Your guide to 2018 Fall Events in the Heartland

Say hello to fall with a pick of the patch

It’s almost fall: the time of year for trips to the pumpkin patch, bonfires, hayrides, and haunted houses.

Good news: the Heartland has plenty of opportunities to get out and enjoy the season.

Fall Events & Festivals



Jump to October

Jump to November

McLeansboro Kiwanis Club Fall Festival
September 6-8

McLeansboro, IL
The annual festival includes three nights of FREE live music, along with a parade, and lots of great food.

Popeye Picnic
September 7-9

Chester, IL
The 39th Annual Popeye Picnic features carnival rides, music, a parade, and a cruise-in.

Rend Lake Car Show
September 8

Benton, IL
Over 175 vintage and classic vehicles will be on hand for visitors to enjoy.  Meet their owners, learn some tricks, and catch the car bug for yourself!  This event is fun for all ages with shops to browse and delicious restaurants featuring local favorites!

SEMO District Fair
September 8-15

Cape Girardeau, MO
Whether you’re coming for the food, the live entertainment, the agricultural exhibits, or the classic midway experience, the SEMO District Fair offers fun and adventure for the whole family. You’ll definitely want to check out Heartland Weekend’s Guide to all things SEMO District Fair.

Riverside Art, Wine, & Blues Festival
September 8

Murphysboro, IL
The biggest little blues festival in the Midwest will take over Riverside Park in Murphysboro, Illinois. You will also find craft vendors along with samples from local wineries and restaurants.

Cache River Days
September 8

Ullin, IL
A full day of fun, free activities focused on the plants and animals of the Cache River and Cypress Creek watersheds. Canoe tours, guided hikes, live wildlife exhibits, nature activities and crafts, Asian carp fry and much more!

9th Annual Fall into Arts Festival
September 8-9

Kennett, MO
The annual festival is packed with great performances and activities. There will also be a LEGO Creation Contest, live music, and plenty of good food to go around.

Cedarhurst Art & Craft Fair
September 8-9

Mt. Vernon, IL
This year’s event includes live glass-blowing demonstrations, art demonstrations, regional musicians, craft beers on tap, and an entire area dedicated to kids that will include story time and other creative fun. There will also be several food vendors and a specialty drink tent that will offer frozen selections like margaritas and strawberry daiquiris.

Fall Quilter’s Week
September 12-15

Paducah, KY
The American Quilter’s Society will host Fall AQS QuiltWeek in Paducah again this year. It’s being held at the Schroeder Expo Center from Sept. 12-15, 2018. The Fall Show features numerous classes to help quilters expand and grow their skills. You can certainly expect everything from how to quilt portraits in fabric to applique to learning to build a quilt around a panel.

67th Annual Murphysboro Apple Festival
September 12-15

Murphysboro, IL
The theme for the festival this year is ‘These Roots Run Deep.” The annual festival includes a parade, marching band competition, a carnival with concessions, and many contests including apple pie eating.

Antique Tractor and Gas Engine Show
September 13-15

Paducah, KY
The McCracken County FFA Alumni present the 40th annual Antique Gas Engine & Tractor Show, Fall Festival and Fall on the Farm, September 13-15, 2018. See antique engines, tractors, cars and trucks on display, many with running engines at Carson Park.

27th Annual Old Greenville Days
September 14-16

Greenville, MO
The celebration includes live music all weekend, 75+ craft vendors, food vendors, Crowley’s Ridge primitive campsite and reenactors, and games and activities for kids.

16th Annual Shrimp Festival
September 15

Golconda, IL
You can look forward to sampling Southern Illinois grown prawn which will be served up a variety of ways. There will also be live music, buggy rides, and a corn hole tournament.

Historic Downtown Wine Festival
September 15

Sikeston, MO
The Downtown Sikeston Wine Festival features the best wines of the region, hors-d’oeuvres and live music.

Rivertales Classic Car Show
September 15-16

Cape Girardeau, MO
Head downtown to check out the beautiful cars that will be on display.  The annual cruise in from Capaha Park to Main Street will take place Friday night.

91st Annual Stoddard County Fair
September 18-22

Dexter, MO
From the midway to the barns, you’ll find lots of things to see and do at the 91st Annual Stoddard County Fair. The parade through downtown Dexter will kick off at 5:30 p.m. on Tuesday, Sept. 18. A tractor pull is slated for Friday night and the 4H & FFA Auction begins at 9 a.m. on Saturday.

2nd Annual Bearcreek Bash Chuckwagon Races
September 20-23

Lowndes, MO
Learn more about the cowboy lifestyle at this MCWRA Finals & Co-Sanctioned ACWRA event. There will be an open trail ride, 4D Barrel Race, Chuckwagon races and more!

