Eat, Sip, Explore — Our Local Favorites
Downtown Winter Garden
Our little town of Oakland is small, quaint, and quiet, making it the perfect place to unwind. But if you’re craving great food, drinks, and live music, you’re only three miles away — by foot, bike, car, or Uber — from one of our favorite spots in Central Florida: Downtown Winter Garden.
We’ve listed a few of our staple stops below, but be sure to wander and explore. The area is full of locally loved restaurants, cafés, and bars, and we’d love to hear if you discover a new hidden gem we should add to our list.
Chef’s Table & The Tasting Room: Enjoy an intimate, preset three-course meal at the Chef’s Table or go for our more casual favorite of small, eclectic plates and craft cocktails at The Tasting Room. We dare you to try the killer Muerto Verde margarita, often missing from the menu so just ask your waiter if you dare.
Thai Blossom: Located next door to the Tasting Room, we often debate between these two as our go-to staples of Winter Garden. If you are in the mood for an Asian flare, this authentic Thai set in the historic Edgewater Hotel building is delicious.
The Attic Door: Just across the street and owned by the Chef’s Table, the small bites are perfect but their wine and music is even better.
The Hangry Bison: A must try for burgers and beer lovers.
Market to Table: Locally sourced and artfully created cuisine with a nice weekend brunch.
Crooked Can in Plant Street Market: Fabulous local Orlando Brewery with so, so food. We usually get a flight and then explore the indoor Plant Street Market for numerous artisan, food and local craft delights.
Three Birds Cafe: Serving breakfast all day long, bottomless mimosas and fresh squeezed orange juice in addition to great, healthy lunch and dinner options as well.
Pilars: Find the art of mixology at this happening martini and music bar.
Press’d: We remember when these guys started out of what seemed like a shoebox in WG. We love how much they have grown and been long time vegetarian and vegan providers to our community and hands down the best pressed juice around.
Gotha
Gotha is small, but it’s worth a stop for one thing — the food. Just a few minutes down the road from upscale Windermere and its lakes, golf courses, and celebrity homes, Gotha keeps things simple, casual, and delicious.
Our favorite Central Florida spot is Yellow Dog Eats, where you’ll catch the smell of smoked barbecue the moment you step out of the car. You can eat inside a Jerry Garcia–themed minivan, sip a drink on the patio, and share your space with the free-range chickens wandering around. It’s quirky, pet-friendly, and unforgettable.
Just nine miles from OMHouse, this little gem is absolutely worth the trip.