Warmer weather signals the arrival of festival season in the Uplands, where communities come alive with an array of vibrant events. Whether you’re a wine lover looking to indulge in tastings in a storybook setting, a comedy enthusiast seeking belly laughs at local venues, or a music lover ready to groove to live performances in scenic outdoor settings, the Uplands offers an enticing lineup of spring festivities to suit every taste and interest.

May 4

Indiana Wine Fair

Brown County

Experience the delightful taste of wine in a picturesque setting as you indulge in a spring day at the Indiana Wine Fair, nestled amidst the rolling hills of Brown County. For two decades, premier wineries, delicious food trucks, and unique local vendors have gathered annually for a day brimming with pours and festivities at the Indiana Wine Fair. The fair returns to the Story Inn on May 4. Enjoy samples and purchase a bottle – or two – for your collection all while enjoying live music and yummy food.

May 11

Barbecue, Blues, and Brews

Greene County

Get ready for a sizzling good time at the thirrd annual Barbecue, Blues, and Brews Cook-Off in Bloomfield! This mouthwatering event will feature some of the finest Pitmasters from the Midwest competing in the cook-off. Indulge in local craft beer and wine while grooving to live blues music. Don’t miss out on the classic car cruise-in, where hot rods and vintage vehicles will rev up the excitement. With top-notch food trucks, craft vendors, and award-winning barbecue to sample, this event promises to be a feast for all the senses.

May 19

Old Jasper Day Strawberry Festival

Dubois County

We don’t know about you, but there is almost nothing sweeter than enjoying a FRESH strawberry on a warm spring day in the Indiana Uplands. Stock up on this sweet fruit bursting with flavor at the annual Old Jasper Day Strawberry Festival, happening May 19 at the Jasper Riverwalk. Plan to spend the whole day in Jasper where you can take a ride on the Spirit of Jasper Train and a horse-drawn wagon, have your face painted, and enjoy live music. The festival will also feature the Patoka 2000 Duck Race, which is just too cute to miss. History lovers will enjoy taking a stroll around Jasper and learning about the past. Did we mention there will be strawberries? Don’t miss it!

May 10-11

Lambrecht Farm Spring Sunflower Market

Lawrence County

Pick the perfect spring bouquet and find unique treasures at this charming farm in the Indiana Uplands! The spring Sunflower Market at Lambrecht Farm in Bedford will feature over 70 vendor booths. Take a break from shopping to enjoy live music and take the kids to the petting zoo. Don’t forget to stop by the food trucks for a tasty treat or two! The farm is home to seasonal markets and other fun events all year long.

May 15-18

Cosmic Songwriter Festival

Monroe County

Get ready for an unforgettable musical journey at the second annual Cosmic Songwriter Festival, kicking off on May 15 in Bloomington. Spanning four days and four venues—the Orbit Room, the Bluebird, the Blockhouse, and the Buskirk-Chumley Theater—this event showcases a fusion of national and local songwriting talent like never before in a “Listening Room Environment” where audiences are expected to be fully present and silent during performances. From intimate acoustic sets to electrifying performances, sit back and immerse yourself in the dynamic atmosphere created by diverse musical styles and genres at one of the many music festivals in the Uplands this year!

May 17-18

Sustain Art and Music Festival

Orange County

Immerse yourself in a harmonious blend of music, art, and sustainability at Sadhana USA’s Sustain Art and Music Festival in French Lick. The two-day festival starts May 17 at the picturesque Elk Ridge Ranch. Over 10 bands are set to perform progressive bluegrass and Americana tunes all weekend. The festival is not just about the music – it’s about making a positive impact with money raised by the festival going to Sadhana USA’s nonprofit initiatives. No music festival in the Uplands is complete without enjoying delicious, locally sourced food and shopping gifted artisan booths. That sounds like a perfect weekend to us!

May 20-June 9

Granfalloon: A Kurt Vonnegut Convergence

Monroe County

Dive into a world of creativity, community, and inspiration at Granfalloon, presented by the Indiana University Arts and Humanities Council. Drawing inspiration from the legendary Hoosier author Kurt Vonnegut Jr., this festival is a vibrant celebration of art, ideas, and the diverse tapestry of humanity. Granfalloon embodies Vonnegut’s spirit by fostering civic engagement, nurturing independent thought, and recognizing art as vital to both personal fulfillment and the strength of our democracy. In partnership with the IU Writers’ Conference and the Bloomington Handmade Market, Granfalloon is a convergence of minds and talents, spanning live music, literary readings, art exhibits, film screenings, theatrical performances, panel discussions, craft workshops, and much more.

May 31-June 2

Cave Country Canoes Paddle Festival

Crawford County

Three days of paddling, peacefulness, and panoramic views? Count us in! Kick off the season of warmer weather by floating along 37 miles of a scenic river in Crawford County during the Cave Country Canoes Paddlefest, happening May 31 to June 2 in Milltown. When you’re not floating you can enjoy live music, delicious food, and warm up at the end of the night by a campfire. Is three days on the river not enough? No worries because there’s a bonus trip on June 3. Hurry and make your reservation today.

May 31-June 2

Limestone Comedy Festival

Monroe County

Get ready to laugh until your sides ache during “Bloomington’s Funniest Weekend.” The Limestone Comedy Festival returns for its 21st year on May 31 with shows planned at seven different venues in Bloomington including the city’s first and only full-time comedy club The Comedy Attic. Performers this year include Jimmy Pardo, Ali Siddiq, Roy Wood Jr, Lace Larrabee, and Ben Brainard. Past festivals have featured comedy legends like Michael Che, Michelle Wolf, Fortune Feimster, Patton Oswalt, and many more!