I have been having the same issue since I got my watch several weeks ago. After spending time with phone support I visited a store and they actually gave me a brand new watch. Unfortunately, it is experiencing the same issues.
I've continued my conversations with Apple phone support and they continue to provide their "techs" my information. I run daily and have sent them screen shots of the AW distance vs. RunKeeper, Nike, and Strava. Apple Watch is always calculating a distance of 10-30% LESS than the other apps that all have extremely close distance measurements to each other, which I know to be accurate as I've run the same trails for years.
At first I thought it might be caused by running on very wooded hilly trails, but after pairing/re-pairing and then calibrating several times on a flat surface...it's still inaccurate. Even when I run on flat surface the AW comes up short on distance.
And like the above, when I run on a treadmill (using indoor run on workout app) it's pretty accurate. Same for biking...distance is very similar to my bike computer.
I'm beyond frustrated at this point because I bought this watch to monitor my running. Basically choosing it over, a Garmin for example, because of the heart rate on the watch and it's just so darn comfortable!
Then you have all the issues with the activity and workout applications...I could go on and on about that. They must have tested all of this with fitness experts so how was all this missed!
Waiting again for Apple to call back with more information from the techs.