Here is our round-up of fun things to do in Toronto this weekend, September 25th to September 28th, 2025.
Things to do in the GTA
Your go-to guide for discovering what’s happening across Toronto and the Greater Toronto Area.
From weekend plans and free activities to seasonal guides, date ideas, and curated experiences
One of the biggest Halloween events in North America, Pumpkins After Dark, returns this Fall to the Country Heritage Park from September 27th to November 1st (just an hour drive from Toronto)
Dress for Success Toronto will host its annual signature fundraising event, Beyond the Suit, on Wednesday, October 8th, 2025, at CIBC Square (81 Bay Street, Toronto). This inspiring evening brings together community leaders, professionals, and supporters to celebrate women and raise vital funds for programs that help women achieve growth and economic independence.
Toronto welcomes its first-ever Water/Fall Festival at the beautiful Toronto’s waterfront providing two action-packed weekends of arts, fun, creativity, and entertainment on September 27th, 28th and October 4th and October 5th from Queens Quay, from Bathurst St. to Bay St.
On September 30th, Toronto’s iconic Caribbean hotspot, The Real Jerk, is turning up the heat with more than just bold island flavours. Guests are invited to experience “Tasting of the Greats”, a premier rum-tasting event at their home location, 842 Gerrard St. E, Toronto.
This weekend, the Common Ground Dance Festival returns to Toronto’s Lee Lifeson Art Park, closing out the summer season in style with three days of dance, workshops, and community celebrations from September 18th to 20th.
This weekend, Canada’s largest vintage fashion event, the Toronto Vintage Show, returns to the grand Exhibition Place from September 20th to 21st, showcasing the very best vintage finds from over 130 vendors and will spotlight the most iconic eras in fashion history.
Taste of Cooksville 2025, one of the largest festivals in Mississauga, returns this weekend, providing two full days of global flavours, food, and live entertainment on September 20th and 21st in Mississauga.
Here is our round-up of fun things to do in Toronto this weekend, September 18th to September 21st, 2025.