In terms of picking the actual show itself, I would suggest The Color Purple. It's 8 blocks, which will be tight, but I think you can make it. Waitress is 2 blocks closer to the theatre, and therefore slightly less of a risk, but I think The Color Purple is a better show. 8 blocks isn't actually that far for NYC, but given the Times Square crowds, it will be tougher.
Other tips for your mad dash:
--MAKE SURE you go to the bathroom at the intermission of your matinee
--Bring some kind of snack with you that you can quickly scarf down between the shows (not DURING either show).
--Have a full water bottle
--Be polite but assertive as you're walking through the crowds on your way to the Winter Garden. Keep to the sides of the sidewalk when possible, and weave through the crowd as best as you can. If you have to, and if it's SAFE, walk just off the curb.
Updated On: 7/3/16 at 10:56 AM