Name: 5th Annual Sanford's Ride To Freedom
Start: 2026-05-16T07:00:00-04:00
Location: Historic Hopper Academy

This year marks our 5th Anniversary, and we’re celebrating in a bigger, bolder way.
On May 16, 2025, we will once again come together to honor Florida’s Emancipation Day with an unforgettable cycling event that both commemorates history and celebrates community. This special ride highlights Sanford’s remarkable Black historic buildings and neighborhoods, fostering awareness, unity, and pride in our shared heritage.
In celebration of this historic date in Florida, this ride will take you through some incredible black communities and historic buildings that help shape Central Florida.
➡️ Hopper Academy: Historic African American School built in 1906 in Historic Georgetown Community; a community established by early black pioneers in 1870.
➡️ Georgetown: The community of Georgetown, a suburb east of Sanford Avenue, and north of Celery Avenue was established circa 1870. It was comprised of lots sold by Henry Sanford to the early black pioneers who had made their way from Virginia, the Carolinas, West Florida, and as far away as the West Indies. In 2020, Georgetown was listed on the National Register of Historic Places.
➡️ Midway/Canaan City: The migrant settlement of Midway/Canaan City was established for blacks during the celery boom of the 1920s, although some people were residing in the area as early as 1865-1890. Midway is also called Canaan City, a section that was joined together with Midway after the “Canaan Land” referenced in the bible. The name Midway is the shortened version of its initial name “The Midway Point” because it was the middle point between two wells located on Sipes Avenue, used to drink from and water livestock.
➡️ Goldsboro: The 2nd African American incorporated city in the United States, founded by William Clark in 1891, brother of Joesph Clark, founder of Eatonville. If the City of Sanford had not annexed Goldsboro, there would have been two all-black incorporated cities in Central Florida—Eatonville and Goldsboro.
Crooms Academy: Seminole County's first high school for African-American students was founded in 1926 by Joseph N. Crooms, currently serving as the Crooms Academy of Information Technology.
➡️ Bookertown: Known as "Monroe's Colored Section", the first African-Americans arrived in this area in 1885 as laborers for two railroads. The streets were named in 1926 for distinguished personalities in African-American history. The community derives its name from the famed Reformer and educator Booker Taliaferro Washington. However, since so many other places were named “Washington” the community was named “Bookertown”.
Additional Community GEMS:
➡️Sanford/Orlando International Airport: Enjoy a one-of-a-kind ride through our local airport, traveling along the terminal curbside for a truly unique perspective.
➡️Sanford RiverWalk: This trail started in 1995 as an idea for a sidewalk along the shores of Lake Monroe but has turned into a multi-use pedestrian trail and destination.