Road Trip Series: Indianapolis, Indiana

Indianapolis, Indiana the second stop on my 2018 Road Trip Series of my “Road to 50” bucket list item. I was on the road for about 2 hours from Louisville, Kentucky before I arrived and checked into my hotel for 2 nights at The Westin. I haven’t put much thought into Indianapolis or about the city, all I knew about Indianapolis was the Indy 500.

After checking into my hotel, I waited for my friend Johnny to drive 4 hours into town from Michigan. When he arrived he told me that Downtown was “poppin'” but the brief moments I was on the streets of Downtown Indy, I thought otherwise. Indianapolis is unlike any major cities, but it does have its charm. Regardless of Indianapolis being on the list of 10 most dangerous cities, I felt relatively safe in downtown since it was heavily patrolled by cops.

Accommodations: All of the events and fun is in Downtown, either on Mass Ave or inside Mile Square. I stayed at The Westin in the Wholesale District, a big area with restaurants and walking distance from all the main attractions.


I recommend staying at The Westin since the rooms are affordable, clean, and convenient. The only complaint I had about it was our toilet was pretty weak (it took a while for the toilet to flush) and parking at the hotel is very costly, which leaves me with my quick tip (ok, maybe I had 2 complaints).

Tip: Street parking in Downtown Indy is convenient and will save you money from expensive hotel parking fees.

There are meters only in operation from Monday through Saturday from 7 am to 9 pm. Since we got in a little late, we only paid for the meter for about an hour right across the street from our hotel. In the morning, we would feed the meter for a couple of hours until we were ready to leave and explore the outskirts of Indianapolis. If you didn’t want to physically go to your car, you could also download the app and pay on your phone for your parking spot. This only cost me about $6-7 to park overnight until noon instead of $45 The Westin was charging.


There are a number of cars that park on the street and I didn’t have any problems with any car theft. Just remember to hide your stuff and bring all of your valuables inside the hotel with you!

Transportation: If you don’t have a car readily available, most things are accessible on foot, but there are ride share services available throughout the city.

Night 1

After dropping off our luggage and finally reuniting after a year, on our first Friday night, we ventured out to have some fun and explore the nightlife of Indianapolis. Two places we were told to visit: Mass Ave and the Mile Square area. We started our journey to Mass Ave on the first Friday night, which felt a lot further than we thought.


We passed by Monument Circle and noticed there was a car event going on. It was actually the Crown Rally!  There were many muscle and exotic cars to admire around the Indiana State Soldiers and Sailors Monument.


When we got to Mass Ave, it was calmer of a Friday night than what I am used to. My first impression of Indianapolis is that it was weird AF. Mass Ave is a very chill street, calm and nobody turning up, yet I still found people throwing up on the side of the buildings and still having a good time. 


We ended up at The Eagle for a drink, which I’m told has great food. Drinks in Indianapolis are very affordable and one thing I noticed is that guys here have no shame in ordering the girly drinks. So cheers to the dude who got the “Bubbles” drink!

We tried for a Jazz bar next but skipped it because of a cover charge. Instead, we decided to go grab a drink at World of Beer. Of course, we had to order some beer, drinks, and wings!

Here, we met some cool Indianapolis locals that we actually spent the rest of the night with. Our new friend thought Johnny looks like Jet Li. (Strange).


World of Beer decided to close down 30 minutes before it’s actual closing time and we decided to take our party elsewhere to Goodfellas Pizzeria! We grabbed some pizza in the front and brought it to the speakeasy tucked away in the back. Wiseguy Lounge is not hard to find or well-hidden by a door or a secret password, but if you aren’t looking for it, you might not stumble upon it. 

Wiseguy Lounge is quiet yet classy with a business casual, upscale vibe. The lights are dim and the couches are comfy. The bartenders are awesome and the cocktails were great. Here, you will find a wide selection of bourbon, beers, and other beverages available. Sometimes they will have hard to find bourbon, like Weller 12!

Afterwards, we were offered a ride back from our friends and ended our first night (Yay! We didn’t have to pay for a Lyft back).

