I frequently cycle between the Heights and Montrose. Often taking the most obvious Heights/Waugh corridor. The stretch of road from Washington south over Buffalo Bayou, then continuing on Waugh past Dallas to W. Gray is a bit harrowing for some. I don’t have issues with it, and have taken the route both day and night.
But there’s another route I take that’s a bit east of that – closer to town. Close and parallel to Studewood/Montrose. It’s a bit less harrowing for those who are timid about Waugh and doesn’t add distance if your endpoints are on the eastern peripheries of these neighborhoods.
Going from the North to South, from the Heights, first take the MKT path south past I-10. Immediately take a right after passing under I-10 on the sidewalk before approaching the Target shopping area. This will lead you along the sidewalk on the south side of I-10, up to Studemont.