This is my favorite time of year for shooting outdoor photos... the nice and cool weather is great so your subjects won't be hot and sweaty, and the fall colors of the leaves add so much warmth and atmosphere to your pics. Also, with the earlier sunset times, we found that the golden hour, the hour before sunset, is a little easier to manage with younger subjects.
The first thing I want to point out is that in spite of your first impulse, do not dress your subjects in orange for photos at a pumpkin patch. It seems most Halloween clothing only comes in three shades of pumpkin orange. Between the orange pumpkins and the orange leaves, you're going to want your subject to really pop out. Blue is the most complimentary, but anything dark and "cool" (blue, green) will help.
Posing the kids in a pile of pumpkins, or a happy couple walking through the leaves is fine and all, but you can get some great, genuine expressions when they're playing around and letting loose. My 4-year-old son goes nuts when he can run, jump, and collapse in hay. Hay rides, hay piles, hay mazes... it doesn't matter. I used a zoom lens for the flying hay pic so I could have a further vantage point and get the action wherever it happened. This time he was all over the place. I particularly love how the falling hay adds a bit more depth and energy to this pic. One note to point out, like I've said before, be mindful of other parents and their children in busy situations like hay piles.
I love love love the backlighting that gives the hair that halo. Basically you shoot with the sun behind your subject. The trick is making sure that their face isn't too dark. If you notice in some of the pics, I also have that golden haze across the entire photo in addition to the halo. That haze is glare from the sun. So sometimes you can nab both. But I find the backlighting halo gives some real warmth and "excitement" to portraits. Either in candid action shots, or posed portraits. It's pretty easy to figure out the right positioning when you're out in the field, or pumpkin patch. Make a note of when sunset occurs, and grab this lighting in that hour leading up to sunset.
Typically its not good to shoot photos in the middle of the day, the lighting is very harsh, and your subjects will be squinting. In addition, there will be harder shadows on the faces, and it's not great for portraits. But sometimes you can get lucky. At the Weber farm market, the roof over the market area was a white translucent tarp strung above the rows of pumpkin bins, acting as a diffuser. It's true, I did add one of those cotton candy washes in photoshop to this particular photo. But this photo was taken moments after the orange shirt photo above.
Another great thing about Fall Festivals and pumpkin patches are all the unique photo ops. Giant plywood pictures with strategic holes cut out seem to be a staple, but I love the unique opportunities, such as posing in this huge tractor wheel hub, or operating an old fashioned hand pump, for interesting photos that you don't typically get. In these cases I prefer Americana/heartland to overly commercialized surroundings in photos. It helps the photos be more timeless. Pumpkin patches, fall fests, farms, and vegetable markets just have a warmer, more human feel. So keep your eyes peeled, you never know when you're going to have a unique moment.
The lighting is just unbeatable right now. The fall colors are fantastic, and the opportunities are everywhere. Get out there and start taking pics that'll impress your friends and family, and you'll keep forever.
Some of my favorite local pumpkin patches are Butler's Orchard, Homestead Farms, Larriland Farms, and Weber Farms (closer to Baltimore). They have lots of activities and great settings for photos.