I really don't have a clue what will work, but this is what my imagination conjured up. I think you're on the right track with a swinging weight. Build a gantry frame in the creek bed from timber, like an A-frame or 4-sided teepee, high enough to suspend a weight and let it swing. The higher the better, as you would get more swing. If you don't get enough swing, it probably won't work. You could also rig a second tower with a pulley on it so you're pulling the ram up was well as back - getting the swing from the maximum height.
Suspend the weight (I was thinking of something more like a battering ram, such as a hunk of RR track). If you attach the ram to the gantry with more than one rope, you can probably adjust the ropes and change the aiming point. Multiple ropes at each end of the ram will also ensure that it swings straight.
Attach a rope to the weight and pull it back ("cock" it) with your tractor. With a long enough rope, you should be able to do it from the bank. Aim the battering ram so it hits low, in the middle of the wall or lower, so it won't damage the bridge itself.
Once you have the ram pulled all the way back, you'll have to rig some sort of quick release clamp for the rope (the trigger). Then, with the rope clamped, back up the tractor until there is enough slack in the rope to let the ram reach the wall. Release the "trigger", and the ram will swing into the wall, taking the slack rope with it, and allow it to be pulled back, cocked and triggered once more. The tractor and the trigger could be a couple of hundred feet from the ram; you should be safe enough.
I think once you break through a middle section, you'll find that the entire wall is weakened enough that you will be able to break whole sections radiating out from the first breach. If there is reinforcement steel in the wall, you'll need a torch or a metal cutting sawzall running on a generator or soemthing to cut it. There are HD rebar hand cutters available that might work if enough steel is exposed.
With someone to help you by clamping and releasing the trigger, you should be able to stay on your tractor, and should be able to get into a rhythm and make a swing every minute or so.
You've already discovered that this is not a weekend project. If you're like me, however, you will get adequate satisfaction when it's over and you can say, "I beat that sucker."