Experience the Region in fall with a one-tank trip with the South Shore CVA
- By: Damon Modglin
- Last Updated: August 13, 2026
The South Shore Convention and Visitors Authority is gearing up for another exciting fall season, and Michiana residents are invited to join the fun! From high-octane air shows and heart-pounding Halloween events to relaxing days picking apples at the orchard, fall along the South Shore is the perfect time to hop in the car for a day trip to the Region.
Gary Air Show
Kicking off on August 21, the Gary Air Show Weekend brings crowds to Marquette Park every year to see aerial acts of daredevilry unlike anything else. This year, the free event will feature over 10 different performers across three days, including a brand new drone and pyro show on Friday evening to get the excitement flowing for the rest of the weekend!
The Greater Kankakee Jamboree
Celebrate the outdoors this August with Backcountry Hunters & Anglers at the first-ever Greater Kankakee Jamboree! This one-of-a-kind experience is happening right in Hebron and will feature a ton of family-friendly fun, like fishing, expert demonstrations, games, and more. The jamboree will be held August 21-22, and if you’ve got a love for the wild ecology of Indiana, you need to be there.
Man’s Man Chili Cookoff
The annual Man’s Man Chili Cookoff at the Indiana Welcome Center is one of Northwest Indiana’s tastiest traditions. Cooks from across the Region gather for the chance to win prizes and show off their skills. All chili is cooked on-site, so visitors have the chance to sample fresh chili as they enjoy the live music and the competition. This year’s cookoff will be held on August 29.
Midwest Region Volleyball Crossover Tournament
If you’re a fan of volleyball, you don’t want to miss the annual Midwest Region Crossover Tournament. The tournament brings together nearly 40 Division II teams from across three conferences for a weekend of heart-stopping plays and fierce competition. In addition to the volleyball fun, your trip can expand with special deals from local businesses just for tournament attendees. This year’s tournament will be held October 16-17.
Wickedly Whiting
When Halloween approaches, Whiting transforms into a festival of wicked terror! Wickedly Whiting brings the most eclectic mix of performers, costumes, and decorations to downtown Whiting for two days of spooky spectacle. This year’s Wickedly Whiting will be hosted on 119th St. on October 2-3.
With fall in Northwest Indiana comes a festival for every occasion. East Chicago’s Kielbasa Fest on August 22 celebrates Polish culture with music, food, and performances, while Whiting’s Empanada Fest on September 12 returns for another evening infused with Hispanic culture and dining. Valpo will celebrate all things Redenbacher during the 47th annual Popcorn Fest on September 12, and the Crown Point Wine Fest on September 12 gives those 21+ a chance to sample some of the finest wineries in the Region. Those looking for something a bit more hoppy can swing by the Valpo Brewfest on September 26, or the St. John Oktoberfest on October 2. No matter what you’re looking to celebrate, the Region has you covered!
Hard Rock Casino Northern Indiana
From world-class entertainment to fine dining to the neon gaming lights, Hard Rock Casino Northern Indiana is the perfect escape from the daily grind. The casino has it all: an on-site sportsbook, shopping, restaurants, and a large performance venue that has seen everyone from comedians to musicians to DJs and more.
County Line Orchard
A trip to Lake County in fall wouldn’t be complete with apple or pumpkin picking at the County Line Orchard. The orchard is a favorite among locals and visitors alike for its friendly service and delicious treats, something you can see for yourself as you travel the Region this autumn.
Harvest Tyme Family Farm
Harvest Tyme Family Farm brings yearly entertainment to the Region, and the fall season is no different. Beginning in September, the farm hosts weekly festivities on Saturday and Sunday featuring hayrides, corn mazes, and a petting zoo amongst other attractions. It also begins its Pumpkin Glow Trail, a half-mile walk with thousands of jack-o-lanterns to light the way. Add a trip to Lowell to your weekend plans once the leaves start to change colors!
Apple Blossom Trails
Sometimes, it’s important even on a trip to slow down and enjoy the world around you. Apple Blossom Trails in Crown Point offers just the opportunity. Tranquil ponds, rolling fields, and peaceful trails among the orchard let you breathe in the fresh air and let go of the troubles of city living. If you want a true rural experience, a trip to the farm is the way to go.
Lake County Parks
The Lake County Parks and Recreation Department maintains a host of beautiful, natural destinations to visit on your drive through the county. From the historic Deep River County Park and its classic Deep River Grinders games to Stoney Run County Park and its 300 acres of explorable outdoor space, you can enjoy the leaves changing in any of the Lake County Parks.
Farmers Markets
You don’t have to go far to find fresh produce, artisan crafts, and local designs in the Region! As fall hits Northwest Indiana, the weekly farmers market provides the perfect shopping experience no matter where you go. Whether it’s Chesterton’s European Market or Crown Point’s Farmers Market on Saturdays, Hebron’s Market on Main or Valparaiso’s Farmers Market on Tuesdays, or Hobart’s Market on the Lake on Thursdays, any day you visit the Region can be one for shopping!
Want to extend your stay? The South Shore CVA has tailor-made guides to help you get the most out of your visit! Restaurant recommendations, hotel suggestions and more are a click away with the South Shore CVA.