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Pittsylvania Wayside Park was first created during the Great Depression as a picnic stop for families that were travelling. The Civilian Conservation Corps, which was established by President Franklin Roosevelt as a way to improve infrastructure and provide work for the unemployed during the Great Depression, built seven Wayside Parks in Virginia, including the park in Hurt.
For people travelling along what is now U.S. 29 business, the park served as a real attraction, especially since there were not as many gas stations and restaurants. Tens of thousands of people visited the park over the years. For locals, many of whom grew up going on field trips to the park and swimming in the Sycamore Creek, the park holds special meaning.
Over the years, the park gradually deteriorated since no organizations maintained it. In recent years, the Pittsylvania County Parks and Recreation Department has completely revitalized the park, enhancing and restoring some of its most distinct features while adding new ones that still reflect the park's history and character. For instance, the new playground has many train-themed elements to match the train trestle that sits right across the street.