Nice to see a fellow "New Englander" ( part time) on the forums . wt1 article is great ... the area with the bridge , I believe, is "bridge street " which crosses the Saugatuck River . I know I have seen that narrow bridge depicted in that stamp . It is metal today not wood.
The church on the hill is still there . I think it is " Greens Farms Church ".
http://www.greensfarmschurch.org/faith_history==========================================================
Driving directions to 70 Hillandale Rd, Westport, CT 06880
Bridge St
Westport, CT 06880
1. Head east on Bridge St toward Compo Rd S
0.1 mi
2. Continue onto Greens Farms Rd
0.8 mi
3. Turn left onto Hillspoint Rd
0.9 mi
4. Turn right onto Hillandale Rd
Destination will be on the right
0.6 mi
70 Hillandale Rd
Westport, CT 06880
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Best John