A list of 30+ fun events in the Kitchener-Waterloo Region during May, including fun family activities, festivals, live music, adult events and more!
Mother’s Day is coming up and you don’t want to be caught empty-handed! But don’t worry, there are tons of ways to make your ... »
Victoria day weekend events & activities in and around Kitchener-Waterloo Region including free fun family & kids’ activities, live music, theatre & performing arts, sports and exhibitions. »
Main Street, Downtown Cambridge
May 31, 2026 To September 27, 2026
Free
Enjoy great musical performances on Main Street on last Sundays from June to October. »
Registry Theatre, 122 Frederick Street, Kitchener
May 31, 2026
Pay-What-You-Can at the Door
Join Green Gables Ukuleles & Friends for their fifth community sing-a-long/play-a-long to raise funds for the Registry Theatre! »
Portuguese Club Of Cambridge, 870 Townline Rd, Cambridge
May 30, 2026
30
Journey of the Monarchs Summit is a not-for-profit, community-driven event designed for professionals, entrepreneurs, and newcomers to build meaningful connections and grow. Featuring 6 speakers, a panel discussion, ... »
Maureen Forrester Recital Hall, 75 University Ave W., Waterloo
May 30, 2026
$10 - $40
Our Gala finale for 2025 2026 – a mash-up exploration of three “eccentric” composers, their incredible influence, in their time, in the world today and upon each other. Originals, re-imaginations…. ... »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 30, 2026
$22.57
Join us for a guided Gardens & Foraging Walk presented by Bob Wildfong through the heritage gardens and surrounding natural areas of Doon Heritage Village. Discover what’s ... »
The Jazz Room, 59 King St. North, Waterloo
May 30, 2026
$20.00 - $32.00
Winner of the International B-Jazz Competition and Winner of Best Solist Prize. The Philippe Lemm Trio is continually proving to be one of the most exciting and ... »
Chudleigh’s Entertainment Farm, 9528 Regional Road 25, Halton Hills, Halton
May 29, 2026 To October 31, 2026
(905) 878-9547
$13 - $14.50
Take a walk in the orchard garden, enjoy a wagon ride around the farm, stop by the playground and run on our haybales, visit friendly farm animals ... »
Various locations, Cambridge
May 29, 2026 To June 13, 2026
Free and ticketed events
Cambridge Pride Week celebrates community, diversity, and self expression with a lively lineup of events. From Pride Prom and screenings to drag bingo, brunches, and parties, the ... »
Waterloo Public Square, 75 King St S, Waterloo
May 29, 2026 To August 14, 2026
Free
Browse through a wide selection of handmade goods created by local artists, crafters, and makers while listening to live music in Waterloo Public Square »
Tapestry Hall, 74 Grand Avenue South, Cambridge
May 29, 2026
$45
Join the CSO for a new annual favorite: a night of music from the movies that make us laugh, cry, exalt heroes and decry villains accompanied by ... »
Fergus Sportsplex, 550 Belsyde AVE E, Fergus
May 29, 2026 To May 30, 2026
$8.92 to $97.31
Meadows Music Festival is one of the best premier music festivals in Ontario, Canada. In addition to the music, Meadows Festival offers an array of local vendors, ... »
Guelph Youth Music Centre, 75 Cardigan Street, Guelph
May 29, 2026
519-993-7591
$20 to $55 single & series tickets available
Cellist Katie Schlaikjer joins violinist Sadie Fields and Guelph Musicfest director/pianist Ken Gee as the new member of the Festival Trio, which has been performing since 2014. ... »
Centre In The Square, 101 Queen Street North, Kitchener
May 29, 2026
$57.50
Don't Be Late for this very important date. Pull up a chair to the most entertaining dance tea party in KW! »
Schneider Haus National Historic Site, 466 Queen Street South, Kitchener
May 29, 2026
$65 per day per child
Join us for this PD Day for a whacky wild art adventure! From painting to sculpting there’s something every budding artist will enjoy! »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 29, 2026
$70.46
Do you hear that? The Wild is calling! Join us in May at Ken Seiling Waterloo Region Museum for a roaring good time at PD Day Camp! »