Day / Night 2

The next morning we dropped by Mass Ave again for lunch at BRU Burger that had pretty sizable burgers that left me feeling so full at the end. The burgers are affordable, priced from $8-13, but does not come with fries (most importantly). We got the Bru Burger and the Melt Your Face Burger. The Bru Burger is their standard burger, with cheese, bacon, tomato jam, caramelized bacon, chopped lettuce, and mayo. The Melt Your Face Burger is their spicy burger. I could always appreciate when a restaurant has a spicy option because I do like a spicy burger, even though this burger did not “melt my face off”.

Mass Ave is also known for all of the artistic things, so make sure to look around for sculptures or art displays.

Mass Ave Sculptures

Also how cute are these fire hydrants?!


These “ndy” signs where you are the I is spread across town. Make sure to look up the locations where they place them.


After lunch, we decided to explore the outskirts of Downtown Indianapolis since we had a car to get around.


The first stop was Newfields: 100 Acres Art and Nature Park (4000 Michigan Rd
Indianapolis, IN 46208). There are several art displays located inside the park. It’s also a great place to get your morning jog in or to explore.


This popular area for all ages to horseplay is called Funky Bones. You can climb on top of these platforms and jump from bone to bone.


It wouldn’t be a park without the swings! The swings at 100 Acres is artsy, looks like you are swinging from a tree.


Even the benches are art displays!

Head deeper into the center of the park, there is a little lake where you can seek tranquility.

After we were done with the park, we headed over to the Broad Ripple area. We were informed that this was a hipster area with a laid-back indie vibe.

Upon arrival, I have to admit that I was a little lost. There wasn’t a strip of stores or anything for you to wander. Everything’s a bit spread out, so if you don’t have a destination planned, you might get lost. But have no fear! Take some time to explore. The things you find will make your experience just that much sweeter!

Whenever I am in a new town, I like to grab a beer at the local brewery like Thr3e Wise Men Brewing Company.  Here, you may get food to pair with your beer. I got the Trail Runner which is a Session IPA and the tasting notes were “Easy drinking, melon, tropical fruit” but… it was definitely not an easy drink. I would suggest to avoid this specific beer and try their other 9 beers available. The beers here are very reasonably priced (under $5 per pint).

Afterwards, we took a small stroll to see what other stores the Broad Ripple had to offer. There was a nightclub, comedy club, and vintage stores.

We got a little hungry and were told that the best wings are over at Chatham Tap. Off we go! Chatham Tap is a British pub filled with a wide variety of different beers from all parts of the world. The Prince Dean’s Angel wings are the ones everyone is ranting and raving about. In my opinion, the wings are good but they aren’t the best I’ve ever had. It is definitely worth a try though if you are looking for a snack!

Did you know Indianapolis has a Canal Walk?

The Canal Walk is a 3 mile-loop, perfect for a calm and casual stroll after a large dinner, walking the dog, biking, or paddling through the canal. Even though Canal Walk is in a residential area, there are still a few restaurants and attractions to check out.

City Market

Another place you can take a walk around is at the City Market. The best way to describe it would be an indoor farmers market with rows of food booths and other products. Unfortunately, when we got there it was closed down for a private event. However, it should be opened Monday through Saturday from as early as 7 AM until 9 PM.

Afterward, I stopped by to pick up a lavender cold brew at Pearings, which was recommended to me by a local. There are other items that are offered here like frozen yogurt, acai bowls, and smoothies.

Downtown Indianapolis has so much history every corner you turn. There are also plaques to inform you of what each statue represents and the history that took place there.

After wandering around the streets of Downtown Indianapolis, it was time for our dinner reservations at St. Elmo Steak House, which is rumored to be the best restaurant in Indianapolis and should not be missed.


This restaurant was JAM PACKED, filled with people from all over the country and different walks of life. It is recommended to make reservations beforehand, otherwise, you will need to wait around for a very long time. The Baltimore Ravens were also in town since they had a game the next day and also had their dinner at St. Elmo’s that night, so you know it’s good!

