Harry would order a screwball, no sorry he is a screw ball. Seriously he would get a a Whiskey and coke. He seems like a nice normal guy, than you get on him and there is some fire in that.
Bert - the mare is a steady eddy, and a little butch she would get a dark, stout beer like Guinness.
Daisy would go for a cherry bounce. Shasta would be asking for a whiskey sour and Ivy I already replied for but she'd go for something fruity, frothy and fun. Preferably with an umbrella and no alcohol. The paint would want an Appletini, Cherry would go for a Shirley Temple, Mac said to heck with the drink he'll take a frozen watermelon hold the vodka. The QH mare said milk for babe and a shot of wheat grass, please. Chili has a request in for Tokillya (orange tequila) and Jasmine claims a Lavender GT might go down nice.
It's hard to stay hydrated in the summer heat, but when those frosty fall evenings come around in October I can picture my mare and I sharing warm spiced cider amply spiked with dark rum and my colt would want a root beer.