This is the first in my “Midwest is Best Series,” where I hope to highlight several more of the gems of cities that the Midwest has to offer! Why should the coasts get all the love, when we’ve got top-notch, charming cities right here in our own back yards? I hope that through this series you will grow your appreciation, discovery of, and love for the Midwest!
EVANSVILLE
Before we planned our trip to Evansville this past month, we were just looking for a weekend getaway within a couple hours from us before my classes started up again for the spring. Since Graham and I live in St. Louis, we are pretty central to a lot of midwestern cities, but Indiana stood out to us since neither of us had really spent much time there, which is crazy because Evansville ended up being only about 2.5 hours from us. Even though I grew up in rural Missouri just 60 miles Northwest of St. Louis, I can’t remember a time that I’ve ever visited Indiana, besides a mission trip where there wasn’t any sightseeing, so I probably thought I was in Illinois. Anyway, Indiana was unchartered territory for us so we chose Evansville and started looking for an Air BnB!
Where To Stay
Choosing an Air BnB is *almost* my favorite part of any trip, and I was pleasantly surprised to find that Evansville has a great selection of charming BnB’s at still small-town prices!

I found the jackpot, if I do say so myself! Without even knowing much about the city, we were right in the heart of the charming historic district and within a mile of everything we wanted to see! I highly recommend staying somewhere in or near the Historic District! There are countless restaurants, coffee shops, stores and even the Ohio Riverfront within walking distance! Find the adorable Air BnB with a cobblestone street and full kitchen that we stayed at here.
Located on historic 1st Street, part of the Historic Preservation District, our stay here allowed us to get a taste of the beautiful Haynie’s Corner Arts District and the surrounding homes.
The Historic Preservation Distric was nothing short of quintessential small town charm. Since the weather was a bit cold and rainy on Saturday, we enjoyed driving through the historic streets and appreciating the beautiful homes!
Where To Eat
DINNER
We had two really great actual meals in Evansville. Since we only stayed one night, our meals were numbered.
After checking into our Air BnB, we headed to Historic Downtown for our dinner reservation at Comfort by the Cross Eyed Cricket. Although oddly named (apparently Comfort is a revised version of an older restaurant, the Cross Eyed Cricket), Comfort was the downtown hot spot. I recommend calling ahead to make a reservation if on a weekend night. Inside, the atmosphere was just that, small town comfort. The menu is full of beloved comfort foods “dressed with a refined flare.”
I didn’t get a photo of our dinners, but we both ordered the fried chicken because, well, comfort food! In addition to their home-style-with-a-twist dinner menu, they also had a wide selection of bourbon and whiskey fueling a creative cocktail menu. I ordered the “Brown Derby,” a Buffalo Trace Bourbon based drink with their house orange honey and grapefruit juice. It was excellent.
DESSERT
After dinner, we found the sweetest dessert spot, Milk & Sugar Scoop Shoppe on the west side of town. It’s a super cute ice cream and cookie dough shoppe with vegan and gluten-free options!
DOUGHNUTS
On Sunday morning, we headed to Parlor Doughnuts for some freshly baked goodies. Parlor is a coffee and doughnut shop off downtown Main Street and the line was out the door when we arrived. Located just next door to Comfort (like I said, everything was super close!), Parlor doughnuts was obviously another local favorite that is a MUST when in Evansville!

LUNCH
For lunch, we stayed in the downtown/Main St. area and found an awesome burger place (Graham’s favorite) inside of an old Greyhound depot. So cool! BRU Burger Bar has locations throughout Indiana, Ohio, and Kentucky, serving local beer and meats at each location. The burgers were BOMB and the atmosphere was great! Definitely go here!
Where To Coffee
Perhaps the most important segment for any city (in my opinion). I’m always on the lookout for local coffee, and luckily Evansville has plenty of it! We were able to visit 2 of the 3 coffee shops on our list. Unfortunately, Proper Coffee is closed on Sundays, so we are definitely planning to come back and try it! It looks amazing!
Our first stop when we got into town was, of course, a coffee shop. We made Honey Moon Coffee Co. our first stop. Located just across the street from the University of Evansville, Honey Moon is a hip college hangout, perfect for study sessions and coffee dates alike. My rule of thumb is that if there’s a university near, the coffee is usually pretty good, and that proved right! In addition to coffee, they also have specialty waffles that are incredible! We ordered the fruit and yogurt waffle, a lavender oat milk latte for me, and a mocha for Graham. The barista was friendly and the space was really comfortable!
On Sunday, we visited River City Coffee & Goods , another must-visit spot in downtown on Main Street. Not only do they serve quality espresso drinks and coffee, but they also serve as a sort of trading post for local vendors and goods. Inside, the shop is filled with gift items, art, apparel, and more from local shops and companies. I purchased the “Midwest Livin” tee from Tribe and Trade, although I could have gotten one of everything in there! Such a unique spot that offers a bright and welcoming place to enjoy a latte and support local business too!
What To Do
Our main goal was to pack as much of Evansville as we could into the 24 +/- hours we were there. That being said, we didn’t want to waste much time driving around, which was perfect because we were able to walk to the majority of our stops. Food and coffee are major parts of traveling for us, so obviously that’s where we invested most of our time. Although the rain made it a bit tricky, we were still able to see a good bit of the town, as I mentioned earlier, by driving through the historic streets and neighborhoods. Later in the afternoon when the rain cleared, we were able to walk down to the riverfront (again, just a few minutes’ walk from downtown, including Comfort, River City, BRU, & Parlor Doughnuts). There’s a nice lookout at the riverfront and it was cool to take a look at the Ohio River before it meets our dear old Mississippi River.
Overall, we enjoyed our little weekend getaway SO much and can’t wait to try another charming Indiana city! We love taking time to just experience another city and its culture and appreciate all the little things along the way! One thing to keep in mind when visiting Evansville is that many of the shops (including Proper Coffee) are closed on Sunday’s, so keep that in mind when planning! Happy trails!
Quick Links
STAY: Air BnB in or near the Historic Preservation District. We stayed here
EAT: COMFORT by the CEC , BRU Burger Bar
SWEETS: Parlor Doughnuts, Milk & Sugar Scoop Shoppe
COFFEE: River City Coffee & Goods, Honey Moon Coffee Co., Proper Coffee Roasters
DO: Eat, drink coffee, don’t expect to shop anywhere downtown on a Sunday!
MORE: Checkout E is For Everyone the official guide to all things Evansville
XOXO
Chelsea

I am a huge fan of the triumphant stories. I love hearing people share about going through what seemed like the darkest depths—when they were so discouraged and weighed down that they never thought they would see the end, but then everything came together and they crushed the obstacles and overcame. I am inspired by the testimony of the couple whose marriage was falling apart, but they somehow persevered and stayed true to their commitment to each other and their hearts began to change; and now, 10 years later, here they are on the other side, talking about their “stronger than ever” love with smiles on their faces. I love seeing confident women telling stories about their past struggles with identity, body image, and believing the lies of the world, and how they overcame those struggles with truth and are on a mission to help other women do the same.
