When I lived in Utah, I had a hard time describing Connecticut to people. It's sandwiched between New York, Massachusetts, and Rhode Island but it truly has its own identity. The shoreline shifts from a suburb of New York to an extension of Rhode Island. The central area (especially around the Connecticut River) is quaint and iconic, filled with old towns and historic homes. The northeast corner has been dubbed the "quiet corner" and it's known for exactly that.
But the northwest corner is my favorite part of the state. It's known for rolling hills, sleepy towns, and boarding schools that resemble college campuses. This tiny corner is where you can find old covered bridges, quiet country stores, and old romantic inns. The Housatonic River snakes through the area and Route 7 offers a scenic drive of fly fishermen and summer sunbathers. Once you leave the river, you can follow 50 miles of the famous Appalachian Trail and hike to the state's highest point. It's a gem year round but my favorite time is fall. The bugs are gone, the leaves are turning, the apple orchards are open, and bonfire season is in full swing. It's an area I keep coming back to, for a day hike any time of year or an overnight excursion in the summer.