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Historic South Brooksville Avenue

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Brooksville, FL
Historic South Brooksville Avenue

✨South Brooksville Avenue Historic District✨

🏠17 Historically Significant Homes
🌳 100 Year Old Oak Tree Canopy
🧱 Paved with Augusta Block Bricks

03/15/2026

just got hail! Right as the Azaleas are blooming and in 77 degree heat, we got dime sized hail! Anything can happen here in Brooksville!

12/25/2025

Merry Christmas from all of us on Historic South Brooksville Avenue ❤️🎄 May you get to spend it peacefully with loved ones!

12/23/2025

✨🎄 THANK YOU, SOUTH BROOKSVILLE AVENUE! 🎄✨

What an incredible night at The Fourth Annual South Brooksville Avenue Christmas Stroll! Our hearts are full, our cocoa cups were never empty, and the Christmas spirit was everywhere.

To everyone who came out to stroll, smile, laugh, and celebrate with us—thank you. This event grows because you show up, bring your people, and spread the word. If you had fun, please tell your family and friends—our goal is to make the Christmas Stroll better every single year, and community is how that happens. ❤️

A huge thank you to:

🚂 The Hernando Historical Museum Assoc. for opening the doors to the Brooksville Historical Train Depot and the Countryman Family One-Room Schoolhouse Museum. Thank you for welcoming everyone in for free while serving hot cocoa and cookies.

⛪ St. John's Episcopal Church of Brooksville for opening their doors, sharing the message of Jesus, and offering free drinks, baked goods, and hot dogs to keep everyone warm and well-fed.

🚗 Michael Kessler and friends for rolling in with their absolutely gorgeous cars decked out in Christmas lights—you truly lit up the Avenue!

🐴 country depot for turning back time with beautiful horse carriage rides, adding that old-Florida, historic magic we all love.

🌭 TJ's Jersey Italian Sausages and Boondoggle Eats for keeping our strollers happy, full, and fueled for the night.

💚 The Grinch for making a surprise appearance and delivering laughs (and a little mischief).

💃✨ Jayne's Dance Academy for sharing their incredible talent and spreading pure holiday joy through their beautiful dance performances. Thank you for bringing movement, music, and magic to the stroll—you truly helped make the night feel alive and unforgettable.

🎅🤶 Santa and Mrs. Claus—a huge thank you for showing up and taking free photos with everyone who wanted one. You made so many memories that will last far beyond the season.

🏡 And finally, to the neighbors of Historic South Brooksville Avenue and Oak Park Avenue—thank you for decorating your homes, for your immense generosity, and for the infectious Christmas spirit that truly makes this stroll feel like something special. This neighborhood is the heart of it all.

From all of us—thank you for believing in this tradition, supporting it, and helping it grow. We can’t wait to do it all again next year… even brighter. ✨

All pictures come from strollers like you! Specifically thank you to Robert Mongold and Stacy The Home Girl 813 Tampa Realtor!
🎄❤️

Merry Christmas to all!

12/19/2025

Don’t miss the dance performances of Jayne’s Dance Academy at The Fourth Annual South Brooksville Avenue Christmas Stroll! They will perform both nights on December 19th and 20th at 7PM at the Treiman House located at 133 S. Brooksville Ave

12/16/2025

We are so honored to have our lovely neighbor read “T’was the Night Before Christmas” at The Fourth Annual South Brooksville Avenue Christmas Stroll! She’ll be in period appropriate dress and reading for all the little ones who want to hear the classic tale!

FREE magnetic bookmarks will also be available for those who listen to the reading!

12/15/2025

CALLING ALL CAR FOLKS! A wonderful group of car guys lead by Michael Kessler will be parked for a FREE car show at The Fourth Annual South Brooksville Avenue Christmas Stroll!

If you’re into cars, Christmas Spirit, FREE goodies and historic homes, you have to check it out!

12/12/2025

We are fortunate enough to have such a lovely church situated nicely on our Avenue. St. John's Episcopal Church of Brooksville will be proudly open during The Fourth Annual South Brooksville Avenue Christmas Stroll!

Please feel free to stop by, say a prayer, get some free hot cocoa & goodies and get some warmth this December 19th and December 20th!

12/10/2025

Want to make a complete evening out of The Fourth Annual South Brooksville Avenue Christmas Stroll this December 19th and 20th, 2025? No need to stop anywhere else! We have two great food options located right on S. Brooksville Avenue! which is our brick and mortar restaurant and returning for the 4th year in a row (They've been to every stroll!) which is our food truck option! So whether you want to sit and eat or walk and chow down, we got you covered!

12/08/2025

Can you believe that The Fourth Annual South Brooksville Avenue Christmas Stroll is NEXT WEEKEND?! Neither can we! While we are putting the finishing touches on our neighborhood, we also wanted to let you know something wonderful! We are very lucky to have two great museums located at the end of our street, The 1885 Historic Train Depot and the Countryman Family One-Room School House! Both museums will be open for free on the nights of the stroll (December 19th and 20th, 2025). Although they are open for free, please strongly consider donating! The train depot was literally built in 1885 and all donations would go to helping with much needed repair! Thank you to for the generosity of being open!

12/07/2025

Here's a look back at previous South Brooksville Avenue Christmas Strolls! What are some of your favorite memories? Tell us as we get ready to put on The Fourth Annual South Brooksville Avenue Christmas Stroll! Our neighborhood loves to put this on for our community. It gives all of us a special feeling in our hearts. There's so much more in store this year, but tell us about your favorite moments!

11/25/2025

Art can be found in the weirdest of places! We love our neighbors!

10/31/2025

Have a Happy Halloween! Since it's a Friday night, we hope to see many trick or treaters this year!

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Brooksville, FL
34601

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