Escape to Bloomington for a weekend getaway


Thousands of Indiana University alum live in Hamilton County, but Bloomington is more than simply a “college town.” It’s also a weekend vacation destination. Activities can include visiting Oliver Winery, seeing live music at The Bluebird, exploring myriad dining options and browsing shops around downtown square.

Where to go:

Visitors would be remiss to skip a visit to Oliver Winery, 200 East Winery Rd. Oliver Winery was established in 1972 by William Oliver Sr. He was a tax law professor at IU Bloomington who played a key role in changing state laws regarding wine sales. His efforts led to the passing of the Indiana Small Winery Act in 1971, which allows people to taste wine on-site where it’s made. That was not permitted prior to the legislation.

Oliver Winery features a vineyard, a winery and a storefront. It is the 28th-largest winery in the nation and is the oldest and largest in Indiana. It also is the largest winery in the U.S. that isn’t on the West Coast.

Tastings are available at the bar, but I suggest reserving a guided tasting in the wine cellar for $21.60 per person. Upgrade the experience with a wine flight tasting plate with cheeses and other delicacies for $6.98 per person.

During the wine tasting, a winery staff member will walk you through a guided tasting of a pre-selected variety of either Oliver’s dry or sweet wines. It’s a fun, hour-long wine boot camp, and you learn the five “S’s” of tasting wine – sight, swirl, smell, sip and savor.

In the evening, especially if visiting on a weekend, be sure to swing by The Bluebird, 216 N. Walnut St. The Bluebird is a rock club the features cover bands and sometimes karaoke. Hairbangers Ball, an ‘80s cover band, was performing when I visited, and the music was rocking loud enough to make my bones vibrate. There is plenty of bar space and dancing space, and the exposed brick archways throughout the building add a cozy touch.

Where to shop:

There are countless adorable boutiques and shops on Bloomington’s downtown square. There’s a store for any style, whether you’re looking for a plant shop, a clothing boutique or something a little more retro like a record store or a used book shop. I stopped by Landlocked Music, a record store at 115 S. Walnut St. Thousands of records are for sale throughout the store, ranging in genres. It also has a dollar bin. Before COVID-19, the store presented live shows once a month, but they haven’t yet returned. The store receives new items in each day, so there’s always something new for shoppers to look at. 

For lovers of all things old and literary, I suggest stopping by Caveat Emptor, 112 N. Walnut St. Caveat Emptor is a used bookstore with everything from ordinary books to an antique and rare selection. There are sliding ladders along the bookcases that make it feel like you’ve stepped into the past.

Where to eat:

Bloomington offers all sorts of dining options spanning culture and diet requirements. At the Table with Anna columns will follow this story with details on a few spots, so keep an eye out for those. They run the gamut from a nice dinner out to a cozy breakfast at a local favorite.

Where to stay:

IU alum might have fond memories of dormitory rooms or other college housing, but when visiting Bloomington for the weekend, there’s no better place than the Graduate Hotel at 210 E. Kirkwood Ave.

The Graduate Hotel has rich wood tones throughout the lobby and plenty of odes to IU basketball history. Its hotel key cards feature characters from the “Stranger Things” science fiction TV show, the setting of which is in Indiana. There’s even a “Stranger Things”-themed room available for reservation, equipped with furniture and decoration similar to that of the show’s set and Eggo waffle boxes, a staple snack of one of the main characters.
For more or to reserve a room, visit