Bloomington / Indiana / North America / United States

What To Do In Bloomington, Indiana on a Weekend Road Trip

What To Do In Bloomington, Indiana on a Weekend Road Trip

It’s easy to get caught up dreaming about all the far away places there are to travel to around the world. But sometimes there’s a hidden gem right in your own backyard. That’s exactly what I discovered when I spent the weekend in Bloomington, Indiana, the traditional ancestral land of the Kiikaapoi (Kickapoo) and Myaamia people. Special thanks to Visit Bloomington for inviting me to explore their city! It’s only about 3.5 to 4 hours from Chicago (depending on what part you’re coming from) to get to Bloomington. What to do in Bloomington, Indiana on a weekend road trip may surprise you — it sure did surprise me!

What To Do In Bloomington, Indiana on a Weekend Road Trip Downtown

While Bloomington may be recognized only as the home of Indiana University, it has so much more to offer. The food scene boasts options from all different cultures, it’s very bike friendly, and it’s even home to Indiana’s oldest and largest winery. Going beyond the surface of the cute, walkable downtown Bloomington, the city welcomes visitors from all countries and backgrounds with open arms.

You may also be surprised to know that there is a Tibetan Mongolian Buddhist Cultural Center in Bloomington, which was visited by the Dalai Lama multiple times. Intrigued yet? To get you started on your trip planning, I’m sharing how I filled my weekend plus a few extra bonus stops!


Lunch at SmokeWorks was one of the highlights of the entire weekend. In fact, I probably would have returned to eat here again (or at least to get a whiskey flight) if I had been in town longer.

What to do in Bloomington Indiana SmokeWorks

They make their food from scratch every day using family recipes, and they smoke their meats for up to 18 hours using locally-sourced Indiana hickory. As our waitress informed us, they make a Memphis-style barbecue, meaning that their meats are served with a dry rub but other sauces can be provided on the side. Before we really dug in, we started off with the meat and cheese tray, complete with house-smoked sausages, a variety of cheese and crackers, spicy brown mustard, and, my favorite part, bourbon cherry spread.

SmokeWorks What To Do In Bloomington, Indiana

If you feel the same way I did and want to try a little bit of everything on the menu, the triple threat sandwich is basically the best of SmokeWorks on a single sandwich. It’s pulled pork, sliced turkey, and jalapeño cheddar sausage all in one.

Bloomington Indiana Weekend Road Trip SmokeWorks

Going back to the whiskey, they have all different kinds of whiskey flights plus three different Old Fashioned options on the menu. Between this and the food, Brandon and I were basically in heaven. My personal favorite was the Smokeworks Reserve Old Fashioned.

Whiskey Bar SmokeWorks

Function Brewing

Over the years, more than 220 unique beers have been brewed at Function Brewing. They had a rotation of twelve to choose from at a time. I ordered the pHruit Drop Midwest Tart — it was listed as a Btown collab beer, so I had to try it! While I enjoyed it, one sour beer is enough for me, so we tried out a flight to get a sample of the other options available while we were there. The verdict? The Cherry Ratio golden ale was my favorite!

What to do in Bloomington Indiana Function Brewing

Even if you are not a beer person, you’re still welcome at Function Brewing! I love this blurb they have published on their drink menu.

Function Brewing

Browse the Shops

When it’s time to walk off all that delicious food and drink, there are loads of cute and interesting shops in the area. If you’re a book worm, don’t miss Caveat Emptor, an impressive used bookstore with rare finds you’ll be unlikely to find anywhere else.

Caveat Emptor

Caveat Emptor

For the music junkies, Landlocked Music has new and used vinyl and CDs. Another store I could have spent hours browsing is Goods for Cooks, which has just about every kind of kitchenware you can imagine, plus gourmet foods as well. They have a great Anthony Bourdain quote on their website that I think sums up perfectly what they are all about.

Food is everything we are. It’s an extension of nationalist feeling, ethnic feeling, your personal history, your province, your region, your tribe, your grandma. It’s inseparable from those from the get-go. – Anthony Bourdain

Goods for Cooks

Goods for Cooks

Oliver Winery

Is there a such thing as a hidden gem within a hidden gem? If so, that’s Oliver Winery. It’s like a little oasis tucked right off of I-69 surrounded by peaceful gardens and a pond out back.

Oliver Winery Gardens Bloomington Indiana

Guided wine tastings are $5 for 8 tastings. We arrived around 4:30pm on a Saturday which is not the best time if you’re trying to avoid the crowds , but we made the most of it. It was about an hour wait for the tasting, so we bought a bottle of wine and some cheese to enjoy out on their patio where they had live music. They have all kinds of meats, cheese, and crackers that you can purchase on site, or you can bring your own snacks.

Bloomington Indiana Weekend Road Trip Oliver Winery

Not only is it Indiana’s oldest and largest winery, it’s also one of the largest wineries east of the Mississippi. If you’re looking to make a day of it, I highly recommend one of their picnic packages. There were a handful of people around us that made use of this option and it looked so inviting!

