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Middletown is home to the World's Largest Jack-in-the-Box that features a giant clown head pop out of a 50 foot (15.24 meters) high structure every minute. Bill Ziegler, owner of Wild Bill's Nostalgia Center, teamed up with artist Chris Hausback and came up with this unique roadside attraction that has thousands of visitors every year. Wild Bill's is a unique place where you will find everything from rare toys, random objects, games, magazines, books and collectibles. Along with the largest jack-in-the-box, Wild Bill's is also home to the world's largest bobbing head which is definitely worth a visit.
Established in 1778 Putnam Memorial State Park is widely considered to be the oldest state park in Connecticut. The park was named for General Israel Putnam, an American Revolutionary War veteran who chose the current site for his troops' encampment. The park is a popular visitor attraction today, with a museum, picnic sites, an interpretative trail as well as outdoor activities like fishing and ice skating.