We know how to throw a party! We’ve been doing this since 1809….there is ALWAYS something to do when you come to Madison. There are home tours, music events, garden tours, holiday events, parades, arts/crafts shows, 5Ks, car shows, food & wine tastings, and beer on tap – just to name a few.
Our largest events include Madison River Jam (formerly RiverRoots), Madison Regatta, Madison Ribberfest BBQ & Blues, Madison Chautauqua Festival of Art, Soup, Stew, Chili & Brew Festival, Nights Before Christmas Candlelight Tour of Homes, and Wonderland in the Park.

March 2021
Girl’s Weekend!
Gather your closest girlfriends for a fun filled weekend in beautiful downtown Madison! We are excited to see you and can't wait for you to join us for a safe & fun filled weekend. Purchase your REDUCED ticket today at https://www.madisonmainstreet.com/event.../girls-weekend-1 . In order to keep our girlfriends healthy & safe for Girl's Weekend, we will not organize large gatherings for this event. This means we will not be hosting a fashion show or organized brunch. BUT, we will have more…
Find out more »June 2021
Music in the Park
Local and regional bands rock out downtown Madison at the Historic Broadway Fountain! Free! Local food vendors and family friendly atmosphere. 5pm-9pm Bring your lawn chair! 812-274-0195 | www.madisonmainstreet.com
Find out more »July 2021
Music in the Park
Local and regional bands will rock out downtown Madison at the Historic Broadway Fountain! Tonight is brought to you by Madison Ribberfest BBQ & Blues, listen to The Doctors Band, and bring your appetite for the "Good to the Bone" rib-eating contest! Free! Local food vendors and family friendly atmosphere. 5pm-9pm Bring your lawn chair! 812-274-0195 | www.madisonmainstreet.com
Find out more »Slice of Summer Sidewalk Sale
Join Main Street merchants for the biggest sale of the summer season! Free lemonade and treats too! Begins 11am Friday and ends at 8pm Saturday, downtown merchants. 812-274-0195. Fri. 11:00am -8:00pm Sat. 11:00am - 6:00pm
Find out more »August 2021
Music in the Park
Local and regional bands rock out downtown Madison at Bicentennial Park! Local food vendors and family friendly atmosphere. 6pm-9pm Bring your lawn chair! 812-274-0195 | www.madisonmainstreet.com
Find out more »September 2021
Music in the Park
Local and regional bands rock out downtown Madison at the Historic Broadway Fountain! Free! Local food vendors and family friendly atmosphere. 5pm-9pm Bring your lawn chair! 812-274-0195 | www.madisonmainstreet.com
Find out more »October 2021
Madison Main Street Downtown Loft Tour
Enjoy a self-guided tour of downtown loft spaces in varying stages of development. For more info 812-274-0195. This event is biennial on odd years.
Find out more »November 2021
Downtown Holiday Open House
Main Street's Signature Event! Elaborate holiday displays, new releases of holiday items, special promotions, and goodies for customers. For more info see the Facebook event here.
Find out more »Small Business Saturday
Shop Small. Shop Local. Shop Madison's downtown. Holiday shopping at its best!
Find out more »If you have an Event or Festival that is not listed here, or if you see a date that is incorrect, contact us.
Dates & Times subject to change. Please call ahead.