The parking lot behind Clermont City Hall has a little more than 100 spaces. On Sept. 22, the City Council voted unanimously to make that lot the site of a proposed downtown parking garage, and the plans could take it past 400 spaces, according to the Clermont Sun.
On Friday, Dec. 4, Light Up Clermont fills City Hall Park at 685 W. Montrose St. It's free, and its event listing plans for a crowd of 10,000 or more. Two weeks later, Santa's Twilight 5K starts from the same park. The garage won't exist for either one. That's why the order of this season's events matters if you live here: November mostly happens on the lakefront, and December comes back to the block that the city has already called its parking problem.
Seven weeks, two hubs
The city's 2026 special events calendar puts almost everything from now through mid-December in one of two places. One is the lakefront pair of Waterfront Park and Victory Pointe. The other is downtown around City Hall Park.
| Date | Event | Where | Organizer |
|---|---|---|---|
| Thu., Nov. 5 | Taste of South Lake | Waterfront Park | South Lake Chamber of Commerce |
| Sat., Nov. 7 | Family Food Fest | Downtown | Clermont Main Street |
| Sat., Nov. 7 | Jack & Allie Superhero 5K and Family Day | Waterfront Park | For Jack and Allie, Inc. |
| Fri., Nov. 13 | Main Street Wine Stroll | Downtown | Clermont Main Street |
| Sat.–Sun., Nov. 14–15 | 46th Horrible Hundred | Waterfront Park | Florida Freewheelers |
| Fri., Nov. 20 | Family Fun Day at the Waterfront | Waterfront Park Field | The River Church |
| Sat., Nov. 21 | Hometown Holidays | Downtown | Clermont Main Street |
| Sat., Nov. 21 | Enchanted Forest of Trees opens | Victory Pointe | City Parks and Recreation |
| Sun., Nov. 22 | Viva Clermont! | Waterfront Park | Ohana Foundation |
| Fri., Dec. 4 | Light Up Clermont | City Hall Park, downtown | City Parks and Recreation |
| Sat., Dec. 5 | Christmas Parade | Waterfront Park into downtown | City Parks and Recreation |
| Sun., Dec. 6 | Chanukah Festival | Waterfront Park | Chabad of South Lake County |
| Sun., Dec. 6 | Ugly Sweater Run: Santa vs Grinch | Victory Pointe | Beastmode Running |
| Sat., Dec. 12 | 4th Annual Trailblazer Bike Ride and Stroll | Waterfront Park Pavilion | Bleeding Disorders Foundation of Florida |
| Fri., Dec. 18 | Main Street Wine Stroll | Downtown | Clermont Main Street |
| Sat., Dec. 19 | Santa's Twilight 5K | City Hall Park, downtown | Sommer Sports |
Thanksgiving weekend is the only open stretch, and several weekends have two or three events. The location column is what shifts. In November the lakefront carries most of the weight, and downtown gets the regular Main Street nights. In December the biggest single nights move to the area around City Hall.
November belongs to the lakefront
The season starts at Waterfront Park, 330 Third St. Taste of South Lake runs Thursday, Nov. 5, from 5 to 8:30 p.m. The South Lake Chamber lists more than 35 restaurants, 35 businesses, live entertainment and voting. It also says shuttle vans will be available. Tickets on Eventbrite start at $30.52. A VIP early-access window runs 4:30 to 5:15 p.m. at the east end of the park.
The next weekend brings the busiest morning of the month to the lakefront. The 46th Horrible Hundred starts with check-in and an expo on Saturday, Nov. 14, from 10 a.m. to 5 p.m. On ride day, Sunday, Nov. 15, parking opens at 6 a.m. and check-in runs 6 to 9 a.m. Riders leave between 7:30 and 9 a.m. in a rolling start, with no mass start. The 35-, 70- and 100-mile options all cost $79.82 through Nov. 13 and $85.14 on Nov. 14–15, according to the Race Roster registration page. The courses measure 35.8, 71.5 and 100.2 miles on Ride with GPS. If you'd like to ride without signing up for the full course, Florida Freewheelers holds a 10-mile family ride from Waterfront Park at 10 a.m. on Saturday, Nov. 14, and says all riders and bikes are welcome.
