The Harvard Library recently released a new interface for their digital collections, and if you have a personal or professional interest, it might be worth checking out. I searched for vintage bicycles and for Salem.
|Columbia-Pope Catalogue, 1895 (Harvard Library)|
|Interior, model 41 (Harvard Library)|
|Sears 1898 Bicycle Catalogue (Harvard Library)|
|Sears competes on price: $35 compare to $100 etc|
|Sears Acme Queen for 1898 (Harvard Library)|
|Sears Ladies' Bicycle Suits for 1898 (Harvard Library)|
|Bicycle Ambulance, Spanish-American War, 1898|
Teddy himself does not seem to be in the photo, but General Frederick Grant, son of Ulysses, is sitting to the left of the detail here.
Images tagged for Salem were a little thin. But there's another version of President Roosevelt at our State Capitol in 1903. (Previous notes on TR here and here.) Some Trowbridge & Livingston drawings for our 1938 Capitol didn't render right, and it was not possible to say if they were anything new.
Maybe you will find something of interest!
Update, July 13th
I should have added some on the Salem agents for the Columbia Bicycle.
|Band and instruments in front of Sroat & Wilson|
dba The Salem Cyclery
This is now the parking just south of the Bike Peddler
circa 1899, detail, State Library Photo Collection
|Sroat & Wilson, agents for Hartford bicycles|
(Wiggins married Myra Albert)
May 8th, 1897
|Sroat & Wilson, and Jos. Meyers & Sons|
April 14th, 1899