Know Before You Go – May 2025 Events in Jackson County

 In Events, General

May is a fun month in Indiana, and especially in Jackson County! The Jackson County Visitor Center has all the events listed right here for you to plan your fun for the whole month!
Click here if you’d like a guide emailed to you each week. 
If your organization has scheduled an event that you’d like to include on this guide, please email Jordan Richart at jordan@jacksoncountyin.com


Thursday, May 1

Open Mic Night – Michael Staublin will host Open Mic Night from 6 p.m. to 9 p.m. May 1, at Brewskies Downtown, 117 East Second Street, Seymour. It’s free to join and open to anyone.


Friday, May 2

Backroad Gypsies – Backroad Gypsies Country Cruise will operate from Noon to 7 p.m. May 2, at three locations in the Reddington Area. Click here for more information.

‘Steel Magnolias’ – Jackson County Community Theatre will present ‘Steel Magnolias’ during performances at 7:30 p.m. May 2 & 3, at the Royal-Off-the-Square Theater, 121 West Walnut Street, Brownstown. Click here for tickets.


Saturday, May 3

Flea Market & Yard Sale – The Norman Station Conservation Club will host its monthly Flea Market & Yard Sale from 8 a.m. to 6 p.m. May 3, at the club, 12157 West County Road 450N, Norman. For booth space, contact Gary at 812-826-6581.

Mother’s Day Craft Show – Stuckwish Farm Market will host its annual Mother’s Day Craft Show from 9 a.m. to 3 p.m. May 3, at the market, 4683 State Road 135, Vallonia.  local vendors, crafts, decor, food, live music, greenhouse, and more.

Downtown Shop Around – The Seymour Main Street Downtown Shop Around will take place from 9 a.m. to 3 p.m. May 3, at participating businesses in downtown Seymour. Visit each location and punch a card for a chance at winning gift cards.

Backroad Gypsies – Backroad Gypsies Country Cruise will operate from Noon to 7 p.m. May 3, at three locations in the Reddington Area. Click here for more information.

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Fantasy Weekend from 10 a.m. to 6 p.m. May 3 & 4, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.

Freeman Army Airfield – The Freeman Army Airfield Museum is open from 10 a.m. to 2 p.m. every Saturday. Appointments can be scheduled through the week by calling 812-271-1821.
Learn more by visiting https://freemanarmyairfieldmuseum.org/ 

Megan’s Wish – The Megan’s Wish Live Auction for Cystic Fibrosis will be held at 4 p.m. May 3, at the National Guard Armory, 1925 1st Avenue, Seymour. The event will feature a taco meal for $12, hot dog meal for kids for $5, and the live auction, which will begin at 5 p.m. For more information, call Rachel at 812-569-4289.

Rails Anniversary – Rails Craft Brew & Eatery will host a 10 Year Anniversary from 6 p.m. to 10 p.m. May 3, at the restaurant, 114 St. Louis Avenue, SEymour. There will be live music, drink specials, and more.

Scott Patman Memorial – The Scott Patman Memorial Super Stock Special will begin at 6 p.m. May 3, at Brownstown Speedway, 476 East County Road 100S, Brownstown. The race will include Super Stocks, ILMS Pro Late Models, Pure Stocks, Crown Vics, and Hornets. Click here for information.

Live music at the Brooklyn Pizza Company – Daniel Wasson will perform at 6:30 p.m. May 3, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Live music at Reed’s Place – Kolton Norton will play from 7 p.m. to 9 p.m. May 3, at Reed’s Place Steak & Chop Shop, 224 South Chestnut Street, Seymour.

Live music at Poplar Street – Brad Treadway will perform at 7 p.m. May 3, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

‘Steel Magnolias’ – Jackson County Community Theatre will present ‘Steel Magnolias’ during performances at 7:30 p.m. May 2 & 3, at the Royal-Off-the-Square Theater, 121 West Walnut Street, Brownstown. Click here for tickets.

Live music at the Eagles – Fred & Tesia will play at 7:30 p.m. May 3, at the Fraternal Order of Eagles, 122 East Second Street, Seymour.

Masquerade Dinner Ball – The Southern Indiana Renaissance Faire will host a formal dinner dance masquerade ball at 8 p.m. May 3, at Swifty Events Center, 351 U.S. 31, Seymour. Dancing will be led by Magpie, and it’s $40 per person. Tickets include parking, one adult beverage, and dinner by Open Flame. The event is 21 years and older only.

