Oakley is a pleasant place. Imagine that you’re Goldilocks but looking for alcohol instead of porridge. If you went up the hill to Mount Adams, you’d probably be all “Mount Adams is too sloppy,” and then if you rode your moped over the viaduct to Northside you’d probably be all “Northside is too cool.” But then if you drove your Honda and parked in Oakley, where you could walk from bar to bar to watch flat-screen televisions and meet a wide variety of people or eat at a nice restaurant followed by a scoop of ice cream, you’d most definitely say, “Oakley is just right.” Follow our step-by-step wining and dining instructions for a fun night that won’t leave you waking up in a wrong-sized bed.
Get in your car at 8 p.m. This seems early, right? It kind of is for a bar crawl, but shut up because you don’t even know what you’re doing yet.
Drive your car down Madison Avenue (or Markbreit if you took the shortcut from Hyde Park) and park before you get to Oakley’s loopy roundabouts. Oakley has some strange traffic circles that are hard enough to figure out when you’re sober. After you’ve parked your car, unbuckle your seatbelt, open your door and step out of the car.
Start walking toward the middle of Oakley, directly at all the lights and businesses. On this journey you’ll pass several restaurants. Go inside one. Doesn’t matter which one, not only because many of the restaurants are Best of Cincinnati winners (which means their food is good) but also because before an evening of binge drinking and walking you must protein-coat your stomach and scarf a few power carbs so you won’t need a nap break in Oakley Laundry.
If you stop by boca (3200 Madison Road), grab a glass of wine and last year’s Best of Cincinnati award-winning Brussels sprouts with diver-caught sea scallop.
If you don’t eat vegetables, go to Dewey’s (3014 Madison Road), winner of Best Pizza (Chain), to watch a guy behind a glass wall make you a cheese pizza while you drink a microbrew with a name that sounds like an Emo song title. This is a great place to stock up on carbs.
Reward yourself for eating dinner with a stop at Aglamesis Brothers (3046 Madison Road) for dessert. This ice cream/candy parlour has been a part of Oakley since 1913. Take a second to absorb the nostalgia of the antique fixtures, sculpted ceiling and Tiffany lamps and then saddle up to the marble-topped counter and order a scoop of Mint Chocolate Chip in an old-timey voice. You can decide what that sounds like. Maybe like Mark Twain? Eleanor Roosevelt? You’ve now had dinner and dessert, you need a drink.
Exit the door to your right and quickly head into Habit’s Cafe (3036 Madison Road). Go up to the bar to order a drink, and while waiting evaluate how nice everyone’s shirts look and whether or not those old people are done with their table. Order several vodka mixed drinks here, comparing the size and cost of each. Although the bartenders make no audible or monetary distinction between the size of the cocktail glasses, spend several minutes figuring out why you paid the same amount for a vodka soda in a rocks glass as you did for a vodka soda in a highball glass. Decide that it’s no big deal and drink them both.
There’s another bar right across the street that looks cute because it has a big sign with beer bubbles on it, so look both ways and run yourself across the complicated intersection. Enter the Oakley Pub & Grill (3924 Isabella Ave.) and appreciate how small and cozy it is while you order a Pineapple Upside Down Cake shot from Jeremy, the bartender in the interesting sweater. After standing there thinking about how good that tasted, realize there’s really nowhere to sit. That’s OK. Sitting for too long can give you blood clots. Order one more shot and leave.
Head back to Madison Avenue, pass Skyline and stop at the Oak Tavern (3089 Madison Road). Look at how shiny and new everything is. Three years ago it was a Chinese restaurant. Can you believe it? Order a shot of tequila from their expansive selection. Try to count all the different bottles of liquor they have. If you’re still able to count above 25, do another shot. Try again. Only 10 or 15 this time? You’re ready to play darts.
All this booze makes you remember how much you love food. And cheese. God, isn’t cheese great? And chili. Chili, too. Didn’t you just pass a Skyline? “Skyline before liquor makes you the sicker, Skyline after beer, nothing to fear.” Exit the Oak Tavern and retrace your steps to find yourself at 3081 Madison Ave., a drive-thru Skyline. Because you’re quite funny, attempt to order through the drive-thru. You can go inside if that doesn’t work.