I've had the good fortune to catch shuutles from the air twice...
The first time was from the cockpit jumpseat on a MIA-DCA flight. The normal overwater routes were closed for the launch and they had us routed up over DAB, JAX, SAV, etc. and we saw the launch from about 60nm away. Awesome!
The second time was enroute SAT-LAX climbing through FL240. There it was below us at 17,000 on the back of the 747, heading for Ellington Field near Houston. Looked sorta strange looking *down* on it..
We had one come over the DFW area a few weeks ago and it left a yellowish-green contrail that looked a little surreal. You could hear it too.. About 10:30 pm.... Cool!
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