Clermont's most famous bike ride gets its reputation from Sugarloaf and Buckhill. Its Saturday program also has a 10-mile family ride on the trail along Lake Minneola, and the organizer's rides page says "All riders and bikes welcome!" The 46th annual Horrible Hundred runs Saturday and Sunday, Nov. 14–15, 2026, at Waterfront Park. Florida Freewheelers organizes it. If you live in town and don't train on hills, the weekend has two halves. Saturday is a lakefront expo with an easy ride attached. Sunday is a long morning of cyclists spread across the roads of South Lake County.
Sunday has no mass start. The Race Roster listing gives a departure window of 7:30 to 9 a.m., so riders leave in waves over 90 minutes instead of all at once on one road.
A Ride Older Than Most of Clermont's Subdivisions
The Horrible Hundred started in 1980. A Florida Freewheelers newsletter from November 2015 called that year's edition the 36th and said the previous year drew more than 2,200 riders. Today Florida Freewheelers calls the ride its biggest fundraiser. The club says almost 2,000 riders typically choose the 35-, 70- or 100-mile course.
That rider count is why the event is built around Waterfront Park. The organizer gives directions from State Road 50: take East Avenue north one mile to Palm Avenue and the park entrance on Lake Minneola's south shore. Everything happens there, including check-in, the expo, breakfast and the post-ride meal. A crowd that size rides out into the county from that one spot.
Saturday Is the Day Built for Locals
Saturday, Nov. 14, opens the Cycling and Fitness Expo from 10 a.m. to 5 p.m. Rider check-in runs during the same hours at the Waterfront Park Pavilion. The familiarization rides leave earlier in the morning, and each one goes somewhere different:
| Saturday ride | Start | Distance and pace | Where it goes |
|---|---|---|---|
| Yalaha Bakery ride | 8:30 a.m. | 50 miles, 17–18 mph average | Part of the course, to Yalaha Bakery and back, with a stop of about 20 minutes |
| Cracker Cove | 8:45 a.m. | 34 miles, 16–17 mph average | Several of the event's hills, on the way to Howey-in-the-Hills |
| Bay Lake Backwards | 9 a.m. | 42 miles, 16 mph average | Into the Green Swamp and through Mascotte, returning on part of the course |
| Family Ride | 10 a.m. | 10 miles | The trail along Lake Minneola |
The bakery ride is the one people talk about. The ride listing tells riders to "bring some $ to get a treat." Yalaha Bakery sponsors the familiarization rides. The family ride runs on home ground. The paved Clermont/Minneola Trail covers 5.2 miles from West Beach along Lake Minneola, through Clermont and Minneola, to the UCF/Lake-Sumter Community College campus. The City of Clermont notes that it connects with the West Orange Trail. A route map is posted on Ride with GPS if you want to check the 10 miles before you show up.
When the organizer's FAQ asks whether you need to be a racer, it answers, "No, riders of any ability can ride." It adds that the 70- and 100-mile routes are very challenging, that they need training rides first, and that you can ride any type of bike.
Sunday Spreads Out Over the Morning
Sunday, Nov. 15, starts early. The organizer's timeline looks like this:
- Parking opens at 6 a.m.
- Check-in runs from 6 to 9 a.m., and breakfast is served from 6 to 8:30 a.m.
- Riders roll out from 7:30 to 9 a.m., with no mass start. Course support is set up for riders who leave before 9 a.m.
- The expo runs from 7 a.m. to 4 p.m.
- Post-ride lunch begins at 11 a.m., catered by Oakwood Smokehouse.
Riders park on downtown streets and at the boat ramp at 140 East Avenue, according to the Horrible Hundred FAQ. For anyone living near downtown, that means early-morning cars on the blocks around the park. The streets clear as riders leave and come back through midday.
Out on the roads, the event runs under ordinary traffic rules. The 2026 rules say riders must stop at all stop signs, obey traffic signals, ride no more than two abreast and not block roadways. In 2015, Spectrum News 13 reported that no roads would close, that drivers should use caution, and that signs at major intersections would warn of possible delays. The club's 2015 newsletter said police monitored major intersections as riders passed through Minneola, Montverde, Ferndale, Groveland, Mascotte and Howey-in-the-Hills. Plans for 2026 may differ, so check with the city and the organizer closer to the weekend.
Last Year's Roads Show Where You'll Meet Them
As of the organizer's Oct. 22 update, the 2026 Sunday route maps and GPS files had not been posted yet. The page says they will be released before the event. Last year's map is the best guide to which roads usually carry riders. The official 100-mile map for Nov. 16, 2025, ran over Sugarloaf and Buckhill Road. It also used stretches of SR 19, SR 33, US 27 and SR 50, plus roads numbered 455 and 561. It had four rest stops:
- Central Turkey Lake
- Sugarloaf
- Independence Way
- Villa City
If your Sunday errands take you north toward Montverde and Howey, or west toward Groveland, the 2025 map is a reasonable sketch of where riders might be until the 2026 files go up on horrible-hundred.com.
Joining In Without Riding
You can take part without a bike. Non-riders can buy a $15 lunch ticket on site. The expo is open at Waterfront Park both days. If you decide in early November that this is your year to ride, registration on Race Roster costs $79.82 including fees from Nov. 1 through Nov. 13. The price rises to $85.14 on Nov. 14 and 15. The 35-, 70- and 100-mile options all cost the same. You can also register in person at Waterfront Park both days. The organizer recommends doing it before Nov. 15 to avoid the rush, and its FAQ says there are no refunds.
Waterfront Park's Calendar Runs Through December
The Horrible Hundred is the largest weekend in a fall season that keeps returning to the same lakefront. The South Lake Chamber's Taste of South Lake fills Waterfront Park on the evening of Thursday, Nov. 5, from 5 to 8:30 p.m. The Chamber lists more than 30 restaurants and more than 30 business exhibitors. After that, the City of Clermont's 2026 events calendar lists:
- Saturday, Nov. 7: Jack & Allie Superhero 5K and Family Day, Waterfront Park
- Saturday–Sunday, Nov. 14–15: Horrible Hundred, 46th annual, Waterfront Park
- Sunday, Dec. 6: Ugly Sweater Run, Santa vs Grinch, Victory Pointe
- Saturday, Dec. 12: 4th Annual Trailblazer Bike Ride and Stroll, Waterfront Park
- Saturday, Dec. 19: Santa's Twilight 5K, downtown
The trail those events depend on is getting longer to the west. FDOT is building Phase III-B of the South Lake Trail, a 1.876-mile, $4.2 million segment in Groveland. It follows CR 565A from Silver Eagle Road to Eagles Crossing, then Eagles Crossing south to SR 50, then SR 50 west to Second Avenue. WFTV reported a Sept. 14 start and about six months of work. FDOT's project page gives Summer 2027 as the estimated finish. Drivers on SR 50 between Second Avenue and CR 565A should expect periodic westbound lane closures, most of them overnight.
The calendar keeps bringing people back to the lakefront at the north end of East Avenue, and that is where the 46th Horrible Hundred starts on Saturday, Nov. 14, with a 10-mile ride along the water at 10 a.m.
The team at Engel & Völkers Lakeland - Lisa Matheny follows South Lake County's calendar as closely as its market. If the Horrible Hundred has you wondering what a home near Waterfront Park or the Lake Minneola trail is worth, we're glad to help with a free home valuation, and you can browse more of what's happening locally on our Clermont neighborhood page.
