It is difficult to provide a general answer to this question since the validity of the annexation will depend heavily on the physical appearance of the particular annexation proposal. However, in general, Wisconsin courts have found that “balloon on a string,” “corridor” or “strip” annexations either do not satisfy the contiguity requirement for annexation or violate the rule of reason. See Town of Mount Pleasant v. City of Racine, 24 Wis.2d 41, 127 N.W.2d 757 (1964); Town of Medary v. City of La Crosse, 88 Wis.2d 101, 277 N.W.2d 310 (1979); Town of Menasha v. City of Menasha, 170 Wis.2d 181, 488 N.W.2d 104 (Ct. App. 1992.) This is particularly true where the municipality is one of the petitioners or where the municipality “is shown to be the real controlling influence in the proceedings.” Town of Pleasant Prairie v. City of Kenosha, 75 Wis. 2d 322, 339-40, 249 N.W.2d 581 (1977). However, the courts have also invalidated an annexation initiated by a private landowner who set the proposed annexation boundaries where the annexation may result in “gerrymandered” or “crazy quilt” municipal boundaries. Town of Medary, supra, 88 Wis. 2d 101, 116; Town of Menasha, supra, 170 Wis. 2d 181, 191, n.3.

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