From about 1860 until nearly 1880, the primary transportation route to and from north Clark County, Wisconsin was by boat via Black River. Early roads were rivers, wagon trails and stagecoach routes. That changed in 1880 when the east/west rail line of the Wisconsin Central was opened between Abbotsford and Chippewa. Once that railroad line opened, rail stops in the north Clark Country area were added at places that eventually became known as Abbotsford, Curtiss, Owen, Withee, Sterling, Thorp and Stanley.

North/South rail connections through northcentral Clark County were added in 1910, when the Spencer Cutoff rail line bypassed Abbotsford, and connected to Owen and points north to Duluth. Connecting westbound rail service became available in 1910 as Owen was established as a key railroad hub. Daily luxury roundtrip passenger rail service between Chicago and Duluth, with passenger rail connection in Owen to Minneapolis westbound was added. The daily “Laker” passenger train service ran through Owen from 1910 until 1965. January 15, 1965, was the last trip of the Laker as it ended passenger rail service through Owen. As logging gradually ended by 1930 and agriculture took over, improved local roads were built over the course of nearly 50 years. The Yellowstone Trail was part of that roadbuilding focus. The Yellowstone Trail was promoted as “A Good Road from Plymouth Rock to Puget Sound.” The Yellowstone Trail to this day travels through the heart of Owen and Withee.

A major historical change in local land transportation took place when “new highway 29” between Abbotsford and Chippewa was opened in October 1963. New 29 was a massive east/west construction transportation project across northcentral Wisconsin. Opening of the new highway in 1963 included a special dedication ceremony on the highway exit ramps for Owen and for Withee by then Governor John Reynolds. The routing of new 29 was such that it bypassed going through downtown Curtiss, Owen, Withee and Thorp. That was controversial, in that it meant travelers on the highway might stop less frequently to shop in the local towns. The new 29 was expanded from two lanes to four lanes of traffic in 2000. The expanded four lane 182-mile segment (Green Bay to Chippewa) of newly improved Highway 29 was dedicated at Edgar, Wisconsin in August 2000 by then Wisconsin Governor Tommy Thompson and Congressman Dave Obey.

Private airplane travel was popular for two decades in Owen-Withee in the 1960s and 1970s. The Withee Airport was constructed south of Withee in 1959. John Isaacs, Lew Bulgrin, Tony Sailer, Harold Braswell and Darrell Marrier were local businessmen, pilots and personalities who hangared planes at the Withee airport. Out of town business executives who conducted executive business in the Owen–Withee area frequented the Withee Airport as well. One of the prominent Owen pilots was Darrell Marrier, who worked the Owen Soo Line depot. Darrell died at Ladysmith in 1960 when his plane crashed and burned. The Withee airport is no longer active.

Local recreational all-season on and off-road land travel became popular in the 2010s with the availability of All Terrain Vehicles known as 3-wheelers, and Quads (4-wheelers). Advanced designs of such vehicles made them hybrids that were nearly like cars and trucks. Some of them with advanced technology are now licensed to be driven on public roads. They are very popular as travel and recreation vehicles.

On the opposite end of technology, some aspects of Owen-Withee area transportation evolved backward from high-speed, high-end autos and trucks. With changing demographics beginning in 1973, Mennonites and Amish settlement in the area brought a return to travel by bicycle and horse and buggy. With the population demographics of the area by the 2020s approaching 50% Mennonite and Amish, bicycle and horse traffic on public roads of the area once again became a very common sight on local roads.