I live in Alpine unfortunately the Target store got torn down last month, drive from Alpine to Fort Davis and then Marfa is really nice.
If you decide to go south from Marfa the park area and river road are also a must, you can down south from Alpine and then along the river to Presidio.
Fort Leaton and BBRSP are right outside Presidio if you take the river road route.
Newsflash Marfa is hipster due to the people who have decided to move out there and flip 1 br adobe casitas for half a mil.
Cant say much about Alpine moved here in 94, then away after I graduated, and back.
The drive to Balmorhea is also not bad, im not sure if the pool will be open by that time.
Marfa I guess if you like artsy stuff, if you go out to the Marfa lights and you have NODs, bring them.
The park area and river road are also a must, you can down south from Alpine and then along the river to Presidio, you will pass BBRSP either way you go.