These are not postcards
Bird's eye views
The second image above shows the devastation caused by the 1937 flood. The Chester Park pool and skating rink can be seen on the lower right.
Winton Place / Chester Park Station
The 4 above show the Baltimore & Ohio Railroads Winton Place Depot. Many of Chester Parks patrons used this depot. The last two are postcards.
Streetcars at Chester Park. The first two images are not postcards. The 3rd image shows a early summer car. If you look closely at the 1st image above behind the streetcar at the arched entranceway (with the two towers on top) you can see the tracks of the roller coaster going up into the arch.
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Chester Park
Entrance
path to the Club
House
ticket
booth
Thanks to Ellis Unger for the last image above. It shows a row of 1932 tickets for some of the various rides available at the park.
The Club House
These are not postcards
Lakeside View of Clubhouse
The Lake first appeared in 1902 in the center of the park, oval in shape it took the place where the old arena was located. Starting now and lasting until the park closed for good the water was pumped into the lake from the city's water main on the north end of the park and was discharged back into the mains on the south side. This fresh water was pumped continuously thus ensuring the lake's water was always in pristine condition. There was a period starting in 1904 when the lake was converted to salt water. It was calculated in 1919 that 100,000 gallons of water passed through the park daily. This was of course a very costly expense for the park and was partly responsible for its closing due to the water bill not being paid.
Various views of the Lake
Bathing
beauties
Scenes along the
Boardwalk
Slide the Slides Ride
The last non-postcard image above is the actual photograph used in the making of the 4th card.
The tickler, installed in 1908, was similar to a roller coaster. Passengers entered a circular tickler car and was pulled up to the top of a steeply inclined platform where it was released and, because of gravity, began to fall through a series of serpentine turns that caused the car to twirl while bouncing off the sides of ride causing the riders to slide into each other. The 3rd image is not a postcard.
I believe this real photo card shows a crowd scene at Chester Park. The poster hanging on the column advertises free vaudeville at Chester Park. The building in the background has a sign over the entrance which also says free vaudeville.