To add to Lester and Brant's postings above here is some more information:
The 1895 Jay County Fair (also called Portand Fair) was held in Portland IN from Monday September 23 through Friday September 27, 1895. The September 21, 1895 issue of
The Daily Democrat (Huntingdon IN) states there were three bicycle races scheduled during the 1895 Jay County (Portland) Fair. The five mile race for which the posted medal is for was to be on Friday September 27, 1895. This is the only reference I can find for bicycle races at this fair. No mention of Major Taylor and no race results.
Since Major Taylor was born on November 26, 1878 he would have been 16 years old during the 1895 Jay County Fair.
I did find a reference in September 21, 1895 issue of
Muncie Evening Press (Muncie IN) that states Major Taylor was scheduled to race at The Big Diamond bicycle races at Greensburg IN on Thursday September 26, 1895. Greensburg is 52 miles southeast of Indianapolis. These races were advertised as the greatest cycling event ever held in Indiana so it makes sense Taylor would be there. Although the race results posted below do not list Taylor placing in any of the 10 races so the question is was he even there. Greensburg is 100 miles south of Portland so the next question is if Taylor did race and not win in Greensburg on Thursday would he have then travelled 100 miles north to race the next day in Portland. Without seeing the race results from the 1895 Jay County Fair it will be hard for someone to state that this medal was won by Major Taylor.
From the September 21, 1895 issue of
Muncie Evening Press (Muncie IN)
The Big Diamond race results from September 27, 1895 issue of
The Indianapolis Journal (Indianapolis IN)