Live music at The Thirsty Sportsman – The River Valley Sons will perform at 9 p.m. May 3, at The Thirsty Sportsman, 205 North Armstrong Street, Crothersville.


Sunday, May 4

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Fantasy Weekend from 10 a.m. to 6 p.m. May 3 & 4, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.


Tuesday, May 6

Live music at Poplar Street – Fred & Steve will perform at 7 p.m. May 6, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.


Wednesday, May 7

Open Mic Night – Dane Darlage will host open mic night at 6:30 p.m. May 7, at The Bearded Hobo, 1029 West Commerce Street, Brownstown.


Thursday, May 8

Slices & Songs – Slices & Songs featuring the Seymour High School Choir will be held at 6:30 p.m. May 8, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Open Mic Night – Michael Staublin will host Open Mic Night from 6 p.m. to 9 p.m. May 8, at Brewskies Downtown, 117 East Second Street, Seymour. It’s free to join and open to anyone.


Friday, May 9

Golf Outing – The Tonya Cassidy Memorial Golf Scramble will be held at 1 p.m. May 9, at Shadowood Golf Course, 333 North Sandy Creek Drive, Seymour. The scramble is organized by F.C. Tucker Real Estate. Click here for more information.

Car Show – The Cruisin’ for a Cause Car Show will be held from 5 p.m. to 7:30 p.m. May 9, in the Seymour High School Parking Lot, 1350 West Second Street, Seymour. The event is free to attend and will include the car show, food by Junkyard BBQ & Kona Ice, music, prizes, and more. It’s $10 to enter a car. Proceeds will go to the Special Olympics Indiana Jackson County.

Live music at Rails – Coleshine will perform at 7 p.m. May 9, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Justin Slager Band will perform at 7 p.m. May 9, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

Live music at the Eagles – Fred & Steve will play at 7:30 p.m. May 9, at the Fraternal Order of Eagles, 122 East Second Street, Seymour.

MayDay Wrestling Match – Supreme Wrestling will host the MayDay Wrestling Match at 7:30 p.m. May 9, at the Knights of Columbus, 118 East Second Street. Tickets are $12 at the door, advance tickets are $10. Doors open at 6:30 p.m.


Saturday, May 10

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Steampunk/Time Travel Weekend from 10 a.m. to 6 p.m. May 10 & 11, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.

Freeman Army Airfield – The Freeman Army Airfield Museum is open from 10 a.m. to 2 p.m. every Saturday. Appointments can be scheduled through the week by calling 812-271-1821.

Friends of the Library – The Friends of the Jackson County Public Library will host sale from 10:30 a.m. to 4 p.m. May 10, at the location in Seymour, 303 West Second Street, Seymour. Members will get access from 4 p.m. to 5:30 p.m. May 9, and a half-hour before opening on May 10.

Race – Saturday Night Racing will begin at 6 p.m. May 10, at Brownstown Speedway, 476 East County Road 100S, Brownstown. The race will include Super Late Models, Super Stocks, Pure Stocks, Crown Vics, and Hornets. Click here for information.

Live music at Brooklyn Pizza Co. – The John Denver Experience will be at 6:30 p.m. May 10, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Live music at Jackson Live – T. Graham Brown – a member of the Grand Ole Opry – will perform at 7 p.m. May 10, at Jackson Live & Event Center, 981 C Avenue East, Seymour. Click here for tickets.

Live music at Rails – Sherianne will perform at 7 p.m. May 10, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Sugar Creek will perform at 7 p.m. May 10, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.


Sunday, May 11

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Steampunk/Time Travel Weekend from 10 a.m. to 6 p.m. May 10 & 11, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.


Wednesday, May 14

Nature Time – The Muscatatuck Wildlife Society will host Nature Time at 9:30 a.m. May 14, at the Muscatatuck National Wildlife Refuge Visitor Center, 12985 East U.S. 50, Seymour. There is a different topic each month, and the program is geared toward preschool-aged children. No registration required.

Open Mic Night – Dane Darlage will host open mic night at 6:30 p.m. May 14, at The Bearded Hobo, 1029 West Commerce Street, Brownstown.


