I found a rather inscrutable use of dateutil recurrence rules in StackOverflow which generates a series of dates corresponding to the third Wednesday of the month: import dateutil.rrule as dr import dateutil.relativedelta as drel dt = datetime.datetime(2012, 1, 1, 0, 0) rule = dr.rrule(dr.MONTHLY, byweekday=drel.WE(3), dtstart=dt, count=12)