How did you hear about us?*

        Please Fill Out the Form Below to See Your Instant Home Value Estimate

        Main Content

        Upcoming Naperville Area Events – May 2024


        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. Get out and enjoy some of the awesome events going on around Naperville. We hope to see you around the neighborhood!


        Origins of Naperville Walking Tour

        Thursday, May 2 | Naper Settlement | 5:30p | $15

        Listen to stories from Naperville’s founding and the impacts of Caroline Martin Mitchell’s generosity to the city on a walking tour of the west side of downtown Naperville. The tour lasts approximately 60 minutes and covers about two miles. Open to all ages. Pre-registration is required.

        To learn more and get tickets, click here.


        Characters on Water Street! 

        Saturday, May 4 | Downtown Naperville | 9:30-11:30a

        The Force will be strong in Downtown Naperville on MAY THE 4TH from 9:30AM-11:30AM as costumed characters from a galaxy far, far away will take over Water Street for a FREE family-friendly meet and greet! Event is weather permitting.

        For more info, click here.


        Naperville Food Truck Festival 

        Saturday, May 4 | Naper Settlement | 12-7p

        Featuring 25+ of the area’s best food trucks, live music entertainment, a Mega bubble Show, Cinco de Mayo beer garden and a local vendor village featuring face painters, balloon artist & kids tattoo artist.

        This is a family friendly event with food & entertainment for kids plus everyone can enjoy the expansive Naper Settlement historical grounds.

        For more info and tickets, click here.


        Cinco de Barko

        Sunday, May 5 | Two Bostons – Any Location

        Arriba! Arriba! Cinco De Barko is coming in hot! Mark your calendars for Sunday, May 5th and head over to any Two Bostons location for some tail-wagging fun. We’ll be serving up FREE Mutt-garitas and our fresh take on a tostada all-day – it’s a fiesta you won’t want to miss! Bring your furry friend along and let’s paw-ty like there’s no mañana!

        For more info, visit twobostons.com.


        2024 State of the City Address

        Wednesday, May 8 | Embassy Suites Chicago- Naperville | 11a-1p

        It is a monumental effort to make Illinois’ fourth-largest city and second-largest economy thrive through investment and redevelopment. The to-do list is big. But together, we’re bigger. Join Mayor Scott Wehrli as he presents his first State of the City address recapping his first year in office with the community he calls #teamnaperville. From our City’s health, economy, and public safety to YOUR local government, you’ll have the chance to learn about the bridges crossed in 2023 and new opportunities being built in 2024. Hosted by the Naperville Area Chamber of Commerce.

        For more info and to register, visit here.


        Weed Ladies Spring Sale

        Thursday – Saturday, May 9-11 | Naper Settlement | 10a-3:30p

        Join The Weed Ladies for their annual Spring Sale featuring Floral design sales. This year’s Spring Sale will be held May 9, 10, and 11 from 10 AM to 3:30 PM. Admission to any Weed Ladies Sale is free. Please enter Naper Settlement’s main entrance and inform the Guest Services team that you are attending the sale. Purchasing a floral arrangement from the Weed Ladies benefits Naper Settlement’s education and preservation programs.

        For more info, visit napersettlement.org.


        Stamp Out Hunger

        Saturday, May 11 | Centennial Beach | 8-11a

        The National Association of Letter Carriers and the National Rural Letter Carriers Association will partner with Loaves & Fishes Community Services during the 32nd Annual Stamp Out Hunger Food Drive. Each year, residents are encouraged to place healthy, unexpired, non-perishable items in bags by their mailboxes on Saturday, May 11, for collection by postal carriers and Loaves & Fishes volunteers.

        For more info and specifics, visit loaves-fishes.org.


        Mother’s Day Paw Printing

        Saturday, May 11 | Two Bostons – Any Location | 12-4p

        Celebrate Mother’s Day with your furry baby at Mother’s Day Paw Paintings. Stop in at Two Bostons locations on Saturday, May 11th between 12:00 PM and 4:00 PM for FREE flower pot paw painting complete with dirt & flower seeds!

        For more info, visit twobostons.com.


        Build a Bouquet Event – Mother’s Day Weekend Event

        Saturday, May 11 | Downtown Naperville | 10a-1p | $40

        Limited tickets will be available (you only need to buy one ticket for Mom) and she and you/your family will get to stroll thru several downtown businesses, and SHE will receive amazing treats and gifts along the way. At each stop, she’ll receive more elements to build her bouquet!

        Staggered start times will allow the fun to be savored while you treat Mom to a fun morning – treats, time with you and keepsakes, too. Check-In at Liam Brex, 222 S. Main Street, Naperville, IL 60540.

        For more info and to register, visit downtownnaperville.com.


        Brook’s Mother’s Day Run

        Saturday, May 11 | The Annex | 8:30a

        Join the Naperville Running Co. on Mother’s Day weekend as they celebrate all families, moms, caregivers, and everyone in between with a two to three mile run along the Downtown Naperville Riverwalk! Start and finish at the Annex with breakfast, coffee, special goodies and demos of the new Ghost 16 too!

        For more info and to register, visit runningcompany.com.


        Naperville Artisan Market

        Saturday & Sunday, May 18 & 19 | CityGate Centre | 10a-4p

        An outdoor market in Naperville, IL showcasing the Midwest’s finest artisans in fashion, food, home goods + art. This curated, 2-day outdoor market celebrates the ingenuity of independently owned, small businesses who channel their passions into creating one-of-a-kind products. Meet & shop with the makers themselves – and learn how they create their unique and functional products. Support small, local, safe & sustainable.

        For more info and tickets, visit napervilleartisanmarket.com.


        Día del Niño (Children’s Day)

        Saturday, May 18 | 95th St. Library | 10a-4p

        Alliance of Latinos Motivating Action in the Suburbs (ALMAS), in partnership with the Naperville Public Library, is excited to announce the upcoming celebration of Día del Niño, also known as Children’s Day. This cherished event is set to take place on Saturday, May 18, 2024, from 10 a.m. to 4 p.m. at the 95th Street Library in Naperville (3015 Cedar Glade Dr.). Día del Niño is a cherished tradition deeply ingrained in the tapestry of Latin American cultures, symbolizing the paramount importance of children in society and celebrating their well-being and happiness. The event is free and open to the public. No tickets necessary, but space is limited.

        For more info, visit naperville-lib.org.


        Centennial Beach Open for Season

        Saturday, May 25 | Centennial Beach

        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. Visit Centennial Beach by purchasing a daily pass or season-long membership.

        For more info, visit napervilleparks.org.


        Memorial Day Parade 2024

        Monday, May 27 | Downtown Naperville | 10:30a

        The Naperville Memorial Day Parade kicks off at 10:30 A.M. on Monday, May 27. The route will be starting at Centennial Beach, east to Jackson to North on Main, East on Benton across Washington, ending at Court Place.

        For more info, visit napervillememorialdayparade.org.




        To see more upcoming events in Naperville, visit the Events page.

        Skip to content