• “Old Settlers” at Neavill’s Grove

    Neavill's Grove 6478-6566 W Deputy Pike Rd, Madison, United States

    Old Settler's Meeting has been held annually on the last Saturday in August since 1885. Antique machinery display, good food, entertainment and fellowship. NO ALCOHOL  and free admission. Deputy Pike, Smyrna Township. 812-866-2891 or 812-701-5834. Kenny Hord 812-273-4130

    Free
  • Play Music on the Porch Day

    Downtown Madison Madison, Indiana

    The Kindred Folk Society brings you Play Music on the Porch Day! Several porches in Historic downtown Madison, Indiana will feature musicians throughout the afternoon of August 29th. Golf cart taxis will be available for porch-to-porch rides for a donation. The event is free, but donations in support of the Kindred Folk Society and our mission to bring quality roots […]

    FREE
  • Chelsea Jubilee

    Saluda Township Park Highway 62, Madison, IN, United States

    Indiana's oldest continuous festival. A Harvest Festival giving thanks to the Creator for his many blessings. Music, tractor parade, games, arts/crafts, flea market, food, fun. Saluda Township Park, Hwy 62.  812-866-4178

    Free
  • Rockin’ on the River Car Show & Concert

    Madison Riverfront Madison, IN, United States

    Rockin' on the River Car Show & Concert River Run Car Show - 10:00 a.m. Featuring classic cars, muscle cars, street rods, antique cars, restored originals, motorcycles, and special interest vehicles. Over 350 machines exhibited. Judging ends at 2pm, and trophies will be distributed at 4pm. Car Show Awards - 4:00 p.m. Best of Show Trophy; Best Class Trophy; Traveler's […]

    Free Admission to Public
  • Unbroken Circle Music Festival

    Bicentennial Park 106 West Vaughn Dr., Madison, IN, United States

    • 3 DAYS • 20 BANDS • 1 CIRCLE | SEPTEMBER 10TH - 12TH, 2025 | BICENTENNIAL PARK LEARN MORE | Follow on Facebook & Instagram for more information and artist announcements!  

    Varies
  • Canaan Fall Festival and Pony Express Mail Run

    Canaan Restoration Council Main Street, Canaan, IN, United States

    Pony express mail run between Canaan and Madison.  Food, stage entertainment, kid's games, exhibits , flea market, arts/crafts.   Admission Free. For more info 812-839-6855 Friday - 3pm - 10pm; Saturday 8am-10:00pm.

    FREE
  • Fall Old Court House Days

    Jefferson County Courthouse 300 East Main Street, Madison, IN, United States

    Unique handmade items, crafts, antiques, collectibles and delicious food selections around the courthouse square, Jefferson & Second St. and the city parking lot. All proceeds go back to the community. Free admission.  Saturday Fish Fry at Fairplay Fire Co. Sponsored by the Madison Pilot Club, www.pilotclubofmadison Fri 11am-6pm Sat - 9am-6pm Sun 10am-4pm

    FREE
  • Harvest Celebration

    Lanthier Winery 123 Mill Street, Madison, IN, United States

    9am-5pm daily.  A cornucopia of of artists, festival food, fall color and wine transforms Lanthier Winery's mammoth gardens.  Enjoy wine tasting, garden tours, live music, strolling the outdoor galleries.

    Free
  • 25th Annual Madison Airshow

    Madison Municipal Airport (KIMS) 3919 W Ims Ln, Madison, IN, United States

    September 26, 2025 Enjoy the Madison Air Show starting at 10AM to experience everything from static aircraft displays, airplane and helicopter rides, aerobatic performances, delicious food, live music, and more! Admission $10/pp, children ages 14 and under are FREE. Parking is off-site. For more information, visit Madison Municipal Airport’s website: www.MadisonMunicipalAirport.com/airshow.html  

    Free – $10
  • Madison Chautauqua Festival of Art

    Historic Downtown Main Street, Madison, IN, United States

    Enjoy Southern Indiana's premier outdoor juried fine arts & crafts show featuring artists & craftsmen from across the nation. Riverfront food fest, entertainment, and children's activity tent. Historic neighborhood between Broadway & Vine Streets and along Ohio Riverfront. Saturday and Sunday 10-5 p.m.  Free admission. 800-559-2956/812-265-2956.  Annual Event www.madisonchautauqua.com

    FREE