The Jazz Room, 59 King St. North, Waterloo
May 29, 2026
$20 - $32
Caleb Khuu presents an electrifying night of jazz, blues, funk, and everything in between. Featuring an exceptional trio performing original music alongside fresh, masterful reinterpretations of beloved ... »
Castle Kilbride, 60 Snyder's Road West
May 29, 2026 To November 8, 2026
$5.25 - $8.25
A guided tour by costumed guide of the exhibits the Trip of 1936 and Vogue Voyages: Fashion on the High Seas Travel Clothes 1912 – 1939. Afterwards create a fabulous fascinator ... »
Uptown Waterloo, 35 King Street N, Waterloo
May 29, 2026 To May 31, 2026
5198974997
50
Back for its 2nd year, this unique experience combines the greatest magicians from around the globe along with professional comedians, actors and improv specialists chosen as tour ... »
Riverside Park, 49 King Street West, Cambridge
May 28, 2026 To May 31, 2026
Free
Get ready for an unforgettable weekend of fun, laughter, and family time at the Cambridge Kin Carnival 2026. Expect exciting activities, great food, and plenty of chances to ... »
Wilmot Recreation Complex, 1291 Nafziger Rd, Baden
May 24, 2026
$13 - $72
Baden Races is the annual road race in the Township of Wilmot out of the beautiful Wilmot Recreation Centre. »
The Registry Theatre, 122 Frederick Street, Kitchener
May 24, 2026
$40 + fees
Jontue’s soulful vocals will delight the audience with renditions of songs of the greatest jazz singers, and backed by the region’s premier big band. »
Registry Theatre, 122 Frederick Street, Kitchener
May 24, 2026
$40.00
Jontue’s soulful vocals will delight the audience with renditions of songs of the greatest jazz singers, and backed by the region’s premier big band. »
The Jazz Room, 59 King St. North, Waterloo
May 24, 2026
$20.00 - $32.00
The Tap Room Gang is a collaborative quartet that brings a fresh and interactive takes on classics and hidden gems from the 1920s and 30s hot jazz ... »
Dickson Centre Arena, 30 Park Hill Rd W, Cambridge
May 23, 2026
2267919897
$7-$25
Please join Whisker Wonderland Cat Show in Cambridge! Fun, Education and Shopping! FUN, Unique and extensive experience for all cat lovers! Door Prizes! Amazing Bid Items! Cat ... »
Dickson Centre Arena, 30 Park Hill Rd W, Cambridge
May 23, 2026
2267919897
$7 to $25
Join us at the Whisker Wonderland Cat Show in Cambridge for a unique, family-friendly celebration of all things feline! Enjoy a full day of fun with door ... »
The Aud, 400 East Ave., Kitchener
May 23, 2026
$23 - $80 (plus applicable fees)
Slamdemonium II returns Saturday, May 23 to the Dom Cardillo Arena at the Kitchener Auditorium for an unforgettable night of professional wrestling. »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 23, 2026
$22.57
Slow your steps, awaken your senses, and reconnect with the quiet wisdom of the woods. Forest Therapy Walk at Doon Heritage Village Step away from the noise ... »
Registry Theatre, 122 Frederick Street, Kitchener
May 23, 2026
$40.00
Music director Simon Wheeldon and the Hamilton based big band pack a punch with traditional and contemporary big band arrangements. »
Registry Theatre, 122 Frederick Street, Kitchener
May 23, 2026
$40.00
Robin and his specially assembled all-star big band deliver the seminal Miles Davis album Birth of the Cool. »
The Jazz Room, 59 King St. North, Waterloo
May 23, 2026
$20.00 - $32.00
GRAMMY NOMINATED & JUNO AWARD WINNING Cuban born/Toronto based saxophonist Luis Deniz, teams up with long time collaborators Adrean Farrugia, Roberto Occhipinti and Mark Kelso, to perform ... »
Bingemans Marshall Hall, 425 Bingemans Centre Dr, Kitchener
May 23, 2026
$5.50
The Waterloo Region Women’s Expo is a vibrant celebration of connection, creativity, and community. Bringing together inspiring speakers, local women-led businesses, and interactive experiences, it’s ... »
Guelph Youth Music Centre, 75 Cardigan Street, Guelph
May 22, 2026
519-993-7591
$20 to $55
Schmaltz & Pepper is a uniquely virtuosic and entertaining chamber ensemble performing original music inspired by Klezmer, Yiddish Swing, Jazz and Classical music. This groundbreaking ensemble features ... »
