Labor Day weekend is the official hand-off from summer to fall, and our communities do it better than most. Summer's marquee events, the Will County Fair in Peotone, the Lake County Fair in Crown Point, Rockopelli over at Bulldog Park, have wrapped up for the year. And you know what? This is my favorite stretch of the season. The air turns crisp, downtown squares fill up, and every community seems to have a tradition worth marking on the calendar. Here is my week-by-week planner for the fall season, with details I confirmed in early September. As always, give the host a quick check before you head out, since dates and venues can shift.
Labor Day weekend: September 5 through 7
Frankfort Fall Festival
The anchor of the South Suburban fall calendar. This is the 58th annual Frankfort Fall Festival on Kansas and White Streets in downtown Frankfort, one of the most recognized arts and crafts festivals in the country, with more than 300 artists, carnival rides, a parade, food vendors and main stage entertainment at Breidert Green. Hours are Saturday and Sunday from 10 a.m. to 6 p.m. and Monday from 10 a.m. to 4 p.m. If the weather cooperates, it is worth every minute.
Weekend of September 12 and 13
Valparaiso Popcorn Festival
Saturday, September 12 in downtown Valparaiso. The town that Orville Redenbacher's popcorn put on the map celebrates with a parade, live music, craft and food booths and the Popcorn Panic race. Admission is free, and it is easily one of the happiest Saturdays in Northwest Indiana.
Crown Point Wine Fest
The same Saturday from 5 to 9 p.m. at Bulldog Park, with pours from wineries in Northwest Indiana, Southwest Michigan and around Chicagoland. A lovely, unhurried evening out in one of our favorite park settings.
Empanada Fest
Whiting hosts Empanada Fest at Lakefront Park on Saturday, September 12, with food, music and community right on the lake. A great excuse for a short drive and a longer lunch.
Also that weekend, the Lofs Lions are hosting an End of Summer bash in the Crown Point area; check the group's page for the exact spot.
Weekend of September 18 through 20
Tinley Park Oktoberfest
September 18 through 20 in downtown Tinley Park's Harmony Square. Traditional German food and beer, polka and oompah music, carnival rides and the ceremonial first keg tap. The official season opener for Oktoberfest lovers across the South Suburbs.
Concerts at the Credit Union 1 Amphitheatre
The B-52s and DEVO play Thursday, September 17, and Breaking Benjamin with Chevelle plays Friday, September 18, at the Credit Union 1 Amphitheatre in Tinley Park. Two excellent chances to catch the last stretch of outdoor concerts as the season turns.
World Cultural Fest
On Sunday, September 20, the region's cultures gather for performances and food from around the world. A wonderful reminder of why this area feels the way it does.
Weekend of September 26 and 27
Portage Harvest Festival
Saturday, September 26 at Founders Square in Portage. A harvest kickoff with vendors, food and family activities; check the city's calendar for the vendor lineup.
Valpo Brewfest
Saturday, September 26 at Central Park Plaza in Valparaiso, with a Biergarten Kick-Off on Friday night, September 25. A dedicated craft beer gathering that draws a great crowd every year.
Fair Oaks Farms Oktoberfest
September 26 and 27. Bavarian fare, fall brews, stein games and farm favorites at one of Northwest Indiana's favorite family destinations. Worth the drive, especially with kids.
Valparaiso University Homecoming Concert
Also Saturday, September 26 at the Chapel of the Resurrection. Pair it with a walk through the downtown square for a lovely autumn evening.
One honest heads-up: Schererville's street celebration has appeared on some calendars for September 18, yet a few 2026 festival guides flag it as possibly on hold, so confirm with the town before you plan around it.
October, already
Mokena Family Fall Fest
Thursday through Sunday, October 1 through 4, at Yunker Park and The Oaks Recreation and Fitness Center at La Porte Road in Mokena. Carnival rides, games, food vendors, a beer tent, kids' activities and live music, with $5 admission. One of the best value family weekends of the season.
Crown Point Oktoberfest
Saturday, October 3 at Bulldog Park. Free, family friendly, with live music, German food, a beer garden, face painting and games. A great way to spend the first crisp Saturday of the month.
Munster Pumpkins, Witches and Hayrides, Oh My!
Saturday, October 3 at Munster's Centennial Park: a pumpkin patch, characters, a pumpkins and pony rides. The friendly kickoff for Halloween season. Munster also hosts an Oktoberfest Beer Scramble at Centennial Golf Course in early October; check the town's parks page for the date.
Valparaiso Fall Harvest Festival
Saturday, October 10 from 10 a.m. to 2 p.m. at Central Park Plaza: pumpkin painting, apple cider and candy apples, bounce houses and face painting. A gentle, happiest way to spend a fall morning with little ones.
Plan ahead, then come see the neighborhoods
Fall dates fill up fast, so if something catches your eye, put it on the calendar now. And there is no better way to test whether a community feels like home than to show up on a festival day: wander the craft stalls, sit on a bench and watch the neighborhood go by. That is when you will know. And when you are ready to make the move, I would love to help you find the right one. You Can With Joanne!™