Wawasee Fine Arts Festival at Oakwood
May 23, 2026
chautauquawawasee.org
(574) 377-7543
Oakwood Resort - Syracuse, IN
The outdoor setting provides a family-friendly environment. Food vendors are onsite for snacks and lunch, with outside seating available. Also, the Pier and Back Porch at Oakwood offers a full menu with both indoor and outdoor lakefront dining overlooking beautiful Lake Wawasee. Children's activities and playgrounds are available. Attendance is free. Stop by the Chautauqua booth for a giveaway.
Strawberry Festival
June 12 - 14, 2026
crawfordsvillestrawberryfest.com
(765) 918-2759
Lane Place Antebellum Mansion - Crawfordsville, IN
Three days of food, crafts, children's booths, athletic events, car shows and fantastic entertainment with Friday and Saturday nights of national-level entertainment shows.
Madison Chautauqua Festival of Art
September 26 - 27, 2026
madisonchautauqua.com
(800) 559-2956
Historic Neighborhood - Madison, IN
Southern Indiana's premier fine arts & crafts festival. Handmade work by exhibitors from across the United States. Activities include entertainment, a food fest, a beer/wine garden, a chalk walk, and kids area.
Bloomfield Apple Festival
October 2 - 4, 2026
bloomfieldapplefestival.org
(614) 600-4218
Town Park - Bloomfield, IN
Come experience autumn magic at one of Southern Indiana's most beloved fall festivals, known for its warm small-town charm and fun-filled variety Enjoy: 🎡Carnival rides, games, and friendly contests, including tractor pulls and wiffle ball tournaments 🍎Tasty bites and local flavors at food booths 🎶 Live music, a parade, and stage performances running all weekend long
Hoosier Fall Festival
October 17 - 18, 2026
hoosierfallfestival.com
(317) 556-5326
Johnson County Fairgrounds - Franklin, IN
We will be offering a wide range of items from local artisans. Crafts, t-shirts, florals, farmhouse decor, jewelry, photography, painted items, clothing, baked goods, jewelry, soaps, holiday decor and so much more. We will have food trucks ranging from tacos and barbecues to deserts and kettle corn. You can purchase your seasonal pumpkins and mums along with other wonderful fall merchandise. The atmosphere will abound with fall vibes and you can take your picture at one of our photo ops. Music, face painting, roaming characters, and balloons will also add to the festivities. Come join us on Saturday and Sunday, Oct.17 & 18.
Events in Madison, IN — upcoming
July 2026 (dates not updated)
Madison Regatta
Downtown Madison Riverfront, Madison, IN
Status: Updated 4/8/2025
This Indiana Boat Auto Camping Show will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art and fine craft exhibitors, and tba food booths. There will be 1 stage with Regional and Local talent and the hours will be . Admission tickets are $20 - $60. This event will also include: fireworks, parade, air show, boat races.
August 2026 (dates not updated)
Madison Ribberfest BBQ & Blues
Bicentennial Park, Madison, IN
Status: Updated 7/10/2025
This Indiana Blues Festival will have commercial/retail exhibitors and 12 food booths. There will be 1 stage with National, Regional and Local talent and the hours will be Fri 5pm-12 midnight; Sat 11am-12 midnight. Admission tickets are $40 - $50. This event will also include: kcb bbq cookoff(state, backyard, and kids), pigmania (concrete pig display), cornhole.
September 26 - 27, 2026
Madison Chautauqua Festival of Art
Historic Neighborhood, Madison, IN
Status: Updated 1/18/2026
This Indiana Art Show will have fine art and fine craft exhibitors, and 24 food booths. There will be 5 stages with Regional and Local talent and the hours will be . This event will also include: entertainment garden with music, beer, community art and kids area.
September 26 - 27, 2026
Harvest Celebration Festival
Lanthier Winery Gardens and Courtyard, Madison, IN
Status: Updated 3/12/2026
This Indiana Wine-Beer Event will have antique/collectibles, commercial/retail, crafts, film, fine art, fine craft and homegrown products exhibitors, and 2 food booths. There will be 2 stages with Regional and Local talent and the hours will be .
September 2026 (dates not updated)
Fall Old Court Days
Jefferson County Courthouse, Madison, IN
Status: Updated 4/7/2025
This Indiana Festival will have antique/collectibles, commercial/retail, crafts, film, fine art, fine craft and flea market exhibitors, and 10 food booths.
November 27, 2026 - December 24, 2027
Madison Indiana's Festival of Trees
Lanthier Winery & Distillery, Madison, IN
Status: Updated 3/12/2026
This Indiana Holiday Celebration will have commercial/retail exhibitors and no food booths. This event will also include: spectacular christmas tree exhibition, wine tasting, holiday shopping, lighted garden.
