The Horrible Hundred is the cycling event that helped earn Clermont its Choice of Champions nickname. Every November, the Florida Freewheelers take over the lakefront for a weekend of rides, a fitness expo, and the kind of community energy that makes the town feel like it is hosting something big. The 46th annual edition runs Saturday and Sunday, November 14 and 15, 2026, at Clermont's Waterfront Park on Lake Minneola.
What the weekend actually is
The Horrible Hundred is a ride, not a race: a century route plus shorter distances that loop through the hills and lake country around Clermont, with rest stops, support, and the finish back at the park. The horrible is the freewheelers' own joke about the hills, and riders from across the Southeast plan their season around it. The expo at Waterfront Park runs alongside the rides with bike shops, vendors, and food.
The local angle
For homeowners and house-hunters, the weekend is a live demonstration of why people move here: hills, trails, lakes, and a town built to host events. The routes pass neighborhoods all over South Lake, and the crowds at the finish line spill into downtown Clermont all weekend.
Make a weekend of it
Waterfront Park is worth the visit even if you never touch a bike: the beach, the pier, the South Lake Trail, and the best sunset in town. Downtown Clermont's restaurants and the Sunday farmers market on Montrose round out the weekend, and the hills riders call horrible are the same terrain buyers ask about when they look at homes with lake or hill views.
Thinking about a home near the trails and the lakefront? Kelly knows the neighborhoods the Horrible Hundred rides through. Book a call and get the local read, no pressure.
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Kelly Wheeler, the Real Estate Ninja, is a Clermont FL Realtor with eXp Realty (SL3352000). He works with buyers and sellers across Central Florida, from Clermont to Winter Garden to Davenport.