My girlfriend is coming up next weekend with our 2 y/o German Shepherd and I was wondering if there are any places I could take him to go hiking? My apartment is in Midland but I wouldn't mind driving an hour or two to someplace for hiking if it was worth it. I looked into Big Bend but unfortunately pets are not allowed on trails...

San Angelo State Park

Have you looked into the Monahans Sand Dunes?
big Spring also has a State Park/ Comanche Trails
San Angelo is nice and has gotten more eateries too
fort Davis- chihuahua dessert nature center is there

i am not sure if there places are pup friendly.

Cloudcroft NM & Ruidoso are getting lots of dog friendly places

In Midland I have taken my pup to The Blue door & Hemingway and sat on the patios.
eaten at Smiling Moose, Free Birds, Starbucks, Jason's Deli, and Jersey. Mikes on the patios.

Midland has a dog park too- just flat and big but good so the pup can run around.

we go on long walks around Green Tree & the duck pond/ old midland .

Thanks you for all the suggestions. I think we are going to try San Angelo St. Park!