Fall is harvest season so I'm into activities that remind me of that even though I don't live somewhere rural. If you can find a cider maker that will do pressings at the fest, that's interesting and educational. Fruit tasting - most people don't know of the different varieties of fruit and how they can taste. You might contact davewilson.com and see if you can set up a tasting in your area (I don't know where that is. Dave Wilson Nurseries focuses on CA but possibly does things elsewhere. You might contact NAFEX for help in setting something up on the East Coast.) A good kid's activity is making butter. They can make it by shaking cream in a jar. Vintage farm equipment, esp. old heritage breed draft animals is cool.

I'm just brainstorming here. This may be way out of the monetary/energy range for what you have in mind.

Ooh, thanks, Spidra.

this is one of those things where we got spanked for staying within our means last year, so now we're in a "spend money to make money" mode, and we'll see what kind of donations/community support we can drum up. But any and all ideas are welcome, as I am too at just a brainstorming stage.

We're a historical estate, used to be a farm, so a lot of that would really work in staying in tune with our history.

pumpkin contest -- or oher biggest veggie contest

Pumpkin catapult? I've seen them on TV news coverage of state fairs a few times. Probably the permits and safety stuff would be too difficult.

You might try contacting Ardenwood Farm in Fremont, CA. They're a historic farm estate. They do all sorts of events that play off their farm history.

Tying in with the locavore movement, it might be good to have a very local farmers market on site during the festival, including folks who make things from local farmed ingredients like local jam, local beeswax, etc. If you ask them to bring demos of what they do, they might be into that.

I love biggest vegetable contests, but most gardeners would like to know in the spring, so they can throw ridiculous amounts of care at one vegetable.

Things like baking and canning competitions (best pie, best chow chow, etc.) are good if you want community participation, and you can make some money from entry fees. It helps if you can corral a local celebrity food person. It would be historically accurate.

Cake and pie sales at county fairs are often done by church groups or PTAs here, so you could invite such groups so that they could raise funds and it would be an inexpensive draw.

Anything in which someone is making something an old fashioned way is interesting, and maybe you have a business in the area that makes cider or syrup or something else that they'd like to promote. (In the South, fall fairs used to have a cane mill with a mule walking around and round and someone boiling down the cane syrup.)

Another possibility is a children's art competition with a fall theme.

I personally like mule pullings, but I think that's mostly just me.

juliebird, you might also want to check out Stone Barns Agricultural Center. I know the executive director if you want someone to call.

Wow. In completely inappropriate coverage of Chelsea Clinton's wedding, from the New York Times: [link]

Arguably the most important question is who will officiate. The groom is Jewish, the bride Methodist. Will there be both a rabbi and a minister? Will vows be exchanged only after the Jewish Sabbath ends Saturday night? Will Mr. Mezvinsky seal the deal with the traditional smashing of a glass? Will Hiram Monserrate be at home taking notes on the proper way to break one?

so many great ideas! Thanks, Cash (hey, it's only a state away!).

What about live music? When I think fall and music, I go to a banjo and fiddle/bluegrass place.

I think about any acoustic music is fine. If you want to push the historical route, go with someone who performs old American folksongs (or sea shanties if you're close to the sea). Contra dancing is also an old form of dancing that was popular in the US in the 18th and early 19th centuries (it's still danced today, though). A lot of the moves are the same as square dancing but it's even more of a mixer dance. The couple will interact with almost every other couple on the floor. If you get a caller who can stick to simple contras, it's a good way to get people moving and involved.