The month of September is always a memorable one in Jackson County! Just take a look at all the fun traditions and events we have to offer as the busiest season of the year arrives! Plan a fun fall in Seymour, Brownstown, Crothersville, Medora, Vallonia and more!

Tuesday, September 27

Live music at Brewskies Downtown – Acoustic Crossroads will play at 6 p.m. at Brewskies Downtown, 117 East Second Street, Seymour.

Wednesday, September 28

SICA Art Club – Join the Southern Indiana Center for the Arts’ Art Club from 2 to 7 p.m. at the center, 2001 North Ewing Street, Seymour. Bring what you’ve been working on and enjoy the company of other artists.

Wednesday Evening Rides – Join the Jackson County Bicycle Club for its Wednesday Evening Ride. The group will leave at 6 p.m. from Central Christian Church, 1434 West Second Street from the parking lot facing Westgate Road. This week’s ride is 10 miles. The group will ride 10 miles every Wednesday through October. Visit the Facebook group for updates and more information.

Live music at Brewskies Downtown – Matt Trimnell will play at 6 p.m. and then Kyle Schryer will play at 8 p.m. at Brewskies Downtown, 117 East Second Street, Seymour.

Thursday, September 29

Seymour Oktoberfest – The Seymour Oktoberfest will be from 11 a.m. to 11 p.m. September 29 through October 1 in downtown Seymour. Check out all the food, vendors, entertainment, biergarten, parade, 5K and so much more. Click here for our official guide to the festival.

Live music at Brewskies Downtown – Jeff, Matt, ‘N Joe will play at 7 p.m. at Brewskies Downtown, 117 East Second Street, Seymour.

Live music at The Eagles – Fred + Steve will play at 7:30 p.m. at the Fraternal Order of the Eagles, 122 East Second Street, Seymour.

Friday, September 30

Seymour Oktoberfest – The Seymour Oktoberfest will be from 11 a.m. to 11 p.m. September 29 through October 1 in downtown Seymour. Check out all the food, vendors, entertainment, biergarten, parade, 5K and so much more. Click here for our official guide to the festival.

Live music at Brewskies Downtown – Six Ways to Sunday will play at 7 p.m. at Brewskies Downtown, 117 East Second Street, Seymour.

Live music at The Eagles – Gene Deer will play at 7:30 p.m. at the Fraternal Order of the Eagles, 122 East Second Street, Seymour.

Fear Fair – Indiana’s Scariest Haunted House – Fear Fair will provide the season’s scariest haunts from 8 p.m. to 1 a.m. at the house, 800 A Avenue East, Seymour. Order tickets by clicking here.

Live music at On the Rox – American Fools – a John Mellencamp Tribute Band will perform at 8 p.m. on the patio at On the Rox, 214 South Broadway Street, Seymour.

Live music at Poplar Street Restaurant – Soul Express will play at 9 p.m. at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

“Blithe Spirit – The Seymour ACTS Theater will present “Blithe Spirit” at 7:30 p.m. at the theater, 357 Tanger Blvd, Suite 208, Seymour. Tickets can be purchased by clicking here.

Beginning of October

Saturday, October 1

Oktoberfest 5K – The Oktoberfest 5K will begin at 8 a.m. at Seymour High School. Register by clicking here.

Seymour Museum Center – The Seymour Museum Center will be open from 10 a.m. to 5 p.m., 220 North Chestnut Street, Seymour. There will be a John Mellencamp exhibit, a disaster exhibit from the Indiana State Museum, and the opportunity to see the progress of the building.

Seymour Oktoberfest – The Seymour Oktoberfest will be from 11 a.m. to 11 p.m. September 29 through October 1 in downtown Seymour. Check out all the food, vendors, entertainment, biergarten, parade, 5K and so much more. Click here for our official guide to the festival.

Championship Night at Brownstown Speedway – It will be Championship Night at Brownstown Speedway. Super Late Models, Pro Late Models, Modifieds, Super Stocks, Pure Stocks, Hornets. Click here for a full schedule, ticket information and more.

Live music at the Fraternal Order of Eagles – Jason Dozier will play at 7:30 p.m. at the Fraternal Order of Eagles, 112 East Second Street, Seymour. 

