If this is your first time in Bloomington, walk up and down Kirkwood until you hit the main downtown square of Bloomington. It offers lots of cute boutique and gift shops, local coffee spots, bars, and a multitude of different cuisine types. If you're new to IU traditions, make sure to stop into Nick's English Hut for a game of Sink the Biz and their famous Biz fries. If you feel like checking out a brewery while exploring the downtown, we recommend The Tap or Upland!
While Oliver is about a 10 minute drive from the downtown, it is well worth the trip. It is Indiana’s oldest winery and one of the largest in the U.S., with outdoor grounds to walk around with a garden and pond, as well as a tasting room and fabulous patio to grab some delicious wine and cheese and sit outside with.
Breakfast/Brunch: Bloomington Bagel (best grab and go, bagels are epic!) Runcible Spoon Village Deli (Talia and Devin's favorite) Lunch or dinner: Buffa Louie's (best wings) Trojan Horse (delicious Greek food) Uptown Cafe (nice sit down American) FARMBloomington (farm to table) Janko's Little Zagreb (upscale steak house) DeAngelo's (Italian) 4th Street Ethnic restaurants: Anatolia (Turkish-one of Talia's favorites) Siam House (Thai) Best snacks or late night: Chocolate Moose (delicious local ice cream spot) Pizza X (no better Pizza around...)
If you are interested in outdoor activities while you are in Bloomington, there are a number of great options. The B line trail is a former rail line that has been converted into a tarmacked path for running, walking, cycling, and skate boarding. The path runs through downtown and beyond, and along the path, you'll find the micro cider distillery and Cardinal Spirits as well as a coffee house. At the far end, as you cross the bridge across past West Grimes is the new Switchyard Park sports and community area. Griffy Lake has lots of hiking trails and boat rental options. Check out https://bloomington.in.gov/parks/parks/griffy-lake for more details. If you have a car and want to drive slightly outside the city limits, Nashville's downtown has tons of local boutique shops and is the perfect place to explore. While you're in the area check out https://www.browncountystatepark.net/hiking_trails.htm for a myriad of hiking trails.
Eskenazi Museum of Art is right in the center of campus and has a number of local exhibits. More details at: https://artmuseum.indiana.edu/ If you are coming in town with little ones, Wonderlab Museum is a wonderful hands on science museum and one of Talia's favorite places from growing up. Find more details at: http://www.wonderlab.org/