While you wait, there is a speakeasy bar upstairs called 1933 Lounge. Here, you are able to order their famous shrimp cocktail and a drink, if you can find a seat. We got an old fashioned at the bar while we waited for our table and sat outside since it was impossible to find an area to claim.

When we finally got to our table, we ordered their World Famous St. Elmo Shrimp Cocktail, Caesar salad, lobster bisque soup, and steak with drinks and wine.

While at the bar, talking to other patrons, they highly recommend the shrimp cocktail. Honestly, when I had it I thought it was just not for me, but if you love horseradish then you will definitely enjoy it.

Overall, I really enjoyed my meal and set to paint the town red for my last night in Indianapolis.


There aren’t many clubs or bars that were “poppin” in the Wholesale District, even on a Saturday night. The club scene at Indianapolis is not anywhere up to par with the ones in the major cities like Los Angeles. We hopped from place to place to find music that we enjoyed listening to, but there weren’t any to be found. All we stumbled upon is mainstream, radio hits songs blaring through the speakers of every bar and club.  


We first went to Social since it was recommended by a friend that lives in Indianapolis. It was pretty empty but there was no cover charge. There was also bottle service here, which I found it to be kinda strange. The DJ was spinning in the corner with not more than 10 people on the dance floor. We also saw a bride and groom party it up here after their wedding. Drinks were about $10 each and they aren’t made very well here, so I suggest just getting shots.

We then left to try our luck at Revel Nightclub and we were told cover charge was $5, but then once we got inside they changed it on us to $10 a person (what?). The employees that we dealt with seemed pretty disrespectful as well. The drinks inside were cheap (about $5 per a small plastic cup), but the music was not very good. Actually, it was really bad. We were there for less than an hour and decided this wasn’t for us. The inside of Revel reminded me of a high school dance party; bad music and awkward dancing. It just didn’t feel like a proper nightclub to me. I would not recommend going here and wasting your time unless you’re into Top 40s.

We decided to make our way back to Mass Ave to try and redeem our busted night out. We went back to Goodfellas to grab a few slices of pizza, ate it, and made our way down the street to find an open bar. We were recommended by an employee to go to Mass Ave Pub but didn’t make it there. Instead, we ended our night at Ralston’s Drafthouse and got some MORE food and beers. The bartenders were super nice and awesome. The food was decent and the beers were good! I would definitely recommend this place for a casual night out.

Indianapolis is a cute, quaint town and great company can make wherever you are so much better.

Day 3

After checking out of our hotel, we went to grab breakfast/lunch at Mesh Restaurant.  

We ordered a bunch of appetizers along with main entrees such as chicken and waffles and chilaquiles. The best thing we had there was surprisingly the calamari. The other dishes were just okay but nothing to write home about. The dinner menu looks better and would recommend having dinner here rather than brunch.

After lunch, went to White River State Park to walk off our meal. Keep in mind you will need to pay for parking here even if the pay machine is broken! I saw a few cars get a parking ticket here thinking that they did not need to pay if the machine was broken. We just paid for an hour of parking to take a stroll around.

This area is filled with the usual park activities such as bike riding, running, and picnicking but also there are several photo opportunities available. When I was researching on places to captivate the charm of Indianapolis, I saw many engagement and family photos taken here. When I visited, it was also no different. There were many photographers spread throughout with their clients for headshots, family portraits, and wedding photos.

The sense of community in Indianapolis was on display when I spotted a cute community library where you take a book and leave a book.

Aside from the many Indianapolis outdoor events such as concerts that take place here, there are other permanent attractions that are available at White River State Park.  There is an IMAX Theater, Indiana State Museum, NCAA Hall of Champions and Indianapolis Zoo, just to name a few, all of which require admission fees to visit.

Final thoughts: The amount of time I allocated to visit Indianapolis was enough for me to see what the city had to offer. There were a lack of great ice cream stores and ethnic foods but everything was pretty affordable. I enjoyed my time here but was ready to move onto the next location, St. Louis, Missouri.

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