The weather should be fairly mild mid-October, but can range quite a bit. Since Bend is at 3800 ft., morning and the evening will be colder, but we are hoping for nice weather during the day. Best to bring lots of layers so you can take off or add on as the temperature changes. Snow is unlikely but definitely not out of the question so check the forecast before you pack!
There is Uber and Lyft in Bend, but can be difficult to get late at night.
There are a few shuttle services from the Redmond/Bend airport which are easy to book if you don't rent a car.