Gliders can go with: Land in the dirt, you won't get hurt. In one sandy loam field my landing run was two fuselage lengths with the glider sitting on the gear doors and hinge fingers pulled off the pin.
For other aircraft, have a look at the size of wheel relative to size/weight of aircraft.
Designers of fixed gear aircraft can squeeze more knots at cruise with smaller wheels. Itty bitty wheels do not take well to plowed fields. A standing or freshly mowed crop will be a better option.