The friendliness of the Midwest feels a million miles away from Southern hospitality on our mental map of the U.S., but the Ohio River acts as a zipper pulling together two seemingly disparate swatches of cultural fabric. As strange bedfellows, the regions temper each other’s known clichés: the grittiness of the Rust Belt is soothed by Kentucky bluegrass; its red-state ranches are cooled by liberal blues. And the drive from Indianapolis to Cincinnati through Louisville and Lexington provides compelling variations of the “Midsouth” theme.
Start: Indianapolis, Indiana. End: Cincinnati, Ohio
Total Distance: 450 miles. Suggested Length: 6 to 8 days.
1) Cultural Trail Indianapolis
A love letter to cyclists and pedestrians, the Indianapolis Cultural Trail meanders between buildings and back alleys, uniting unexpected outdoor art installations and a bevy of local businesses. Swap your four wheels for two at the city’s expansive bike share program and pedal past the Murat Theatre, with its Islamic architecture and tiki lettering; pause at Indy Reads Books, an independent seller promoting literacy in central Indiana; then refuel at Public Greens, which focuses its profits on feeding at-risk and food-insecure children in the community.
2) Milktooth Indianapolis
With more arm tats than Popeye, chef-owner Jonathan Brooks does what we love best — he challenges our definition of deliciousness with a shortlist of dissonant menu items served on mismatched china. A plate of green olive-soaked cauliflower next to a tarte tatin Dutch baby sounds like culinary Frankenstein-ing, but it’ll prove to be the most memorable meal in town.
The university campus–sized Newfields devotes its 152 acres to massive outdoor sculpture work, elaborate gardens, a biergarten (in season), and a dedicated museum complex with an impressive collection of international oeuvres spanning most continents and eras.
4) Gallery Pastry Shop
Imagined as an atelier for high-end pastries, Gallery started to morph into a hangout when brides-to-be hankered for a glass of wine while taste-testing their wedding cakes. Today, the baking station shares its garage-style real estate with several long tables. It’s become the go-to brunch spot in the city, in spite of itself, fueled by a Beyoncé playlist and free-flowing champers on weekends.
5) St. Elmo Steak House
Visiting Indy and not checking out the Motor Speedway is like going to Paris and not swinging by the Louvre. But the ultimate boys’ club experience in town is St. Elmo’s, an old-school steak house with tux-clad waiters, ribeyes that would make Sinatra weep, and a shrimp cocktail with enough freshly grated horseradish to make your sinuses explode.
6) 21c Museum Hotel
The 21c was dreamed up as a way to help revitalize Louisville’s downtown wasteland over a decade ago. The concept — fusing compelling accommodation with a contemporary art space — took off, and now both Lexington and Cincinnati have spinoffs, though they hardly feel like a chain as each version inhabits a historic building that helps dictate the variations in their layouts and style. The galleries are worthy of a dedicated visit (even if you’re not a hotel guest). And don’t be shy about taking one of the giant plastic penguins by Italian design firm Cracking Art — molded in a different color at each property — up to your room for a selfie session in bed.
Located in the most sprawling of the four cities on this tour, Louisville’s NuLu district (“New Lou,” get it?) may only be a couple of small city blocks, but it’s a good first stab at a walkable small-business thoroughfare, complete with standouts like LGBTQ-owned Mahonia, a shrine to succulents and general good taste; Revelry, with its quirky, locally made art and jewelry; and Joe Ley Antiques (615 E. Market St.), a warren of forgotten trinkets housed in an Addams Family–style manse.
8) Kentucky Bourbon Trail
Worthy of the reverence ascribed to Napa and Sonoma, the valleys between Louisville and Lexington are the heartland of America’s bourbon country. Park your car and let Mint Julep Tours take you on a chauffeured tasting of some of the region’s top tipples. Get some face time with the mom-and-daughter owners of Jeptha Creed — they’re about to release their first batch of straight bourbon (aged two years). And don’t miss the VIP speakeasy treatment at whisky powerhouse Stitzel-Weller Distillery. The tour will even throw in a brewery stop — try lunch and an IPA pairing at Monnik Beer Company.
The two most important things in Kentucky are bourbon and horses, and no trip to the Bluegrass State would be complete without exploring both. And it is quite literally the bluegrass — fields of vitamin-rich plants and cereals — that fortified the local equines and helped establish the Lexington area as the country’s premiere region for stallions. Owned by the son of Graham Beck (of South African winery fame), Gainesway is of particular interest for its pristine grounds, including several English-style gardens, and its prize horse Tapit, considered the most desirable sire in America.
10) Distillery District
A derelict campus of distilleries and warehouses is now Lexington’s hangout hive, as each of the area’s structures are refurbished piecemeal. Spoil your dinner at Middle Fork Kitchen Bar with bourbon-infused ice cream at Crank & Boom and don’t miss a visit to the newly opened James E. Pepper Distillery. A local entrepreneur with a passion for history has resurrected the brand — a crucial part of pre-Prohibition Americana — in its original bourbon-making location.
The fact that Cincinnati is known as the “Queen City” should be enough of a draw for the gays, but if you’re in need of some extra convincing, the Over-the-Rhine neighborhood will do the trick. Known as the most dangerous district in America only a decade ago, “OTR” has become a viable Brooklyn contender, even beating out its New York counterpart by prioritizing small businesses and sustainable growth. Today, the Italianate row homes feature design boutiques like Deerhaus (DeerhausDecor.com) and Elm & Iron, and darling eateries like the New American kitchen at Salazar. A street car service, with hilariously corny recorded announcements by Cincy native Nick Lachey, links the downtown to OTR with stops throughout the neighborhood including Findlay Market, a boisterous conglomeration of artisanal vendors.
Connected by a food tube — a tunnel that pushes burgers from one establishment to the next — these Over-the-Rhine hangouts pack the perfect one-two punch for a night out on the town. Order the pickle-brined fried chicken at Sartre OTR amid Gatsby-esque surroundings — thick black paint, scuffed mirrors, and plenty of Art Deco gilding — then head next door to Rhinegeist. Meaning “ghost of the Rhine,” the vaulted beerhall inhabits an old brewery from the glory days of German settlement and cranks out its own recipes on draught (including cider!) that pair perfectly with a game of cornhole.
13) Casablanca Vintage
A point of pilgrimage for thrift shop aficionados, Casablanca anchors the alternatively flavored Northside neighborhood, a civic transport junction that has been a quiet sanctuary for the city’s LGBTQ crowd since the so-called “white flight” to suburbia in the 1970s.
14) American Sign Museum
More a monument to nostalgia than a didactic museum space, this warehouse is filled to the brim with a private collection of commercial signs spanning the age of American consumerism. From mirrored glass and light bulbs to curlicues of pulsing neon, the ASM’s highlights include old ads for KFC and McDonald’s, and a retro road sign for a now-shuttered HoJo’s.
Could America’s best Italian restaurant be in Ohio? Sotto makes a compelling case. This Cincy favorite bookends its primis with house-made charcuterie boards and puffy ricotta doughnuts in a cavernous wood-beamed basement in the heart of downtown. The feather-light, freshly made pasta here is a poignant reminder that the shells of Barilla macaroni in your pantry are better suited for arts and crafts.