Castle Kilbride, 60 Snyder's Road West, Baden
May 22, 2026 To September 20, 2026
$22/p.p. + taxes and fees
Castle Kilbride's popular tea and tours inspired by the museum's special exhibit Vogue Voyages: Fashion from the High Seas 1912-1939. »
Marden Park, 7384 Marden Rd, Guelph
May 22, 2026 To May 28, 2026
$15.00 per student
The Waterloo Wellington Children’s Groundwater Festival is an annual week-long event that brings government, industry and educators together to teach children the importance of groundwater and ... »
Registry Theatre, 122 Frederick Street, Kitchener
May 22, 2026
$30.00
The Registry’s Karl Kessler and Andy Macpherson bring poets and musicians to the stage for a magical evening where poetry and music swirl together in the ... »
The Jazz Room, 59 King St. North, Waterloo
May 22, 2026
$20 - $32
Based in Montreal since 1984, Yves Léveillé is a celebrated pianist and composer renowned for bridging the gap between cerebral complexity and lyrical beauty. Over a career ... »
Guelph Youth Music Centre - Recital Hall, 75 Cardigan Street, Guelph
May 22, 2026 To June 19, 2026
Full Concert Series $90 - $240
It’s Guelph Musicfest’s 20th Anniversary! In celebration, this season features a dynamite lineup of great composers and superlative musicians, all designed to lift your spirits ... »
Cambridge Newfoundland Club, 1500 Dunbar Rd, Cambridge
May 21, 2026
5195904511
FREE
The ‘Spotlight on Seniors Health and Info Event’ is a FREE annual event focusing on providing information and connection with our local senior community members and their ... »
Atmosphere Cafe, 24 Carden St, Guelph
May 21, 2026
$ 29.99
Join Single in the City for Connection & Cocktails Singles Night in Guelph. An evening for singles to meet, mingle, and enjoy great conversation over drinks.—no ... »
St. Jacobs Country Playhouse, 40 Benjamin Rd, Waterloo
May 20, 2026 To June 7, 2026
$38 - $62
Put your sleuthing skills to the test as the best-selling crime novel of all time takes centre stage in this darkly foreboding and masterfully suspenseful thriller that ... »
New Dundee Community Centre, 1028 Queen Street, New Dundee
May 17, 2026
Free
Join us on Sunday, May 17th 2026 for an evening of spectacular fireworks, food, music, and community fun. »
Clovermead Honey Shop & Adventure Farm, 11302 Imperial Road, Aylmer
May 16, 2026 To November 1, 2026
519-773-5503
Season Pass $89.99; Daily Pass TBA
Connect with nature, create lasting memories and build family traditions. Come enjoy the family fun farm with your family! »
Plant Sale, 9042 Wellington Rd. 22, Hillsburgh
May 16, 2026
Free
This is the Hillsburgh Garden Club’s only fundraising event, featuring a wide selection of annuals, perennials, herbs, tomato plants, hanging baskets and more. Club members will ... »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 16, 2026
No registration required!
A selection of the flower and vegetable varieties found in the gardens of the Doon Heritage Village are available for purchase while supplies last. The plant sale ... »
The Jazz Room, 59 King St. North, Waterloo
May 16, 2026
$20.00 - $32.00
With six albums to their credit – Auguste, Sphère Réflexion, Bluesy Lunedi (finalist at ADISQ and JUNO in 2010), Homo Pugnax, Circum Continum and Exalta Calma (awarded ... »
THEMUSEUM, 10 King Street West, Kitchener
May 15, 2026
$20
Join Vixens and Tease for a sultry installment of burlesque! With extra special guest Neil E. Dee, a Canadian daredevil and expert sword swallower, featured in Ripley’... »
The Jazz Room, 59 King St. North, Waterloo
May 15, 2026
$20 - $32
Valérie Lacombe is a Montreal-based jazz drummer, bandleader, and composer whose work centers on original music for chordless quartet. Her debut album, State of Garden and ... »
Retro Remix, 64 Grand Ave. S., Cambridge
May 14, 2026
$159-199
Join us at the Retro Remix studio to transform a retro game controller into a unique shadow-boxed work of art. In this hands-on workshop, you’ll build ... »
Grey Silo Golf Course, 2001 University Avenue East, Waterloo
May 12, 2026
519-279-4669
Complimentary
