With spring on its way out and summer finally peeking over the horizon, Illinois' weather usually warms up in May. Our real estate agents can't wait to make the most of the late-spring days ahead, and outdoor events are among the things they're most excited about. Luckily, there are more than enough fun festivities to fill their calendars in Belleville this May.

5 Outdoor Events to Kickstart Festival Season in Belleville

Bellevue Park Nights 

Address: 401 Bellevue Park Dr., Belleville, IL 62226 

Bellevue Park Nights is a beloved city tradition that offers a free concert and movie on the second Friday of each month from May to September. The May 8 event is the first of the 2026 series. It features music by indie band FanFare at the Bellevue Park bandshell, followed by a screening of Sing.  

There will also be:

• Dancing 
• Activities and games for kids 
• Local food trucks 

The concert starts at 7 p.m., while the movie starts an hour or two later at sunset. Both parts of the event are free. 

Belleville Woofstock 

Address: 110 N 6th St., Belleville, IL 62220 

Calling all dog lovers! Belleville Woofstock is coming to town on May 9 at the Rotary Park dog park near our Belleville homes for sale. This celebration of all things canine will feature: 

• Live music  
• A pet parade
• Food vendors serving hot meals and snacks, including pup-friendly options 
• A market full of locally sourced pet items 
• Kid-friendly activities
• A kids' dog show with prizes and special treats

Head over to the park from 11 a.m. to 3 p.m. with your furry friend and join in for free.

Eckert's Belleville Farm Strawberry Festival 

Address: 951 S Green Mount Rd., Belleville, IL 62220 

Nothing beats biting into a sweet, juicy strawberry that was grown right here in Belleville. That's exactly what you'll get at Eckert's Belleville Farm Strawberry Festival. Every May weekend starting on the 9th, the farm will be overflowing with ripe strawberries for guests to pick. Festivities include: 

• Strawberry-flavored treats and appetizers 
• Strawberry-themed cocktails 
• Festival foods
• A kids' play area 
• Pony rides and a petting zoo 
• Carnival rides 

You can visit anytime between 10 a.m. and 5 p.m. on either day. Admission is included with standard tickets.

Art on the Square 

Address: 401 Bellevue Park Dr., Belleville, IL 62226 

Art on the Square is Belleville's nationally recognized annual juried arts show, drawing artists and art lovers from all over the state to celebrate the joy of creation.

This year's three-day exhibition will take place on May 15, 16, and 17 at the Veterans Memorial Fountain in Public Square. There will be hundreds of works of art and a chance to speak to the talented artists who created them. Additional attractions include:

• A Wine Court
• Local food and drink vendors 
• Live entertainment  
• A Children's Art Garden for budding artists to work on their own masterpieces 

You can visit the show from 4 to 10 p.m. on May 15, 10 a.m. to 8 p.m. on May 16, and 10 a.m. to 4 p.m. on May 17.

Belle-Clair Fairgrounds Flea Market 

Address: 200 S. Belt East, Belleville, IL 62220 

The Belle-Clair Fairgrounds Flea Market visits the park of the same name on the third weekend of every month. This May's market is scheduled for the 16 and 17. Hundreds of vendors will be on-site selling:  

• Antique furniture, toys, household items, and other vintage goods
• Rare collectibles 
• Used books and magazines 
• Clothing and accessories 

The market is open from 9 a.m. to 4 p.m. on Saturdays and 9 a.m. to 3 p.m. on Sundays.

Gear Up for Summer Event Season in Your New Belleville Home 

Think these May events sound fun? Wait until you see what's happening in Belleville over the summer.  Now is the perfect time to settle into a new local home where you can watch it all unfold. Contact us today to get the inside scoop on the best Belleville homes on the market.