This overlooked midwestern town is sneaky cool

Indianapolis is simply a delight, from its compact and tourist-friendly downtown to its charming neighborhoods hiding an array of cool under-the-radar dive bars, hip restaurants, burgeoning distilleries and wineries, and lively music venues. Indy’s charms may not be fully apparent at first glance, but like any good travel destination, the more you explore, the more you fall in love.

Here’s our suggested itinerary of how to have a can’t-miss weekend exploring the Circle City’s lesser-known gems, from an alarmingly fun minor league baseball stadium to a leafy beer garden-equipped art museum.

A collection of tall buildings that make up the Indianapolis skyline — Indianapolis is simply delightful © John J. Miller / Getty Images

Get out and explore Indy’s neighborhoods

While many visitors tend to stick to the downtown tourist district, Indy boasts a number of hip neighborhoods tailor-made for more offbeat exploration. The Fountain Square District is home to several standout bars, restaurants, and music venues as well as the historic Fountain Square Theatre Building, featuring the addictively fun Atomic Duckpin Bowling on its fourth floor in addition to a picturesque rooftop garden cocktail lounge overlooking the city.

Head over to the Mass Ave Cultural District to snap a photo of the 38-foot-tall Kurt Vonnegut mural (the famous novelist was raised in Indy) before making your way into Mass Ave’s bustling bar and nightlife scene, which includes the glorious outdoor patio located at the laid-back German-style Rathskeller. North of the city, the Broad Ripple neighborhood (where David Letterman was raised) plays host to funky shops, a variety of ethnic cuisine and a thriving nightlife offering a more collegiate feel thanks to the presence of nearby Butler University.

See a live show in a mosque-styled Shrine Center

Certainly, no one is going to confuse Indianapolis with Nashville or New Orleans, but Indy’s music scene more than holds its own (with its central location making the city an ideal stopover for national touring acts as well). Local, independent, and smaller touring acts grace the stage at the homey 195-capacity Hi-Fi, where you’ll find everyone from college-aged hipsters to grizzled old farmers rocking to the sounds of bands like Indy’s own eccentric bluegrass/Americana favorites Bigfoot Yancey. Grab a spot with great sight lines to the right of the stage and enjoy a night out commiserating with a friendly crowd from all walks of life.

Larger touring acts gravitate more towards venues like the Old National Centre, a stunning and wholly unique multi-purpose historic structure modeled after a Moorish mosque and owned by Shriners International. The venue portion, the 2,500-seat Murat Theatre, features an Egyptian vibe while the building itself constitutes the largest Shrine Center in North America. Smaller venues like the hip Radio Radio and old-school blues bar Slippery Noodle Inn keep the tunes flowing throughout the city, while downtown’s underrated 6,800-capacity Farm Bureau Insurance Lawn at White River State Park hosts vibrant outdoor concerts in one of the most picturesque settings in the Midwest.

Drink up in an Indy dive bar (or a veteran-owned distillery)

There are dive bars. And then there is Dorman Street. Located in a residential section of town seemingly in the middle of nowhere with an exterior reminiscent of notorious New Orleans dive Snake & Jake’s and a locals-heavy crowd of bar and restaurant industry workers, Dorman Street is slinging a surprisingly excellent selection of expertly crafted cocktails in a dark, laid-back oasis of drinking well past the point at which good decisions are made.

Melody Inn and Red Key Tavern are other classic Indy dives, while those looking for something more upscale can head over to the unique veteran-owned distillery Hotel Tango for standout spirits served in a historic carriage house. Easley Winery is a fun urban winery offering daily tastings of seven wines for just $5 that attracts a diverse mix of clientele, while the Inferno Room is Indy’s go-to spot for exotic tiki drinks and America’s largest collection of artwork from Papua New Guinea outside of a museum.

Eat at one of the world’s best restaurants

Indy’s “fine diner” Milktooth has been praised everywhere from Bon Appetit to Food and Wine as one of the best restaurants headed by one of the best chefs in the US. Whether or not that’s true, Indy’s long underrated food scene is booming.

In addition to the inventive rotating breakfast and lunch offerings at the always-packed Milktooth (housed in a former garage space), Indy’s food scene goes far beyond stereotypical Midwestern meat-and-potatoes fare. The hip Bluebeard, serving contemporary American dishes in a 1924 factory warehouse, is owned by a member of Jimmy Buffett’s touring crew and earned a James Beard Award nomination for “Best New Restaurant in America” in its first year (2012). It hasn’t looked back since.

Over in the charming residential neighborhood of Herron Morton, the almost unbelievably adorable Tinker Street puts you in the right mood immediately with a small pour of free sparkling wine as you are seated. From there, it’s time to dig into an affable menu stacked with seasonal farm-fresh heavy hitters ranging from squash tacos to ramen to Great Lakes walleye and duck and pumpkin waffles.

Indy is also home to the only non-Illinois location of Chicago’s epic heavy metal burger joint Kuma’s Corner as well as downtown’s iconic St. Elmo Steak House, which has attracted everyone from AC/DC to Dan Quayle since opening in 1902.

Hit an art museum beer garden (or a park overlooking the highway)

Despite its buttoned-up reputation, Indy isn’t afraid to do things a little differently. For proof, look no further than the city’s stunning 152-acre art gallery/garden campus Newfields, which houses the Indianapolis Museum of Art, a 100-acre art and nature park, and the historic Lilly House estate. They also have s a beer garden. Grab a beer or a glass of wine from the leafy outdoor beer garden (open April-October) and stroll around this breathtakingly beautiful campus with drink in hand.

And in case you think Indy doesn’t have a sense of humor about its Indy 500 reputation, think again. Sure, you could pay good money to watch cars do laps at the world-famous Indianapolis Motor Speedway. Or you could take a walk to a small neighborhood park called The Idle, where three rows of bright orange stadium seats suddenly pop up on a small hill with a bird’s eye view of…traffic along the interstates. While upon first entering the park it comes across as a joke, it’s hard to deny the peaceful nature vibe (soundtracked by the soft whirl of highway traffic) the longer you sit there. Like most things in Indy, first impressions are rarely equivalent to final determinations.

Experience the best of small-town life (in the city) at a minor league baseball game

Nowhere is Indianapolis’s intriguing mix of small-town charm and urban city life on more perfect display than at the family-friendly Victory Field, home to the minor league-affiliated Indianapolis Indians baseball team. Located in the heart of the downtown tourist district but often overlooked in favor of larger pro sports arenas, there’s not a bad view to be had at one of the best minor league ballparks in America.

Watch the sunset’s reflection over Indy’s downtown buildings surrounding the ballpark as you take in a game on a breezy summer night, while all of your preconceived notions about this city float away like a deep home run hit over the fence onto the stadium lawn.

Jay Gentile traveled to Indianapolis with assistance from Visit Indy. Lonely Planet contributors do not accept freebies in exchange for positive coverage.