Old City

Philly is bordered on the east by the Delaware River (you can see New Jersey on the other side), and the city has taken great pains to activate the areas along the waterfront. One of our personal favorites: the kid-friendly wonderland that takes over Penn's Landing during the summer months. Between Memorial Day and Labor Day, the Delaware River Waterfront organizes an outdoor roller skating rink, with other carnival activities like mini-golf, games, and a Ferris wheel. Food-wise, you can pick up hard-shell crabs and cheesesteaks with a side of old-school crinkle fries at Chickie and Pete's, and there's an ice cream stand from Franklin Fountain in the summer. They recently debuted a winterized version around the holidays, when the roller rink gets covered in ice, and ice cream gets swapped out for egg nog and hot chocolate.