Praise the Lard BBQ Cook-off
September 20-22

Murphysboro, IL
The Praise the Lard cook-off is a qualifying event for the World Food Championships, so you can bet there will be lots of delicious BBQ! There will also be a Bloody Mary Contest and a Kids Que team cookoff.

East Perry Community Fair
September 21-22

Altenburg, MO
“The Best Little Fair in the Land” includes a parade, 4h & FFA exhibits, live music, a truck pull, and a lawn and garden tractor pull.

Frontier Days
September 21-22

Cave-In-Rock, IL
Cave-In-Rock Frontier Festival is held on the banks of the beautiful Ohio River. The festival, which commemorates the extensive and colorful history connected to Cave-In-Rock and the surrounding community, is an entertaining and fun-filled community event. There will be a parade, free inflatables, kids games, a washer pitching tournament, a band, a live play, fireworks and more!

Dragon Boat Festival
September 22

Paducah, KY
The dragons are coming back to Paducah’s riverfront for the 7th Annual Dragon Boat Festival in 2018. Gather your team or watch as the River Discovery Center hosts dragon boat races on the Ohio River.  Family fun activity with a kids area and food vendors.  Races run in heats beginning at 9 am.  Colorful dragon boats with 16 paddlers and a creatively dressed drummer race 3 races each.  Proceeds benefit the educational programs of the River Discovery Center.

The Delta Fair
September 25-29

Kennett, MO
The annual fair features a parade, midway, demolition derby, tractor pull, and a demolition derby. There will also be numerous exhibits in the American Legion Building, Youth Building, and FFA Building.

American Legion Cotton Carnival
September 25-29

Sikeston, MO
Celebrated since 1945, this 5-day festival honors military veterans of all branches and celebrates the annual cotton harvest.  Enjoy carnival rides, games, pageants, and entertainment.

Butler County Fair
September 26-29

Poplar Bluff, MO
The 157th Annual Missouri Butler County Fair will take place at Ray Clinton Park. Fairgoers can look forward to live music, a demo derby, weenie dog racing, rides, games, and food.

Barbecue on the River
September 27-29

Paducah, KY
Can you think of a better way to spend an early fall weekend than enjoying great BBQ, lively entertainment, exquisite crafts, a charming downtown and a great time with 40,000 of your closest friends? 35 plus BBQ teams from Western Kentucky and beyond cook up over 80,000 pounds of pork and chicken in hopes of taking home the coveted Grand Champions trophy. Along with delicious mouthwatering food and fabulous fun, you will be helping out many local charitable organizations.

Reynolds County Fair
September 27-29

Redford, MO
This family-friendly event features an ATV rodeo, pet talent show, team roping, a parade, a mud run, and a rodeo.

Bollinger County Fall Festival
September 28-29

Marble Hill, MO
You can look forward to a parade, cow chip bingo, garden tractor pull, kiddie tractor pull and a sand volleyball tournament at this annual event.

Family Weekend Craft Sale
September 28-29

Carbondale, IL
Local craft vendors have come together for the last 30 years to sell their professional and quality handmade wares. Just head to The Craft Shop at the Student Center to find unique crafts and gifts.

Magpie Market Days
September 28-30

Marion, IL
Join us for a vintage market like no other! It’s held at the Williamson County Fairground. You’ll see vendors from all over the U.S. who will sell things like shirts, boutique items, vintage finds, and handmade items. There will also be food trucks & live music. Kids under 10 will receive free admission!

Mount Vernon Fall Festival
September 28-30

Mount Vernon, IL
This year’s Fall Fest theme is “Illinois Proud” and will focus on the state’s bicentennial. 2018 is Illinois’ 200th birthday and Mt. Vernon’s Fall Fest will participate as an official bicentennial event for the state. The festival kicks off Friday at 5 p.m. with entertainment, food, and craft vendors. Saturday will again include the 5K for Special Olympics, Cruise-In Car Show, 100+ entry parade and marching band expo, Great Pumpkin Contest, Tri-State Treasure Hunt, musical entertainment, and more. The FREE Kids Zone, food and craft vendors, and beer and wine tent will be open all three days of the festival.

71st Annual Soybean Festival
September 29-October 5

Portageville, MO
Main Street Madness is Saturday, September 29 from 9 a.m. until 3 p.m. There will be booths set up with baked goods, arts and crafts, jewelry, raffles, fundraisers, beauty products, and home items. You’ll also be able to take in a magic show at 9:30 a.m. and 12:30 p.m.

Fall Harvest Festival
September 29-October 31, 2018

Sikeston, MO
Beggs Family Farm opens for the season on Saturday, September 29. Activities include a corn maze, pig races, cow barn play area, wooden play fort, wagon rides, and you can pick your own pumpkins. It’s open Wednesday-Sunday each week through October 31 (closed on Oct. 3).

