A container on private property, on your own driveway or on your own farmyard, clear of the road and any sidewalk, needs no Village permit in Caledonia.
The road is the part to plan for, because Caledonia has no published route for a container there. The only street permit the Village publishes is written for block parties and similar neighborhood events, and it must be denied where the proposed use is primarily for private or commercial gain. It also needs a petition signed by most of the adult residents along the block, a review by the chief of police, possible insurance and a possible performance bond, and it cannot run past ten at night. None of that is designed for a roll-off container.
What that means in practice: plan the placement on private ground. If there is genuinely nowhere on the property to put it, talk to the Village before you book, because an administrative route may exist that is not written down. We will never promise a road placement in Caledonia on the strength of the published rules alone.
On the hauler side, Caledonia is refreshingly simple. The Village grants no collection franchise, keeps no approved-hauler list and licenses no haulers of its own. It contracts a cart service for household trash and recycling and leaves everything else to the property owner, and its code sets only timing rules: material out at the roadside by seven in the morning on collection day, no earlier than fifteen hours before, and containers off the roadside within twelve hours after collection. The baseline on a roll-off operator in Wisconsin sits at state level, as a Department of Natural Resources transportation license, and your account manager confirms that side of things before delivery.
One local rule does reach the customer directly, and it is worth knowing if you own property on both sides of a municipal line: it is unlawful to place out for collection in Caledonia any waste or refuse that was not generated inside the Village. Debris from a job in Racine or Mount Pleasant should not be brought over to a container at a Caledonia address.
Village Hall sits at 5043 Chester Lane and is open weekdays from eight to five; the Village's own garbage and recycling page covers the household arrangement.