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Tonight we’re exploring Old Town Kissimmee, one of Central Florida’s most unique entertainment districts — and home to what’s officially recognized as America’s longest-running weekly car show and cruise night. Opened in December 1986, Old Town was designed to recreate a classic Florida Main Street — complete with brick roads, vintage storefronts, neon lights, and old-school Americana charm. But what truly put Old Town on the map? The cars. Every week, classic cars cruise down the brick-paved street in a tradition that’s been going strong for over 36 years. From restored antiques and hot rods to muscle cars and custom builds (1985 and older), this isn’t just a car show — it’s a rolling time machine. And the best part? It’s completely family-friendly. Located in Kissimmee, Florida, just minutes from Walt Disney World, Universal Orlando, SeaWorld, and International Drive, Old Town feels like stepping into a different era — a nod to pre-theme-park Florida and classic Saturday night cruise culture. In this video, we explore: • America’s longest-running weekly car cruise • Kissimmee’s cattle-town roots • Old Town’s 2019 renovation & 86-foot Ferris wheel • The giant swing ride • 70+ locally owned shops and restaurants • Fossils, gem mining & rock shop treasures • Mortem Manor haunted house • Retro shooting gallery • World Food Trucks — one of Orlando’s largest permanent food truck parks Old Town blends nostalgia, nightlife, family fun, and Florida personality into one walkable 18-acre district — and it’s a must-visit if you’re looking for something beyond the theme parks. If you’re visiting Orlando or Kissimmee and want a free, family-friendly night activity — this might be it. Thanks for exploring with us — and as always… never stop exploring. 🚗✨ ⏱ CHAPTERS 00:00 Welcome to Old Town Kissimmee 02:12 America’s Longest-Running Weekly Car Show 03:30 Classic Cars Cruise Down Main Street 05:55 Muscle Cars & Kissimmee’s Cattle Town Roots 08:09 The Rides – Ferris Wheel & Giant Swing 09:30 Exploring 70+ Local Shops 10:20 Fossils, Gem Mining & Rock Shop 11:15 Window Shopping & Tattoo Studios 11:46 Retro Shooting Gallery 12:13 Mortem Manor Haunted House 12:35 Curiosity Shop Oddities 13:06 World Food Trucks – 100+ Flavors 14:19 Neon Night Walk Wrap-Up #oldtown #kissimmeeflorida #classiccarshow #thingstodoinorlando #familytravel 📌 PINNED COMMENT Have you ever been to Old Town Kissimmee? We love that this place feels completely different from the theme parks — brick streets, neon lights, classic cars, and real Florida cruise culture that’s been happening here for 36 years. If you’re visiting Orlando and want something FREE and family-friendly at night, this car show is absolutely worth it. 👇 Drop a comment: Classic muscle car… or modern supercar? What’s your pick? Would you rather do Disney at night — or cruise a classic car show like this? 👨👩👧👦 ABOUT US We’re a family of four traveling full-time in our RV — Jeff (Dad), Monica (Mom), and our two kids, Dean and Gertie. We explore America’s history, national parks, hidden gems, and unique attractions while roadschooling on the road. ⚠️ DISCLAIMER This video is not sponsored. We were not paid or hosted by Old Town Kissimmee. All opinions are our own based on our personal experience. 🔗 CONNECT WITH US 📺 YouTube: / @deangertieexploretheworld 📸 Instagram: / deanandgertieexploretheworld 💻 Facebook: / deanandgertie 🎥 TikTok: / deanandgertie 🌐 Website: https://www.deanandgertie.com 💌 Email: ExploreTheWorld@DeanandGertie.com 📬 Postcard Club (Patreon): / deanandgertieexploretheworld 🛒 RV Travel Must-Haves: https://www.amazon.com/shop/deanandge...