By Molly Snyder Senior Writer Published Apr 09, 2014 at 5:21 AM Photography: Royal Brevvaxling

Recently, we spent three days discovering Indianapolis and determined that, in general, it felt somewhere between Milwaukee and Chicago in size and vibe.

With roughly 800,000 people, Indy is actually closer to Milwaukee’s population of just under 600,000 as opposed to Chicago’s 2.5 million, but when walking and driving around, it felt like the Midwestern love child of the Windy and Brew Cities.

We had never been to Indy before, so we really weren’t sure what we’d find or what we’d think of the city, but after a long weekend and a lot of investigating, we came home eager to share our findings with Milwaukeeans who might want to give Indy a whirl.

"Even as the nation’s 13th largest city, first-time visitors are always surprised to see just how abundant the cultural offerings are in the city," says Morgan Greenley, senior communications manager for Visit Indy. "We're more than just racing." 

Indianapolis was co-designed by Alex Ralston, who had previously assisted Pierre L'Enfant as he designed Washington, D.C. and, consequently, the layouts of the two places are often compared.

For Indianapolis, Ralston created a circular Downtown design that originally was to include the governor’s mansion, but instead became the location of the city’s now-famous Soldiers’ and Sailors’ Monument. 

Hence, the city is sometimes called The Circle City, and other times Naptown, but it is more commonly nicknamed simply, Indy.

In the '80s and '90s, Indy faced many of the same challenges as many other medium-sized cities, including urban decay and "white flight." However, at the end of the 20th century, the Downtown neighborhood underwent a major revitalization effort which has allowed the city to host numerous large-scale conventions and sporting events, including the Indianapolis 500 and the Big Ten Conference football games. 

Perhaps the most impressive and innovative aspect of the city is the Cultural Trail, an eight-mile urban path for bikers and pedestrians that was completed in 2013 and connects the city's five downtown districts, neighborhoods and entertainment offerings. 

From its inception, the Cultural Trail was dedicated to supporting public art and more than $2 million in private funding was allocated to allow for many public art displays along the trail.

One of the most appealing aspects of road tripping to Indianapolis is how easy it is to get there. With only 280 miles between the two cities, we made it there from Milwaukee in under four hours without any major traffic issues either way.

It is also a fairly easy city to navigate and, best of all, we found the parking to be cheap or free and plentiful.

Also, even though it is just a few hundred miles to the south of Milwaukee, Indianapolis'  March weather was 10-15 degrees warmer the entire time, with one of the days during our four-day visit reaching into the 70s.

There are many hotel and motel options in Indianapolis, including the 1,005-roomed JW Marriott, which is why the city is able to welcome such large conventions. (In 2003, GenCon, the largest gaming convention in North America, moved from Milwaukee to accommodate the massive increase in attendees.)

We stayed at the smaller, more boutique-y Conrad Indianapolis and had a fantastic experience. 

The five-star hotel is a mix of history and contemporary luxury (case in point: there was a television in the our bathroom) with an eclectic collection of art in the lobby, hallways and rooms.

"We pride ourselves on offering both world class and local art," says Jacqueline Cromleigh, the Conrad’s PR and marketing manager.

The Conrad features a self-serve wine bar, Tastings, and The Capital Grille, very similar to the one in Milwaukee except the Indianapolis location also serves breakfast.

We spent an evening at Tastings chatting with Cromleigh. We had enjoyed self-serve wine in Milwaukee at Black Sheep, however with 150 different wines on tap, Tastings is the sommelier’s or amateur sommelier’s smorgasbord.

Tastings also offers small plates, including delicious, moist crab cakes.

The Conrad staff was so genuinely fun and friendly that we sought out their input and conversation on numerous occasions.

Conrad concierge Lee Ann Parrotte provided print-outs of maps, but even more valuable, the kind of local insider information that is gold to us. With a solid and insightful understanding of Indianapolis neighborhoods, she was able to suggest locales that were not already on our radar.

"There’s an unmatched heart and soul in the Fountain Square neighborhood," says Parrotte. "And I hope it stays."

And indeed, our visit to the Fountain Square neighborhood was one of the high points of our weekend. The neighborhood is just southeast of Downtown and home to a funky mix of entertainment offerings, galleries, studios and living spaces. It reminded us of Milwaukee’s Walker’s Point neighborhood.

