Where are you going to be and when? There are several places to pick apples on the North Shore. It's a little early for most of the apples and definitely early for pumpkins. Some farms actually ship in pumpkins and lay them out on their "pumpkin patch" (I saw this at Russell Orchards in Ipswich), so call and confirm if they grow their own if that's important to you. Also, call the orchard and see which trees are open that day. Some only allow limited choices on weekdays (again, Russell). All that said, these are the ones I know a bit about:
Russell - on the road to Crane Beach. Very nice farmstand w/ their own cider donuts, cider, and wines. I think they have a playground and a petting zoo.
Connor's Farm - in Danvers. Smaller, a nice sandbox for kids to play in, lots of different types of apples in a small area, but they aren't labeled, so you have to try them all and see what you like.
There's one in Peabody that I know a lot of people like. I can't think of the name, but I'm sure someone else will provide it or a search would easily find it. I've heard they're very generous w/ their pesticide sprays, though.
Cider Hill - in Amesbury. IPM so they use less spray than most. Lots of different types of apples. I've had their fruit but never been there.
There's a certified organic orchard in Harvard that someone here recommended. They have a website so I'm sure you can easily find it.
Enjoy!