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
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 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.
September 2026 (dates not updated)
Harvest Celebration Festival
Lanthier Winery Gardens and Courtyard, Madison, IN
Status: Updated 8/31/2025
This Indiana Wine-Beer Event will have 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 .
November - December 2026 (dates not updated)
Madison Indiana's Festival of Trees
Lanthier Winery & Distillery, Madison, IN
Status: Updated 10/30/2025
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.
