Featured Events in Windsor in May, 2025 (April Updated)

Information Source: WINDSOR ESSEX LEAMINGTON JERK FEST | eventbrite

Hollywood Zoo is bringing their 80's Hair Metal Tribute to The Cherry, Friday May 2nd. Relive the glory days of big hair, big shoulder pads and neon everything, everywhere as they take you on a nostalgic rock ride thru your favorite 80's hits! Information Source: The Cherry Rock Lounge | eventbrite

Hot Hiit with Hayley Come join us for an intense workout session with the amazing Hayley! Get ready to sweat and burn those calories in this high-energy Hiit class. Hayley will push you to your limits and help you achieve your fitness goals. This event is perfect for anyone looking to challenge themselves and have a great time doing it. Don't miss out on this opportunity to get fit and have fun! Information Source: Hayley | eventbrite

Welcome to the Symphonic Prog Rock event of the year! The 65 piece Thames Valley Festival Orchestra with conductor Stephen Ellery returns to Windsor Parish Church of St John the Baptist for an evening filled with the mesmerizing sounds of progressive rock music by the legendary composer and arranger, Dee Palmer. Immerse yourself in the intricate melodies and complex rhythms of the music of legendary prog rock bands such as Jethro Tull, Yes, Genesis, Pink Floyd and Queen via the amazing arrangements for a 65 piece symphony orchestra with rhythm section. The programme will feature full orchestral arrangements of perennial favourites from the 70s and 80s such as Follow You, Follow Me (Genesis), Owner of a Lonely Heart and Roundabout (Yes), Another Brick in the Wall and Wish You were Here (Pink Floyd), Elegy and Aqualung (Jethro Tull), Tie Your Mother Down, Somebody to Love and We are the Champions (Queen) and much more. Information Source: Thames Valley Festival Orchestra | eventbrite

Whether through melodies or lyrics, music transforms stories into immersive, emotional experiences. The Windsor Classic Chorale invites you to experience the awesome power of music to bring stories to life by enhancing emotions and setting the mood, drawing listeners deeper into the narrative. There will be a reception immediately following the concert. Information Source: Windsor Classic Chorale | eventbrite

Sweetwood Mac is the “must see” Fleetwood Mac / Stevie Nicks Tribute band based out of London Ontario. Voted Top Tribute Artist (FCLMA) 2024 Top Tribute Artist Nominee (FCLMA) 2022, 2023, 2024, 2025 Information Source: The Cherry Rock Lounge | eventbrite

Toss Bags. Raise Funds. Have Fun! Join us for the 3rd Annual Tailgate Takeout Charity Cornhole Tournament ! Hosted at Walkerville Brewery , this exciting event supports the Canadian Mental Health Association - Windsor Essex County (CMHA) - helping to make a real impact in our community. What’s in Store? Cornhole Tournament – Run by Windsor Cornhole , featuring a single elimination swap-style format (randomized partners for round robin games…play with pros, friends, and fellow cornhole enthusiasts!) Cash Bar – Enjoy local craft brews from Walkerville Brewery and other local libations Eats by local vendors Live music Raffles + 50/50 Draws **CASH PRIZES FOR TOP 3 TEAMS!** Tournament Registration $35 per person Open to all skill levels Don't miss out on this incredible day of friendly competition, community spirit, and giving back! Sign up now and secure your spot! Information Source: Walkerville Brewery x Tailgate Takeout | eventbrite

✨️ One Night Only! ✨️ Join your hosts Angelina Lepore & Venom Von Snaps and their talented cast as they celebrate their birthdays through homages in their likeness! You can expect performances that are fun and flirty, sexy and sultry by the talented Blossom Kink (@theblossomdrag), Bellvyra (@bellevyra), Cecil Cecropia (@cecil.cecropia), Miss Mercury Retrograde (@miss.mercury.retrograde), Hudson Bae (@kinghudsonbae), Remedy (@remedy.cures), and the birthday girls Angelina Lepore (@theangelinalepore) and Venom Von Snaps (@venomvonsnaps)! Tickets: Preorder $15 + fee online or $20 at the door Seating is limited, reserve your seat now! Questions? Reach out to thehouseofcures@gmail.com Information Source: The House of Cures | eventbrite