Fountain Square Theatre Building features bars, restaurants and two duckpin bowling facilities. Action Duckpin Bowling  – a 1930s vintage alley that’s similar to Koz’s Mini Bowl in Milwaukee but has eight lanes and electric as opposed to human pinsetters. Also, Atomic Bowl – a ‘60s-style alley — is located in the building.

Across the street, Funkyard Cafe features coffee, tea, gelato, local art and second-hand books and records. We spent an hour or so people watching and witnessed this great conversation between two 30-something men.

"Can I borrow that Etch-A-Sketch?" one man asked, nodding to the toy on the table.

"Absolutely," the second man said, handing it to him.

On the topic of coffee shops, we also visited Bee Coffee Roasters, a hand-brewed coffee and espresso shop with two locations. It reminded us of Milwaukee’s Valentine Coffee and we took home a pound of beans as our souvenir.

We also took home a variety of peculiar sodas from Rocket Fizz including hot chicken wing, peanut butter, cookie dough, ranch dressing and jelly and pumpkin pie. We don’t recommend the chicken wing variety, but the others were oddly tasty. 

Must-visit Fountain Square nightspots include intimate live music venue Radio Radio and the burlesque and bingo bar, White Rabbit Cabaret.  

Our other favorite Indianapolis watering holes were the Slippery Noodle Inn, the oldest continuously operating bar in Indiana that once served as a stop on the Underground Railroad, and the Red Key Tavern, which we stumbled into simply because the vintage neon sign was appealing. 

Located in what’s referred to as the SoBro neighborhood (south of the party-hardy Broad Ripple ‘hood), the Red Key has been around for 63 years and three generations. Dusty model airplanes still hang from the ceiling and Bing Crosby’s still blasting from the jukebox.

Today, the Red Key is a mix of hipsters, students and old guys who remember the original, late owner, Russ Settle, and his numerous, now legendary house rules that included no standing, no moving of chairs, no putting your feet on chairs, no cursing and no coats on furniture. 

His grandchildren still enforce the rules today.

"We keep everything just the way my grandpa Russell wanted it," says Leslie Settle.

For the sake of travel experience, we visited the Broad Ripple neighborhood on an energized Friday night and stopped into a sports bar called Chumley’s for a beer and to catch a few minutes of a basketball game. (Go Hoosiers?)

At night, Broad Ripple is a fun, college-y neighborhood ideal for thirsty sports lovers. During the day, the cafes, shops and galleries are also a draw.

Like Milwaukee, Indy offers a plethora of excellent restaurants, from the chic to classic.

Our favorite meal of the trip took place at Bluebeard, located in a renovated factory warehouse in the Holy Rosary neighborhood.

Bluebeard, named after a novel by the Indiana-born Kurt Vonnegut, serves contemporary American cuisine with a local and seasonal focus. Everything was presented so beautifully and the food was so delectable we didn’t leave a single scrap on our rectangular, white plates.

We started with Mezcal mules – a take on the Moscow mule that’s made with Mezcal, bitters and ginger beer – along with a noshy assortment of pickles, olives and radishes.

We went on to have a scrumptious roasted beet salad tossed with mushrooms, greens, feta, crunchy shallots and a balsamic truffle vinaigrette, roasted Brussels sprouts and small plates featuring fresh sashimi, pork chops, an incredible bouillabaisse (octopus, shrimp, mussels, tomato, semolina crouton and saffron rouille) and, even though we are usually not dessert people, finished with vanilla bean chess pie.

The following night, we juxtaposed our contemporary food experience with Indy’s iconic St. Elmo Steak House. St. Elmo’s is best known for its shrimp cocktail – which is the "world’s spiciest dish" according to the Travel Channel – and as full-on Sriracha floozies we were impressed with the amount of heat in the dish.

We also enjoyed steaks, salads and a side of asparagus along with fascinating conversation with our server who not only provided us with tales of famous folks he’d waited on over the years, but also took us on a private tour of the multiple wine cellars.

Other eateries that were highly recommended to us that we did not have time to check out include The Libertine Liquor Bar and R Bistro.

