Niagara Grape & Wine Festival: Niagara Grape & Wine Festival is a staple of the Niagara community, celebrating Niagara’s finest VQA wines, culinary creations, and Canadian entertainment for over 70 years. Drawing over 150,000 visitors each year, the Niagara Grape & Wine Festival is now the largest and oldest wine festival in Canada and has become embedded in the hearts and memories of Niagara natives and travelers across the globe. https://niagarawinefestival.com/

Multicultural Council of Windsor & Essex County – Carrousel of Nations: The award-winning Carrousel of the Nations is one of Ontario’s largest and longest-running multicultural festivals, celebrating the rich diversity of Windsor and Essex County. Over two weekends each June, Cultural Villages across the region welcome visitors to experience authentic cuisine, vibrant music & dance, traditional attire and cultural experiences from around the world, all with free admission. Welcoming hundreds of thousands of guests each year, Carrousel is a unique celebration of cultural heritage, community, and hospitality. Celebrating more than 50 years of cultural diversity, Carrousel of the Nations offers a unique opportunity to travel the world without leaving the region of Windsor & Essex County. www.carrouselofnations.ca

Stonebridge Wasaga Beach Blues, celebrating its 14th anniversary, is an international, award-winning music event featuring three days of top entertainment on two main stages, welcoming thousands of music fans each year. On the weekend of September 18, 19, and 20th come and experience an evening, day, or full weekend of top musical talent, with food trucks, vendors and beverages sold at the Beer Garden. For the BEST deal come for a weekend and enjoy the world’s longest freshwater beach while you’re here! www.wasagabeachblues.com

Toronto Burlesque Festival: The Toronto Burlesque Festival invites you into a world beyond the ordinary. Showcasing four different nights of dazzling, dreamlike entertainment at the iconic Buddies and Bad Times Theatre. The festival includes a VIP cocktail reception, burlesque classes, vendors marketplace, Sunday high-tea brunch and an exclusive Legend and Learn talk series. Whether you’re a seasoned burlesque aficionado or a first-time attendee, TBF offers a transportive journey through world-class burlesque, cabaret, and drag, featuring artists from Toronto, across Canada, and around the globe. https://www.torontoburlesquefestival.ca

Niagara Falls Winter Festival of Lights: From November 14, 2026 to January 10, 2027 the most enchanting of Niagara Falls attractions, the annual Winter Festival of Lights is Canada’s largest FREE outdoor light festival. Experience the spectacular displays with millions of lights and larger than life displays across the tourism districts. https://wfol.com/

The Canadian National Exhibition (CNE) is Canada’s largest community event and one of the top ten agricultural fairs in North America. Founded in 1879 as the Toronto Industrial Exhibition, the CNE is a not-for-profit organization that has enjoyed a distinguished history as a showcase of the nation. The CNE continues to be one of Ontario’s great annual traditions and an event that offers substantial entertainment value for money. Taking place over the 18 days leading up to and including Labour Day, it is affectionately embraced as an end-of-summer ritual by more than 1.4 million visitors annually, visitors who reflect the rich diversity of Toronto and the region. www.theex.com

Kingstonlicious: Kingstonlicious is Kingston’s premier prix fixe culinary celebration, held annually in February and March across 40+ restaurants, cafés, breweries, and the Memorial Centre Farmers' Market. Each seasonally inspired edition showcases the city’s vibrant food scene through curated menus, immersive dining experiences, and a spirit of community connection. Along with mouthwatering prix fixe offerings, Kingstonlicious features signature events hosted by local chefs and special guest collaborators—from winemakers and brewers to chefs and musicians—who come together to craft one-of-a-kind culinary moments. Whether you're a passionate foodie, a casual diner, or a visitor discovering the city’s historic charm, Kingstonlicious invites you to taste your way through the flavours that define Kingston as one of Ontario’s top culinary destinations. kingstonlicious.ca

Peterborough Musicfest: Canada’s Longest-Running Free Admission Music Festival. Set against the backdrop of scenic Del Crary Park, Peterborough Musicfest brings the community together every summer for award-winning, family-friendly concerts featuring top Canadian and international acts alongside local talent. Running from late June to mid-August, the festival offers 16 nights of free music by the lake—making it a must-visit destination for music lovers of all ages. ptbomusicfest.ca