The Woodlands

Trail Running Calendar near The Woodlands 2026-2027

Explore the top trail runs near The Woodlands for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026

Last Man Standing - Willis

Willis | 18 mi from The Woodlands

Backyard Ultra 5 km

Two races in Willis, Texas combine a family friendly 5K with a Last Man Standing ultra where runners repeat a 5K loop every 50 minutes until one remains.

Two races in Willis, Texas combine a family friendly 5K with a Last Man Standing ultra where runners repeat a 5K loop every 50 minutes until one remains.

Bigfoot Running Company - Cypress

Cypress | 19 mi from The Woodlands

Road Race Trail Run 3 mi 6 mi

Gingerbread Lane at John Paul Landing Park in Cypress features Kids Dash, 1 Mile, 5K, 10K and a virtual option with shirts, medals and a holiday costume contest.

Gingerbread Lane at John Paul Landing Park in Cypress features Kids Dash, 1 Mile, 5K, 10K and a virtual option with shirts, medals and a holiday costume contest.

January 2027

The ReRun 5x5 Trail Run

Plantersville | 26 mi from The Woodlands

Trail Run 25 km

A 5x5 trail challenge at Magnolia Hill Ranch where runners complete a 5K every hour for five hours on fast pinewood trails by a lake.

A 5x5 trail challenge at Magnolia Hill Ranch where runners complete a 5K every hour for five hours on fast pinewood trails by a lake.

February 2027

Houston Ultra Trail

Houston | 28 mi from The Woodlands

Trail Run 5 km 10 km ... 50 km 50 mi

Loop-based trail races at Memorial Park in Houston on February 13, 2027, with distances from a free Kids 1K to a 50 Mile ultra, supported aid stations, chip timing, medals and 50 Mile belt buckles.

Loop-based trail races at Memorial Park in Houston on February 13, 2027, with distances from a free Kids 1K to a 50 Mile ultra, supported aid stations, chip timing, medals and 50 Mile belt buckles.

Bernhardt Wine Run 5k

Plantersville | 26 mi from The Woodlands

Trail Run 3 mi

A chip timed 5k at Bernhardt Winery in Plantersville Texas with a volunteer 3.1 mile option and race kit items including a finisher medal and a wine pour.

A chip timed 5k at Bernhardt Winery in Plantersville Texas with a volunteer 3.1 mile option and race kit items including a finisher medal and a wine pour.

March 2027

Bigfoot Running Company - Cypress

Cypress | 19 mi from The Woodlands

Road Race Trail Run 5 km 7 mi 13 mi

Western themed running event in Houston with races from 50 m to 13.1 miles, a custom race shirt, a belt buckle finisher medal, music and a photo opportunity.

Western themed running event in Houston with races from 50 m to 13.1 miles, a custom race shirt, a belt buckle finisher medal, music and a photo opportunity.

Bigfoot Running Company - Cypress

Cypress | 19 mi from The Woodlands

Road Race Trail Run 3 mi 7 mi 13 mi

Community race in Cypress, TX on March 13, 2027 supporting the Outdoor Disabled Veterans Program with in-person and virtual distance options.

Community race in Cypress, TX on March 13, 2027 supporting the Outdoor Disabled Veterans Program with in-person and virtual distance options.

April 2027

Spring Fling - Houston

Houston | 28 mi from The Woodlands

Road Race Trail Run 3 mi 6 mi

Spring Fling Houston on 04/18/2027 in Sugar Land offers a Kids Dash, 1 mile, 5K, 10K and a 13.1 mile virtual race with music and a Bigfoot theme.

Spring Fling Houston on 04/18/2027 in Sugar Land offers a Kids Dash, 1 mile, 5K, 10K and a 13.1 mile virtual race with music and a Bigfoot theme.