There are several farms in the Woodstock area. Greig Farm in Red Hook (about 30 minutes from Woodstock) has some great picking and friendly staff. Click here to find out what fruit is available each month.
Jenkins-Lueken Orchards in New Paltz (30 mins) starts off with cherries in the early summer followed by raspberries and blueberries with blackberries around mid-August. Minard Farm in Clintondale (45 minutes) has pick-your-own apples and pumpkins starting at the end of August.
Kedler's Farm, Kerhonkson (40 mins) have strawberries available during the first week in June. Plan to visit the farm early for the best pick-your-own strawberries. These are followed up by blueberries and then a ton of other fruit and veg.
Many of the farms have markets, cafes and activities for kids especially during holiday weekends.