A Look at Downtown Tavares Ruby Street Restaurants

Stand on the rooftop of the Citrus on the Lake Boutique Hotel around 7 p.m. on a clear evening and you can watch a seaplane taxi up to the dock below while the sun drops behind Lake Dora. That view is the whole pitch for Citrus Sky Bar, the rooftop bar that opened on the hotel's fourth floor at 199 W. Ruby St. in early 2025 and is still marketed as Lake County's only rooftop bar. What the view doesn't tell you is that almost everything else on that block, the coffee shop, the cocktail lounge, the steakhouse, the ice cream counter, belongs to the same two people who built the bar you're standing on.

That's the part worth knowing if you live here and have started noticing Ruby Street feels different than it did a couple of years ago. It's not a citywide restaurant boom. It's a couple who kept building on the same short stretch of sidewalk.

One block, one ownership group

David and Hillary Perry, working with business partner Emad Shahid, own The Citrus Hotel itself plus four other operations built around it: Nautilus Coffee Co., The Argonaut Bar & Lounge, Ironworks Steakhouse, and Poppy's Ice Cream. Citrus Sky Bar is their newest addition, built on a roof they already owned. That's a coffee shop for the morning crowd, a themed cocktail lounge for the evening, a steakhouse for dinner, an ice cream counter for families walking the waterfront, and now a rooftop bar to close the night, all reachable without moving your car.

When the Perrys opened the rooftop bar, David Perry framed it as filling a gap for the whole county, not just the hotel. Hillary Perry has talked about it more simply, as a sunset-over-Lake-Dora kind of place. A year in, David Perry has described the bar's role during the city's public events, including a July Fourth fireworks show where rain moved in but the crowd stayed put because they had somewhere dry to keep drinking and watching. His read on it: "We believe in this downtown and the direction it's going. The waterfront district is truly special and we're excited to be part of its growth."

That's a business owner's confidence, and it's backed by six properties pointed in the same direction. But it also means a big share of downtown Tavares's new energy runs through one operator's decisions about hours, pricing, and what gets poured behind the bar. If you want a night out that isn't tied to that name, you have to look a few doors down or across the park.

The city built a second option, and it doesn't run on the same clock

That's where Wooton Park comes in. In March 2026 the city launched something genuinely new: the Tavares Lakefront Food Trucks & Market, a monthly evening event billed from the start as a brand-new addition to the calendar. The first one ran March 20 from 5 to 9 p.m. with live music, food trucks, corn hole, and vendors selling wellness products and local goods. By June 19, the event had grown a second identity, rebranded for that evening as the Tavares Lakefront Cars, Food Trucks & Market, with a classic car show folded into the same waterfront strip.

The contrast matters more than the novelty. Ruby Street's revival is privately built and open every night the Perrys choose to keep the lights on. Wooton Park's new market is a single scheduled evening a month, city-organized, free to attend, and built around vendors and trucks rather than a fixed menu. One is a business bet. The other is closer to a civic experiment in giving people a reason to walk the park after dark that doesn't require a dinner reservation.

If you live in Tavares and are trying to figure out what to do on a given Friday, that distinction is the actual useful information. Ruby Street works any night you want a sit-down meal or a rooftop cocktail. The Wooton Park market only works on its one night a month, and that night has been shifting in format as the city figures out what draws a crowd.

The rest of the map, if the block isn't what you're after

Ruby Street and Wooton Park aren't the only options downtown, and it's worth knowing what else is in easy walking distance if a rooftop bar isn't the plan for the evening.

• Ruby Street Grille, a straightforward downtown option a short walk from the hotel complex.
• The Goblin Market Restaurant & Lounge, one of the area's more distinct dining rooms.
• Puddle Jumpers, with an outdoor patio near the seaplane base, close enough to watch the same water traffic the rooftop bar looks down on, just from ground level.
• Fish Camp, out toward Lake Eustis, for something further from the Ruby Street cluster entirely.

None of these are owned by the Perrys. If the goal is variety rather than convenience, that's where to start.

The older calendar is still doing the heavy lifting

None of this is replacing what already worked. Wooton Park has hosted the city's Planes, Tunes & BBQ festival for eighteen years running, most recently on March 7, 2026, with an air show, a drone show, live music, and the Seaplane-A-Palooza flying contests as the event's signature feature. That festival isn't new and isn't trying to be. It's the anchor event the newer monthly market is building around, not competing with.

The Tavares Farmers Market follows its own separate rhythm. As of this August, the city's own listing marks it as the last market of the season, with a return promised for fall. If your Saturday mornings downtown have felt a little emptier lately, that's why. It's not gone. It's between seasons, the same way it is most years.

What this actually means if you live here

The honest version of what changed in downtown Tavares this year isn't "there's more to do." It's that the additions split cleanly into two categories that don't overlap on the calendar or the ownership chart. One category is Ruby Street, a small, ambitious cluster of businesses built by one couple who keep adding to what they already own. The other is Wooton Park, where the city is testing a new monthly event that's still figuring out its own format, car show one month, straight food trucks the next.

Knowing which is which changes how you plan around it. If you want a reliable Tuesday night dinner, Ruby Street's businesses are open on their own schedule regardless of the city's events calendar. If you're hoping to catch the Lakefront Food Trucks & Market, check the date first. It's not a weekly fixture yet, and its next iteration might look different from the last one.

Either way, the block and the park are both proof that downtown Tavares is still adding things worth walking to, just not from the same source, and not on the same night.

If you're watching this corner of Lake County change and want a read on what it means for property values or timing, Gabriella Nystrom tracks these shifts across Tavares and the rest of the Golden Triangle as part of her day-to-day work in the area. Reach out anytime to talk through what you're seeing on your own street.