Harvard Square
Then: The Bow & Arrow Pub and Baskin- Robbins-Dunkin’ Donuts at the corner of Massachusetts Avenue and Bow Street were institutions in the neighborhood, and they provided the setting (though the bar interiors were actually filmed at the Upfront Bar & Grill in Toronto) for the memorable night when Will meets Skylar.

Now: Both establishments closed shortly after filming, and the Grafton Street Restaurant and Bar has taken their place. A new Baskin-Robbins-Dunkin’ Donuts opened three years ago next door to the old location.