On Nov. 21, the season starts using both hubs on the same day. Clermont Main Street holds Hometown Holidays downtown, and the Enchanted Forest of Trees opens at Victory Pointe Park, 851 Victory Pt. The city's EventHub page describes the Forest as a walk-through display of more than 100 decorated trees that you can visit by day or at night. The listing runs from Nov. 21 through Jan. 1, 2027. Decorating slots cost $110 for a business or family tree and $55 for an eligible nonprofit, and both are sold out. Groups that decorate a tree have to maintain it every week, so the display gets looked after for the whole six weeks rather than being set up once and left.
The Forest is the one piece of the season that stays put. Every other event lasts a day or a weekend. The trees are lit by the lake for six weeks, and the December events downtown pass right by them.
December moves to City Hall Park
Light Up Clermont on Dec. 4 is the city's tree lighting and street party at City Hall Park, with events spreading through downtown. The city's listing gives the hours as 5:30 to 9 p.m. and promises live entertainment, food, family activities and vendors. The 10,000-plus attendance figure on that listing compares with the 100-some spaces in the lot behind City Hall.
The next morning, Dec. 5, the Christmas Parade starts at 10 a.m. It leaves Waterfront Park and goes through Historic Downtown, so it's the one event that uses both hubs. This year's theme is "Christmas Rewind: Holiday Mixtape," and the lineup includes floats, marching bands and local groups.
On Sunday, Dec. 6, events go back to the lakefront. Chabad of South Lake County holds its Chanukah celebration at Waterfront Park, with a menorah lighting, entertainment, winter-wonderland activities, and crafts and treats for children. Chabad's event page expects more than 400 people. That same day, the Ugly Sweater Run starts at Victory Pointe.
The AdventHealth Santa's Twilight 5K on Dec. 19 brings the season back to City Hall Park and connects the two hubs on foot. The live run and walk is listed from 6 to 9 p.m. The race page describes a downtown course with an LED tunnel, holiday lights, cheer zones and a pass by the tree forest at Victory Pointe. Entry costs $49, or $44 for ages 1 to 17 and 70 to 99, and the price goes up after Nov. 30.
Where the garage plan stands this season
The South Lake Tablet reported in August that parking "has become an increasingly important issue during downtown events, waterfront activities, and peak restaurant hours." That's when Council created a citizens advisory committee to compare possible garage sites. South Lake Tablet
The Clermont Sun covered the outcome. Two sites were in the running:
- The lot behind City Hall. It has a little over 100 spaces now and could hold more than 400 as a garage. Council picked it on Sept. 22.
- The public lot near West Minneola Avenue and Seventh Street. It would have held a five-story garage with about 300 spaces. The city decided not to build there.
The vote doesn't authorize construction. City staff are now working on preliminary engineering, detailed plans, costs and a proposed budget. All of that goes back to Council before the city looks for contractors. The garage's design, budget and timeline are still open.
So this holiday season looks a lot like the case Council used to pick the site. The nights with the biggest crowds are right next to the lot the city plans to expand, and for now it's still a surface lot.
The next parking conversation is already at Victory Pointe
Some of the lakefront crowding may also be addressed eventually. The South Lake Tablet describes the proposed $45 million Lumberyard District on 12.3 acres beside Victory Pointe Park, the South Lake Trail and the Lake County Rowing Association. Its second phase includes a two-story parking garage meant for both residents and visitors. Fully built, the project would have 392 apartments and "The Sawmill," a commercial district of about 53,000 to 55,000 square feet. South Lake Tablet That's a proposal, though, and it's further off than the City Hall garage. This year, the Enchanted Forest and the Ugly Sweater Run will use Victory Pointe as it is now.
Dates to put on the fridge
- Through Nov. 13: Horrible Hundred registration is at its lower price of $79.82.
- Nov. 15, 6 a.m.: Horrible Hundred parking opens at Waterfront Park.
- Nov. 21 through Jan. 1: The Enchanted Forest is open at Victory Pointe by day and at night.
- Before Nov. 30: Twilight 5K entry is $49 until the price goes up.
- Dec. 4, 5:30 p.m.: Light Up Clermont starts at City Hall Park.
- Dec. 5, 10 a.m.: The parade leaves Waterfront Park. Check with the City of Clermont for route and street details as the date gets closer.
At The HomePlace Team, we follow downtown Clermont projects like the City Hall garage because they affect how people get around the neighborhood every day. If you're wondering how downtown changes like the garage or the Lumberyard District could affect your own home, ask us for a free home valuation and we'll go through it with you.
