Exploring big cities can be exhilarating but I love spending a few days in a small town every now and then. There are so many great small towns in Connecticut but Madison holds a special place in my heart. First settled in 1641, Madison is full of historic homes and a charming downtown district. It occupies a central location on Connecticut’s Long Island Sound shoreline which means it boasts both tree lined streets filled with New England charm and stunning beach views. Since it’s a small town, most of it is quite walkable, especially on a beautiful day. It’s definitely a sweet little town to visit for a long weekend and I can’t wait to escape to it again soon.