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Hawthorne Race Course is a venue that offers both live racing and simulcasting. It is a thoroughbred horse racetrack with a one-mile dirt oval and a seven-furlong turf oval. The homestretch on the main track is 1,320 feet long, making it one of the longest in the country. Founded in 1891, Hawthorne Race Course is the oldest sporting venue in Illinois for horse racing, considered America's original sport. The business is family-owned and operated, now in its 4th generation, and has been hosting racing events on the City's border for over a century. The track is famously known as "Chicago's hometown track." Hawthorne is also the only race course in the nation that hosts both Thoroughbred and Standardbred racing. Additionally, they have the largest network of off-track betting bars in Illinois and offer two PointsBet Sportsbooks and a sportsbook at the track.

The Wells Street Art Festival is an annual event on the second weekend of June. It is located in Old Town's popular Wells Street corridor and attracts around 50,000 visitors yearly. The festival showcases talented artists from across the continent specializing in traditional painting, sculpture, artisan woodworking, metalsmithing, jewel crafts, digital arts, and more. Additionally, there is a dedicated performance stage where local musicians, performance artists, and cover/tribute bands entertain the crowd throughout the weekend. Moreover, at the corner of Wells Street and Evergreen Street is a children's play area where kids can participate in arts and crafts, watch a performance, or have fun. The festival also has over 20 food and drink vendors who sell a variety of tasty treats. Visitors can try something from all the excellent Old Town restaurants participating.

History and nature enthusiasts must visit the Field Museum in Chicago. The museum boasts an impressive collection of over 21 million specimens that showcase the history of human and animal life in different regions. One of the museum's key attractions is Sue, the most complete Tyrannosaurus Rex skeleton worldwide. The Field Museum offers permanent and rotating exhibits that provide an insight into the world's natural history. The museum features a wide range of exhibits, including Mammals of Asia, Mammals of Africa, the Grainger Hall of Gems, Underground Adventure, Inside Ancient Egypt, Evolving Planet, The Ancient Americas, DNA Discovery Center, McDonald's Fossil Prep Lab, and the Regenstein Laboratory. The Field Museum Library is home to over 275,000 volumes of research collections, which are fundamental for the museum's scientific staff. The Library provides information on biology, anthropology, botany, geology, archaeology, museology, and other fields of study.