25 summer events in Oshkosh that can't be missed, from Waterfest to AirVenture & XRoads41

AI-assisted summary
• Oshkosh hosts a variety of summer events, including music festivals, art shows and a circus.
• Waterfest, a concert series at Leach Amphitheater, features numerous artists throughout the summer.
• EAA AirVenture, a major aviation event, takes place at Wittman Regional Airport from July 21-27.
• The XRoads41 music festival, held Aug. 7-9, features country and other music acts.
• Many free events are available, such as the Oshkosh Jazz Festival and free Tuesday night concerts.

OSHKOSH – Woodcarving, a circus, wrestling, toys, comics, music concerts, festivals, a poker run, art, airplanes, jazz — Oshkosh has it all this summer.

Here are 25 events happening between May and August to put on your summer bucket list.

May: Spring Wine Walk, Wrestling Con & Toy and Comic Show

• May 3: Downtown Oshkosh Spring Wine Walk. 1-5 p.m. Check in at Time Community Theater, 445 N. Main St., before starting the Woodstock-themed walk. 20-plus wine samples will be featured at different businesses throughout downtown Oshkosh. Participants can sample up to 18 wines, or one sample per location. Some businesses will be offering specials, coupons and opportunities to win prizes. Tickets are $35 and include a souvenir wine glass.
• May 4: 49th Annual Artistry In Wood Show. 9 a.m.-4 p.m. at Oshkosh Convention Center, 2 N. Main St. Features 80 woodcarvers, pyrography artists, and various artists from Wisconsin and the Fox Valley area. The event includes a bucket raffle, demonstrations, tool and wood vendors, “how-to” books, food concession, and artwork for sale. Admission is $5 for adults and free for ages 12 and younger.
• May 15: Glow Circus presented by Carden International Circus. 7 p.m. at Oshkosh Arena, 1212 S. Main St. Aerial acrobats, elephants, camels, buffalo, zebras, horses and more. Tickets start at $18.
• May 17: ACW Wisconsin Water City Wrestling Con 2025. 3:30-10 p.m. at Oshkosh Convention Center, 2 N. Main St. Live wrestling matches, vendors and merchandise, and appearances by JBL, Shelton Benjamin, Demolition, Santino Marella, Kelly Kelly, Jinder Mahal, Brian Myers, Heath Slater and Colt Cabana. The event usually sells out, so tickets, $25-$60, may be limited.
• May 17: Festival of Spring. 9 a.m.-4 p.m. at Paine Art Center & Gardens, 1410 Algoma Blvd. A free outdoor event featuring the Paine’s annual spring plant sale and numerous vendors of original art, fine crafts, plants and garden supplies.
• May 24: Quad Con Oshkosh Toy and Comic Show. 10 a.m.-5 p.m. at Oshkosh Arena, 1212 S. Main St. More than 90 booths with artists, authors and vendors selling posters, comics, video games, Pokemon, Star Wars, Transformers, anime, action figures, Funko pops and comic books. Plus, a cosplay contest.

June: George Thorogood at Waterfest, The Glam Band & Bago Big Bet

• June 12: Hairball! at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include The Michael Weber Show and Brett Newski & the Bad Inventions. Standing-room-only VIP is $30, general admission $20 and $10 for fans in line before 6 p.m. Opening night is free for teachers with a school ID.
• June 17: The Glam Band - Free Tuesday Night Concert. 5:30-9 p.m. at Leach Amphitheater, 303 Ceape Ave. Includes family entertainment, bounce houses and food trucks. Admission is free.
• June 19: George Thorogood and The Destroyers at Waterfest. Gates open at 5:30 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include The Jay Edward Band and The Pocket Kings. Standing-room-only VIP is $45 and general admission is $20.
• June 25-28: The Bago Big Bet 2025. 10 a.m.-8 p.m. each day. Oshkosh Marriott Waterfront Hotel & Convention Center, 1 N. Main St. High-stakes poker, boat display and boat parade.
• June 26: The Cat Empire at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include Copper Box and Kate Voss & The Hot Sauce. Standing-room-only VIP tickets are $30; general admission is $10 for fans in line by 6 p.m., $15 before 7 p.m. and $20 after 7 p.m.

