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Winston Bridge


Winston RR Bridge Tunnel South entrance 69 highway level

the grass at the bottom of the photo is the narrow shoulder of 69 highway. The tunnel is just a few steps from 69 Highway but driving by you will not see it unless you know to look for it

Photo taken by Paul Hamby in April 2015


BH Photo #323323


Historic Significance 

Written by Paul Hamby

Tunnel under Rock Island railroad near Winston, Missouri. Jesse James and his gang hid in this stone arch tunnel while waiting to hold up the train at Winston.

On July 15, 1881, Frank and Jesse James, Wood and Clarence Hite, and Dick Liddil robbed the Rock Island Railroad near Winston, Missouri of $900 (equivalent to $14,000 in 2015). The train Conductor William Westfall and a passenger John McCullough were killed.

William Westfall’s grave bears an inscription reading: “Killed by train robbers July 1881. His grave site is in Plattsburg Missouri about 35 miles SW of Winston.

This spur is long abandoned and the tracks were removed. However the Train Depot still stands in good condition and is maintained by the local historical society. The depot is approximately .4 miles west of the tunnel.

The tunnel is built from hand cut rocks and it is a testimony to the quality of workmanship that it still stands in excellent condition 150 years later


Abandoned stone arch bridge over a tributary of Dog Creek on former Rock Island Railroad
Daviess County, Missouri
Very Good Condition
- Chicago, Rock Island & Pacific Railroad (CRIP (1866-1920); RI (1920-1975) ROCK (1975-1980))
Stone arch
Approximate latitude, longitude
+39.87678, -94.12622   (decimal degrees)
39°52'36" N, 94°07'34" W   (degrees°minutes'seconds")
Approximate UTM coordinates
15/403692/4414688 (zone/easting/northing)
Quadrangle map:
Inventory number
BH 67230 (Bridgehunter.com ID)


19th Century (7,667)
Abandoned (3,729)
Arch (12,239)
Built 1871 (118)
Built during 1870s (1,129)
Chicago, Rock Island & Pacific Railroad (1,116)
Daviess County, Missouri (81)
Deck arch (11,477)
Missouri (6,317)
Railroad (15,663)
Stone arch (3,099)

Update Log 

  • April 26, 2015: New photos from Paul Hamby
  • April 25, 2015: Essay added by Paul Hamby
  • April 25, 2015: Added by James Baughn based on a tip from Paul Hamby