1. Larriland Farm
Woodbine, Md.
Drive time from D.C: About 1 hour
Larriland Farm has been a go-to place for locals to pick their own pumpkins, apples, berries and peaches since 1973. Picking isn't just business as usual here; you can get to the pumpkin field via a hayride that'll see you ford a stream and snake through the woods.
Time Out tip: On weekends, be sure to pick up an apple fritter or two at the market—they're made from the owner's family recipe. Food trucks are also available on Saturdays and Sundays.