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#1 – 205 E Fort Dade Avenue
Lirit wanted to get an aerial view of the city as well as a prime spot to hear the music from the bandshell. A friendly eagle carried her up and dropped her off on a high perch where she could see everyone coming and going! If you listen closely when bands are playing, you can hear her singing along.
#2 – 111 N Main Street
Binda had never been attracted to going to the surface of the water but preferred the deep – exploring caverns and swimming with sea monsters. Binda found the sun blinding and the feel of dry hair on her back was so itchy! She’d wandered into the hardware store to escape the sun and had a lovely talk with the owner, who told her stories about the women in her husband’s family who had founded the store over 100 years ago! She gave Binda some water to wet her hair and sent her away happy. But immediately upon going outside again Binda found the sun so bright and hot she searched for shade. She found a shaded spot right next to the nice hardware store. Humans liked to rest there as well and she met many interesting people as the days went by.
#3 – 101 N Main Street
Many years ago Inna heard a story about a terrible fire in the city. The three story building was too high for firefighters to effectively battle the blaze. The building lost its third floor to the fire and the city forever banned any buildings above two stories. Rumor is (even though the building is only two stories now) you can see the Gulf from the roof! Inna liked knowing she could get up there anytime for a glimpse of home.
#4 – Courthouse, 20 N Main Street
Halimeda missed the water. She was having trouble understanding why anyone would choose to live out of sight of the ocean – especially when it is only 30 minutes away! She did love the old brick buildings, especially the Courthouse. And then she saw it – the water that so reminded her of home! And that is where she stayed. (Halimeda had a spa day and received beauty treatments at Teal Plank Workshop).
#5 – 26 S Broad Street
Jauhera heard a rumor that a mermaid had come to Brooksville before she and her friends arrived. But no one had heard from her for years, and chances were good it was just a fable. Imagine her surprise, then, when she found Chalsie, that long-lost mermaid! They quickly became friends and Jauhera plastered Chalsie with questions about mermaid life in the old days. Jauhera considered her new friend a treasure beyond any other she might find elsewhere.
#6 – 10 S Main Street
When at Weeki Wachee, Neri woke early each morning and swam to her favorite rock to watch the sunrise. She was curious to see how a Brooksville sunrise would compare and found herself a nice ledge from which to watch. Neri reveled each morning in watching the sun slowly bringing color and light over the beautiful brick buildings in front of her.
#7 – 36 N Broad Street
Kelsey had always loved finding a comfortable spot near a port and watching the ships come in and the dolphins chase fish. As she turned onto Brooksville Avenue, her eyes were immediately drawn to the Water Tower because it reminded her of a port. She was too shy to go to the Tower itself and found a comfortable spot on a building a block away. She’d been right about the port; besides its function as a water tower, it was also the Good Neighbor Trailhead. Cyclists and walkers came and went, resting and chatting before getting back on their bikes to cruise the brick-lined street to the downtown restaurants and shops.
#8 – 26 S Brooksville Avenue
Muirgheal loves to learn. She can often be found researching the history of the sea and volunteers at the Gulf Library under Bimini Island, organizing documents and interviewing old timers. After finding out the new City Hall was not the original, Muirgheal set out to find the old one! She was delighted to find it covered with murals of fire responders and decided that she’d discovered the best building in Brooksville!
#9 – 302 S Brooksville Avenue
Takara is obsessed with sparkle and color and was immediately drawn to a tower that housed a massive chandelier. Built in 1884, the Frazze family bought it in 1913 for a whopping $2500! Mr. Frazze served as Train Station Master and used the tower to keep an eye on the trains when he came home from work. The chandelier is a new addition to the home, but it made this home Takara’s favorite!
#10 – 70 Russell Street
Arcelia loves treasure in all its forms and found herself at the place where treasures arrived and departed from Brooksville. The Railroad Station started bringing Brooksville the goods in 1885 thanks to the diligent persistence of John Hale. This meant Brooksvillians no longer had to trek their wagons 30 miles to Wildwood. The Station was critically important to Brooksville’s economy – exporting Tangerines during our citrus boom, “potatoes” during Prohibition, and lumber.
#11 – 1112 E Jefferson Street
Aria can’t get enough of American Human pop culture! While she can sing along to all Beach Merboys Songs, they can’t compare to the decades of influence of Frank Sinatra, Madonna, and the Jackson Family. So imagine her delight when she found out Elvis had been to Brooksville! Aria promptly found herself a good location to watch people coming and going from the building. She wouldn’t miss another celebrity visit!