Get ready for an unforgettable in-person event where luxury meets adventure. Dive into the world of high-end travel with exclusive experiences, top-notch destinations, and expert advice… all ... »
St. Jacobs Farmers' Market Station, 330 Farmers Market Road, Waterloo
May 10, 2026
$139.10
Celebrate Mother’s Day in style with a scenic train ride and a delightful high tea experience! Step aboard our heritage train and relax in the cozy ... »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 10, 2026
$31.53
Learn all there is to know about starting a garden! A hands-on overview of soil preparation, essential tools, methods of watering, fertilizing and preventing weeds. »
Castle Kilbride, 60 Snyder's Road West, Baden
May 10, 2026
$6.66 -$9.85
Children of all ages are invited to treat their mom to a 30-minute costumed guided tour of Castle Kilbride and the special exhibit The Trip of 1936. A ... »
Crowne Plaza Kitchener-Waterloo, 105 King St E, Kitchener
May 10, 2026
2269724226
$24 -$55
Celebrate Mom in style this Mother’s Day Join us for a delightful brunch experience at the Grand Ballroom, Crowne Plaza Kitchener-Waterloo—featuring a delicious buffet, warm ... »
Whistling Gardens Ltd., 698 Concession 3, Wilsonville
May 9, 2026 To October 12, 2026
519.443.5773
$8.95 to $16.80
If you haven't been to the Whistling Gardens before, plan a trip and see why Whistling Gardens is voted as one of Canada’s Best Botanical Gardens. »
The Kitchener Auditorium, 400 East Avenue, Kitchener
May 9, 2026
519-571-1418
$2 to free
Everyone is welcome at the KW Gem & Mineral Show & Sale. You will find rocks, minerals, gemstones, fossils, fluorescent specimens, beads, and gemstone jewelry. Activities for children. »
SydFIT Health Centre , 180 St Leger St, Kitchener
May 9, 2026
$35 - $50
12 Olympic style amateur bouts – 1 great night Join your Destiny Boxers for a full night of high impact, high energy amateur boxing matches, right here at SydFIT! Who ... »
St. Jacobs Farmers' Market Station, 330 Farmers Market Road, Waterloo
May 9, 2026
Mothers are free
Celebrate MOM aboard the Mother’s Day Heritage Hopper! Today only, mom rides FREE with the family!* Spend special time with Mom aboard our heritage train, where ... »
Kitchener Farmer's Market, 300 King St E, Kitchener
May 9, 2026
$45
Celebrate Mother's Day with something extra sweet! In this hands-on mini cake class, our budding chefs will bake, decorate, and personalize adorable mini cakes made with love ... »
Gaukel Block, Kitchener
May 9, 2026
Free to attend
Poyo Fest is a free fan-run celebration dedicated to everyone’s favourite pink hero! »
rare's Slit Barn, 1679 Blair Rd, Cambridge
May 9, 2026
Free
On Saturday, May 9, from 8:00 a.m. to noon, join us at rare's Slit Barn at 768 Blair Road for our annual Spring Plant Sale & EcoMarket! »
Centre In The Square, 101 Queen Street North, Kitchener
May 9, 2026
$31.50
Catch the hottest standups from Toronto’s world-class comedy scene for one night only, featuring comedians seen on Just For Laughs, Hulu, Crave, CBC & more! »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 9, 2026
$19.38
Visit Doon Heritage Village and meet some baby goats! Chance to interact with and learn about goats and environmentally friendly grazing. »
Ken Seiling Waterloo Region Museum, 10 Huron Road, Kitchener
May 9, 2026
$22.57
Join Region of Waterloo Forester Andrew Puchalski for an immersive guided walk through the beautiful woodlands surrounding Doon Heritage Village, located at the Ken Seiling Waterloo Region ... »
The Jazz Room, 59 King St. North, Waterloo
May 9, 2026
$20.00 - $32.00
The Gordon Sheard Trio is an exciting, dynamic contemporary jazz ensemble that has been stunning audiences with virtuosic performances grounded on strong original compositions for over fifteen ... »
HH - J.G. Hagey Hall of the Humanities, 200 University Avenue West, Waterloo
May 8, 2026 To May 10, 2026
$41.28
Don't miss this electrifying concert series featuring over 150 of Canada's most exciting young performers - backed by a full live band - as our incredible Senior & Junior ... »
Centre In The Square, 101 Queen Street North, Kitchener
May 8, 2026
$50.75 - $85.25
