We use the AllTrails App on our phones! Download it, put in your location, and look for a trail that is at your level. They are all rate from easy, moderate, difficult, and very difficult. You can download the map from the app and do this before you hike because service does get spotty!
Sisters, Oregon is a small town of about 2500 people. Uber and Lyft may be difficult to get at times, but taxis are available. I've checked Uber at various times to see their availability at the Redmond Airport and it appears there is always 1-2 available. Renting a car would be our recommendation or pairing up with someone else who may have similar flight times.
For a detailed local weather forecast, see www.noaa.gov The average weather is low-mid 70's this time of the year for a high, but better to check the website above or your weather app!
For current road conditions, please go to www.tripcheck.com. This will show you live cameras and traffic jams.
If you need to schedule a ride from the Redmond Airport, please call The Redmond Airport Shuttle at (541) 382-1687.