I had a quick look for the tricycle. I found a few similar ones on ebay and such, without any firm date information. The most useful example appears to be this auction for an "Antique Vintage Wooden Kiddie Kart Child's Bike trike Riding Toy Tricycle", which states:
Age: Quite Old - Maybe 60-80 years old???
Marked: Kiddie-Kar (Kart)
The age range isn't terribly helpful, and the design could certainly be older still. The manufacturer/model might be worth following up. There seem to be quite a few different Kiddie Kar(t) tricycle designs though.
Edit: I was reluctant to click on a "tricycle fetish" website but it appears harmless enough. This "1918 H.C. White Kiddie-Kar" page looks about right, but may be too early to help pin down a date.
H.C.White Kiddie Kar http://www.tricyclefetish.com/imagemagic.php?img=images/20090818213919-DSCF7016090818.jpg&w=220&h=222&page=prod_info
Edit 2: There's a Flickr page by "Okinawa Soba (Rob)" showing an advert for the Kiddie-Kar and some history of the H.C. White company.
in 1919 ... [White expanded] output to 2 million Kiddie-Kar “automobiles” per year.
After more than a decade of tremendous success, the company failed in the Great Depression
So this tricycle, was made between roughly 1918 and 1930. They were hugely popular and some could easily have lasted many years. So if the one in your photo is a Kiddie Kar, it can't be earlier than 1918 but it could be much later.