‘Blithe Spirit’ – The Seymour ACTS Theater will present “Blithe Spirit” at 7:30 p.m. at the theater, 357 Tanger Blvd, Suite 208, Seymour. Click here for tickets.

Fear Fair – Fear Fair – Indiana’s Scariest Haunted House will be from 8 p.m. to 1 a.m. at the house, 800 A Avenue, Seymour. Click here for tickets.

Live music at Poplar Street – Bad Medicine will play from 8 p.m. to midnight at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

Live music at Brewskies Downtown – Brent James & The Vintage Youth will play at 8 p.m. at Brewskies Downtown, 117 East Second Street, Seymour. ‘

Movie Night At Tiemeyer’s Farm Market – Tiemeyer’s Farm Market will show ‘The Haunted Mansion’ at sundown on the lawn of the market, 3147 South 300W, Vallonia. It’s free to attend and those who do should bring lawn chairs and blankets.

‘Chasing Bubbles’ – There will be a free public viewing of the documentary ‘Chasing Bubbles’ that shows the late Alex Rust’s sailing trip around the world at 9 p.m. at Schwatzer’s German Restaurant, 113 Indianapolis Avenue. 

Live music at On the Rox – Kill’n Smalls will play at 10 p.m. at On the Rox, 214 South Broadway Street, Seymour.

Sunday, October 2

Fear Fair – Fear Fair – Indiana’s Scariest Haunted House will be from 8 to 10 p.m. at the house, 800 A Avenue, Seymour. Click here for tickets.

Monday, October 3

Scarecrow Stroll – The Seymour Main Street Scarecrow Stroll is a self-guided tour of scarecrows put together by participating downtown businesses! Follow to each location where you can scan a QR code to vote for your favorite.

Tuesday, October 4

Rise Above Exhibit – The Rise Above Exhibit will be available for the public to view from 5:30 to 7:45 p.m. at the Seymour Airport, 1025 A Avenue. The exhibit is part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Freeman Army Airfield Museum – The Freeman Army Airfield Museum will be open from 6 to 8 p.m. as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen. The museum is located at 1035 A Avenue, Seymour.

‘The Freeman Field Mutiny’ – Reginald DuValle will make a presentation on The Freeman Field Mutiny during the Evening Speaker Series at 7 p.m. Emanuel Church, 1849 First Avenue, Seymour, as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Wednesday, October 5

Rise Above Exhibit – The Rise Above Exhibit will be available for the public to view from 5:30 to 7:45 p.m. at the Seymour Airport, 1025 A Avenue. The exhibit is part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Freeman Army Airfield Museum – The Freeman Army Airfield Museum will be open from 6 to 8 p.m. as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen. The museum is located at 1035 A Avenue, Seymour.

Wednesday Evening Rides – Join the Jackson County Bicycle Club for its Wednesday Evening Ride. The group will leave at 6 p.m. from Central Christian Church, 1434 West Second Street from the parking lot facing Westgate Road. This week’s ride is 10 miles. The group will ride 10 miles every Wednesday through October. Visit the Facebook group for updates and more information.

‘Sculptor’s Talk’ – Matt Glenn will make a presentation about the sculpting the Tuskegee Airmen statues during the Evening Speaker Series at 7 p.m. Emanuel Church, 1849 First Avenue, Seymour, as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Thursday, October 6

Rise Above Exhibit – The Rise Above Exhibit will be available for the public to view from 5:30 to 7:45 p.m. at the Seymour Airport, 1025 A Avenue. The exhibit is part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Freeman Army Airfield Museum – The Freeman Army Airfield Museum will be open from 6 to 8 p.m. as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen. The museum is located at 1035 A Avenue, Seymour.

‘The Photograph that Changed American History’ – Bryan Patrick Avery will discuss the ‘Photograph that changed American History’ during the Evening Speaker Series at 7 p.m. Emanuel Church, 1849 First Avenue, Seymour, as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Free Family Movie Night – Schuler Bauer Real Estate will offer up a free family movie night with a showing of Hocus Pocus at 7 p.m. at Steinker Platz in downtown Seymour. There will be popcorn and candy available.

28th annual Fun Fest at Brownstown Speedway – Click here for information, tickets, schedule and more about Fun Fest at Brownstown Speedway.

