Litchfield County, Connecticut

Due to the fictional hamlet of Star's Hollow, which was modeled on the actual town of Washington Depot, Gilmore Girl fans will be familiar with this region. But it wasn't just movie magic that gave this area a Rockwellian feel; many of the tiny hamlets are also worth exploring. The various communities take pleasure in their expertise and exude that classic New England vibe.

You should plan a meal at Al Tavolo (the menu is constantly changing, but if you can, request the chestnut soup), then save space for the Dairy's justly renowned ice cream. Since this is New England, there are many opportunities for winter activities, including the 400+ acre Black Rock State Park for cross-country skiing and Mohawk Mountain, the oldest ski and tubing resort in the state. After that, stop by a Mano for coffee and pastries to recharge.

From New York City, it takes around two and a half hours to go to this picturesque area of Connecticut. Take Route 7 which meanders through much of the county from the Hutchinson River Parkway to I-684. The majority of the state's northwestern region, which borders New York, is covered by Litchfield.

Location: northwestern Connecticut