May 9
Sidewalk Sale
When: May 9, 2026 (9:00 AM – 2:00 PM)
Where: Main Street, Evansville, IN
☀️ Join us for Evansville's longest street sale! The sidewalks of Main Street will be lined with 150+ shops, makers, residents, and community members selling their items. Come ready to shop and find great bargains!
After shopping, visit our restaurants and shops for lunch, coffee or adult beverages, gifts for mom, and more. Guests 21 and older can also purchase alcoholic beverages in official Downtown Evansville DORA branded cups and enjoy them as they explore the event.
May 9
Evansville Anime-Fest
When: May 9, 2026 (10:00 AM – 5:00 PM)
Where: Evansville, IN
⭐️ Ready to geek out? It's time to assemble your squad and show off your best cosplay at the Evansville Anime-Fest! This family-friendly convention brings all your favorite fandoms together under one roof. Get ready to browse exhibitor booths overflowing with comic books, toys, manga, and one-of-a-kind artwork. Plus, you won't want to miss the cosplay contest, anime trivia, and epic lip-sync battles. It’s a guaranteed blast! Admission is just $20, and little sidekicks 11 and under get in free with a paid adult.
May 12
EVPL Riverfront Reads
When: May 12, 2026 (6 PM – 7 PM)
Where: Evansville Riverfront Pagoda, Evansville, IN
📖 Bring the whole family out for an evening of stories, dancing, and community fun! Along with interactive activities for all ages, local community partners and food trucks will be on site to make the night even more memorable. Grab a blanket, bring your dancing shoes, and enjoy a fun-filled evening together, weather permitting.
May 16
5th Annual SummerFest
When: May 16, 2026 (Festivities begin at 5:00 PM)
Where: Downtown Henderson, KY (Water and Second streets)
Pop across the river for a fantastic evening of free live jams and good ol' community fun. The 5th Annual SummerFest is back, and it's bringing the party with a massive free concert, a hopping beer garden, and tons of activities for the kiddos. The best part? It's all for a good cause, supporting local charities.
May 21
Summer Sunsets
When: May 21, 2026 (5:00 PM)
Where: 2800 Kotter Ave, Evansville, IN
Summer Sunsets presented by 3rd Shot Pickleball is the perfect community evening out. Enjoy food trucks, outdoor games, vendor booths, and refreshing beverages. Leashed pets are welcome, making it a great excuse to get the whole family out of the house and mingle.
May 31
2026 Strawberry Social
When: May 31, 2026 (12:00 PM – 4:00 PM)
Where: 525 State Rd 662 E, Newburgh, IN
🍓 Good, old-fashioned fun, for all ages! Historic Newburgh, Inc. is hosting its sixth annual Strawberry Social! Close out the month with a massive dose of sweetness at the region’s favorite Strawberry Social. Historic Newburgh is shutting down the road for an afternoon of family fun. Indulge in the famous strawberry shortcakes and Strawberry Derr's Sodas. There will also be a ticket raffle, kids' activities, live music, and a vendor mart. It's the ultimate way to kick off summer.
Get Out & Play in the Sunny Days of May
May is officially bursting with reasons to get out of the house. We've got the food, the tunes, and the perfect Midwest weather waiting for you. Text your friends, scoop up the family, and go support these amazing local events.
