In Downtown Clermont, the Trail Is the Business Plan
September 17, 2026
September 17, 2026
Every Saturday at 7:30 a.m., a few dozen runners gather at Lake Hiawatha Preserve for the Clermont Waterfront parkrun, a free timed 5K that anyone can join with no registration fee. When they finish, most of them don't get in a car. They walk over to Cheeser's Palace for coffee, still in their running shoes, still catching their breath. It is a small ritual, but it says something about how this city works now that would have sounded strange five years ago: the trail decides where people eat, drink, and spend their Saturday, and downtown Clermont has rearranged itself around that fact.
This is not a story about a new coffee shop or a seasonal calendar. It is a story about why the businesses opening and closing along West Montrose and West Desoto Streets over the past year look nothing like the businesses they replaced, and why that shift traces back to a stretch of asphalt most people think of as recreation rather than infrastructure.
Clermont has spent the better part of a decade building toward this. The city earned a Trail Town designation from the Florida Department of Environmental Protection's Greenways and Trails System in 2018 and was later named Florida's Bicycle-Friendly Community of the Year. Neither award was about scenery. Both were about connection, specifically the Legacy Loop Trail, a short but deliberate piece of infrastructure completed as part of Phase 2 of the city's Downtown-Waterfront Master Plan that links the 13-mile South Lake Trail directly into the downtown core.
Before that connector existed, a cyclist finishing a ride on South Lake Trail had to choose between continuing on toward Minneola or driving downtown separately. Now the trail routes riders straight past Victory Pointe Park and into the restaurants and shops clustered around Waterfront Park. The South Lake Trail itself ties into 36 miles of continuous riding once it links up with the West Orange Trail at Killarney Station, and Clermont sits at the rough midpoint of the statewide Coast-to-Coast Trail. None of that matters to a downtown business owner in the abstract. It matters because it means a meaningful share of the people walking into a bar or bike shop on any given Saturday arrived on two wheels, not four.
The clearest evidence of what that shift demands from a business sits at 750 W. Desoto Street, where Clermont Brewing Company operated for six years before closing on Halloween night last year. The space reopened six days later as The Station, under new owners Bob and Linda Zimmardo, who purchased the business after Bob wandered in on what general manager Jessica Kelyman has described as an ordinary Saturday night and asked enough questions that she told him to make an offer by Monday.
What The Station kept from Clermont Brewing Company was the building and a few menu staples, like the buffalo chicken dip and pretzel bites. What it dropped was the identity of a brewery built around a product people traveled to buy. What it added was pool tables, a sixteen-foot LED wall for watch parties, live music several nights a week, and a patio being enclosed and air-conditioned for year-round use. The math behind that pivot is simple once you think about who is actually walking in. A destination brewery competes on the beer itself. A gathering spot competes on how long people are willing to stay once they're already there, on foot, with nowhere else booked for the afternoon.
"They're not just stopping in and leaving. They're hanging out for hours, listening to music, talking, dancing."
That's Kelyman describing what changed. It is not a complaint about slower turnover. It is a description of a business model built for people who arrived without a car and have no reason to rush back to one.
If The Station shows what an existing business looks like once it adapts to trail traffic, Midpoint Rec shows what a business looks like when it is built for that traffic from day one. The bike, kayak, and paddleboard rental startup launched this year with no permanent storefront. Bookings happen online in advance, and pickup and drop-off happen at Triangle Vinyl, the record shop downtown, while the company plans a shipping-container shop as its eventual home base.
That is an unusual way to open a rental business in a tourist-adjacent city that has plenty of vacant retail space to fill. It only makes sense if the founders are betting that the customer base already exists on the trail itself, cyclists and paddlers who need gear for an afternoon and will find a container shop through word of mouth and an Instagram feed rather than a storefront window. Midpoint Rec is explicit about its own positioning too: it markets itself as sitting at the center of the Florida coast-to-coast bike trail, inside the downtown district, with direct access to the South Lake Trail and Lake Minneola. That is not incidental language. It is the entire business case.
The same logic shows up in how the city has scheduled its fall calendar, all of it converging on Waterfront Park, the point where the trail effectively ends and downtown begins.
None of these events happen because downtown Clermont has extra weekends to fill. They happen because the infrastructure now supports back-to-back gatherings that draw people who are already downtown for other reasons, whether that's a bike ride, a lunch reservation, or a walk along the water. A calendar this dense only works if the foot traffic to sustain it already exists, and the trail is where that traffic comes from.
If you already call Clermont home, the practical takeaway is less about any single opening and more about how to read the pattern. The businesses succeeding downtown right now are the ones built for people who show up without a car, whether that means a bar designed for a long stay rather than a quick pour, or a rental company that skipped a storefront because the trail already delivers its customers. The events calendar reflects the same bet, stacking five major gatherings into an eleven-week stretch because the crowd is already walking distance from the park on most weekends anyway.
The next time you finish a ride at Historic Village Station or wrap up a Saturday parkrun at Lake Hiawatha Preserve, take a slower look at what's actually opened around you this year. The pattern isn't hard to see once you know what you're looking at. Downtown Clermont didn't get more restaurants. It got a downtown that finally understood who its customers are and where they're coming from.
If you're curious about what else is changing in this pocket of Lake County, or you'd like a closer look at how neighborhoods near the trail are holding their value, Marcelo Teixeira and the team at Glasstone Real Estate track these shifts closely and are always happy to talk through what they're seeing on the ground.
