LORELAI: I gotta tell you Kirk, these are really good for amateur shots.
KIRK: Thanks. That’s me and my parents on vacation in the Berkshires.
The Berkshires are a highland region in the western part of Connecticut and Massachusetts. More specifically, The Berkshires is often used to refer to the part of the Green Mountains that extends into Massachusetts, while the part that goes into Connecticut is called the Northwest Hills or the Litchfield Hills. Because of this, I suspect Kirk and his parents were in Massachusetts.
The Berkshires is a popular tourist area, with picturesque towns, hiking trails (including part of the famous Appalachian Trail), and waterfalls, as well as numerous cultural and artistic activities.
The Annotated Gilmore Girls 