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History
editIn terms of history, I think there are three sections of the current route to think of. These are 1) east of Wellsboro (from US 15 to Wellsboro), 2) west of Wellsboro to the split with PA 362, then 3) the little windy backroads west to Leonard Harrison State Park.
As for the three sections, both the 1883 History of Tioga County and the 1897 History of Tioga County mention the first east-west state road in the county (approved in 1807) was from the boro of Covington (now Putnam Township) to Wellsboro, which basically is the eastern portion of 660 today (section 1). The road continued west out of Wellsboro towards Potter County, but it is not clear to me if it followed what is now 660 (section 2) or US 6. Both roads meet up near Ansonia to cross Pine Creek, as the gorge makes crossing it further south impossible for many miles. So at least much of 660 east of Wellsboro and perhaps part of it west of Wellsboro were laid out in the ealy 1800s. There was a plank road, but it ran from Wellsboro to Tioga (along what is now PA 287).
Here is a 1915 highway map of Tioga County that shows that almost all the roads involved in 660 today were already in place by 1915. For comparison here is the most recent PennDOT map of the county.
As for the last, windy part of 660 to the park (section 3), it is clear from the 1915 map that the roads were mostly there at that time. If you look at the Leonard Harrison State Park article there is a section on Nessmuk, who died in 1890: "He also described a trip to what became Leonard Harrison State Park: after a 6-mile (9.7 km) buggy ride, he then had to hike 7 miles (11 km) through tangles of fallen trees and branches, down ravines, and over banks for five hours." (It is about 10 miles from Wellsboro to the park today). I have to look at the book again, but my guess would be that his trip was in the 1850s or early 1860s at latest.
Then the lumber era came and the gorge was clear cut - most of the lumber would have been floated out or perhaps moved by railroad. Leonard Harrison bought the land that became the park in 1906, developed it as a park, and donated it to the state in 1925. The Wellsboro Library has the newspaper archives online which is searchable. I found a July 22, 1936 article on paving 660 in the park here.
Hope this helps, it is about all I have / could find easily. Ruhrfisch ><>°° 19:12, 22 December 2011 (UTC)