Thursday, May 15

Open Mic Night – Michael Staublin will host Open Mic Night from 6 p.m. to 9 p.m. May 15, at Brewskies Downtown, 117 East Second Street, Seymour. It’s free to join and open to anyone.

Seymour City Jam – Seymour City Jam will be at 6:30 p.m. May 15, at Crossroads Community Park in downtown Seymour. The featured band is Blackwater Revival – a Doobie Brothers Tribute Band. Junkyard BBQ will be the featured food truck. Food and drinks will be available at 6 p.m. The event is free.


Friday, May 16

U.S. 50 Yard Sales – The U.S. 50 Yard Sales will operate on May 16. There are no designated locations or hours.

Golf Outing – Anchor House will host its 10th annual Golf Outing at 8 a.m. May 16, at Shadowood Golf Course, 333 North Sandy Creek Drive, Seymour. Click here to register.

Hen & Chicks – Hen & Chicks Barn Market will host its Spring Market from 11 a.m. to 7 p.m. May 16, at the Three Bin Farm, 5602 East County Road 100N Seymour. There will be more than 70 vendors, food, and entertainment. It’s $5 to enter.

Live music at Brooklyn Pizza Co. – Chris Gantt & Friends will perform at 6:30 p.m. May 16, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Live music at Rails – Brad Treadway will perform at 7 p.m. May 16, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Custom Blend will perform at 7 p.m. May 16, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

Live music at The Eagles – Doug Dillman will play at 7:30 p.m. May 16, at the Fraternal Order of Eagles, 122 East Second Street, Seymour.


Saturday, May 17

U.S. 50 Yard Sales – The U.S. 50 Yard Sales will operate on May 17. There are no designated locations or hours.

Hen & Chicks – Hen & Chicks Barn Market will host its Spring Market from 10 a.m. to 4 p.m. May 17, at the Three Bin Farm, 5602 East County Road 100N Seymour. There will be more than 70 vendors, food, and entertainment. It’s $5 to enter.

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Pirate Weekend from 10 a.m. to 6 p.m. May 17 & 18, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.

Freeman Army Airfield Museum – The Freeman Army Airfield Museum is open from 10 a.m. to 2 p.m. every Saturday. Appointments can be scheduled through the week by calling 812-271-1821. Learn more by visiting https://freemanarmyairfieldmuseum.org/ 

Race – Saturday Night Racing will begin at 6 p.m. May 17, at Brownstown Speedway, 476 East County Road 100S, Brownstown. The race will include ILMS Pro Late Models, Super Late Models, Super Stocks, Pure Stocks, Crown Vics, and Hornets. Click here for information.

Glow Foam Party – The Glow Foam Party will be at 6:30 p.m. May 17, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Live music at Jackson Live – Billy Keith will perform at 7 p.m. May 17, at Jackson Live & Events Center, 981 C Avenue, Seymour. Tickets are available at the door.

Live music at Rails – Kolton Norton will perform at 7 p.m. May 17, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Brian Hopkins will perform at 7 p.m. May 17, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

Live music at The Thirsty Sportsman – Ragtop Deluxe will perform at 9 p.m. May 17, at The Thirsty Sportsman, 205 North Armstrong Street, Crothersville.


Sunday, May 18

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Pirate Weekend from 10 a.m. to 6 p.m. May 17 & 18, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.


Monday, May 19

True Crime Club – The Jackson County Public Library’s True Crime Club will meet at 5 p.m. May 19, at the Seymour location, 303 West Second Street, Seymour. Th event is limited to 20, and registration should be completed by 5/15. The group will discuss a cold case file that will be provided ahead of time. Registration: 812-522-3412.


Wednesday, May 21

Open Mic Night – Dane Darlage will host open mic night at 6:30 p.m. May 21, at The Bearded Hobo, 1029 West Commerce Street, Brownstown.


Thursday, May 22

Open Mic Night – Michael Staublin will host Open Mic Night from 6 p.m. to 9 p.m. May 22, at Brewskies Downtown, 117 East Second Street, Seymour. It’s free to join and open to anyone.

Live music at Brooklyn Pizza Co. – Charlie Morgan & Friends will perform at 6:30 p.m. May 22, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.


Friday, May 23

Live music at Brooklyn Pizza Co. – Chris Bell will perform at 6:30 p.m. May 23, at The Brooklyn Pizza Company, 753 West Second Street, Seymour.

