Hillstone in Winter Park, Florida lakeside culnary delight

Hillstone in Winter Park can easily be missed, but don't let this delicious setting pass by. Photo Rori Paul
Growing up in northern Illinois I had the great pleasure of spending many happy hours across the state-line in Wisconsin, home to the Wisconsin State Fair, cheese, and beautiful lakes. My family had a home in Lake Geneva, home to many of my most joy-filled memories, where the lake sat center stage and nature was the backdrop to countless hours of play, laughter, and fun. Meals at one of the area’s restaurants or supper clubs meant darkened rooms against silhouetted back lighting, fine food, and a warm and inviting atmosphere. The lakeside setting meant sparkling waters, birds at play, and a view that enriched the soul.
Stepping through the doors to Winter Park’s Hillstone was like stepping back to home, where lakeside dining enriched my life and memories flooded back as old friends.
Winter Park, Florida is out of the tourist zone so many identify Central Florida with. Yet locals have known it as their place, one of the many “neighborhoods” that make up the Orlando area, and while off the beaten path for most, this typical suburban town should not be overlooked. That it offers up a handfull of the area’s best means that plenty is on tap to enjoy.

The entry says it all: hip and cool in a warm, friendly, welcoming setting that harkens to my favorite days at Wisconsin lakeside eateries. Photo Rori Paul
Hillstone should be at the top of that list.
Set back from the road one can easily pass by without even noticing – we had on a previous area visit – only the low slung handsome sign to give it away, though nondescript within its strangely natural surroundings.
Set lakeside at the edge of one of Central Florida’s natural watery spots, the low rise of dark wood blends among the surroundings as naturally as the lake itself. Harkening to that supper club feel of Wisconsin I’ve so loved, even the art – a sculpture of two birds in action greets you inside the door – reflects what I so adore of these settings. Textures, colors, and feel round out an ambiance of warmth, homey friendliness that could be as much movie background as neighborhood eatery.
The clientele is as ranging as any you’d find at a theme park, mostly regulars who know a good thing, and while the tradition of going where the cops go to eat (no cops during our visit) by the steady flow through out our visit, most who seemed to know the menu by heart, tells me these are people who are not like us, first timers.

The Cesar Salad was a surprise with rock shrimp that gave this hot-cold treat a pop of flavor. Photo Rori Paul
Culinary Treats
We’d been invited by the find folks of Hillstone to meet this locale, their guests on this day, and happily greeted from our entry. As often happens for such visits, we were treated to a range of tasty delights, all so that we can get to know them and in turn, share with you. But as always, I wouldn’t share if I didn’t care and I can tell you that Laura and I both were excited beyond delight. So much so we have at least two future visits planned, one to include mom who’ll soon be moving to town.
Hillstone is an open and friendly place, that tip of the hat to hot and trendy, while homey and everyone-knows-your-name seems the feel, but the food is where its at, and this food is worth your consideration.
Price points hit the range so most any budget will find something here, but the portions and taste makes any price a secondary thought.
We’ll share more in other articles, but to get you off and running, my favorite of the day was the Famous French Dip. My personal dining out favorite – inherited from mom – the Famous part here is well deserved, with a beef so tempting and tasty it melts in your mouth. Thin shaved and cooled to pink perfection, the combination with the buttery toasted bread makes this memorable.
Served with the tempting and fun thin fries, these too were a delight and a perfect side to the meal, though our actual favorite side overall (think comparing apples and oranges) was the couscous. I’d eat the fries easily with any sandwich again, but the couscous – something I so rarely enjoy or even want – was amazing.

I loved the Famous French Dip (now my favorite in the area) and the fries were yummy, but we think our favorite overall side was the couscous - who knew! Photo Rori Paul
With so many enjoyable elements, I think Laura would come to the easy conclusion that her favorite was the Caesar Salad with crispy rock shrimp. As I crave the French Dip, she craves this fresh and crispy salad not merely for the fresh greens with ideally proportioned dressing, but the exciting shrimp that literally pop in your mouth. A limited seafood loving fan, I too adored these treats, but Laura was over the moon.
More to come… we’ll share more of the menu in future articles and look for more photos, but needless to say, Hillstone’s kitchen can cook up a storm that your taste buds will be looking forward to time and again.
The Setting
Remember that lakeside setting I mentioned? An ideal backdrop to this culinary experience, I was at once captivated and relaxed. Stunned that in a city so engrained in its high energy themed attractions and go-go travel extravaganza, one could find a spot so relaxing and laid-back, all I wanted to do was nap, eat a little more, watch the passing day, nap…
I found myself often looking out the windows of the room, a smartly designed set up with tiered seating and all tables facing the lake, moving through the day from sunlit to diners and staff silhouetted against the lake, I would be called back into the moment by another course or Laura asking how I was enjoying myself. So too did I notice how so many seemed to be missing out on the beauty of the setting.
But this is that kind of place, where your meal and your experience is what you need and what you make of it.
Inside its easy to let the backdrop slip unseen into the background like one of the prints on the wall, but outside, where tables offer a closer overview of the setting, or along the grassy yard where appetizers and drinks can be enjoyed, Hillstone provides a range of experiences. Families, gatherings and couples sat on chairs or on the pier to enjoy their time, some sipping drinks, others eating, some just having fun watching the kids at play, all a part of this offering.

A reminder of the places of my childhood and young adulthood, when family and friends would gather in Lake Geneva, Wisconsin, Hillstone was at once a relaxing respite from life, a culinary delight, and old friend come to visit. Photo Rori Paul
Hillstone is something for everyone, and a tip of the hat to those places where family dinners out were as common place as Sunday’s at Grandma’s.
Check Please
I’d gone that day not feeling up to my job, but quickly found myself resting, restful, delighted, and indulged. The setting was charming and memorable, touching in me the memories and fondness of times gone by, a meal so incredibly wonderful I cannot wait to return again and again. Mom will be here soon…
For the pricing, the food, and the atmosphere – as a rule I do not like to give places a 5 star rating when I’ve not paid, as I cannot feel like its the right thing to do, but we enjoyed our time at Hillstone so much, that not only do I give it a 5 star, if I had it in my rating system, I would give it a 5 plus!
If you are looking for a place the locals know and love, a place where you can wear business casual to jeans or shorts, a place where you can enjoy a lakeside cocktail, your special event, or a diner with someone special, Laura and I highly recommend Hillstone.
And for the record… Hillstone is my first choice for my 45th birthday dinner this year.
I believe they called it a Moroccan couscous – but whatever they name it, Yummy fits!
There is something special about enjoying your meal, looking out over a lake, and watching the smooth, sweet pass of a kayak. Hillstone is a setting for relaxing, rejuvenating, and reconnecting.
The on-site garden means many ingredients are so fresh, they come right from here. Stroll with a drink in hand and enjoy the setting, including the garden, or host a gathering including weddings in this peaceful spot.
Drinks or dinner or both, relax in this setting for a peaceful escape from Orlando, and enjoy the natural beauty of Florida.
Hillstone in Winter Park is an exciting spot for a culinary treat in the Orlando area.
All photos are copyright Rori Paul with permission of Hillstone. For more about Hillstone and other Florida dining options, please visit us on Rori Travels Florida at Travelers Taste Of…





