July: LiFEST, AirVenture & the county fair

• July 4: Fourth of July Celebration. 9 a.m.-10 p.m. at Menominee Park, Hazel Street and Merritt Avenue. Food trucks throughout the park from 3 to 10 p.m. Reetz Ball Diamonds Concessions from 3 to 10 p.m. Lakefly Cafe from 10 a.m. to 6 p.m. Children’s Amusement Center from 11 a.m. to 7 p.m. Festival Foods Fireworks Show at dusk. Admission is free.
• July 10-13: LiFEST. One of the nation’s largest Christian music festivals. Held at the Sunnyview Expo Center, 500 E. County Road Y. More than 100 acts across six stages. Featuring Matthew West, Ben Fuller, Sidewalk Prophets and more. More info at Lifest.com or call 920-738-5588.
• July 10: Marcia Ball at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include The Jimmys, Alex McMurray Band with Paul Sanchez and Rising Phoenix. Standing-room-only VIP is $25; general admission is $10 before 7 p.m. or $15 after 7 p.m.
• July 13: Faire on the Green. 9 a.m.-4 p.m. at Paine Art Center & Gardens, 1410 Algoma Blvd. The largest summer art and craft fair in Oshkosh. More than 100 artists showcase their creations, from photography and jewelry to watercolors and pottery. The free event includes a Corner Market with imported items and fair food, as well as live entertainment. The Paine’s gardens are also open for free.
• July 15: American Platinum - Free Tuesday Night Concert. Gates open at 5:30 p.m. at Leach Amphitheater, 303 Ceape Ave. Includes family entertainment, bounce houses and food trucks. Admission is free.
• July 17: Big Bad Voodoo Daddy at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include Cigar Store Indians and Fox Menagerie. Standing-room-only VIP tickets are $30; general admission is $10 before 7 p.m. and $20 after 7 p.m.
• July 21-27: EAA AirVenture Oshkosh 2025. EAA AirVenture Oshkosh will run July 21-27 at Wittman Regional Airport, 525 W. 20th Ave. It’s the world’s largest annual gathering of aviation fans, with people visiting from more than 90 countries. Day and night air shows, static displays, presentations, demonstrations and more are featured. Additional information, including advance ticket and camping purchase, is available at www.EAA.org/airventure, or call 800-JOIN-EAA (800-564-6322).
• July 30-Aug. 3: Winnebago County Fair. Held at Sunnyview Expo Center, 500 E. County Road Y. Barns open at 8 a.m. daily; gate charge begins at 9 a.m. daily; expo building opens at 9 a.m. daily; and family and kids’ entertainment begins by 11 a.m. daily. Midway/carnival rides run 4-10:30 p.m. Wednesday-Thursday; 1-10:30 p.m. Friday (closed 4-5 p.m. for a safety check); noon-10:30 p.m. Saturday (closed 4-5 p.m. for a safety check); and noon-4 p.m. Sunday (fair closes at 4 p.m.). Daily tickets are $12 in advance or $15 at the gate. More details: winnebagocountyfaironline.com.
• July 31: Vic Ferrari at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include Shining Star and Rose Canyon Band. Standing-room-only VIP is $20; general admission is $5 for fans in line by 6 p.m., $10 before 7 p.m. and $15 after 7 p.m.

August: XRoads41, Waterfest & Jazz Festival

• Aug. 7: Steely Dane at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include The Producers and Twistin’ Egyptians. Standing-room-only VIP is $25; general admission is $10 for fans in line by 6 p.m., $15 before 7 p.m. and $20 after 7 p.m.
• Aug. 7-9: XRoads41 music festival. Held at Ford Festival Park, 4125 S. Washburn St. Artists include Cody Johnson, Kane Brown, Parker McCollum, Jessie Murph, Nelly, Koe Wetzel, Ian Munsick, Rodney Atkins, The Castellows and more. Single-day tickets, three-day tickets and campsites are on sale now. More info: xroads41.com.
• Aug. 14: Loverboy at Waterfest. Gates open at 5:45 p.m. at Leach Amphitheater, 303 Ceape Ave. Openers include Mt. Olive and another act to be announced. Standing-room-only VIP is $50; general admission is $20.
• Aug. 19: Road Trip - Free Tuesday Night Concert. Gates open at 5:30 p.m. at Leach Amphitheater, 303 Ceape Ave. Includes family entertainment, bounce houses and food trucks. Admission is free.
• Aug. 23: Oshkosh Jazz Festival. Free event in downtown Oshkosh between the 100 and 700 blocks of North Main Street. Featured artists include The Son Reis Project at 1 p.m.; Eric Jacobson at 1:55 p.m.; B.D. Greer’s Divas at 3 p.m.; Jane Monheit at 5 p.m.; and headliner John Pizzarelli at 6 p.m.

Contact Brandon Reid at breid@gannett.com.