In Partnership with the Southern Weekend

The Cincy Weekend Guide To: Oakley

Here in Cincinnati, we're lucky to have 52 unique and interesting neighborhoods, each with it's own history and community. Go even further, and we've got more than 200 neighborhoods in the whole Tri-State! Our goal is to explore each one and give you a guide to what to do if you're there.

For our first ever Cincy Weekend neighborhood guide, we present: Oakley. Originally a popular spot for wagon drivers in the 1800's, and even called home for famed markswoman Annie Oakley (how's that for some history), things have changed quite a bit. Now you'll find a quiet but vibrant neighborhood with plenty to do, great food and great people.

While you're in Oakley you should...

Eat wings at The Oak Tavern

Not only are these the best wings in Oakley, they could be the best in the whole city. “The Oak Tavern” lies just off Oakley square further down Madison road. Walk in and you’ll find a great bar with good beer, a couple tables and a perfect patio spot when the weather is nice.

As for the wings, well… if variety is your goal, you’re in the right place. Smoked, grilled and served plain with a caddy featuring 6 different (and all delicious) sauces like Teryaki Garlic, Spicy BBQ, BuffalOAK and more. This is the perfect spot to watch a game, catch up with friends and enjoy amazing wings.

Get directions to The Oak Tavern.

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Get brunch at the Sleepy Bee Cafe

Odd’s are you’ve had someone tell you how great the Sleepy Bee Cafe is, and for good reason. Locally sourced ingredients made well every time by incredibly talented chefs. There’s probably gonna be a line to get it, but it’s well worth the wait to have a brunch far above the rest. That includes an array of different pancakes, delicious omelets made with fresh eggs and produce (trust us, try the “Greek Bee”) and some breakfast sandwiches that are out of this world. We love “the Broakley” with thick cut bacon, sprouts, avocado and a broken egg on a brioche bun. Yes, please.

Get directions to the Sleepy Bee. 

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Get a cup of coffee at Deeper Roots

In the grand scheme of things, it seems like fewer and fewer places can do a straight-up, classic, no-frills solid cup of coffee well. Deeper Roots is perfecting it. Whether it’s their rotating list of daily brews or one of their pour-over offerings, we can’t recommend this spot enough (and we can’t recommend the “Cabin Fever” brew enough either.) And this high praise for doing the basics well shouldn’t take away from the fact that they also make some pretty great espresso drinks too. So, if you’ve got the time, stop in for a cappuccino and hang out for a while in this beautiful little shop. Or maybe just grab a cup to go and take a scenic walk around the square right outside.

Get directions to Deeper Roots. 

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See a show at the 20th Century Theater

If Oakley had a mascot, a symbol, an icon of some kind, it would probably be the 20th Century Theater with it’s bright red sign illuminating the square at night. Opening in 1941, the theater has a long and interesting history, even closing in 1983 due to the rise of big multi-plex theaters. After it came close to being torn down, even becoming a flooring company at one point, the theater went back to being a theater, even turning on the light again in 2010 for the first time in 30 years! Needless to say, it’s a place you’ve gotta see in person. Whether it’s a concert, wedding or even the OFF market, the 20th Century Theater is an important piece of Cincy history worth seeing.

Get directions to the 20th Century Theater. 

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Grab a beer at Madtree 2.0

MadTree 2.0 is finally here! We don’t need to explain to you how great their beer is because you probably already know, but this new space is definitely a spot you need to check out. Much bigger than the previous taproom on Kennedy, there are more taps, more tables, an outdoor beer garden and even some private event spaces. MadTree started in a basement in Oakley, now one of the neighborhoods most iconic businesses. We can’t think of a better story of the community supporting good beer and good people.

Oh yeah, we took a tour right before 2.0 opened. You can check it out here. 

Get directions to MadTree Brewing 2.0

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Stop by the Oakley Pub for late night drinks and apps

The Oakley Pub feels like a place where everybody knows everybody, and that’s probably true on any given night. Cheap beers, good vibes and great appetizers. That includes the Buffalo chicken dip (a fan favorite), great crab cakes and your choice of the “Oakley” (chili, classic toppings, black olives) or “Anderson” nachos (queso, pico and pickled onions.) Drop in sometime.  We’re sure it won’t disappoint.

Get directions to the Oakley Pub and Grill.

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Indulge at Aglamesis Bro's

Walking into Aglamesis after a night out on the square is really something special. When you open the door, you’re immediately immersed in an authentic vintage ice cream parlor where everything lives up to the hype. Most importantly, from the marble fountain to the tin ceiling, everything is authentic and that’s important. They’ve been around for more than 100 years made famous by delicious, small batch ice cream and fine handmade chocolates you’ll be dying to take home. With all these things combined, this is pretty much a required date spot.

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Go healthy at Rooted Juicery + Kitchen

This list proves that there are a ton of great places to indulge in Oakley. But on the flip side, the neighborhood also has a handful of great healthy and natural options.

That includes Rooted Juicery + Kitchen. You’ve probably seen the bottles of colorful goodness around town. Their juices are all made with organic products often sourced from farms right here in Ohio. Also, there are a BUNCH of flavors with something for everyone. But don’t sleep on their food offerings. This is  a great spot for a healthy lunch where you can get salads, wraps or bowls (we love the grab-and-go Buddha bowl).  End it all with a smoothie and a walk around the square on a nice day.

Get directions to Rooted Juicery + Kitchen.

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Keep an eye out for more neighborhood guides coming soon!