Stay & Play Inspiration Itinerary
Florida’s Adventure Coast is brimming with history. Our many historic sites include eight locations listed on the National Register of Historic Places, among others. This itinerary is sure to excite both the curious journeyer and the history buff.
Explore this two-day itinerary and learn about the many cultures that took part in our Florida’s history – from early Native Americans, to the first settlers who risked everything to uproot and make this their new home.
Discover the localities, marked by history, and enjoy the attractions along the way!
Have breakfast at the local Southern Harmony Café close to the Fort King Road marker or at one of the familiar restaurants near the intersection of I-75 and Cortez Boulevard.
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Starting Point: FORT KING ROAD
The marker is located on the southwest corner of Cortez Boulevard and US-301
US Highway 301 now crosses the course of what was once a major road in Florida’s history. One of the oldest transportation routes in Florida, its construction began in 1825 as a military road connecting two forts: Fort Brooke near the mouth of the Hillsborough River, and Fort King in present day Ocala. In time, it was developed and became known as the Fort King Road, an important route for the Second Seminole War of 1835-42 and development in the 19th century.
From here, head west on Cortez Boulevard / US-98 for 13 miles, and turn left to continue on Cortez Boulevard. The marker is on your left before passing Emerson Road.
- CHOCOCHATTI HISTORIC MARKER
Location: On Cortez Blvd. east of Emerson Road
This sign marks what was once a major settlement for Upper Creek Indians who emigrated from present day Alabama and Georgia. This Muskogee speaking branch of Upper Creek established a colony by 1767 called “New Yufala.” For the Upper Creek Indians, who eventually transformed into Seminole, the area of Brooksville was prime land for farming, cattle, and hunting.
The settlement became known as Chocochatti, meaning “Red House” which is sometimes thought to mean “War Town.” With the passage of the Indian Removal Act (1830), and the onset of the Second Seminole War, Chocochatti’s residents were forced to decide whether to leave Florida or resist. By 1836, some of the Chocochatti Seminoles decided to move to Oklahoma. Others resisted and remain part of the Seminole Tribe of Florida today.
Interested in Native American culture or the meaning behind the Seminole names throughout the county? Check out Florida's Adventure Coast Native American Place Names. And, be sure to attend the annual Brooksville Native American Festival, a large celebration held the first weekend of February.
From the Chocachatti Marker, head west on Cortez Boulevard and use the middle lane to continue onto Jasmine Drive. Turn left onto Olmes Road. The main entrance to the Brooksville Cemetery located in less than a mile on your right.
- GRAVE OF CHARLOTTE WYNN PYLES CRUM
Location: Brooksville Cemetery, 1275 Olmes Road, Brooksville, FL 34601
Space 2, tier 3, lot 18
The Brooksville Cemetery, once referred to as the Chocochatti Cemetery, is the resting place of over 5000 souls from throughout Brooksville’s history. The earliest known burial is that of Charlotte Wynn Pyles Crum, and one of Brooksville’s first white settlers. Charlotte and Richard Crum settled in Chocochatti in 1842 through the Armed Occupation Act. On September 12, 1842, soon after the Second Seminole War’s end, Charlotte Crum and a party, including her daughter and granddaughter, were fired upon by Seminoles while traveling. Charlotte was killed in the attack, and her death became sensationalized. She is buried in the Brooksville Cemetery.
Exit the cemetery and turn right onto Olmes Road. Turn right onto US-98 / E Jefferson Street, and continue for 1.8 miles. The Hernando County Courthouse is on your left.
- HERNANDO COUNTY
Location: Designated by the County Courthouse, 20 N Main Street, Brooksville, FL 34601
Today, Hernando County encompasses Brooksville, Weeki Wachee, and other neighborhoods on Florida’s Adventure Coast. However, in the mid-19th century, the county was actually much larger, encompassing all of present-day Citrus, Hernando and Pasco counties.
Established in 1843 and named for Hernando DeSoto, the county placed the first county seat in Brooksville, which was then referred to as DeSoto. The county changed its name in 1844 to Benton County, in honor of Senator Thomas Hart Benton, but later changed it back to Hernando during the Missouri Compromise. The county was split into three counties in 1887, giving Hernando County the boundaries that it has today.
Brooksville has many historic homes to look at and a few museums including the May-Stringer House Museum and the 1885 Train Depot Museum. You can learn even more about the history of the city of Brooksville and Hernando County during the annual Heritage Day Festival in late February.
Turn north on Main Street, which soon turns into Howell Avenue. Continue 1.9 miles to Broad Street / US-41 and turn left (north). After 2.2 miles, turn left onto Snow Memorial Highway. Take the first left onto Chinsegut Hill Road. The marker is on your right.
- CHINSEGUT HILL
Location: 22495 Chinsegut Hill Road, Brooksville, FL 34601
Chinsegut Hill is one of few plantations that have survived Florida’s history. In 1842, just following the Armed Occupation Act, Colonel Bird M. Pearson from South Carolina built the first section of the house on the 5,000-acre property he had claimed. The slave plantation produced sugarcane, tobacco, cotton and Florida citrus crops. The plantation switched hands twice before being renamed Chinsegut Hill in 1904. “Chinsegut” is an Inuit word meaning “a place where lost things are found.”
