Headhouse square borders on Old City and Queens Village in Philadelphia. It is a beautiful historic area with cobblestones and many delicious restaurants and bars. We lived in the square a couple years ago and it is our favorite part of the city. We also were engaged underneath the Head House shambles. A couple of our favorite restaurants and bars in the square are the Twisted Tail and Pizzeria Stella. Both have delicious food and Twisted Tail has great cocktail options.