End of US highway 14
View a map showing this route.
Photo credits: Tom
Grier, Don
Hargraves; Matt Majewski, Greg
Osbaldeston; Jim
Teresco; me
Additional research: Monte
Castleman
| Approx. time period | East terminus | West terminus |
|---|---|---|
| 1926-1928 | Winona, MN | Phillip Jct. SD |
| 1928-1929 | Winona, MN | (near Spearfish, SD) |
| 1929-1932 | Winona, MN | Rapid City, SD |
| 1932-1933 | Winona, MN | Phillip Jct. SD |
| 1933-1934 | Chicago, IL (Addison) | Phillip Jct. SD |
| 1934-1935 | Chicago, IL (Addison) | Cody, WY (?) |
| 1935-1938 | Chicago, IL (Addison) | East entrance Yellowstone National Park, WY |
| 1938-1952 | Chicago, IL (Broadway) | East entrance Yellowstone National Park, WY |
| 1952-1978 | Chicago, IL (Michigan) | East entrance Yellowstone National Park, WY |
| 1978-present | Chicago, IL (Broadway) | East entrance Yellowstone National Park, WY |
US 14 was an original 1926 route, but at the time its east end was at US 61 in Winona MN. The photo below is looking south on modern US 61...
Teresco, Oct. 2004
...and although this junction serves as today's functional equivalent, this is a newer bypass of sorts around Winona, and it hadn't yet been built back when US 14 ended here. Originally US 61 followed 6th Street through Goodview, which becomes 5th Street in Winona (that road runs parallel to this highway, about three blocks to the left at this point). The 1927 map I've seen is a bit unclear, but it appears at some point (either Vila Street or Johnson Street) traffic jogged one block to the south and followed 6th Street (or Broadway) through downtown Winona. Meanwhile, US 14 split off today's route by going east on Gilmore Street (via a bridge that no longer exists), then north on Vila. Depending on the routing of US 61, US 14 would've ended either at 6th or 5th. The photo below is looking south on Vila at 5th:
Grier,
July 2006
Southbound US 61 came in from the right on 5th. It may have continued to the left, in which case the beginning of US 14 was straight ahead. But US 61 might have gone straight ahead here before turning left at the next block, in which case the photo below shows the original east beginning of US 14:
Grier,
July 2006
That's one block ahead from the previous photo (use the pedestrian skywalk for reference). It's possible that US 61 came south on Vila to this point, and then turned left on 6th (or Broadway). If so, then US 14 would've begun straight ahead. (Incidentally, the bluffs visible in the background mark the edge of the Mississippi River floodplain, in which Winona is situated.)
After 1933, US 14 was extended eastward via southbound US 61 (just as it is today, albeit via the newer highway described above). The two routes don't diverge again until Readstown WI (about 76 miles distant).
Early maps make it look like no one quite knew what to do with the west end of US 14: it wasn't until about 1934 that it was assigned a routing through the Black Hills distinct from US 16 (or more accurately, US 16 was rerouted to go through the Hills, while US 14 was given US 16's old path around the north edge of the Hills). Originally US 14 ended at a lonely junction with US 16 outside Phillip SD. I photographed that spot in March 2004; click here to view photos and more info.
Two years later, the US 14 designation may have been extended west with US 16 to the SD/WY state line near Spearfish. Even if so, that was the west terminus of US 14 only briefly, because the next year the designation was truncated to Rapid City. It's difficult to speculate exactly where signage would've ended there, but my guess is that the terminus would've been at the same intersection where US 216 ended. You can view photos from there on this page.
In 1932 the west end of US 14 was back at Phillip Jct; and in 1934 it was extended either to Rapid City again or to Cody WY (you can view photos from there on this page). In 1938 US 14 was extended west again, this time to the east entrance of Yellowstone National Park, where it remains to this day (you can view photos from there on this page).
Now, back to the east end: as I said, it was 1933 when the east end of US 14 was extended to Chicago. Traffic came in on Addison Street, and state highway maps from 1934 through 1938 (scan below courtesy of Neil Bratney) seem to indicate that US 14 ended at its junction with US 12/41 (Lake Shore Drive):

The photo below is looking east on Addison at Lake Shore:
Hargraves
That was the original Chicago endpoint of US 14. The next shot is a view up westbound Addison, at the former beginning of US 14...
Hargraves
...but that was the situation for only about four years. The 1939 map shows US 14 coming in on Broadway and ending at Foster Avenue. Yep, same intersection where US 14 ends today. We'll see photos from there below, but first I want to note: that junction hasn't been a continuous endpoint since 1939. The first time, US 14 ended there only until 1952. The 1953 map shows that US 14 had been extended down to a common endpoint with US 54 (you can view photos from there on this page). That was the case until 1978; the 1979 map was the first to show US 14 back at its Broadway/Foster endpoint, where it remains to this day:
Osbaldeston, June 2000
That's looking south on Broadway at Foster. The photo below is looking east on Foster:
Majewski, Aug. 2011
US 14 begins to the north on Broadway. Below we're heading the opposite direction (west on Foster):
Majewski, Aug. 2011
If you turn right on Broadway, you're at the east beginning of US 14, and you're greeted with the sign shown below:
Hargraves
If you keep following US 14 from there, you'll intersect US 41 again in a couple miles.