Do you think your oaks will produce sometime in the 4th season? How about timeframe for chestnuts? Have you done this in the past / have pictures of a 4 year old or older you have planted?Exo,
Those came from a guy in Missouri but, they do live in northern zones too.
I actually have purchased nice bur oak and swamp white oak seedlings from the Missouri Dept of Conservation (MDC) but, they are sold out for this year. They post online in late October -early November. They just arrived Saturday so I'll be busy this weekend. I think they worked out to $.50 a piece including shipping. They have an oak called the Concordia that is supposed to be a fast grower and producer and has lived in zone 4 Wisconsin. May try them next year.
If you're looking for acorns then I'd check with Oikos in Michigan
They usually have them available for a couple weeks in November
If it were me I'd also try chestnuts. I get them in late October from Pike County Illinois. Chestnuts are easy to germinate and grow. Same as how I showed here. They'd do well in Mass.