Friday, October 7

Rise Above Exhibit – The Rise Above Exhibit will be available for the public to view from 5:30 to 7:45 p.m. at the Seymour Airport, 1025 A Avenue. The exhibit is part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Ghouls & Goblets – Seymour Main Street will offer Ghouls & Goblets from 6 to 9 p.m. in downtown Seymour. There will be multiple breweries, wineries, and distilleries throughout tasting locations downtown where participants can get samples and make purchases. There also will be locations for spooky stories and music. Click here for tickets.

Concert – The Salute to the 75th anniversary of the U.S. Air Force concert will be at 6:30 p.m. at Crossroads Community Park in downtown Seymour. The evening will feature the ‘Band of Flight’.

Live music at the Fraternal Order of Eagles – Rich Hampton will play at 7:30 p.m. at the Fraternal Order of Eagles, 112 East Second Street, Seymour.

Fear Fair – Fear Fair – Indiana’s Scariest Haunted House will be from 8 p.m. to 1 a.m. at the house, 800 A Avenue, Seymour. Click here for tickets.

28th annual Fun Fest at Brownstown Speedway – Click here for information, tickets, schedule and more about Fun Fest at Brownstown Speedway.

Saturday, October 8

Fly In Benefit – Join the Southern Indiana Flying Eagles for a Fall Fly In from 9 a.m. until dusk at the RC Field, at Freeman Field. This fly in benefits the Jackson County Humane Society. Hot Dogs, drinks, and chips are available at the field.

5K – The Muscatatuck National Wildlife Refuge will host the 5K Your Way from 9 a.m. to 3 p.m. at the refuge, 12985 East U.S. 50, Seymour. The 5K is a way to celebrate National Wildlife Refuge Week and gifts for completion will be given. The closed area of the refuge will be open and volunteers will be at trailheads. Stop by the refuge visitor center for information.

HOPE Medora Goes Pink – Hope Medora Goes Pink will be from 9 a.m. to 4 p.m. in downtown Medora. The day will feature health information, screenings, food, entertainment and more.

Houston Fall Festival – The Houston Fall Festival will be from 9 a.m. to 4 p.m. at the historic Houston School House, 9830 North County Road 750W, Norman. The day will feature vendors, food, entertainment and more.

Stuckwish Farm Market Fall Craft Show – The Stuckwish Farm Market Fall Craft Show will be from 9 a.m. to 3 p.m. at the market, 4683 State Road 135, Vallonia.

D.A.R.E. Ride – The Seymour Police Department’s annual D.A.R.E. Jeep Ride will start at 9 a.m. from Freeman Field Recreation Area. For information, call the department at 812-522-1234.

Small Town Fall Market – The Small Town Fall Market will be from 9 a.m. to 3 p.m. at Shields Park in Seymour.

Rise Above Exhibit – The Rise Above Exhibit will be available for the public to view from 9 a.m. to noon, and then from 2:30 to 4:30 p.m., at the Seymour Airport, 1025 A Avenue. The exhibit is part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen.

Stuckwisch Pumpkin Patch U Pick – The Stuckwisch Pumpkin Patch’s annual U Pick Weekend will be from 10 a.m. to 6 p.m. at the patch, 1416 North State Road 11, Seymour. The day will featuring picking your own pumpkin, hay rides, a corn maze, farm animals, live music, food from Stag’s Mobile Kitchen and ice cream from Kovener’s Korner. It’s $5 for a family pass for the hay rides and corn maze.

Freeman Army Airfield Museum – The Freeman Army Airfield Museum will be open from 10 a.m. to noon, and then from 2:30 to 4 p.m., as part of the dedication week of the new Freeman Field Mutiny Indiana State Historical Marker and two life-sized statues of Tuskegee Airmen. The museum is located at 1035 A Avenue, Seymour.

Tuskegee Airmen Memorial Dedication – The Tuskegee Airmen Memorial dedication will take place at 1 p.m. at the Freeman Municipal Airport, 1025 A Avenue, Seymour.

Fear Fair – Fear Fair – Indiana’s Scariest Haunted House will be from 8 p.m. to 1 a.m. at the house, 800 A Avenue, Seymour. Click here for tickets.

28th annual Fun Fest at Brownstown Speedway – Click here for information, tickets, schedule and more about Fun Fest at Brownstown Speedway.