Considering doing "Hale on wheels" in Plainview Texas this september. I'm originally from the other Plainview in New York and thought it might be fun to finally visit the sister city for a bike event. Has anyone done this ride?
https://site.haleonwheelsbikeride.com/Home.html

Could be fun.
Plainview is primarily a cotton area as I recall, and won't be too pretty that time of year. Expect a lot of flatness and potentially a lot of strong steady winds on straight roads with zero shelter other than the telephone poles.
You're not too far from Palo Duro Canyon, and (assuming they don't have a route going up there), a side trip up there would be worthwhile.

Oh, music for the theme:
https://www.youtube.com/watch?v=fdG7d3-r3YY

I went to school at Texas Tech in Lubbock about 50 miles south of there. My brother is a biochemistry professor at Wayland Baptist University in Plainview. I worked summers while in school at the Highway Dept in that area, and also do a little pheasant hunting around there in the CWP lands. I'm pretty familiar with the area. Let's just say there probably won't be a lot of climbs unless the route goes way east or way north. Also, count on a lot of vibration inducing chip sealed farm to market roads, high winds, 100+ temps common even in September, and low humidities. Great people though.

For sister cities, this would be the ugly sister...

Thanks. I looked at the list of Texas rides at wheelbrothers and it appears ft. Davis cyclefest is the same weekend. I know that is a scenic and popular event, and I haven't done it before.

As a lifelong Texan, the area around Fort Davis is my favorite part of the entire state. I'm new to cycling and have never done the ride, but that part of the state is fantastic. If you've ever seen the wide open vistas and mountains in the movie "No Country for Old Men" or the old James Dean movie "Giant", they were filmed in the Marfa/Fort Davis/Alpine area.

Looking at these places on google maps, it looks like the Alpine / Marfa / Ft. Davis triangle would be an awesome loop ride scenery wise. With a stop up in Davis Mtns State Park. Anyone ever done that before?

One catch in the Marfa area is there's pretty much zero between towns out there, so if the towns are too far apart for you, you don't have much of a supply point.
There's a Fort Davis Cyclefest out there in the fall.
Bikin' Mike has had some group rides out there in the past, maybe Fort Worth Bicycle Association has too, come to think of it.
There's a "No Country For Old Men" race out there with 200 and 384 mile versions- put on by Dex Tooke.

I've never ridden it (still relatively new to riding), but that is my absolute favorite part of this state. We usually stay at Indian Lodge in Davis Mtns State Park as a base for everything around there, hit Marfa and Alpine (great restaurants in Alpine), spend a night at McDonald Observatory, and go snorkeling and scuba diving (yes, believe it or not) at Balmorrhea State Park. The open spaces and silence out there is awe inspiring. You don't have the crowds of the Hill Country. We get out to the Davis Mtns area at least every other summer.

Cheers.