I pulled this out of a larger cycling article. The fact that the Globe published the inner workings of this local club is interesting. In 1886 they would have been riding on dirt roads, and I believe Weld street was still farmland at the time.
So when was the last time there was a bicycle race in the streets of Jamaica Plain?
Boston Daily Globe November 7, 1886
Jamaica Plain Pedalers.
A Club Road Race in Which all Members Must Run or Pay.
The members of the Jamaica Plain Bicycle Club have watched with no little envy the road races given by the different clubs about Boston during the past month. At one of the recent meetings a member of this club was heard to remark that if his club could not give a better conducted series of road races than those in progress they would sell out. Accordingly, at the next meeting of the club road racing formed the chief subject of debate, and it was finally decided to hold a series of club races on Tuesday afternoon, November 9. A number of schemes for the improvement of the present methods of conducting road races were decided upon, chief among which was that of fining of all members of the club who failed to start in the race. They fully appreciated the fact that there were some among their members who were by no means "flyers" on the road, but a large field of starters they must have, and this seemed the most practical method of attaining the end desired. Among the more worldly-minded members there was considerable objection to this race or "ante up" scheme, for, as they expressed it, it would be "deuced hard to collect the fifty cents." However, it was decided to give the scheme a trial, and as the club is young and very enterprising it may prove a success.
There are to be two races. The first is to be for ten miles, and the three first men in are to receive for prizes a bicycle lantern, a pair of ball pedals, and a bicycle saddle. The start will be made at 3 p.m. and the course will be as follows: Start at club house, Centre street, left to Pond street, left to May street, right on Centre street, right to Weld, left to Corey, left to Centre, left to May, right to Pond, right to Orchard, right to Centre, to May, right to Pond, right to Centre, to finish at club house.
The second race will be five miles over the following course: Start at 3:05 p.m., from clubhouse, Centre street, right to Burroughs street, seven times around Burroughs, Pond, Eliot and Brewer streets, to Burroughs, to Centre and finish at clubhouse.
The member who is looked upon as the most likely winner is McCausland, president of the club, and a sergeant of the local police force. McCausland is a fine rider, and would have made a good showing in the recent races of the Massachusetts club had it not been that he broke his Star bicycle.