7th Annual Craft Beer Festival
September 29

Cape Girardeau, MO
The Community Counseling Center Foundation Board will host the Seventh Annual Cape Girardeau Craft Beer Festival at the First State Community Bank Pavilion in the Arena Park. Admission includes samples from microbreweries, along with a souvenir pilsner glass, live music and great food.

9th Annual Iron Horse Festival
September 29

Poplar Bluff
Live entertainment all day, free kids zone, 5 & 10K races, dog show, car show, flag ceremony, food vendors, craft vendors, farmers market, tons of demonstrations, Union Pacific train on display, and so much more.

September 29

Ste. Genevieve, MO
Oktoberfest in Ste. Genevieve will highlight local German culture, traditions, activities, and foods.

Saluki Comic Con
September 29-30

You’ll see vendors, comic artists, a costume competition and more. You can also win cash prizes and trophies!

Click HERE for Trick-or-Treat & other Halloween events



Jump to November

Madison County Fair
October 5-6

Fredericktown, MO
The Madison County Fair is the first weekend of October and includes rides, music, games, booths and various animal exhibits and competitions.

DeSoto Daze
October 5-7

DeSoto, IL
There will be live music, trivia, a 50/50 raffle, inflatables, and a corn hole tournament. It’s all at the DeSoto Community Park.

Liberty Days 2018
October 5-7

Bloomfield, MO
This is an educational event for the whole family. Visitors can experience the past and the present as re-enactors show how uniforms, weapons, military tactics have evolved throughout the years. A living history encampment area is open to the community. It includes food and other activities.

Uptown Jackson Oktoberfest
October 6

Jackson, MO
The Oktoberfest is presented in the style of a German Oktoberfest. It features live music, authentic food and beer, family-friendly activities and more to give one the sense of adventure that a trip to Munich would provide!

Fall Festival & Twisted Cat Tournament
October 6

New Madrid, MO
Activities include a petting zoo, car show, great food, music, a youth fishing rodeo, mini golf, touch-a-truck, old-fashioned wagon rides, arts and craft vendors, bouncy house, and the Twisted Cat Fishing Tournament. All the fun takes place in downtown New Madrid from 9 a.m. until 5 p.m.

Mounds Fall Festival
October 6

Mounds, IL
There will be a parade, lots of food, and baseball games at this annual event at the city park. The parade will start at 11:30 a.m.

Heritage Festival
October 6-7

Mt. Vernon, IL
The Jefferson County Historical Village will host its annual Heritage Festival the first weekend of October. Demonstrations of old-time crafters will be on the grounds, as well as costumed docents to provide tours of the Historical Village. Food and drink will also be available moderately priced. There will be a church service at 10 a.m. Sunday in the Mt. Olive Church. Musical performances are scheduled throughout both days.

Fluorspar Festival
October 6-7

Rosiclare, IL
Hardin County Fluorspar Festival celebrates the influences brought to the area by the Fluorspar Mining Companies. The festival features an ever-growing list of activities and things to do, including a Queen’s Pageant, a carnival, hickory-smoked barbeque, a pet parade, kid’s games, karaoke, food and craft vendors, a quilt show, an open house at the American Fluorite Museum, a car, truck and motorcycle show and a large parade featuring local school bands, groups, floats, a Grand Marshall and horse clubs. There will also be local musical talent on hand and the finale is held Saturday evening at the City Park on the Ohio River.

Chaffee German Days
October 12-13

Chaffee, MO
There will be rides, food, pageants and other entertainment for the whole family. The event takes place at Frisco Park.

Union County Colorfest
October 12-14

Anna, IL
Enjoy the fall color of the Shawnee National Forest and guided home tours. Shop at local orchards, farm markets and art and craft fairs. You can also sample wine along the Shawnee Hills Wine Trail, watch the wiener dog races at the kid’s fest at the Anna park on Saturday.

Dexter Fall Festival
October 13

Dexter, MO
Our Annual Fall Fest will have great food vendors, entertainment, crafts and games for all ages.

Annual Fall Festival
October 13

Frohna, MO
A day of history, food, crafts, drinks, meeting old friends and making new ones. The event runs from 9 a.m. until 3 p.m. It’s held at the Saxon Lutheran Memorial in Frohna.

Golconda Fall Festival
October 14

Golconda, IL
The festival is at the courthouse from 12-4 p.m.

Blackcat BBQ Showdown, Flea Market & Fall Fest
October 19-20

Goreville, IL
The Village and Goreville School’s Fall Fest have joined forces for one big Fall Event. Chili Supper, BBQ Cook-off, Flea Market, Kids’ & Teen Cook-off, Hay Rides, Games, Parade and LOTS LOTS More!!!

