September is packed with family-friendly fairs and festivals across Toronto, the GTA and Southern Ontario! Celebrate the start of fall with traditional agricultural fairs, harvest festivals, cultural celebrations, street festivals and plenty of live entertainment. Families can enjoy midway rides, delicious food, kids’ activities, music, local vendors and more. Check back often—we’ll continue adding great September events as we find them!
Family Fairs & Festivals in September
GTA and Southern Ontario
Toronto Dragon Festival
Sep 4
to Sep 6, 2026
Nathan Phillips Square
Toronto, get ready for an unforgettable spectacle! The sixth annual Toronto Dragon Festival (TDF) returns to Nathan Phillips Square from Friday, August 29 to Sunday, August 31, igniting the city with a thrilling fusion of tradition, technology, and imagination. This year’s Festival promises mythical encounters and futuristic thrills. ...
Orillia Pirate Party
Sep 4
to Sep 6, 2026
Port of Orillia
Prepare to batten down the hatches — the Pirates of the Orillian Sea are setting their course for Orillia’s Downtown Waterfront! Word on the wind is they’ll make landfall just in time for Labour Day weekend, bringing a treasure chest full of swashbuckling fun, live entertainment, and high-seas ...
Toronto International BuskerFest for Epilepsy
Sep 4
to Sep 7, 2026
Woodbine Beach Park
It’s spontaneous, it’s outrageous; it’s fun, funny, and fabulous – there is something for everyone at the Toronto International BuskerFest for Epilepsy. For four exhilarating days, the festival showcases an array of mind-boggling circus acts, daring acrobatics, mesmerizing magic shows, hilarious comedy performances, and much more. In addition ...
Bark In The Park TO
Sep 4
to Sep 7, 2026
Woodbine Beach Park
Join in the fun at Bark in the Park TO, a four-day event dedicated to dogs and dog lovers! This unique festival is packed with fun activities, exciting performances, and pet-centric vendors, all set against the scenic backdrop of Woodbine Park. Expect interactive play areas, special photo ops, ...
Carnival Barrie
Sep 5
to Sep 6, 2026
Will Dwyer Park
Barrie’s Most Vibrant Latin Festival Returns September 5-6, 2026! In the rich tapestry of Latin American traditions, from the rhythmic music to the tantalizing cuisine. Every moment is a celebration of culture. Experience two days of music, food, dance, and culture at the Barrie waterfront.
Egyptian Coptic Festival
Sep 5
to Sep 6, 2026
Mississauga Celebration Square
Established in 2018, the Egyptian Coptic Festival is the 1st event showcasing Canadians from Egyptian Coptic origin in North America. You will have the opportunity to connect with more than 40 local businesses and thousands of attendees who are expected to attend the event over 2 days. You ...
Uxbridge Fall Fair
Sep 11
to Sep 13, 2026
Elgin Park
We’re thrilled to have you joining us for another year of fun, food, and fantastic activities. The focus of this year’s Uxbridge Fair is upon crops, crafts and traditional farm animals. Without these areas of agriculture our society would not exist. Highlights: Midway Tractor Pull Demolition Derby 4H Lawn ...
Georgetown Fall Fair
Sep 11
to Sep 13, 2026
1 Park Ave in Georgetown
The Georgetown Fall Fair is back for 2026! Visit the fair for live music, Battle of the Bands, Beer tent, Demolition Derby, Truck Pull, Agricultural Education Tent, Family Friendly Midway, The Ultimutts Hollywoof Stars Show, Petting Zoo, Free Children’s Games and Activities, Entertainment, Homecraft Exhibits, local vendors and ...
Kerrfest Kids
Sep 11
to Sep 13, 2026
Westwood Park
Celebrate the start of fall at Kerrfest & Kerrfest Kids, returning to Westwood Park in Oakville for its 10th anniversary! This popular three-day community festival brings together live music, great food, local vendors, an artisan market and plenty of family-friendly fun. Friday and Saturday feature an impressive lineup ...
Philippine Festival Mississauga
Sep 11
to Sep 13, 2026
Mississauga Celebration Square
Experience the vibrant spirit of Filipino heritage at PhilFest Sauga, a lively 3-day fiesta filled with joy, dance, and delicious traditional cuisine. Celebrate community, culture and connection with us. Come with your smile, move to the rhythm and indulge in unforgettable flavours! You’ll be glad you came!
Tim Hortons Southside Shuffle Blues & Jazz Festival
Sep 11
to Sep 13, 2026
Port Credit Memorial Park
The 28th Annual Tim Hortons Southside Shuffle, a non-profit, award-winning blues and jazz festival, takes place September 11-12-13 2026, in the village of Port Credit and Port Credit Memorial Park, Mississauga, Ontario. The three-day event features two free stages, one ticketed stage, and a free Saturday afternoon street ...
Taste of The Kingsway 2026
Sep 11
to Sep 13, 2026
Bloor Street West between Montgomery Rd and Prince Edward Dr
Taste of The Kingsway returns September 11 – 13, 2026, bringing three unforgettable days of food, entertainment, shopping, and family fun to South Etobicoke. Presented by Mantella Corporation, the neighbourhood’s largest annual street festival transforms Bloor Street West from Prince Edward Drive to Montgomery Street into a celebration ...
