What you will find with Garmin GPS is it records a position every now-and-again along the route. Each point has an accuracy of, as you say, +/- 30ft. Sometimes, when the signals are being interupted or deflected, the accuracy decays and the thing thinks its sitting on the fence and not on the road.
Study the Track and you might see the plotted Track zig-zags along the road and sometimes detours off the road. The true distance will be according to Pythagoras' theorum and 'finite element' construction.
The 'Trip distance' displayed is an accumulation of all the straight lines between data points at changes in direction, speed or elevation. If the data points are laterally inacurate, the errors will accumulate uncontrollably therefore lengthening the distance.
Also, you may ride round a slow sweeping curve. The two datapoints at each end of the curve are at the distance of the straight line, not the arc. Thus shortening the indicated distance.
One may say the law of averages will sort it out, but I wouldn't trust that. GPS distance determination is inherently inacurate.