At 7:30 on a Saturday morning, a few dozen people are walking off a 5K along the paved path at Lake Hiawatha Preserve, sweat drying in the lake breeze, timing barcodes still clipped to their shoes. The Clermont Waterfront parkrun has been doing this every week for a while now, free, volunteer-run, open to whoever shows up. After the run, the crowd drifts the same direction it always has: toward Cheeser's Palace for coffee.
What's changed is everything on either side of that walk.
A few years ago, the stretch between the lake and Montrose Street was mostly empty storefronts and a handful of longtime holdouts. Today it's a working list of names that didn't exist the last time most residents checked: a wine bar, a Cuban sandwich counter, a sports bar that lets your dog off the leash. Meanwhile, out on the highway frontage that rings the historic core, a different kind of growth has been happening in plain sight, and it looks nothing like what's happening downtown.
That split is the actual story. Not "Clermont is growing." Everywhere is growing. The question worth asking if you live here is who's doing the growing, and where they're choosing to put their money.
The Highway Picked the Chains
Highway 50 has become Clermont's answer to a national rollout map. Longhorn Steakhouse opened its doors at 1275 Highway 50 back in September 2024, part of the same wave that brought Mission BBQ into its hiring phase that fall. This spring, White Castle cut the ribbon on its Clermont location, with Mayor Tim Murry crediting the chain with bringing 75 new jobs to the area, and fourth-generation family member and CEO Lisa Ingram joining the ribbon-cutting in person. Portillo's has announced a location at 1251 East Highway 50, adding another Central Florida address to its growing list.
None of this is a knock on any of those businesses. It's just a pattern. Highway frontage brings traffic counts, traffic counts bring corporate real estate teams, and corporate real estate teams bring the same handful of national brands that are also opening in Kissimmee, Winter Garden, and every other fast-growing edge of Central Florida. If you drive Highway 50 through Clermont, you're seeing the same expansion logic playing out here that's playing out everywhere else in the region.
Two Blocks Doing Something Different
Now walk instead of drive. Head into the two or three blocks bounded by Montrose Street, West Avenue, and 7th Street, the same blocks the parkrun crowd passes through on the way to coffee, and the pattern flips entirely.
Back 40 Wine Co. opened at 719 West Avenue, run by a husband and wife, Wesley and Karen Hime, who built the space out of a building that had previously been a florist and, before that, a nail salon. It's one of the few downtown spots with weekend hours that run to midnight, later than most of its neighbors.
A few doors over, Fumao Table opened at 646 7th Street on June 28, 2026. It's a family operation, the Diaz family serving Cuban street food built on recipes they describe as passed down rather than invented, croquetas and cafecito served the way they grew up eating them.
Pups Pub Clermont opened this year at 898 West Montrose Street with an off-leash dog park attached and weekday doggy daycare launching this month. Down the block, Huarike Peruvian has built a loyal following at the corner of Montrose and West, and The Station took over the space on West Desoto Street left behind when Clermont Brewing Company closed, now running its own menu and live entertainment lineup.
That's five distinct, independently run businesses inside a walk you could make in under ten minutes. None of them are franchises. All of them are somebody's name on a lease.
The Restaurateur Who Already Had a Restaurant
The clearest example of what's actually driving this sits just south of downtown on Highway 27, in a spot that used to be Grace O'Malley's Irish Pub. That's where chef Uday Kadam opened The Venue this June, a catering and special-events space, right across the courtyard from Guru Indian Restaurant, the restaurant he's owned since 2014 and built into a spot recognized among the top 10 percent of restaurants worldwide, with multiple Tripadvisor Certificates of Excellence along the way.
Kadam isn't an outside investor scouting Clermont for its growth numbers. He already had a restaurant here. He watched it earn its reputation over more than a decade, and then he opened a second business a few steps from the first one.
The highway is where national chains place a bet on a market. Downtown is where people who already live in that market place a bet on themselves.
That's the difference worth sitting with. The businesses filling in downtown Clermont aren't chasing Clermont's growth from the outside. They're already part of it, and they're reinvesting.
Growth Doesn't Mean Everything Survives
It would be dishonest to describe this as pure addition. The Station exists because Clermont Brewing Company closed. Somebody's business didn't make it, and somebody else took the space and tried again. That's not a footnote to the growth story, it's part of it. A downtown filling in with new operators is also, by definition, a downtown where some previous operators didn't make the rent, sold the concept, or closed for reasons that never made the local paper.
If you live near Montrose Street, you've probably already watched at least one storefront change hands more than once in the past few years. That churn is normal in a commercial district finding its footing, and it's worth knowing about before you assume every new sign out front means unlimited momentum.
What This Actually Changes About a Saturday
Here's where the two threads meet. Clermont Main Street runs a monthly Wine Stroll through more than 20 participating downtown businesses, and that route now passes storefronts like Back 40 and Fumao Table that weren't on the map the last time most people walked it. The weekly Farmers Market still sets up in the same spot it always has, but now it's flanked by places that didn't exist when the market started drawing crowds.
A few of the dates on the downtown calendar worth knowing if you haven't been paying attention:
- Clermont Main Street Wine Stroll, monthly, sampling from more than 20 downtown businesses
- Clermont Waterfront parkrun, every Saturday at 7:30 a.m., free, at Lake Hiawatha Preserve
- 2026 Clermont Family Flavor Weekend, September 11, Historic Downtown Clermont
- AdventHealth Cool Sommer Mornings Triathlon-Duathlon-5K series, ongoing through the fall at Waterfront Park
Family Flavor Weekend in particular is going to be the real test of how much has changed. It's the kind of event that pulls people through the entire downtown footprint in a single weekend, and this year that footprint includes a wine bar that didn't exist a year ago and a Cuban sandwich counter that's barely two months old.
The Part That Matters If You Live Here
None of this means downtown Clermont has "arrived" or that the highway corridor is somehow lesser. They're just doing different jobs. The highway is where Clermont absorbs the same national growth that's landing across every fast-growing edge of Central Florida. Downtown is where the people who already had something invested here are doubling down on it, one storefront at a time, with their own names on the lease and their own money on the line.
If you've lived in Clermont for a while, that distinction probably already matches what you've noticed without being able to name it. The highway feels like it could be anywhere. Montrose Street increasingly does not.
If you're weighing what any of this means for your own plans in Clermont, whether that's understanding how a changing downtown affects your street, or just wanting a local read on where the momentum actually is, Garcia Group is happy to talk it through. Let's Connect.
