Several tasty events happening in Windsor-Essex this weekend, including the Caboto Club’s Grape Fest to the Teutonia Club’s Oktoberfest. Here’s a look at events from Sept. 17-20, 2026. Caboto Club Grape Fest Friday September 18 to Saturday September 19 Caboto Club’s Grape Fest 2026 brings the community together for a weekend celebrating Italian heritage, great food, wine, live music and the traditions that have been shared across generations. Come hungry! Enjoy Caboto favourites including fresh pasta, BBQ specialties, wood-fired pizza, Italian crostoli, Sicilian cannoli and more. Pair your meal with a selection of Italian wines or grab a cold beverage in the Beer Garden. And of course, no Grape Fest would be complete without our signature Grape Stomping and Spaghetti Eating Competitions, happening throughout the weekend! Grape Fest is a licensed 19+ event. A portion of Grape Fest proceeds supports the Giovanni Caboto Club Scholarship Fund, helping local students pursue their educational goals. Teutonia Oktoberfest Saturday September 19 5:00 pm The Teutonia Club Oktoberfest is Windsor’s oldest and original Oktoberfest celebration! Join us on Sept. 19th for authentic Food, Beverage, Music, Games, Live Performances, and a live band, all to be shared with your friends and family in our community! With over 50 years of Oktoberfest celebrations and counting, hundreds of thousands of Windsorites have experienced the Teutonia Club, a staple of the community. Scarehouse Windsor Haunted Experiences Friday September 11 to Saturday October 31 Scarehouse Windsor is back for another season, and it’s more haunting than ever! Stone and Sky Music & Presents: Coming Together – A Collaborative Arts-Based Reconciliation Celebration Monday September 14 to Sunday September 20 Come experience all the sights and sounds at the Stone and Sky Music & Art Series! All My Sons at Kordazone Theatre Thursday September 17 to Saturday September 19 In 1947, Arthur Miller exploded onto Broadway with his first major work, ALL MY SONS, winning both the New York Drama Critics’ Circle Award for Best New Play and the Tony Award® for Best Author. Bring-a-Friend Night! Thursday September 17 5:00 pm to 8:30 pm Bring-a-Friend Night at Art Windsor-Essex takes place Thursday, September 17 from 5–8:30 PM. Enjoy the gallery spaces and a self-guided art activity, with admission $10 for guests while AWE members get in free. Amherstburg Uncommon Festival Friday September 18 to Sunday September 20 Step into a world where steampunk meets magic. Gears, gadgets and enchantments abound at the extraordinary Amherstburg Uncommon Festival. Mean Girls Friday September 18 to Sunday September 20 Come Experience ‘Mean Girls’ based on the Paramount Pictures film! Death of a Salesman at the Bank Theatre Friday September 18 to Sunday September 20 The Bank Theatre presents - Death of a Salesman by Arthur Miller Oktoberfest at Walkerville Brewery Friday September 18 to Saturday September 19 Dust off your lederhosen, because Walkerville Brewery’s Oktoberfest celebration is back! Join us in our transformed ‘Bier Hall’ for all the Oktoberfest festivities! 9th Annual Klapa Concert Friday September 18 7:00 pm to 8:00 pm Experience authentic Dalmatian klapa singing (a cappella) with Croatia’s Klapa Bošket and Windsor’s Klapa Kartolina. Seven Drunken Nights: The Story Of The Dubliners Friday September 18 7:30 pm Proudly celebrating its incredible 10th Anniversary Seven Drunken Nights - The Story of The Dubliners is back for 2026! Sauve’s Country Market Fall Vendors Market Saturday September 19 to Sunday September 20 Expect many different vendors from all across Windsor-Essex from local craft makers to perfectly crafted treats and much more! Erie Street GastroPub Block Party Saturday September 19 to Sunday September 20 5 Weekends of Music with Great Food, Patio and Drinks, extended patio and festival. Full details of schedule and entertainers. Lakeside Market Saturday September 19 8:00 am to 1:00 pm Don’t miss the Lakeside Market! Downtown Windsor Farmers’ Market Saturday September 19 9:00 am to 2:00 pm Discover fresh local produce, artisan foods, family fun, and community events at the Downtown Windsor Farmers’ Market. Festival of Hawks Saturday September 19 to Sunday September 20 Join experts from the Holiday Beach Migration Observatory for this amazing natural spectacle. Watch thousands of birds of prey flying overhead. Colchester Markets Saturday September 19 10:00 am to 3:00 pm Celebrate local makers, history, and community at the 6th annual Colchester Markets, a lively vendor event supporting the restoration of Colchester Schoolhouse #2. End of Summer Peche Island Guided Tours Saturday September 19 10:00 am to 1:00 pm Last chance to explore Peche Island this season with a guided tour! Museum Windsor Presents: Downtown Built Heritage Walking Tour Saturday September 19 11:00 am to 1:00 pm Explore and learn about a selection of downtown Windsor’s buildings that have withstood the test of time. Wolfhead Distillery Tour and Tasting Experience Saturday September 19 1:00 pm to 4:00 pm Get an exclusive behind-the-scenes look at our den, where we craft award-winning whisky, vodka, and gin. Teddy Bear Picnic Saturday September 19 6:00 pm Come out and join us on Saturday September 19 for a fun evening of activities and our last outdoor movie of the season. Live Music at Parkside Grille Saturday September 19 Experience summer nights the way they’re meant to be at Rochester Place. London Knights V.S. Windsor Spitfires – Home Opener Saturday September 19 7:05 pm Head on out to the WFCU Centre, for an exciting OHL Matchup as the Spitfires matchup against one of their rivals the London Knights at this Home Opener! Foreign Journey – The Best of Foreigner & Journey Saturday September 19 7:30 pm Prepare to be transported back to the golden age of arena rock! Danny Martinello LIVE Comedy At Tipsy Toucan Saturday September 197:30 pm to 9:00 pm Danny Martinello live at the Tipsy Toucan! Tecumseh Farmers Market Sunday September 20 9:00 am to 1:00 pm Discover fresh, locally grown produce, handmade goods, and unique treasures from our talented local vendors. Open Streets Windsor 2026 Sunday September 20 10:00 am to 2:00 pm Join us as Open Streets Windsor returns for its annual celebration of community, culture and wellness, this year with a new format featuring two distinct routes and seven vibrant community hubs throughout Windsor’s east end. Board Game Bazaar Sunday September 20 12:00 pm to 3:00 pm Sell games, buy games, swap games, at the board game bazaar! Come ready to shop or try and sell off some games you’re ready to part with. Leamington Raceway Horse Races Sunday September 20 1:00 pm Head out to the Leamington Raceway for a thrilling day filled with excitement and lots of fun!
