In 1936, as Bridgeport celebrated the centennial of its founding in 1836, the city's Chamber of Commerce sponsored a exposition/exhibition of local manufacturers and other businesses. The exposition was held within the buildings of the Remington Arms Company (a major manufacturer of guns and ammunition in Bridgeport at the time) between May 15 and 23, 1936.
The event was definitely a local business-focused fair; it did not include a midway with games and rides or a variety of live entertainment options. Instead, local vendors such as the Acme Shear Company, Bridgeport Brass, Crawford Laundry Company, Hoffman Fuel and Murphy's Signs had exhibit booths for their wares and/or services. Visitors also had the chance to see multiple wards of the Bridgeport Hospital, a dental clinic (with patients), an active high school classroom (with students) and a reproduction of an old-time nickelodeon (i.e., early motion picture theater). Also on display were replicas of a selection of freaks and oddities - human and animal - whose original/living versions were included by PT Barnum in his shows. The Exposition also included displays of live manufacturing of many of the products produced in Bridgeport at the time.
The Bridgeport Chamber of Commerce produced a commemorative medal for its Exposition; the Chamber did not sponsor the commemorative half dollar, the coin was sponsored by Bridgeport Centennial, Incorporated.
The medal's obverse, depicting a kneeling male figure reading a page labelled "HISTORY", is meant to symbolize the accomplishment's of Bridgeport during its first century. Behind the central figure is a parallel "Then (1836) and Now (1936)" scene of Bridgeport ('Then" is the top scene.). The reverse design featuring a female figure seated on a blank page while holding a quill pen is meant to represent Bridgeport's still-to-be-written future.
The medal was designed by Alice Harvey, a local high school student; it was produced by the local Jennings Brothers Manufacturing Company - a producer of fine metal crafts such as bookends, candlesticks, clocks, figurines, flatware, jewelry boxes and picture frames. Mintage was specified as being limited to 2,500. (The leaflet that accompanied the medal [shown below] has additional information.)
I've seen reference to the medal being silver, but I believe it is actually a base metal piece with a silver wash; the medal is 70 millimeters in diameter. Also, my medal is edge-marked "1" but I doubt very much it is the first of the medals produced; it wouldn't surprise me to learn that all such medal have a "1" on their edge.
IMO, the medal does not rise to the level of the coin in artistic merit, but it does make a nice supplement to the Bridgeport half dollar.
1936 Bridgeport Centennial Exposition Medal

1936 Bridgeport Centennial Half Dollar

For more on the Bridgeport half dollar, check out:
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1936 Bridgeport, CT Centennial-
1936 Bridgeport, CT Centennial - RevisitedFor other of my posts on commemorative coins and medals, see:
Commems Collection.