Records indicate Taylor made these stamps in 1864 while still in Montreal
Winslow & Co. was a genuine carrier operating a service from Boston to Portland in the 1850's.
The company was taken over by Eastern Express in 1857.
Although the genuine Winslow & Co. operated out of Boston, Taylor gave them an office in Montreal with an actual address
I have copies of 3 types - note the main difference in the size and type of the "No 3"