Maywood Fest 2025: Everything You Need to Know
Get ready to celebrate community spirit Labor Day weekend—Friday, August 29, through Sunday, August 31—at Maywood Fest! What started as a simple neighborhood picnic has blossomed into the largest event in Maywood, IL, attracting thousands of attendees daily. This year, the Village of Maywood and PowerMove Presents are bringing something different to Maywood Fest with the addition of Summer Jam 2025.
This year, there will be more entertainment—on two stages—and even more food and retail vendors!
MAYWOOD FESTIVAL: HOW IT ALL STARTED
Maywood Fest started with a simple idea: to bring the community together for a day of fun at Maywood Veterans Park. What began as a small community picnic with just a few activities has grown into the largest event in the Village of Maywood. Now a three-day celebration filled with diverse vendors, live entertainment, and activities for people of all ages, it attracts more than 5,000 attendees each day.
The festival's popularity comes from its ability to serve the whole community. Kids enjoy the fun zone, with inflatables, face painting, and games, while music fans look forward to a lineup of live performances. Over the years, Maywood Fest has become a cherished tradition, showcasing the best of what Maywood offers and serving as a symbol of the village's dedication to unity and community spirit. As it continues to expand, Maywood Fest remains a great example of how a simple idea can bring a community closer together, year after year.
WHAT TO EXPECT AT MAYWOOD FEST 2025
Maywood will be buzzing Labor Day weekend with live music from nationally renowned artists, including the Isley Brothers, Tank, Tyrese, Keke Wyatt, and Lyfe Jennings. Comedians including Lil Rel Howery and Damon Williams will also perform, and favorite local performers will take to the community stage. Enjoy offerings from more than 40 food vendors, as well as games and other activities for the whole family. Even teens will be entertained with gaming and activities in the Teen Zone. Whether you're a long-time resident or visiting for the first time, Maywood Fest provides the perfect chance to come together and enjoy the best of this vibrant community.
The festival kicks off at Maywood Veterans Park, located at 5th Avenue and Oak Street, on Friday, August 29, running from 5:00 p.m. to 10:00 p.m., followed by a full day of festivities on Saturday, August 30, from noon to 10:00 p.m. The celebration wraps up on Sunday, from 10:00 a.m. to 11:00 pm. Summer Jam stage gates open at noon on Sunday.
Visit the official Maywood Fest 2025 website for information and tickets.
Amazing Entertainment
Enjoy a variety of live music, comedy, and other entertainment on two stages.
Friday, August 29
Maywood Fest Community Stage, 5:00 p.m. to 10:00 p.m.
HBCU, Divine 9, and a house music takeover (FREE)
Saturday, August 30th
Maywood Fest Community Stage, noon to 10:00 p.m.
Latin, hip-hop, and Chicagoland talent (FREE)
Summer Jam Stage; gates open 5:00 p.m. to 10:00 p.m.
Summer Jam Comedy Show
Lil Rel Howery will host performances by Marlon Mitchell, Mike Samp, M. Dubbs, B. Cole, Sean Morgan, Uncle Rail, DJ Leon Rogers, DJ Kool Ant, and KJ Cliff.
Bring your family and lawn chairs for laughs at Maywood Veterans Park. Show starts at 7:00 p.m. First 1,000 tickets for Maywood residents are free, with a limit of two per household; upgrades are available upon request.
Get information and buy Summer Jam Comedy Show tickets here.
Sunday, August 31
Maywood Fest Community Stage, 10:00 a.m. to 9:00 p.m.
Gospel Fest, local Chicagoland talent, and TeenZone (FREE)
Summer Jam Stage, gates open noon to 11:00 p.m.
Summer Jam R&B Family Food Festival
Lil Rel Howery will host an incredible event with unforgettable performances by the Isley Brothers, Tyrese Gibson, Tank, Keke Wyatt, Lyfe Jennings, Silk, Jacquees, Koffee Brown, 3-Piece, Unk Nem, and others.
Bring your family and dress to impress. Show starts at 3:00 p.m. First 500 tickets for Maywood residents are free, with a limit of two per household; upgrades are available upon request. Get information and buy Summer Jam R&B tickets here.