As Brew City natives, it was crucial to us that we went on a brewery tour, and so we picked Sun King Brewing

The bustling brewery and tasting room is owned by Clay Robinson and Dave Colt – self-described "hop heads" – who started the company in 2009.

And the business has grown beyond their yeastiest dreams.

In 2010, Sun King brewed 5,000 barrels and this year is on track to produce 28,000 barrels – five times what was originally projected. Not surprisingly, during our visit, the brewery was under another expansion renovation.

Sun King offers three year ‘round beers and three to four seasonal beers every month. 

And it’s only available in Indiana.

"Every ounce of beer we make gets sold in Indiana," says Robinson. "We believe beer is best when fresh and we only distribute close to home."

Sun King looks and feels somewhat like the Milwaukee Brewing Company – plus, both distribute primarily in cans with environmentally-friendly plastic can toppers and have similar tasting room areas.

However, Sun King’s tasting room features brewery mascot, Zaius, who is named after the orangutan in the "Planet of the Apes" and is made from the roof of the Hoosier Dome.

"He’s a piece of Indiana history," says Robinson. "We try to have fun here."

At times during our weekend in Indy, we went full-on tourist. (You have to when visiting a new city, right?) We squished a souvenir penny or two and went to the top of the aforementioned Soldiers’ and Sailors’ Monument in the epicenter of Downtown. 

Visitors can climb the 331 stairs to the 360-degree observation deck at the top of the monument or, for $1, take a tiny elevator. 

Despite issues of minor claustrophobia and an unnatural fear of elevators, we still decided to skip the stairs. It was completely worth it – the view of the city is incredible.

Also, a trip to Indianapolis would not be complete without some tribute to racing culture. With this in mind, we visited the Indianapolis Motor Speedway, home of the Indianapolis 500 and the Brickyard 400.

"On race day, we’ll have 300,00 people in this facility. It’s an astounding thing to be a part of," says Tom Sturber, public relations and media manager for the speedway. "It should be on everyone’s bucket list – whether you like racing or sports or not. It’s an American cultural icon and it’s quite something."

Indeed, it is. Not only is it the largest outdoor seating facility in the world and includes an incredible nine-tour viewing pagoda, but standing on the racetrack, imagining all the action that has taken place there, is a complete thrill.

During our visit, we learned that when drivers win the Indy 500 they drop to their knees and kiss the part of the track that is still brick. (When it was built in 1909, the entire track was brick but over the years it was replaced with asphalt.)

After we, too, kissed the bricks for good luck, we went to the Dallara Car Factory and explored 23,000 square feet of racing-focused exhibits. We also took a wild spin in a street-legal IndyCar 2.

Finally, we visited the Eiteljorg Museum of American Indians and Western Art — which is 25-years-old this year — and checked out photographer Ansel Adams’ exhibit as well as a fascinating collection of photos by Blake Little called "Photographs from the Gay Rodeo."

We heard that the Children’s Museum of Indianapolis was excellent, too, but being that we were on an "adult trip," we did not swing by and stopped off for beers and barbecue in Fountain Square on our way out of town instead. 

Molly Snyder grew up on Milwaukee's East Side and today, she lives in the Walker's Point neighborhood with her partner and two sons.

As a full time senior writer, editorial manager and self-described experience junkie, Molly has written thousands of articles about Milwaukee (and a few about New Orleans, Detroit, Indianapolis, Boston and various vacation spots in Wisconsin) that range in subject from where to get the best cup of coffee to an in-depth profile on the survivors of the iconic Norman apartment building that burned down in the '90s.

She also once got a colonic just to report on it, but that's enough on that. 

Always told she had a "radio voice," Molly found herself as a regular contributor on FM102, 97WMYX and 1130WISN with her childhood radio favorite, Gene Mueller.

Molly's poetry, essays and articles appeared in many publications including USA Today, The Writer, The Sun Magazine and more. She has a collection of poetry, "Topless," and is slowly writing a memoir.

In 2009, Molly won a Milwaukee Press Club Award. She served as the Narrator / writer-in-residence at the Pfister Hotel from 2013-2014. She is also a story slam-winning storyteller who has performed with The Moth, Ex Fabula and Risk!

When she's not writing, interviewing or mom-ing, Molly teaches tarot card classes, gardens, sits in bars drinking Miller products and dreams of being in a punk band again.