The biggest draw for me to Milestone's is its reliability and consistency. I've yet to have an unpleasant experience at this location, which has a gorgeous interior and great outdoor patio (note: outdoor seating arrangements are limited to groups of 4).
The girl and I almost always order Spinach & Artichoke Dip. This item has been on Milestone's' menu for years, and with good reason.
Beer: Milestone's used to promote their own Palomino beer, but they have phased it out and now offer the usual suspects on tap: Guinness, Keith's, Creemore. Bellinis are always popular with the ladies.
I never stray too far from the Grilled Mediterranean Chicken for a main. It's not too adventurous, but the combination of goat cheese and pomegranate molasses is hard to ignore.
Milestone's is a bit steep for the food, but the location and consistency keep me coming back.