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[Bruce]

This Wikipedia article claims that there was a US 20 Business loop in Bend prior to the construction of the Bend Parkway, as its route description would not be possible on modern roads due to the expressway's construction. Did it actually exist?

[stevashe]

Old Oregon state maps from the 90s before the parkway was built do show a Business US 20 in Bend (source). But it's only a spur along Greenwood and Newport, which does align with the end of the route from Wikipedia. As for the rest of the route, even looking on historical aerials in Google Earth (the Bend Parkway opened in 2001 and a 1994 aerial is available), Deschutes Place did not connect to Wall St and E 1st St did not connect to main US 20, so the rest of that route is either made up or a guess.

Edit: Looks like Division St was renamed at some point, because looking at the 1980 Oregon state map, it does show a full business loop with the same street that is called Division St on the 90s maps marked as E 1st St:

[NE2]

20 Business and 97 Business were the original state highways as defined through Bend in 1935 (pre-1927, future US 97 seems to have gone south on Hill from Franklin). The cutoff on 3rd north of Franklin was added after 1960.

[Bruce]

Old Oregon state maps from the 90s before the parkway was built do show a Business US 20 in Bend (source). But it's only a spur along Greenwood and Newport, which does align with the end of the route from Wikipedia. As for the rest of the route, even looking on historical aerials in Google Earth (the Bend Parkway opened in 2001 and a 1994 aerial is available), Deschutes Place did not connect to Wall St and E 1st St did not connect to main US 20, so the rest of that route is either made up or a guess.

Edit: Looks like Division St was renamed at some point, because looking at the 1980 Oregon state map, it does show a full business loop with the same street that is called Division St on the 90s maps marked as E 1st St:

D'oh. Totally forgot that Oregon has a good map archive to search through. Thanks for doing the heavy lifting!