Top Local Events Happening This May You Don’t Want to Miss

May is filled with exciting local events, making it the perfect time to get out and enjoy the spring season. From outdoor art shows and artisan markets to food festivals and Memorial Day parades, communities across the western suburbs have plenty of activities for you to explore.

1. Naperville Artisan Market at CityGate – Naperville (May 16-17 | 10AM - 4PM)

The Naperville Artisan Market returns to the scenic 30-acre campus of CityGate Centre, bringing together more than 115 talented local and Midwest artisans for a vibrant spring shopping experience. Visitors can spend the day exploring a thoughtfully curated open-air market filled with handcrafted goods, including unique gifts, home décor, jewelry, original artwork, boutique fashion, and specialty foods. Each booth offers something different, giving guests the chance to discover one-of-a-kind items while meeting the makers behind them and learning more about their craft. Whether you’re looking for a meaningful gift, refreshing your home décor, or simply planning a fun weekend outing, the event offers something for every interest. With its mix of creativity, small business support, and community spirit, it has become one of the most anticipated seasonal shopping events in the area.

For more info, and to RSVP, click HERE.

2.  Food Truck Fest – Aurora (May 15 | 5-9PM)

Get ready for a flavorful evening at the Food Truck Fest where you can explore a wide variety of mobile cuisine from some of the best local food trucks in the region. From savory street food and global flavors to sweet treats and creative comfort dishes, there’s something for every craving in one lively, open-air setting. Whether you’re a dedicated foodie looking to try something new, a family planning an easy night out, or a group of friends meeting up for a casual evening, the festival offers a fun, laid-back atmosphere built around great food and community. Come hungry and plan to sample your way through multiple vendors while enjoying a relaxed spring evening. Admission is free, and everyone is welcome to attend.

For more info, click HERE.

3. Mac Fest – Wheaton (May 16 | 1-5 PM)

Attention all mac-and-cheese lovers! Mac Fest in downtown Wheaton is a unique food-centered event brings together local restaurants and vendors serving up creative mac and cheese dishes, from classic comfort food favorites to gourmet creations featuring BBQ, lobster, buffalo chicken, and more. Enjoy unlimited mac and cheese tastings, live entertainment, craft beverages, shopping specials throughout downtown Wheaton, and fun activities for all ages. Mac Fest has quickly become a favorite spring tradition for food lovers looking for a casual, fun, and family-friendly day out! Tickets are $25, so secure yours now, bring your appetite, and head downtown for an afternoon full of flavor, fun, and community at Mac Fest!

Purchase tickets HERE.

4. Wine Tasting in Lilacia Park – Lombard (May 16 | 7-9 PM)

Looking for a date night idea? Join the Lombard Park District and Lynfred Winery for an evening of guided wine tasting and discovery in beautiful Lilacia Park. Guests will enjoy a curated selection of wines chosen by expert hosts while learning about what makes each variety distinctive, from flavor profiles and aromas to the winemaking techniques behind them. The experience is designed to be both educational and enjoyable, making it a great option for couples or friends looking for a relaxed night out with something a little different. Tickets are $42 to $51 and include six wine samples, a tasting glass, and a complimentary glass of wine. Pre-registration is required, so be sure to reserve your spot in advance!

For more info and to register, click HERE.

5. St. Charles Fine Art Show – St. Charles  (May 23 | 10AM - 6PM & May 23 | 10AM - 5PM)

The St. Charles Fine Art Show transforms downtown St. Charles into a vibrant open-air gallery, bringing together painters, photographers, sculptors, jewelry makers, and artists from across the Midwest. Held Memorial Day Weekend, this juried outdoor event features more than 100 artists showcasing original work in a variety of mediums along scenic S. Riverside Avenue beside the Fox River. Visitors can stroll through downtown while discovering one-of-a-kind artwork, from contemporary paintings and handcrafted jewelry to striking sculpture and photography, all while enjoying the charm of the riverfront district. The event also pairs perfectly with St. Charles’ popular restaurants, local breweries, cafés, and riverfront patios, making it an ideal way to spend a spring afternoon supporting independent artists, exploring the community, and finding unique pieces for your home or collection.

For more info, click HERE.

6. Downtown Wheaton French Market – Wheaton (Saturdays | 8:00AM – 2:00PM, April through November)

The Wheaton French Market transforms downtown Wheaton into a lively, European-style marketplace filled with fresh flowers, artisan foods, pastries, handmade goods, and specialty items from regional vendors. Run by Bensidoun USA and inspired by the charm of traditional French outdoor markets, it features a rotating selection of vendors each week, so there’s always something new to discover, from fresh produce and baked goods to jewelry, crafts, and specialty foods.

Strolling through the market offers a relaxed, walkable experience through downtown, with plenty of opportunities to stop into nearby coffee shops, boutiques, and local restaurants before or after browsing. It’s a favorite weekend destination for families, couples, and shoppers looking for unique, locally made finds in a welcoming community setting.

For more info, click HERE.

7. Local Memorial Day Parades – Aurora, Naperville, Plainfield & Oswego

Don’t miss the Memorial Day parades happening across the area as communities come together to honor fallen heroes and celebrate local traditions. From patriotic ceremonies to marching bands and community floats, each parade offers a meaningful way to spend the holiday weekend with family and friends.

• Aurora – Annual Memorial Day Parade | Monday, May 25, 10:00 AM | Downtown Aurora | MORE INFO
  
  
• Naperville – VFW Memorial Day Parade | Monday, May 25, 10:00 AM | Starting on Jackson Ave. | MORE INFO
  
  
• Plainfield – Memorial Day Parade | Monday, May 25, 10:45 AM | Ira Jones Middle School to Settlers’ Park | MORE INFO
  
  
• Oswego – 2026 Memorial Day Parade | Monday, May 25, 10:00AM | Downtown Oswego | MORE INFO
  
  

There’s plenty to look forward to this May! Be sure to take advantage of the spring season and enjoy all the local happenings while they’re in full swing.