This photo is most likely from the Brighton Bicycle Club’s annual race from Glendale to Hamilton. The race start was at the old toll-gate (which is still there if you look closely at the intersection of Springfield Pike and Congress Ave) and proceeded up what is now route 4 to Hamilton, Ohio.
The Cincinnati Enquirer reported in 1895:
There will be large crowds at Glendale and Hamilton as well as along the line to see the annual handicap road race of the Brighton Bicycle Club members to-day. The start will be at the first toll-gate near Glendale and the finish at Hamilton. The start will be promptly at 10:30 AM. The race has been the sole topic of conversation of the Brighton boys, and they have worked hard to get everything in shape for to-day’s event. The best racing talent of the club is entered for the prizes in to-day’s race, and there will be some hot work on all sides. Theo Bruckner, Billy Windisch, the Burger boys, Will and Al Lieman, Eddie Poorman, and Will Billen are among those carded to start.
The first prize for the 1895 race was a diamond pin.
The building in the background is the Century Inn on Springfield Pike, which was built in 1806. In the 1870’s the inn was renamed “Wheelmen’s Rest” to capture the bicycle traffic between Cincinnati and Hamilton.