Help dating photos? LS&MS

Researching family genealogy, and I came across these photos. No idea who the men in the photos are or even when they were taken. Hoping someone who knows about the trains, can help me narrow it down, by figuring out at least ballpark when or where the pics were taken? I have a fourth picture, which does not show as much of the train, but also has a part of the NY Central logo.

It's a little bit of a shot in the dark. My family is from Cattaraugus County, NY, if it helps at all. I'm not even sure these men are family, thought my ancestors were all farmers! But they're neat photos anyway, would be fun to know a little more.

Thanks in advance,
Emily

Well, the caboose is marked LSMS, which is Lake Shore and Michigan Southern, the former New York Central's mainline from Buffalo to Chicago via Cleveland. The Lake Shore had some branches too.

There's a New York Central System Historical Society in Gates Mills, OH (outside Cleveland). They probably have a website and people who can date it fairly precisely. Their annual meeting is the 6th & 7th of May in Marlboro, Ma.

Hi edbear
The locomotive in the photo is a 2-6-2 type, built by Brooks Locomotive 1n 1905, the LS&MS had 35 of these types. The 2-6-2 's last until 1947, finally scrapped.
As for the cabooses, I could not find any information on them, I tried looking up rolling stock information etc. So as for dating photo, just a guess 1935 to 1947? Pat

In the first photo, the guy leaning out the window just looks to me like it's earlier than 30's or 40's. I'd take a guess at teens.

Obviously the rolling stock did not all get re-lettered immediately, but since the LS&MS became part of NYC at the end of 1914, I'd say no later than mid 1920's - the cabooses would probably have become NYC by then.

I have no specific useful knowledge, but… my impressions looking at the photos were in line with BR&P's. The style of clothing makes me think of early rather than mid-20th C. The wooden caboose lettered for LS&MS (with fairly old-fashioned looking trucks) is clearly in service. The LS&MS was a subsidiary of the New York Central by the late 19th C, but was later (as BR&P notes) consolidated into the parent company. I don't know how often cabooses got re-painted, but I doubt it would have been repainted with LS&MS lettering after the consolidation.

Having a life-long interest in cabooses, I have accumulated various data from multiple sources. Sometimes it all fits, sometimes it contradicts. But for what it's worth I have the following.

I show NYC cabooses 17384 - 17406 rebuilt from LS&MS between 1914 and 1918. I also show that NYC's short cabooses, found in the lower 18000 series, were ex LS&MS. No exact number of how many there were. These cabooses, after rebuild, resembled the typical NYC lines east cabooses with the low cupola, but only had 2 windows instead of 3 on each side. But I don't know if there were two separate groups of LS&MS cabooses rebuilt - one onto the 17000 series and one integrated into the 18000 series - or if there was a second rebuilding.

But the key point for THIS discussion is that if that source is accurate, after the December 22 1914 date for LS&MS becoming a part of NYC itself, it took about 4 years to assimilate their equipment.

So using Pat Fahey's built date of 1905 for the loco and the 1918 estimate for caboose relettering I'd say we have a range which should work. Of course nothing says those pics were all taken at the same time - the first caboose pic, with the older clothing and appearance, could have been let's say 1895 while the loco shot might be 1910.

Thanks everyone for all your comments! Early 1900s sounds like a good starting point, I'll check against what census records i can find and see if it matches anyone!

The fourth pic I mentioned is also attached. It focuses more on the men, than on the train, but thought you may like anyway.