes fall in The Woodlands stand out is how much is happening beyond any single venue. A weekend can include an art show at Market Street, a morning run through Northshore Park, an evening along The Waterway and a concert at The Pavilion, all within the same community.
As temperatures begin to cool, the miles of trails, parks, outdoor dining destinations and entertainment venues throughout The Woodlands also become an even bigger part of everyday life.
For residents, these events are part of what makes The Woodlands such an active place to call home. For visitors or those considering a move to the area, fall is an ideal time to experience the community firsthand.
Looking for a home in The Woodlands? Explore available properties and discover more about living in one of the Houston area's most sought-after communities.