#12 – 924 E Jefferson Street
In 1763, Spain traded Florida to Great Britain. Those British settlers became known as Florida Crackers, cowboy types who bragged a lot. Maritza thought anyone who braved the unknown like they had could brag any time they wanted. Beyond not knowing where their next meal was coming from, they didn’t even know what kinds of food was native to the area! They had to learn so much so quickly in order to survive and deserved our admiration.
#13 – 770 E Jefferson Street
Peninnah had always loved reading “The Little House on the Prairie” books, and had yearned to step back in time and experience life on the frontier. She was shocked to find a log cabin right in the middle of a busy street and stopped to explore. Turned out the building wasn’t that old, but it sure looked like the real thing! The house across the street was a real pioneer house though, and she found a nice spot where she could sit on the log cabin and gaze at the pioneer home.
#14 – 103 S Saxon Avenue
Wanwisa loves her family more than anything. Raising a large school of merchildren has been her focus for most of her life. She works to create lasting memories by making holidays special and bringing everyone together for family events. Wanwisa was astounded at the significance of the house – first a turn of the century home, then the County’s first library, then part of the legendary Rogers’ Christmas House, and now a favorite party venue. Just her kind of place – one that creates meaningful memories for all who enter.
#15 – 510 E Liberty Street
Mettalise couldn’t believe how hilly Brooksville is – all she’s known before now are the flat west coast shores. Mettalise heard you could see the west coast if you went high enough. So she went to the top of a hill and climbed to the top of the building – but it made her nauseous and she couldn’t bear to look. She climbed down to the first floor, hoping she could see the gulf, but ended up facing the wrong way! Mettalise didn’t mind though, she had a lovely view of the museum and all the comings and goings of the people coming to shop and eat.
#16 – 701 Museum Court
Lyndal had toured Chinsegut Hill and been fascinated by the Ederington family. She wanted to learn more about the kind of people that would leave a successful plantation in South Carolina to come to the unknown wilds of Florida. So when she heard about the house Frank Ederington bought in town, she knew she had to see it. The house was also famous for having the first basement in Brooksville! She found a nice place to stay where she could enjoy the beautiful landscaping and still see people as they came to visit.
#17 – 601 Museum Court
Maridith spent her days in the sea exploring their unmapped depths. She loved the thrill of being somewhere that no one had ever been before. And she admired anyone who dared to leave the comfort of established life for a frontier experience. That admiration drew her to the May-Stringer museum. Housing over 11,000 artifacts, the museum is a tribute to the brave pioneering spirit of Brooksville’s founding families. As Maridith walked the grounds, she came upon a little round structure and took a seat. She didn’t know what this round place was for (humans have such odd buildings) but she loved that she could see both the house and the garden from where she sat.
#18 – 503 E Jefferson Street
Calliope came from a long line of seaweed farmers. The first week of harvest was always her favorite week of the year. Seeing the ripe fields, with the seaweed waving at her, brought such a feeling of satisfaction. The long harvesting days were finished with a banquet each night that brought all her family together. Her grandmother told a story each night and Calliope always listened intently so she would not forget even the smallest detail. Someday it would be her job to share these stories and she wanted to do it well. Imagine her joy when she came across a piece of human farming equipment! It would never do for a seaweed harvest, but it sure was cool looking!
#19 – 191 E Jefferson Street
Undine found herself missing the waves! Her favorite water past time is riding the waves and seeing how long the wave can push her without having to move her tail. As she explored the city, a heavy rainstorm blew in, refreshing her scales and skin. She noticed what looked like a waterfall or crashing wave in the front of a building and decided to check it out. Water poured out of this thing-a-ma-jig but Undine could not tell where the water came from. She set her back to the water thing-a-ma-jig, relaxed, and watched the cars come in and out of the Courthouse.
#20 – 100 N Brooksville Avenue
Anahita’s first stop had been the city water plant – she still couldn’t really grasp how people had figured out how to clean the water and put it inside buildings. But they had – and done it so well that in 2017 Brooksville won an award for the Best Tasting Water in Florida. Anahita then went to visit the former site of the Vernada Hotel – the first hotel with indoor running water. The hotel had 30 guest rooms, and each floor had a couple bathrooms that guests shared. It would have been quite a novelty then. For a mermaid, the idea was still a novelty! The hotel was long gone, but the magic of the place remained in the quirky building that took its place.
Short on time or want to do less walking?
You may want to consider the short route instead.
Recommended Starting Location
Florida’s Adventure Coast Visitors Bureau
Brooksville Welcome Center
205 E. Fort Dade Ave.
Brooksville, FL 34601
Paper maps available for pickup.
The trail is open daily from sunrise to sunset.
Always use crosswalks!