Sorry about the typo.

A Diamond climb from Middletown/Wurtsboro is definitely doable. But a low notch near Wurtsboro is definitely required. Would be tricky to do it over Middletown Airport.

Regarding a 1000km flight, if you take a high tow near High Point, it would be doable to connect with the Blairstown ridge. You might not make Middletown at the end of the day, but the task need not be a closed circuit.

All the best,
Daniel