When Greek guitar virtuoso Pavlo teams up with powerhouse vocalist Daniel Emmet, an America’s Got Talent finalist, the result is a one-of-a-kind concert experience. Together, they ... »
Centre In The Square, 101 Queen Street North, Kitchener
May 8, 2026
$31.50
Big & Tall Comedy Tour is a high-energy stand-up showcase featuring a stacked lineup of touring comics, including CJ Erwin, Billy Squires, Jonny P, Tim Reaburn, and Curtis ... »
Registry Theatre, 122 Frederick Street, Kitchener
May 8, 2026
$30.00
Father and Son Duelling Pianos is a high-energy, narrative-driven musical production featuring Juno Award-winning pianist Eddie Bullen and his son, the multitalented Quincy Bullen. More than a ... »
The Jazz Room, 59 King St. North, Waterloo
May 8, 2026
$20 - $32
Top Pocket is a fusion band playing 100% original material written by 4 of the 5 band members. The bands fusion combines funk, rock, Latin and jazz/swing styles. »
The Donkey Sanctuary of Canada, 6981 Concession 4, Puslinch
May 3, 2026 To October 25, 2026
519 836-1697
$0 – $20
Come out and experience the DSC! »
Starling Children's Mental Health Centre, 285 Benjamin Road, Waterloo
May 3, 2026
(519) 623-9380 ext.1137
Free
Join us on Sunday May 3rd, as we lace up our shoes and walk for Children’s Mental Health at Starling’s (formerly Lutherwood) annual Steps for ... »
African Lion Safari, 1386 Cooper Road, Hamilton
May 2, 2026 To October 11, 2026
519-622-8144
$26.95 - $53.95
Canada's Original Safari Adventure - Get Closer Than You Ever Imagined to lions, giraffe, cheetah, rhinos and over 1,000 other exotic birds and animals! »
THEMUSEUM, 10 King Street West, Kitchener
May 2, 2026 To May 3, 2026
Early-bird tickets are now on sale
Immerse yourself in all things pop culture, sci-fi, comics, anime, visual art, digital technology, interactive tech-art, and more! »
Comic Book Stores, Canada
May 2, 2026
Free
Get a free comic and swag on Free Comic Book Day 2026 from your local comic shop. Free Comic Book Day is a single day – the first Saturday ... »
St. Jacobs Farmers' Market Station, 330 Farmers Market Road, Waterloo
May 2, 2026
$144.45
Step aboard our heritage train and take a journey through the picturesque countryside between St. Jacobs and Elmira, where cherry-inspired delights await. Settle into the cozy ambiance ... »
RIM Park, 2001 University Avenue East Waterloo
May 2, 2026
Free
Is it your time? If you\’ve ever thought about running for municipal office — even just a flicker of curiosity — this afternoon is for you. The Waterloo ... »
Brae Ridge Farm & Sanctuary, 7667 Maltby Rd E, Guelph
April 26, 2026 To September 27, 2026
2269244065
$60 per person
Alpaca Yoga! Escape to our enchanting farm and immerse yourself in a truly unique experience like no other. Picture this: You arrive at our serene farm, greeted ... »
Drayton Entertainment Youth Academy, 145 Northfield Dr W, Waterloo
April 21, 2026 To June 13, 2026
519-804-1100
$88-$152
Spring Session kicks off April 21! Step into 8 weeks of creativity, confidence, and hands-on theatre fun. From high-energy Musical Theatre to imaginative Acting & Improv and behind-the-scenes magic ... »
Our Lady of Mount Carmel Academy, 2483 Bleams Road, New Hamburg
April 18, 2026 To June 16, 2026
226-698-7982
$15 to $20
Our Lady of Mount Carmel Academy (2483 Bleams Rd, New Hamburg, Ontario) is holding its 2nd Annual Licensed Raffle Licence No. RAF1529638), featuring a brand-new 2026 Chevrolet Trax and $4,000 ... »
Township of Wilmot, 60 Snyder’s Road West, Baden
April 11, 2026 To October 24, 2026
855-844-6787
$16.75 + tax
Enter a beautiful and haunted mansion in the spookiest way… at night! From haunted antiques, to playful spirits and the artist who was dead. Featuring… A house ... »
Various stations
April 9, 2026 To October 29, 2026
$21.49 - $42.79
Enjoy the picturesque countryside aboard our heritage train ride! »
Brae Ridge Farm & Sanctuary, 7667 Maltby Road East, Guelph
January 14, 2026 To December 31, 2026
2269244065
$125 - $195
Embark on an unforgettable adventure with our exclusive private tour, designed for up to 5 guests (expandable to 8 for a small additional fee). Experience the thrill of meeting ... »
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