World of Jazz Festival: Live Jazz and Paint Night
Sep 11
to Sep 11, 2026
Peel Art Gallery Museum and Archives
Enjoy an inspiring evening of live jazz and creativity with the Duncan Wilson Trio. Tour Abstract Art in Canada, then create an abstract painting guided by a PAMA educator. No experience required. Part of B-Jazzed’s World of Jazz Festival.
The Cabbagetown Festival
Sep 12
to Sep 13, 2026
Cabbagetown
The Cabbagetown Festival is more than just an event; it’s a celebration of our community’s spirit, diversity, and history. Whether you’re here for the mouthwatering food, the eclectic shopping, the energetic performances, or simply to soak in the atmosphere, we can’t wait to see you in September. So, ...
Markham-Milliken Children’s Festival
Sep 12
to Sep 12, 2026
Aaniin Community Centre Park
Join us on Saturday, September 12, 2026 from 10 AM to 6:30 PM outside of Aaniin Community Centre – 5665 14th Ave(External link) for this year’s Markham-Milliken Children’s Festival (MMCF), presented by Tim Hortons. There are a variety of fun and free activities and live entertainment for the ...
Oro World’s Fair
Sep 18
to Sep 19, 2026
Oro-Medonte Fairgrounds
The Oro Agricultural Society is a group of dedicated volunteers working to promote an understanding of the agricultural heritage of Oro-Medonte, as well as providing opportunities for recognition of the talents and skills of members of our local communities, through participation in the Oro World’s Fair. Highlights include: ...
Bloor West Village Toronto Ukrainian Festival
Sep 18
to Sep 20, 2026
Bloor West Village
The Bloor West Village Toronto Ukrainian Festival welcomes you to come and enjoy everything the Ukrainian culture has to offer. Discover Ukrainian culture in Canada and share the Ukrainian spirit at North America’s largest Ukrainian Street Festival.
Cultural Festival 2026
Sep 18
to Sep 20, 2026
The ROC
Celebrate the cultures, traditions and stories that make Georgina unique at the Town of Georgina Cultural Festival, taking place September 18–20! This three-day, family-friendly celebration features a different theme and experience each day. Kick off the weekend Friday evening at The ROC with music, family activities and a ...
Beeton Fall FAir
Sep 18
to Sep 20, 2026
Beeton Fairgrounds
Celebrate 170 years of fall fair tradition at the Beeton Fall Fair, September 18–20, 2026! One of Canada’s oldest agricultural fairs, this popular community event offers three days of family fun, entertainment and classic country fair experiences. Enjoy unlimited midway rides and amusements, agricultural and 4-H shows, homecraft ...
Roncesvalles Polish Festival
Sep 19
to Sep 20, 2026
Roncesvalle Village
Toronto’s Polish street festival returns for its 20th anniversary, celebrating food, music, and culture in the heart of Roncesvalles. Come celebrate Roncesvalles Village and the unique heritage of this neighbourhood at the Roncesvalles Polish Festival. Returning September 19 and 20, 2026, this milestone 20th edition builds on the ...
Harvest Fest
Sep 19
to Sep 19, 2026
Clinton Harvest Fest
Harvest Fest is coming to Clinton on September 19! Planning is underway for another amazing day. Featuring: Vendor market Classic car show Live music on the OLG Stage Sensory-friendly zone Rock climbing Bouncy castles Pony ride carousel Giant inflatable slide Face painting Food trucks Live Entertainment
Milton Fall Fair
Sep 25
to Sep 27, 2026
Milton Fairgrounds
A favourite fall tradition since 1853, the Milton Fall Fair brings three days of family fun, agricultural heritage and classic fair excitement to the Milton Fairgrounds! Explore livestock shows and agricultural displays, browse homecraft exhibits and competitions, enjoy live entertainment and tasty fair food, and take a spin ...
The Great Northern Exhibition
Sep 25
to Sep 27, 2026
GNE Fairgrounds
Get ready for a weekend of classic fall fair fun at the Great Northern Exhibition (GNE)! This long-running agricultural fair returns to Clearview Township September 25–27 with the 2026 theme “Country Roots and Cowboy Boots.” Bring the whole family to enjoy midway rides and games, farm animals and ...
Arts of the Middle East Festival
Sep 25
to Sep 26, 2026
Mississauga Celebration Square
The Arts of the Middle East Festival brings people together to celebrate the rich culture, vibrant traditions, and incredible flavours of the Middle East. This year, join us for unforgettable performances, cultural experiences, and delicious cuisine that highlight the beauty and diversity of the region. Step into a ...
Fall Celtic Festival
Sep 26
to Sep 27, 2026
Toronto Rock Athletic Centre
Celebrate Celtic music, dance and culture at the Oakville Fall Celtic Festival, a free two-day festival for all ages! Taking place September 26 & 27, the festival brings Celtic traditions to life with live music, pipe bands, Irish and Highland dancing, cultural performances, food and plenty of family ...
The Word on the Street 2026
Sep 26
to Sep 27, 2026
David Pecaut Square
The Word On The Street’s 37th Annual Festival returns to its iconic fall weekend, September 26th and 27th, at David Pecaut Square. The festival will feature over 100 exhibitors and six stages of programming for book-lovers of all ages. Spend the weekend meandering through the vibrant marketplace, where ...
