From ancient cypress forests to Victorian homes and baseball legends, explore the places where Seminole County’s history helped shape the American story.
As the United States prepares to celebrate America’s 250th anniversary, communities across the country are reflecting on the places where history still lives in everyday landscapes.
In Seminole County, that history isn’t confined to textbooks or monuments. It unfolds along the St. Johns River, inside preserved historic buildings, and even at a baseball stadium where some of the sport’s greatest legends once stepped onto the field.
Through the statewide America 250 Florida Road Trip, travelers are invited to explore historic destinations across Florida — including several meaningful stops right here in Seminole County. The layers of history here reflect the many chapters that make up the American story.
Ready to explore? Here’s how to spend two days experiencing the places where Seminole County’s history helped shape the American story.
Day One: Historic Sanford & America’s Pastime
Start your morning in Historic Downtown Sanford, one of Central Florida’s most well-preserved historic districts. Founded in the 1870s along the St. Johns River, Sanford quickly became an important transportation hub connecting Florida agriculture to markets across the country.
For breakfast, step into The Colonial Room Restaurant, a Sanford institution that has served the community for generations. Often cited by locals as one of the oldest continuously operating restaurants in downtown Sanford, the diner is known for classic breakfast plates and a loyal following of longtime residents.
After breakfast, visit the Museum of Seminole County History, housed in a 1926 building originally constructed as the county’s “Old Folks Home.”
Inside, visitors can see an 800-year-old Native American dugout canoe, a re-creation of founder Henry Sanford’s library, and for those interested, there’s a “paranormal tour” of the historic building. Exhibits also highlight the area’s agricultural past, including celery farming, which once earned Sanford the nickname “Celery City.”
Next, continue through Sanford’s historic district to admire one of the city’s most recognizable landmarks: the Mayfair Hotel.
Built in 1925, the Mayfair became one of Florida’s most prestigious winter destinations during the early tourism boom. The Mediterranean Revival-style hotel welcomed presidents, celebrities, and athletes who traveled to Sanford during Major League Baseball spring training.
For lunch, head to Henry’s Depot, a modern culinary collective located on one of Sanford’s most historically significant sites.
The property sits along one of Florida’s first railroads, the original route of the Orange Belt Railroad. It was first laid in the 1880’s to connect Central Florida’s citrus industry with northern markets. Railroad entrepreneur Henry B. Plant purchased the line in 1885, expanding the rail network that helped Florida agriculture reach the rest of the country.
The depot itself was rebuilt in 1940 and later transformed into Henry’s Depot in 2019, where historic elements of the rail structure remain visible today.
After lunch, visit one of Seminole County’s official America 250 Florida Road Trip stops: Historic Sanford Memorial Stadium.
Originally built in 1926, legends such as Babe Ruth and Jackie Robinson appeared at this field during Sanford’s early spring training era. The stadium was rebuilt in 1951 to honor veterans of both World Wars and later hosted Major League spring training for teams including the New York Giants and Boston Braves. Today, it remains active as the home of the Sanford River Rats and local Babe Ruth baseball programs.
Before dinner, take a short drive to Midway, one of Seminole County’s oldest historically Black communities. Founded by formerly enslaved families after the Civil War, Midway later grew into an important agricultural center during Sanford’s celery farming boom.
Visitors can explore sites connected to the community’s farming heritage, including Meriwether Farms — the birthplace of Commissioner Bob Thomas, Seminole County’s first Black elected official — and Andres Flowers Farm, where owner Christa Andres continues operating the 13-acre property in honor of her late husband.
For dinner, return to downtown Sanford and step inside one of the city’s most unique historic buildings: The Old Jailhouse Restaurant.
Originally constructed in 1890, the building later served as the Seminole County Jail from 1914 to 1959. Today, the restaurant preserves many of the original architectural details, including historic brick archways and the former jail bars that still remain inside the building.
Day Two: Oviedo, Longwood, and the Deep Roots of Seminole County
Begin your second day in Historic Downtown Oviedo with a southern-style comfort breakfast at the Town House Restaurant, a longtime local diner that has served Central Florida for decades.
After breakfast, stop at the Lawton House, a historic home built around 1890 that now serves as headquarters for the Oviedo Historical Society. Built by members of one of Oviedo’s founding families, the house is a classic example of Florida Cracker architecture, known for its wood-frame construction, raised foundation, and wide wraparound porch designed to keep homes cool in Florida’s climate.
Next, drive towards Sanford to visit Fort Mellon Park, located along the St. Johns River.
The park sits on the site of Fort Mellon, a U.S. Army outpost established in the 1830s during the Second Seminole War. At the time, the fort helped protect settlers and steamboat traffic traveling along the St. Johns River, which served as one of Florida’s most important transportation routes during the 19th century.
After exploring the park, head to the Central Florida Zoo & Botanical Gardens.
Among the animals visitors can see is the American bald eagle, the national symbol of the United States since 1782. The rehabilitated birds in this exhibit area powerful reminder of the wildlife that has long represented freedom and resilience throughout American history.
For lunch, stop at Christo’s, a Sanford favorite that has been serving the community since 1971. Located in the heart of Historic Downtown Sanford, the family-owned restaurant has welcomed generations of residents and visitors alike.
In the afternoon, continue to one of Seminole County’s official stops on the America 250 Florida Road Trip — Big Tree Park in Longwood.
The park was once home to the legendary Senator Tree, a massive bald cypress estimated to be more than 3,500 years old. Long before Florida became a state, the towering tree had already stood for centuries and was recognized as one of the oldest standing trees on earth.
In 1929, President Calvin Coolidge visited the site and dedicated a plaque recognizing the tree’s national significance. The original tree was lost to fire in 2012, but visitors can still see its preserved remains and a cloned successor growing nearby, along with Lady Liberty — the Senator’s “sister” tree, a 2,000-year-old bald cypress that still stands 89 feet tall.
Next, take the Longwood Historic District Walking Tour. It’s a self-guided walk that takes about an hour and passes many of the district’s preserved historic structures.
Highlights include the Bradlee-McIntyre House, built in 1885, and the unique Inside-Outside House, a historic structure from 1873, known for its unusual architectural design and connection to Longwood’s early residential history.
As evening approaches, end the day at Enzo’s on the Lake — a transformed mid-century Italian-style villa that has become a Central Florida culinary landmark, known for its lakeside setting and classic Italian cuisine.
Where America’s Story Lives On
From a 3,500-year-old cypress tree to historic homes, military outposts, railroad towns, and ballparks where legends once played, Seminole County offers a remarkable window into the many layers of American history.
As the nation celebrates America’s 250th anniversary, exploring these places reminds us that the American story isn’t only found in famous monuments, major cities, and libraries.
Preserving these places ensures that Seminole County’s history remains more than something written in books. These landmarks allow people to stand beside history, walk through it, and experience it for themselves — today, and for generations still to come.
About the Author:
Daniella Hume, the owner of Mastropieces Productions, is a versatile creative professional specializing in writing, photography, digital media production, social media management, and video creation. With a deep passion for her community, Daniella’s work aims to inspire and uplift her audience while celebrating the beauty and vibrancy of the people and places around her. Her published work can be found throughout Central Florida and beyond, showcasing her commitment to the Sunshine State and dedication to sharing a positive message.