Live music at Rails – Bob Layhe will perform at 7 p.m. May 23, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Ruben Guthrie will perform at 7 p.m. May 23, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.


Saturday, May 24

Freeman Army Airfield Museum – The Freeman Army Airfield Museum is open from 10 a.m. to 2 p.m. every Saturday. Appointments can be scheduled through the week by calling 812-271-1821. Learn more by visiting https://freemanarmyairfieldmuseum.org/ 

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Viking Weekend from 10 a.m. to 6 p.m. May 24 & 25, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.

Race – Saturday Night Racing will begin at 6 p.m. May 17, at Brownstown Speedway, 476 East County Road 100S, Brownstown. The race will include ILMS Pro Late Models, Super Late Models, Super Stocks, Pure Stocks, Crown Vics, and Hornets. Click here for information.

Live music at Brooklyn Pizza Co. – Happy Accident will perform at 6:30 p.m. May 24, at The Brooklyn Pizza Company, 753 West Second Street, Seymour. Joe Persinger also will perform.

Live music at Rails – Ruben Guthrie will perform at 7 p.m. May 24, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Colt Wienhorst will perform at 7 p.m. May 24, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.


Sunday, May 25

Southern Indiana Renaissance Faire – The Southern Indiana Renaissance Faire will host its Viking Weekend from 10 a.m. to 6 p.m. May 24 & 25, at Swifty Farms, 351 U.S. 31, Seymour. Click here for ticket information.


Wednesday, May 28

Live music at Brooklyn Pizza Co. – Ruben Guthrie will perform at 6:30 p.m. May 28, at The Brooklyn Pizza Company, 753 West Second Street, Seymour. Joe Persinger also will perform.
Open Mic Night – Dane Darlage will host open mic night at 6:30 p.m. May 28, at The Bearded Hobo, 1029 West Commerce Street, Brownstown.

Thursday, May 29
Summer Kick Off – The Jackson County Public Library will host a Summer Kick Off from 2 p.m. to 6 p.m. May 29, at the location in Seymour, 303 West Second Street, Seymour. There will be community agencies, games, a bouncy house, and more. The event is free and open to all ages.

Open Mic Night – Michael Staublin will host Open Mic Night from 6 p.m. to 9 p.m. May 22, at Brewskies Downtown, 117 East Second Street, Seymour. It’s free to join and open to anyone.


Friday, May 30

Free Summer of Fun Kickoff – WJAA Radio 96.3’s Free Summer of Fun Kickoff will be from noon to 1 p.m. May 30, at the Jackson County Visitor Center, 100 North Broadway Street, Seymour. A free lunch will be provided and those who attend can spin the prize wheel and tour the visitor center.
Crothersville Library Kickoff – The Jackson County Public Library will host a Summer Kick Off from 3 p.m. to 5 p.m. May 30, at the location in Crothersville, 120 East Main Street, Crothersville. There will be community agencies, games, a bouncy house, and more. The event is free and open to all ages.
Live music at Rails – Michael Duvall will perform at 7 p.m. May 30, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Kolton Norton will perform at 7 p.m. May 30, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.


Saturday, May 31

Freeman Army Airfield Museum – The Freeman Army Airfield Museum is open from 10 a.m. to 2 p.m. every Saturday. Appointments can be scheduled through the week by calling 812-271-1821. Learn more by visiting https://freemanarmyairfieldmuseum.org/ 

Hoosier Dirt Classic – 42nd Annual Hoosier Dirt Classic will begin at 6 p.m. May 31, at Brownstown Speedway, 476 East County Road 100S, Brownstown. The race will include Northern All-Stars Super Late Models, Pure Stocks, Crown Vics, and Hornets. Click here for information.

Live music at Jackson Live – Chapel Hart will perform at 7 p.m. May 31, at Jackson Live, 981 C Avenue East, Seymour. The group was featured on America’s Got Talent, and will not be performing in Seymour. Click here for tickets and information. 
Live music at Rails – Justyn Underwood will perform at 7 p.m. May 31, on the patio at Rails Craft Brewery in Seymour. In the event of rain, music will be moved indoors.

Live music at Poplar Street – Dwight Hendrix will perform at 7 p.m. May 31, at Poplar Street Restaurant, 513 South Poplar Street, Seymour.

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