Then owned by Colonel Raymond Robins, the house became host to many guests including Thomas Edison, Marjorie Kinnan Rawlings, J.C. Penney and Helen Keller. During recent times, Chinsegut Hill has become a museum and retreat center, with cottages near the manor house for guests to stay in.
Just up the road from the historic marker is Chinsegut Hill Manor itself, where visitors can take a tour of the house and grounds, and learn about the residents and people who made history here.
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Breakfast at Riverside Restaurant
Address: 7224 Shoal Line Blvd, Weeki Wachee, FL 34607
Phone: (352) 515-55871. BAYPORT'S EARLY HISTORIC/POST CIVIL WAR ERA
Location: 4140 Cortez Boulevard, Weeki Wachee, FL 34607
There are two historic markers at Bayport Park, a scenic spot on the Gulf of Mexico with a boat ramp and nature viewing deck. In the mid-19th century, this area functioned as a shipping port; cotton, timber, and other goods from Brooksville were brought by wagon and shipped to Cedar Key to be sent by rail to other areas.
Bayport became an important port for Confederate troops to receive salt and beef during the Civil War, leading Union troops to land there and set fire to nearby plantations during the “Brooksville Raid” (1864). After the war, Bayport was rebuilt and remained in use as a port until 1885.
- BAYPORT AREA: EARLY CIVILIZATION
Location: 4140 Cortez Boulevard, Weeki Wachee, FL 34607
The second historic marker describes early history of Bayport up to 9,000 years ago. A burial mound found in the area contained artifacts of multiple Native American cultures that had lived in the area up to 1,700 years ago, who were present when Spanish explorers led by Panfilo de Narvaez and Hernando de Soto landed on the Gulf shore in the early 16th century.
From Bayport Park, drive east on Cortez Boulevard for 6.4 miles. Turn right onto Commercial Way / US-19 and make the first right at Weeki Wachee Springs State Park.
- WEEKI WACHEE: PRE CIVILIZATION
Location: 6131 Commercial Way, Weeki Wachee, FL 34602
Although Weeki Wachee Springs is not listed on the National Register of Historic Places, it contains a wealth of history, some of which is referred to on the markers at Bayport; “Large mammals, such as mammoths, mastodons, ground sloths, and saber tooth cats roamed these coastal lowlands. Their fossilized remains have been found in Weeki Wachee Springs.” Two burial mounds were found at Weeki Wachee, resulting in excavations where human bones were found linking to the Timucuan culture. Pottery and other items have been found at the site dating between 1200 and 1700 A.D.
Weeki Wachee Springs is celebrating 70 years of live mermaid shows. This classic Florida attraction began in 1947 when Newton Perry, a former Navy diver and trainer, turned stunt swimmer and promoter, scouted out Weeki Wachee, envisioning pretty girls performing in the Spring. He designed the underwater breathing system used by the mermaids, which allows them to perform synchronized ballet and stunts while breathing through air hoses hidden in the scenery. The attraction reached its heyday in the 1960s, as girls traveled from as far as Tokyo to become a mermaid, and visitors included Elvis, Don Knotts, Esther Williams, and Arthur Godfrey.
While visiting the park and traversing the grounds, you will notice a few historic signs in the park. You may also catch a Sirens show, bringing former mermaids back to Weeki Wachee Springs to swim again – once a mermaid, always a mermaid!
From Weeki Wachee, turn left (north) onto Commercial Way / US-19 and turn right onto Cortez Boulevard. Continue 5.8 miles, and turn right onto the Florida 589 Toll South ramp. Continue on 589 for 6.4 miles. Take Exit 37 for County Line Road and turn left. Continue for 1.5 miles and turn left onto US-41 / Broad Street. Stop at Cafe Masaryktown located on your right.
Location: 398 Broad Street, Masaryktown, FL 34604
East of Weeki Wachee and south of Brooksville lies a small town called Masaryktown, named by the Slovak and Czechoslovakian immigrants who moved in between 1924-26. The town was named after Thomas G Masaryk, the first president of the recently formed Republic of Czechoslovakia (1918).
By August of 1926, the town had at least 300 residents, but many would leave within the next two years. The colony had counted on citrus trees, most of which did not endure two winter freezes of 1926-27. Those who chose to remain in the town turned to other means of producing; by the 1960s, the town was revived by chicken farming and is a popular location for retirees.
From the National Register of Historic Places marker: “The building on this site was erected in 1925 as the "Masaryk Hotel" for initial housing of newly arrived settlers, and retained that name until 1997.”
The building remains and is known as Café Masaryktown, a great restaurant for lunches and dinner serving Cuban cuisine.
End your journey here with a Cuban sandwich, and take the time to soak in the history from your historic touring adventure!