From meaningful community initiatives to luxury fashion and spine-tingling Halloween experiences, October is bringing plenty to look forward to. Whether you’re looking to support an important cause, discover a new shopping destination or embrace spooky season, here are three events worth adding to your calendar.
Pink Pearl We Step Together
Photo provided by Pink Pearl Canada
Grab your friends, lace up your walking shoes and get ready to make a difference on October 18th! Pink Pearl Canada’s We Step Together returns to Niagara-on-the-Lake for a unique passport-style walk supporting young women facing cancer. Forget your traditional 5K! This experience takes participants along a curated route filled with delicious local bites, sweet sips and charming stops, all while raising awareness and funds for Pink Pearl Canada’s free support programs. Register individually or gather your favourite people for a team, and enjoy a beautiful fall day for an even more beautiful cause. Can’t make it in person? Join the fun from anywhere with their virtual Walk in a Box!
Harry Rosen’s new Flagship opens in Toronto
Photo provided by Jaime Eisen Communications
Luxury menswear has a stunning new home in Toronto! On September 22, Harry Rosen opened its new flagship at 153 Cumberland Street in the heart of Yorkville. Spanning nearly 38,000 square feet across three storeys, the space brings together wardrobe essentials, contemporary fashion and renowned designer names including ZEGNA, TOM FORD, Giorgio Armani and more. Inspired by the Grand Tour of Italy, the beautifully designed flagship features an expanded made-to-measure experience, an immersive Creed fragrance destination and an outdoor patio overlooking the Village of Yorkville Park. More than just a place to shop, it’s a destination for discovering personal style, experiencing exceptional tailoring and enjoying a little luxury.
Intimissimi and Calzedonia to open at CF Sherway Gardens
Photo provided by Oniverse
Two of Italy’s most recognized fashion labels are officially making their Canadian debut. Intimissimi and Calzedonia are set to open their first Canadian boutiques at CF Sherway Gardens this October. Their arrival in Canada is led by ILT Group Inc., international retail partner for Oniverse, the Italian parent company behind both brands. Both brands are known for their meticulous approach to fabric and craftsmanship, from Calzedonia’s fashion-forward legwear and swimwear to Intimissimi’s signature silk and lace. Their arrival at CF Sherway Gardens marks the first step in a broader Canadian expansion, giving shoppers the opportunity to experience both brands’ quality and design firsthand.
Motionball x Daniel Nestor Pickleball Social
Photo provided by Duet Public Relations
Join the motionball team for an afternoon of friendly competition at the Daniel Nestor Pickleball Social on Friday, October 16 at Fairground Racket Club – Leaside! Hosted by Canadian tennis legend Daniel Nestor and motionball co-founder Paul Etherington, teams of 4-6 players will hit the pickleball courts and play alongside our Special Olympics athletes in competitive and recreational brackets. The tournament will kick off at 3:30 p.m. with activations from Toronto and National brand partners and motionball-themed activities running throughout the day. Participants are welcome to join the on-site social afterward for snacks and beverages to celebrate a full afternoon of games, connections, and fundraising.
Legends of Horror Casa Loma
Photo provided by Duet PR
This October, the grounds of Casa Loma will once again be transformed into Legends of Horror, an immersive Halloween theatrical experience celebrating its 10th anniversary. From October 3 through October 31, 2026, guests will wind through two kilometres of interactive sets across the iconic castle’s lower gardens and haunted underground tunnels. “Legends of Horror is Toronto’s most comprehensive Halloween night-out experience, combining world-class immersive theatre, elevated food and cocktails, and live entertainment all within Casa Loma’s iconic setting,” said Nick Di Donato, president & CEO, Liberty Entertainment Group. “It’s thrilling to see the castle transform into this kind of theatrical space where every corner becomes a scene, inviting audiences to experience Casa Loma in a way they never have before.” Tickets start at $35 and are now available at legendsofhorror.ca. For more information, visit casaloma.ca and follow on Instagram @casalomatoronto.
Rise at The Ritz with Hina Khan
Photo provided by Duet PR
Rise at the Ritz is an exclusive full-day experience designed to help you unlock your rich identity and rise to the next level of your personal, professional, and financial life. Hosted by renowned Identity-Led Transformation Coach Hina Khan on October 24th, this transformative event explores how your current results are a reflection of your inner image, and how to shift that image to align your thoughts, feelings, and actions with your deepest goals. Throughout the day, you’ll experience a powerful blend of mindset coaching, guided exercises, community connection, and elegant touches that include a red carpet welcome, curated marketplace, and a welcome drink – all set within the luxury of The Ritz-Carlton Toronto. A portion of the event’s proceeds will be donated to Baby Love, Canada’s largest diaper donation program dedicated to ending diaper need so every baby can thrive.
