From Montrose, head west up Buffalo Bayou thru Memorial Park. Take Woodway, Memorial Drive or side streets west outside the loop, then follow Memorial until you reach Boheme. Go left on Boheme then south along Beltway 8 a quarter mile to Terry Hershey Park.
Terry Hershey park runs all the way from BW8 to Barker Dam and has both paved multi-use and dirt trails. Once you get to the dam, go north then west either on the top of the dam (gravel) or next to it (paved) end of the dam at Barker-Cypress and the 10. From there, take Barker-Cypress north or a couple blocks further west, alternatively go on Fry Road. Both Fry and Barker-Cypress are straight shots all the way to Cypress.