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  • 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

  • St. Michael the Archangel Tour

    Recurring
    St. Michael the Archangel Church 521 E Third St., Madison, United States

    St. Michael's is one of the oldest buildings used as a Catholic church in the state and the oldest Gothic Revival-style building in Indiana. The pointed-arched windows are a key component of this style of architecture. Inside the building, the ceiling is a rare ogee-arch “open book” ceiling. The building also houses a 1895 organ, numerous beautiful statues, and many […]

    $10

  • 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

  • Architectural Walking Tour

    Recurring
    Historic Madison, Inc. 301 West 2nd Street, Madison, IN, United States

    Explore the nation's largest contiguous National Historic Landmark District the Third Saturday of each month, May - October. Meet at the Historic Madison, Inc. office on to learn about Madison’s unique National Historic Landmark District. This FREE guided tour will explore the stunning styles, amazing architecture, and rich history of Madison’s downtown. No registration is required. This tour is also […]

    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

  • Clifty Day on the Madison Trolley Line

    Recurring
    Clifty Falls State Park 2221 Clifty Drive, Madison, IN, United States

    Enjoy a day in the great Clifty Falls State Park! We will board the trolley & leave at 1PM from the Visitors Center - 601 W. 1st Street, Madison, IN. Tickets include: ride & admission to the park 1-hour guided tour with the park naturalist free time to explore the trails, Nature Center, and gift shop Grab your tickets by […]

    $15

  • Tri Kappa Tour of Homes

    Historic Downtown Main Street, Madison, IN, United States

    Biennial tour of Historic sites in downtown Madison. Presale tickets (Until Sept. 30th) Adult $22 Child (5-10 yrs) $6 After Sept. 30th Adult $30 Child $8 Begins at 10am on Friday Oct 2nd and Ends on Sunday Oct 4th at 5pm. For more information call: 812-599-2638 

    $22 – $30