Gypsy Hill Park is a recreational park situated in the center of Staunton, Virginia, United States, where Churchville Avenue (off of route 250) and Thornrose Avenue intersect each other. The park itself contains various public services and attractions, including football and baseball fields, the Thomas D. Howie Memorial National Guard Armory, a large bandstand pavilion, a golf course, a basketball court, a gym, and the central duck pond equipped with food dispensers, allowing visitors to feed the ducks and fish. Throughout the expanse of the park are multiple sites complete with picnic tables, grills, and covered pavilions. Constitution Drive, an almost -mile-long (2.4 km) road, encircles the duck pond, runs through the entirety of the park, and is often used as a walking and bike path by visitors.
The miniature train, the Gypsy Express, is another classic part of the park's long history. Beginning in 1958, the train has carried passengers from May to October, with tickets costing only one dollar.
Presently, the train is maintained and operated completely by volunteers. Unique to the Gypsy Express is an Easy Access Car designed and built by volunteers to accommodate handicapped riders. A documentary recounts the history of the train. 
During the mid-1800s, the area now known as Gypsy Hill Park served as the water supply for the city of Staunton via a local pumping plant that utilized the many underwater springs found in the area. In order to protect the surrounding area, Staunton city ended up purchasing around 30 acres of land by 1876. By 1890, the city had purchased sixty more acres. Since all of this land had been purchased, a proposal was formed and mailed to the city's council which moved that a public park be created with the current resources. After the proposition was passed, the lands between Churchville Avenue and the Baldwin Fair Association were designated as the perimeter for the new park, thanks to the planning of Staunton resident, Captain W.P. Tams, along with others. It came to be known as Gypsy Hill Park due to the high traffic of wandering gypsies that passed through the area on their nomadic trips. In order to accommodate more park features, Staunton City bought Baldwin Fairgrounds, a local park which already had a repertoire of activities that drew people to the site. As the park grew, so did its attractions, including an in-park zoo that became a prominent feature to visitors in 1893.
The Stonewall Brigade Band, a community-based band, has undergone various name changes during different periods; it was also known as the 5th Regiment Band (Civil War era), Second Corps Band, and Turner's Silver Cornet Band. In the mid-1800s, founder David W. Drake convinced his professor, A. J. Turner, to move to Staunton. Over the years, the band performed throughout Staunton, including Gypsy Hill Park. They performed for President Grant when he was in Staunton and have traveled and played at prestigious venues in cities such as New York and Chicago. The Stonewall Brigade Band has remained intact and still performs today.
In 2008, a documentary about Staunton during the Jim Crowe Era debuted revealing the truth behind segregation laws in the city. Staunton citizen Rita Wilson, who eventually became a member of the city council and served for 16 years, spoke out about the issue. She recalled not being allowed into the park's premises. One day out of the year, African American people were allowed entrance. Since 1988, Staunton City has held an African American Heritage Festival which focuses on various aspects of African American culture including various types of live music, crafts, presentations, and displays.
During summer months, the park draws large crowds with a variety of free concerts and activities. Every Monday night, the Stonewall Brigade Bandstand performs their music at eight pm. Tuesday night is "Praise in the Park," where musicians perform faith based music starting at seven pm. Wednesday nights are reserved for bluegrass music, and Thursday nights are reserved for jazz performances, which are both held at seven pm. On every other Friday night, a family friendly movie is projected onto the pavilion at dark. The Staunton Parks and Recreation departments funds and supports all of the activities that take place throughout the course of the week and last until the end of August. The renowned country group, The Statler Brothers (also from Staunton), performed their music at the annual Fourth of July festival at the park. During winter months, Gypsy Hill Park is adorned with lights and decorations for the Christmas and holiday season. In addition to all of all of the live music, Gypsy Hill Park hosts an annual festival throughout Memorial Day weekend called Art in the Park where local artists, musicians, and vendors set up tents showcasing their artwork and wide array of crafts. An array of performers take stage on the bandstand, and a designated children's craft station allows kids to participate in multiple activities.
In the fall of 2015, sixteen-year-old Isaiah Stuart was convicted of the second-degree murder of twenty-six-year-old Julian Parrott in May 2014. Parrott was stabbed thirty-six times by Stuart and was left to die near Gypsy Hill Park's golf course. The next day, a jogging man spotted Parrott's body and informed city workers, which led to a police investigation in which Stuart ultimately ended up confessing to the murder. Evidence showed that Julian had not put up any sort of resistance.
Famous Shenandoah folk artist Grandma Moses, who was a resident of Augusta county for eighteen years, painted a picture of Gypsy Hill Park which sold on January 31, 2016 for almost six thousand dollars at the Augusta Expo in Fishersville, Virginia.