May is the perfect month to get out, explore, and take in the season of full bloom. From floral festivals and fashion-forward experiences to all the Mother’s Day celebrations, there are plenty of ways to find moments of joy this month, and here are a few we are excited to join in on.
NOTL in Bloom Festival
Celebrate Mother’s Day Weekend in Niagara-on-the-Lake this year! The town will be in full bloom as the NOTL In Bloom Festival returns, transforming the town into a vibrant celebration of flowers, food, wine, and community. With stunning floral displays, charming streets, and special events throughout the weekend, it’s the perfect excuse to plan a spring day trip—or a full weekend escape—in one of Niagara’s prettiest destinations.
Fashion Art Toronto
Pink Pearl We Step Together Newmarket
Pink Pearl Canada is bringing We Step Together to Newmarket on Sunday, May 24th. It’s a meaningful community walk in support of young women facing cancer. This event invites participants to come together, raise awareness, and fundraise for Pink Pearl’s free support programs, which help young women feel less alone throughout their cancer experience. Whether walking as an individual, with friends, or as part of a team, every step helps create connection, hope, and practical support for those who need it most.
Spring Market Sip ‘n’ Shop at The Kimpton Saint George
The Spring Market Sip ’N’ Shop is taking place at the Kimpton Saint George Hotel in Toronto on Saturday, May 3, 2025, from 11 a.m. to 4 p.m. Guests can browse a curated mix of luxe local vendors featuring candles, pet accessories, sustainable goods, vegan cookies, plantable greeting cards, chocolates, flowers, perfume, ceramics, skincare, jewelry, and more. The event also includes live music by Jesse Maxwell, plus dog-friendly treats and slushies for furry friends.
The Art of the Pivot
In May, Art of the Pivot with Shantelle Bisson is happening at the Kimpton Saint George Hotel in Toronto on Sunday, May 3, 2026, from 11 a.m. to 1 p.m. Hosted by best-selling author and speaker Shantelle Bisson, the event features an inspiring panel conversation on reinvention, resilience, and turning life’s challenges into new opportunities. Guests will hear from local women entrepreneurs, including Jordana H. Goldlist and Emily O’Brien, with the conversation moderated by Taylor Buckley of the Golden Hour Collective. Proceeds support Elizabeth Fry Toronto, which works with women and gender-diverse people who are, or may be, at risk of being in conflict with the law.
motionball’s Marathon of Sport Toronto in Support of Special Olympics Canada
Canada’s largest sporting event, motionball in support of the Special Olympics Canada Foundation, is back on May 23rd at the University of Toronto’s Varsity Stadium. Everyone is welcome to sign up and join us on the field for the 2026 motionball Marathon of Sport Toronto—a full day of inclusive sports where participants of all abilities come together to compete, connect, and raise funds for an incredible cause. On event day, your team will be paired with 1-2 local Special Olympics athletes who will compete alongside you throughout the day. Together, you’ll take part in a variety of sports and activities, including Soccer, Football, Basketball, Ultimate Giant pong, Benchball, and more.
Mother’s Day High Tea at the Castle 2026
Casa Loma Experiences is offering a special Mother’s Day High Tea at the Castle on Sunday, May 10, 2026. Guests can enjoy an elegant afternoon tea inside Toronto’s iconic castle, featuring premium teas, scones, gourmet pastries, and tea sandwiches in a historic Edwardian-inspired setting. The reservation also includes access to tour Casa Loma, making it a memorable Mother’s Day outing that combines food, history, and a beautiful castle experience.
Mother’s Day at Elora Mills
Elora Mill Hotel & Spa is celebrating the season with special events and experiences in the village of Elora. Highlights include Mother’s Day dining from May 7 to 14, with a three-course lunch prix fixe and a four-course evening tasting menu, as well as Elora’s Plein Air Festival on May 17, a four-day art competition that welcomes artists and visitors to experience the charm of Elora, Fergus, the river gorges, and the surrounding Grand River landscape. It’s a beautiful spring getaway for dining, art, nature, and small-town charm.
Afternoon Tea at Overlea
Spend the afternoon celebrating Mom at Afternoon Tea at The Overlea in The Postmark Hotel in Newmarket. Reservations are welcomed between 1:00 – 4:00 p.m.. It’s simly a lovely way to celebrate Mom.
Pop-up flower market and Sunday Mother’s Day Brunch at The Broadview
On Sunday, May 10th, The Rooftop will treat moms to a complimentary glass of prosecco and dessert, alongside live music from the Stuart Brignell Organ Trio from 6 to 9 p.m.
Sunday Brunch Sessions at Cassette
Cassette’s signature Sunday Brunch Sessions, from 10 a.m. to 3 p.m., will feature live music, family-style mimosas, and $10 espresso martinis, creating an energetic yet intimate setting.
