At the very southern end of town off of Rt 7B South were two bridges over the Otter Creek giving road access to the Wylie and Smith households. That access may have extended to a couple other homesteads in Wallingford as the roadway shown on the 1869 map below seems to indicate. At the time these bridges were built Creek Rd did not extend south of Walker Mountain Rd. There was no road access from Clarendon to properties on the west side of Otter Creek prior to these bridges being built.
The history of the bridges is not known, including whether both existed at the same time or one succeeded the other. It is also not known how many times these bridges may have been rebuilt but the abutment for one of them was raised indicating at least one rebuilding. That final iteration of that bridge also used railroad ties as support beams rather than wood. That might help date that final reconstruction.
The Wylie house was built in 1791 for James Wylie (1746 - 1791) and his wife Prudence Crary (1746 - 1813) who had started farming on that site in 1777. It then passed down for two additional generations ending with William Wylie (1833 - 1888) who died unmarried and without children. The Wylie home still exists and now fronts Creek Rd. It has been substantially expanded and altered and is not easily recognizable as having a core as old as it is.
The Smith household appears for the first time in this location in the 1840 census. This was Perry Smith (1814 - 1871) and his wife Lovina Button (1816 - 1899). Perry's parents Lemuel Smith (1792 - 1859) and Azuba Parker (1789 - 1861) were in Clarendon but it doesn't appear that they were in this spot. Perry and his family were there again in 1850. In 1860 22 year old son Lucian is living there as head of household with his wife Laura and sister Emma. Perry is living just below the town line in Wallingford on what is now North End Drive with the rest of his family. In 1870 Perry is still in Wallingford and Lucian is found in Illinois.
The Smith house is still there and is said to date to 1820. If that is correct then another family preceded the Perry Smith household in this location.
Based on the dates associated with the Wylie and Smith families, the first bridge construction likely goes back to the early 1800's or even earlier.
The cover photo shows the abutment for the bridge that was raised up higher (see the cement on top of the stones) and whose final iteration used railroad ties for supports. The original stone abutment is very substantial for servicing just two farms which begs the question as to whether the roadway shown on the map below was in fact a road going down into Wallingford.
Below is a segment of the 1869 map showing these two households and the lines indicating perhaps a farm road extending down into Wallingford. Below that are two photos of the other bridge. The first shows the abutment which is not in as good condition as the one in the cover photo. The other photo shows a rock wall side to what was an elevated roadway built going from the bridge towards what is now Rt 7B South. The land fronting Rt 7B South appears to have been significantly altered and thus this elevated roadway does not extend all the way to Rt 7B South. Perhaps the land was too soggy in that area or flooding precipitated the need to build the elevated roadway.