September
2026

September is not quite summer, not quite fall and that is exactly what makes it so good. It is patio weather, festival season, game-day energy, back-to-routine momentum, and an open invitation to get out and see what is happening around town.

Home/ Events
September 4 -6
maywood fest 2026 event page-1

Maywood Fest

Maywood Fest 2026 will be held the weekend of Friday, September 4th through Sunday, September 6th at Maywood Veteran's Park. Get ready for an exciting entertainment line-up on the main entertainment stage, food and retail vendors, and other enjoyable festival activities for attendees of all ages. We are looking forward to another fun-filled Maywood Fest!

Location: Maywood

September 4 - 6
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Taste of Melrose Park

The 2026 Taste of Melrose Park Entertainment Lineup Has Arrived!

Labor Day Weekend is shaping up to be another unforgettable celebration as the Taste of Melrose Park returns September 4–6, 2026 with an incredible lineup of live music, entertainment, food, and family fun.

This year's schedule features tribute bands, classic rock favorites, live DJs, comedy, dance performances, cultural entertainment, and much more across multiple stages throughout the festival grounds.

September 4–6, 2026 at the Melrose Park Civic 

 
 
 
 
 

 

Location: Melrose Park 

September 11 - 12
oaktoberfest events page

Imperial Oaktoberfest

The Oompah is back and better than ever! 
Get ready for an unforgettable weekend packed with:
Live Music: Non-stop German bands and festive tunes starting Friday.
Authentic Food: Sizzling bratwurst, soft pretzels, and more!
Cold Beer: Pouring the finest traditional brews all weekend long. The long wait for Das Boot Marzen & Das Prost Fest Bier is over!
2026 Event Steins & merch: Take home the brand-new, limited-edition official glassware or cool logo tee!
Cornhole Tournament: Grab a partner and kick off the fest with our bags competition on Thursday.

Location: Brookfield

September 12 - 13
west end arts 2026

West End Arts Festival

Celebrate the arts at the 30th annual West End Arts Festival, a juried art festival that brings together fine artists, families and art lovers for a vibrant weekend in La Grange. From 10 a.m.–5 p.m. Saturday and Sunday, browse and shop original artwork while enjoying live art demonstrations, creative activities, food, wine and beer, kids’ activities and acoustic music. Set next to Metra’s BNSF Stone Avenue Station, the festival offers free admission and free parking, making it an easy and entertaining fall outing for all ages.


Location: La Grange

September 19
glow fun run events page

Glow Fun Run

Ages 6+ The Glow Run PRE-PARTY will include a DJ, a black light photo op, glow body paint, and a t-shirt decorating station!   
This fun, non-competitive event kicks off at sundown, so make sure to wear light up running gear or any glow items you can find!  
 
Check-in/activities:  6:00pm
Race Start:  7:00pm 

Location: River Forest

September 25 - 27
la grange oktoberfest event page

La Grange Oktoberfest

The inaugural La Grange Oktoberfest brings together local restaurants, live entertainment, family activities, and community spirit for a weekend celebration in Downtown La Grange. Built around local businesses and designed to encourage visitors to explore the entire downtown, Oktoberfest celebrates both Bavarian traditions and everything that makes La Grange special.

Location: La Grange

September 20 & 27
Gangster Tour

There Goes The Neighborhood Tours

This exterior tour visits 13 houses in these two suburbs which were previously owned by major hoodlums, including Tony Accardo, Paul Ricca, Sam Giancana, “Tough Tony” Capezio, and "Machine Gun Jack" McGurn. I will discuss the criminal careers of the former owners, the interesting features of each home (I've now been in 10 of them), the family's time there, and answer all questions from the audience. The tour lasts about two and a half hours and is a deep immersion into the history of organized crime in Chicago from Prohibition to about the 1990s. It is by coach bus with no walking required.

 Location: Oak Park & River Forest

September 25 - 26
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Downtown Oak Park Oaktoberfest

Celebrate the changing seasons at Oaktoberfest in Downtown Oak Park. Enjoy an exciting live music lineup, delicious food from local restaurants, specialty craft beers, and kids’ activities.

Located at Marion Street and North Boulevard, South of Lake Street.

Friday, Sept 25: 4:00 PM – 10:00 PM

Saturday, Sept 26: 12:00 PM – 10:00 PM

Location: Oak Park

September
chef events september event page

September events at Chef Shangri-La

Chef Shangri-La has an incredible line up of entertainment this month! Sip and Paint, Hula Show, Drag Brunch and a great list of tribute artists! 

Location: North Riverside 

September 26
hop stop events page

Riverside Hop Stop

Hop Stop is back in another undefeated collaboration between Riverside Foods and the Olmsted Society. With your commemorative tasting glass, you’ll be able to sample over 20+ offerings from local brewers, cideries and cocktail crafters, including Riverside’s own Quincy Street Distillery. Make use of the free bicycle valet, bring a designated driver, or take the Metra, which drops you right outside. There will be local food vendors, art activities for children (under 12 are admitted free with ticket), and music to round out a wonderful outdoor family friendly setting in the arboretum Village of Riverside.

Location: Riverside

September 27
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Olmstead Society Walking Tour - North

With homes by William LeBaron Jenney, Frank Lloyd Wright and Howard Van Doren Shaw, the North tour includes Michaux, Gatesby, Longcommon, Shenstone, Cowley, Herrick, and Nuttall Rds as well as the historic village water tower. Advance reservations may be purchased here. Please select the appropriate price for your tour category. You may also pay with cash or check on the day of the tour.

 

Location: Riverside