Plus, the annual Car, Bike, and Truck Show will kick off at 10:00 a.m. on Sunday. There will be prize drawings and trophies will be awarded to the best in 10 categories. There's no charge to enter. Categories include Trucks, Motorcycles, Best Exotic Paint and Sound System, and more! Plus the coveted Mayor's Choice Trophy. Awards will be presented at 2:00 p.m. Register on-site or in advance.
Incredible Food
Come hungry! With such an amazing variety of food, you’ll definitely want to try everything. Be sure to check out the vendors, including:
A&M Italian Ice
Antojos Pablanos El Carmen
Caseras
Chi Town Foods
The Food Dude
Foster’s Shrimp
Haire’s Gulf Shrimp
Jerkbyli
Josephine’s Cooking
Juicy Jubilee
Jay’s Backyard BBQ
Jazzy Jerk Grill
Just Like Mama’s Restaurant
Jessie Old Fashion BBQ
Kingston Market
Legend’s Grill
Lickle Jamaica
Mia’s Vegan Cuisine
New Era Restaurant
Polly Ann Cakes
S2 City Grill
Scrumptious BBQ
Shark Ruby’s Restaurant
Soulful Delight
Turn Lemons
Windy City BBQ
Visit the official Maywood Fest 2025 website for information and tickets.
Specialty Retail Vendors
Support a fantastic array of retail vendors, including:
Africa and Bank
The Aughtry Connections
Bomb Beauty Boutique
Diva’s Destination Travel Agency
Emma Genes Hair Heaven
Goddess Accessories
KamKia Designs
Legacy Letterman
Naturals ByNette
Olive & Oak
QC Shades LLC
Scotty’s Clothing
Sharlee Luxe
Sherrie’s Rings and Things
Sincerely Yours Candle Co.
Snatched Angels
Soap and Happiness
Tresses V Loc Lounge
Unbothered 2
Nonprofit supporters include the Cook County Clerk’s Office, Triton College, Way Back Inn, Able Ministries, Campaign for a Drug-Free Westside Inc., Speaker Emanuel Chris Welch’s Office, and the Launching Pad Worldwide.
Visit the official Maywood Fest 2025 website for information and tickets.
GETTING THERE
Getting to Maywood, IL, is easy, no matter where you're coming from, as it’s located just 11 miles west of downtown Chicago. You can hop on I-290 West from the city and reach Maywood in about 20 minutes. If you're coming from the northern suburbs, take I-294 South and connect to I-290 East for a quick trip. From the west, I-88 East will get you there, while visitors from the south can take I-55 North, then connect to I-294 North.
For those using public transportation, the Metra Union Pacific West Line has a stop in Maywood, making it convenient for city dwellers and suburban commuters alike.
Wherever you're coming from, Maywood is easily accessible and ready to welcome you!
WHILE YOU’RE IN TOWN
Outside of the festival, the Village of Maywood offers a wealth of local history and culture to explore. Embark on your own walking tour through the town’s neighborhoods, where you'll discover an impressive variety of architectural styles, including Italianate, Queen Anne, Prairie, and Mid-Century Modern. These homes, designed by notable architects such as John Van Bergen and William Drummond, showcase the skill and creativity of their eras. Be sure to visit the Historic Maywood Home for Soldiers’ Widows, a unique landmark that serves as a poignant reminder of the town's past.
Maywood has deep roots in African American history. Established in 1995, the West Town Museum of Cultural History is dedicated to preserving the local Black heritage. The museum shares the stories of notable figures, such as Fred Hampton, the leader of the Black Panther Party, who grew up in Maywood. It also highlights the town's significant role in the Underground Railroad. Visitors can see a monument near 1st Avenue and Lake Street that marks the site of the Ten Mile Freedom House, which once served as a refuge for enslaved people on their journey to freedom.
For outdoor enthusiasts, Maywood is the starting point of the Illinois Prairie Path, a 61-mile trail ideal for hiking, biking, or simply taking in the beauty of restored prairies and natural landscapes.
Learn more about Maywood’s rich blend of history, architecture, and outdoor activities at OakParkandBeyond.com