Things to do in Bloomington Indiana Oliver Winery

The tasting itself was so much fun and also educational. The staff helping with the guided tastings are very informative and helpful throughout the tasting, making the experience even better. My top three in order of preference were the Creekbend Chambourcin Rosé, Creekbend Traminette, and Creekbend Crimson Cabernet. We enjoyed our visit and the wines so much that we ended up walking out of there with 6 bottles of wine to take home!

Oliver Winery Tasting Room Bloomington Indiana

Scholar’s Keep

Hungry for a snack? Stopping by Scholar’s Keep for the Totchos alone is worthwhile. Totchos = tater tots + nachos. Basically fried potato-y goodness smothered in chili-cheese sauce all in one dish. If deciding between restaurants I’d opt for SmokeWorks, but the Totchos are worth a visit on their own!

Totchos from Scholar's Keep

Totchos from Scholar’s Keep

Village Deli

Waking up to a rainy morning led us in one clear direction… to Village Deli for a traditional breakfast. In a classic diner-style fashion, you can indulge in eggs and home fries, biscuits and gravy, or their famous oversized “ginormous” pancakes. To make it even sweeter, they serve breakfast all day long!

What to do in Bloomington Indiana Village Deli

Two Sticks Bakery

The full parking lot of people waiting for Two Sticks Bakery to open told me everything I needed to know. This is a bakery worth the wait.

Two Sticks Bakery Bloomington Indiana

They have fresh baked goods daily, made from scratch with local and organic ingredients whenever possible. The spread they had available when we walked in made my mouth water instantly, but what instantly stole my heart was their classic chocolate chip cookie.

Two Sticks Bakery Cookies

Bonus Ideas for What To Do In Bloomington, Indiana

There’s only so much you can do in one weekend, but there are so many more things I would have done if I had the time. Try stopping for kombucha on tap from Bloomingtea, momo’s at Anyetsang’s Little Tibet, a good laugh at Comedy Attic, or canoeing or kayaking at Griffy Lake Boathouse.

What To Do In Bloomington, Indiana - Weekend Road Trip

SpringHill Suites by Marriott Bloomington

Finally, for a centrally located place to stay, the SpringHill Suites by Marriott Bloomington is right in the center of it all. It’s under a 10-minute walk from most of the above places, and I love Marriotts to begin with so it’s a win-win!

SpringHill Suites by Marriott Bloomington

All SpringHill Suites properties specifically pay close attention to the little things that can make all the difference in a hotel room, and this one was no exception. A few of my favorites from this stay are the built-in luggage rack, having a light in the shower, and extra lighting surrounding the mirror.

SpringHill Suites by Marriott Bloomington Little Things

The room also had a nice living room space next to a desk which is a special touch especially when I’m working from the road. They also had bikes available that guests can rent for free so you can explore the town on two wheels!

SpringHill Suites by Marriott Bloomington Indiana

Before my visit I had no idea how much I was missing out on in Bloomington. The food, breweries, wineries, cute shops, and so much more kept me plenty busy when planning what to do in Bloomington, Indiana on a weekend road trip. It’s a city with such a big heart and uplifting vibe that I know it won’t be long before I return.

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Special thanks to Visit Bloomington, who facilitated this trip! Note that this did not affect my views and all opinions are my own.


  • Rhythm
    May 16, 2024 at 5:16 am

    Thanks for sharing this awesome guide! Bloomington sounds like the perfect weekend getaway destination. Can’t wait to explore the hiking trails and indulge in some delicious local eats. Your suggestions have definitely inspired me to plan a road trip there soon!

  • Sowjanya
    April 11, 2024 at 4:43 am

    I would like to thank Visit Bloomington for the amazing weekend! I fell in love with Bloomington, Indiana, from the wonderful Two Sticks Bakery to the delectable SmokeWorks.

  • E Gear Lab
    July 19, 2023 at 12:50 am

    This captivating blog on “What to Do in Bloomington, Indiana – Weekend Road Trip” is an absolute gem for wanderlust souls seeking the perfect getaway! Packed with a delightful mix of insightful recommendations, hidden gems, and must-visit attractions, it paints an enticing picture of Bloomington’s charm and allure. From exploring the picturesque landscapes at Indiana University’s campus and immersing in the vibrant arts scene to savoring the delectable local cuisine and embracing the natural beauty of nearby state parks, this well-crafted guide leaves no stone unturned. The author’s passion for the destination shines through, igniting the reader’s curiosity and wanderlust, making it a true source of inspiration for planning an unforgettable weekend road trip. A captivating read that undoubtedly sparks the desire to embark on a Bloomington adventure!

  • Esther Harris
    September 17, 2019 at 10:00 am

    Excellent post! I really love the suite in the Marriot it seems very comfortable! Also, the Smoke Show seems to be a place to go and spend some good money to try the food in a unique way!

    • Marissa Sutera
      September 17, 2019 at 11:41 am

      Thank you Esther! Yes, both are definitely highlights of Bloomington. I hope you get to visit soon!

  • Christian
    August 5, 2019 at 8:20 am

    I would love to go to Oliver Winery and wants to take a photo in the garden and pond.

    • Marissa Sutera
      August 7, 2019 at 8:25 pm

      It’s so peaceful there! And with a glass of wine in hand, even better!

  • Jennifer Hamoy
    June 25, 2019 at 1:23 am

    good blog. Thanks for sharing..


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