I contacted the Glenn H Curtiss Museum to see if they had any information on the motorcycle as suggested by Heather Rojo. They said they didn't have anything like it, but they thought it was about a 1910 Indiana.
Does anyone know anything about this motorcycle and sidecar? What year is it from? I think it says Indian on the side. I tried looking it up and didn't find anything exactly like it. Some looked similar but the sidecar was different.
Oh, by the way, the riders are my grandparents, Jim & Ethel Hoover.
Please leave a comment and let me know someone is looking at this. I haven't had a comment yet so it feels like no one is reading anything.