Maiden Alley Oktoberfest
October 19-21

Paducah, KY
This festival is made special with attention being paid to providing great beer, awesome food, regional and national live music acts, art vendors and more.

American Thresherman’s Fall Show
October 19-21

Pinckneyville, IL
This annual event features steam & gas engines, tractors, steam train rides, a pony ride carousel, and many demonstrations including burr milling, and cider & apple butter making. It’s held at the Fairgrounds, so we hope to see you there!

Bernie Fall Festival
October 20

Bernie, MO
The festival kicks off at 10 a.m. with a parade. Entertainment begins at 12 p.m. There will also be food, games, shopping, giveaways and more!

Missouri Department of Conservation’s Fall Festival
October 20

Cape Girardeau, MO
Come on out for a fantastic fall harvest festival. We’ll celebrate the bounty that Missouri has to offer in the fall both through human and wild animal eyes. Taste a few fall treats, enjoy a campfire, try out crafts and games, or join us for a hike. There’s so much to do at our festival! The event is at the Cape Girardeau Nature Center and runs from 4-8 p.m.

Vulture Fest
October 20-21

Makanda, IL
Each fall, vultures fly over Makanda and the surrounding areas and signal the beginning of fall and the arrival of the incredible fall colors of Makanda and southern Illinois. Vulture Fest also features live music, food, shopping, and art by local artists for purchase.

45th Annual Fort Massac Encampment
October 20-21

Metropolis, IL
Step back in time to the turn of the century and celebrate the heritage of Fort Massac State Park. Attend one of the largest events in Illinois. Join Illinois Department of Natural Resources, Fort Massac, the Greater Metropolis Area CVB and City of Metropolis as we welcome thousands back to the late 1700’s. Taste the of the foods, see the sights of the day and hear the cannons boom and music play. Most importantly, experience History Come to Life at the Park!

Benton Fall Fest
October 27

Benton, IL
Break out your Halloween costumes – the Fall Fest is here! The 2018 Fall Festival will be held on the Benton Square on October 27th 4 p.m. through 7 p.m. The event is family friendly and free to the public.

96th Annual Pinckneyville Mardi Gras
October 27

Pinckneyville, IL
The celebration begins bright and early on Saturday morning where you will find a run hosted by Pyramid running club, a pancake breakfast hosted by the Lion’s Club, a flea market stretched across Walnut street, a car show over-flowing on Mulberry Street, live entertainment, children’s games, marching band field competition, and Illinois’ oldest night-time parade featuring floats, costumed marchers, bands and more.

Rural Heritage Day
October 27

Ste. Genevieve, MO
A day of history, reverie, and reminiscence! Come see how it used to be done, whether it’s farming with antique tractors, corn grinding, cooking, spinning, leatherworking, soap making, wood carving, gardening, or maybe take part in some good old-fashioned games. Tour the historic homes and enjoy live entertainment from fiddlers, cloggers, and comedians.
A donation of $3 is appreciated.



Jefferson County Candlelight Tour
November 3

Mt. Vernon, IL
Enjoy an evening walk by candlelight and experience what life was like before electricity. The Jefferson County Historical Village walkways will be lined with candles. Candles will also be lit in the buildings. The buildings will be open with costumed interpreters. Following your tour of the village by candlelight, partake of gingerbread and cider in the Schweinfurth Museum.

41st Annual Heritage Festival
November 3-4

Harrisburg, IL
The festival focuses on locally handcrafted items and delicious food. More than 100 vendors will have wares to sell, kicking off the holiday shopping season.  Items include handmade jewelry, handmade 18-inch doll clothes, wooden creations, Christmas items, handmade purses, candles, honey products, antiques and collectibles homegrown vegetables and many more.

Taste of the Holidays
November 10

Various Wineries
Get in the spirit of the holidays and experience the flavors of three local wineries: Apple Creek Vineyard & Winery in Friedheim, Missouri; Hemman Winery in Brazeau, Missouri; and The Barrens Winery in Perryville, Missouri.

Autumnfest Arts & Crafts Show
November 10-11

Carterville, IL
AutumnFest is an annual juried event for handcrafted arts, crafts, and specialty foods.

Golconda Deer Festival
November 15-17

Golconda, IL
The Pope County Deer Festival is a local tradition, held during the 1st shotgun deer season in Golconda, the ‘Deer Capital’ of Illinois. Held Thursday thru Saturday featuring vendors, food & music. A Deer Queen coronation on Friday night, a parade on Saturday at 2 pm. On Sunday morning, a community breakfast and town sweep are held.

If you know of other fall events or see an error, please let us know! CLICK HERE to contact us.