How Do I Loop Through a Date Range in Reverse?

Try upto/downto :

irb(main):003:0> sd = Date.parse('2010-03-01')
=> #<Date: 4910513/2,0,2299161>
irb(main):004:0> ed = Date.parse('2010-03-15')
=> #<Date: 4910541/2,0,2299161>
irb(main):005:0> sd.upto(ed) { |date| puts date }
2010-03-01
2010-03-02
2010-03-03
2010-03-04
2010-03-05
2010-03-06
2010-03-07
2010-03-08
2010-03-09
2010-03-10
2010-03-11
2010-03-12
2010-03-13
2010-03-14
2010-03-15
=> #<Date: 4910513/2,0,2299161>
irb(main):006:0> ed.downto(sd) { |date| puts date }
2010-03-15
2010-03-14
2010-03-13
2010-03-12
2010-03-11
2010-03-10
2010-03-09
2010-03-08
2010-03-07
2010-03-06
2010-03-05
2010-03-04
2010-03-03
2010-03-02
2010-03-01
=> #<Date: 4910541/2,0,2299161>