Why the obligation leaks away
Covenants come in two kinds. A restrictive covenant — do not build, do not use for trade — can bind later owners of the burdened land. A positive covenant — pay, repair, contribute — generally does not.
An obligation to contribute to the cost of maintaining a track is a positive covenant, so it does not run with the land. The original covenantor remains contractually bound for ever, which is of limited use once they have sold and moved on.
The result is a deed that reads as though everyone shares the cost and a road where nobody does.