Discover Naperville: Monthly Local Events – May
There’s so much to do in and around Naperville this May! From Cinco de Mayo to the annual Memorial Day parade and everything in between, you’ll find something to do for everyone. We hope to see you around the neighborhood!
Weed Ladies Floral Sales
Thursday, April 30 – Saturday, May 3 | Daniels House at Naper Settlement
Discover the artistry of the Weed Ladies of the Naperville Heritage Society at our annual Spring Floral Sale! Each one-of-a-kind, hand-crafted arrangement features beautiful silk and dried flowers designed to brighten your home while supporting local history!
In honor of the upcoming 250th anniversary of the United States, this year’s sale features a curated selection of commemorative arrangements celebrating the American spirit!
For more info, visit napersettlement.org.
Shop the Block
Saturday, May 2 | Block 59 – 404 IL Rte. 59, Naperville
A Market For Mom And More is your go-to shopping event of the season! Set outdoors on the green at Naperville’s must-visit destination, Block59, and happening just in time for Mother’s Day—when spring is in full bloom— this curated market brings together a lineup of local makers, artists, and small businesses. It’s the perfect place to find thoughtful handcrafted gifts, local luxuries, and treats for anyone and everyone!
For more info, visit theblock59.com.
Walk MS – Naperville
Sunday, May 3 | Riverwalk Grand Pavilion
The Walk MS: Naperville 2026 includes both 1-mile and 3-mile route options, making it accessible for everyone to get involved. The purpose of the event is to build awareness and generate funds that help improve the lives of people living with MS.
For more info, visit nationalmssociety.org.
Naperville Garden Club Plant Sale
Friday, May 8 & Saturday, May 9 | Aero Estates | 9a-4p
hop a selection of hanging baskets, plants, and herbs—perfect for spring gardens and Mother’s Day. Event held rain or shine; cash or check only. Proceeds support local scholarships and community programs.
For more info, visit napervillegardenclub.org.
Mother’s Day Weekend – Build A Bouquet Event
Saturday, May 9 | 10am | Downtown Naperville
Celebrate Mom! For each ticket purchased, one participant will receive a bouquet and special treats! As you stroll through select downtown businesses, you’ll collect fresh flowers, unique gifts, and sweet surprises—creating a bouquet as beautiful as MOM.
Check-in location – 144 W. Jefferson Avenue. Limited tickets available! Staggered start times ensure a relaxed and enjoyable experience.
Make it a perfect day by starting with breakfast or wrapping up with a special lunch downtown. After all, she deserves to feel like the queen she is!
For more info, visit downtownnaperville.com.
Naperville Food Truck Festival
Saturday, May 9 | 12-7pm | Naper Settlement
Calling all food lovers! Get your appetites ready for a culinary adventure as the Naperville Food Truck Festival returns to the heart of downtown Naperville. This annual event is a vibrant celebration of food, fun, and community, bringing together a diverse lineup of Chicagoland’s best food trucks for a day of delicious discovery.
More Than a Meal — It’s a full-day family experience packed with live music, three spectacular Mega Bubble Shows, a Bluey Character Meet & Greet, face painters, balloon artists, and a vibrant vendor village.
For more info and to get tickets, click here.
BLOCK 59: Welcome to the Block Party
Wednesday, May 13 | 4-7p | Frontier Park Sports Complex
Block 59 is kicking off the season in style with Welcome to the Block on Wednesday, May 13 from 4–7 PM! Set on the Green, this lively community celebration features a special appearance by Mayor Scott Wehrli and showcases everything Block 59 has to offer—from its standout tenants to an exciting year of events ahead.
Guests can soak up live music from Bucket Number Six while enjoying family-friendly fun like face painting, crafts, and balloon artists. Plus, there’s no shortage of delicious bites with favorites like Stan’s Donuts, Shake Shack, Yard House, Lazy Dog Restaurant & Bar, Velvet Taco, Crisp & Green, Piccolo Buco, and more.
It’s the perfect excuse to gather the family, connect with neighbors, and celebrate the start of a vibrant season at Block 59.
For more info, visit theblock59.com.
Naperville Walking Tour – Public Art
Thursday, May 14 | 5:30pm | $15
Listen to stories from Naperville’s founding to the generosity of Caroline Martin Mitchell on a walking tour of the west side of Downtown Naperville.
Tours last approximately 60 minutes and cover about two miles. Ticket sales end at 4 PM on each tour date. Tickets cannot be purchased at the door. Guests are encouraged to dress for the weather and wear comfortable walking shoes. Open to all ages.
For more info and tickets, visit napersettlement.org.
Distinguished Gentleman’s Ride
Sunday, May 17 | 9am | Downtown Naperville
The Distinguished Gentleman’s Ride is a global event uniting classic and vintage motorcycle riders in support of men’s health. Its purpose is to raise awareness and critical funds for prostate cancer and men’s mental health.
For more info and to register, visit gentlemansride.com.
Author Event with Hayden Panettiere/This Is Me
Wednesday, May 20 | Anderson’s Bookshop | 7pm | $37
Join Anderson’s Bookshop for an author event with Hayden Panettiere, to celebrate the release of This Is Me: A Reckoning, on Wednesday, May 20th at 7:00 pm in our Naperville store.
Check in will begin approximately 30 minutes before the start time. This event will consist of a signing and photo line. There will be no presentation or Q&A.
For more info and tickets, visit andersonsbookshop.com.
Centennial Beach Opening Day
Saturday, May 23
Jump into summer as you swim in Centennial Beach’s historic stone quarry. It’s not a swimming pool, it’s not a lake, but rather it’s an experience like no other! Wade into the zero-depth entry and swim to depths of 15 feet. For generations, Centennial Beach has been the local “swimming hole” for many Naperville residents and their guests. It’s a great place to meet friends, gather with family or simply relax and enjoy! Centennial Beach is open annually from Memorial Day weekend through Labor Day.
2026 Naperville Memorial Day Parade
Monday, May 25 | Downtown Naperville | 10:30am
Naperville’s Memorial Day ceremonies start at 7:45am and continue throughout the morning including the Memorial Day Parade and Riverwalk Ceremony. The parade route is east on Jackson, north on Washington, east on Benton.
For more info, visit napervillememorialdayparade.org.
Welcome to Naperville’s Monthly Events Hub, your go-to resource for staying connected with all the exciting happenings in this vibrant community! Whether you’re a longtime resident, a new neighbor or just visiting, Naperville offers something for everyone throughout the year. From cultural festivals and family-friendly activities to outdoor adventures and seasonal markets, there’s always something to look forward to.
Each month, Naperville is buzzing with special events and gatherings that bring people together. You can expect a diverse range of events, such as:
Live Music and Concerts
Enjoy performances featuring local bands and nationally recognized artists at venues like the Naperville Riverwalk or North Central College.
Farmers Markets
Fresh produce, local goods, and artisanal crafts are available weekly at our bustling farmers markets, perfect for those who love supporting local businesses.
Family-Friendly Fun
From outdoor movie nights to interactive exhibits at the DuPage Children’s Museum, there are plenty of events to entertain kids and adults alike.
Festivals & Fairs
Whether it’s the beloved Last Fling over Labor Day weekend, the Naperville Ale Fest, or the holiday lights at Naper Settlement, our town knows how to celebrate.
Stay in the Loop
Naperville is always evolving, with new events popping up every month. Check back regularly for the latest updates on concerts, art shows, fitness events, and more. Don’t miss out on seasonal festivals, neighborhood fairs, and exciting happenings right in your backyard.
Be sure to stay connected and make the most of everything Naperville has to offer by following us on social media!