Things to Do in Waterloo Region in May 

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…plus a May Long Weekend road trip idea!

by Alex Kinsella | April 2024

We’ve got our fingers crossed that the April showers we experienced will bring May flowers across Waterloo Region. There’s lots to do in May, from spring maker markets to the summer festival kick-off with WelcomeFest KW. We’ve also put together a weekend road trip for you and your friends this Victoria Day long weekend that’s sure to be vintage! 

Here’s our list of amazing events to check out this May across Waterloo Region! 

Jane’s Walks | May 3–5 

Jane’s Walks Waterloo Region returns on May 3, 4, and 5. Jane’s Walks started in 2006, the year after Jane Jacobs died, as a way to honour her life and activate her ideas. Although she had no formal training as a planner, Jacobs changed the approach to city planning through her book, The Death and Life of Great American Cities. There are 21 free walks to choose from, learn more at

Spring Ayr Market | May 4 

Looking for something special for the mom in your life? Head to the North Dumfries Community Complex for the Spring Ayr Market. It has over 40 vendors with everything from baked goods to beauty products. 

Wonderfully Made Market | May 4 

Just in time for Mother’s Day, discover one-of-a-kind gifts and meet the makers who bring them to life! The Wonderfully Made Market returns to Catalyst 137 with a curated selection of nearly 50+ makers and talented artisans from across the Waterloo Region.  

Green Room Barbers Spring Market | May 5 

A market in a barber shop? Yes, that’s exactly what the Green Room Barbers are doing on May 5. Enjoy one of Belmont’s best cups of coffee while you shop amazing deals from local makers. 

Anne of Green Gables | May 9-12 

The Community Players of New Hamburg are celebrating their 40th anniversary with a production of Anne of Green Gables: The Musical. This family-friendly classic features the story of Anne, a precocious redhead who comes to live with a family on a farm in Prince Edward Island. Tap your toes and laugh along with this energetic performance! 

Waterloo Food Tour | May 10 

Stroll Walking Tours wants to tantalize your taste buds in Uptown Waterloo! This three-hour food tour dives into the heart of the city’s vibrant culinary scene, including independently-owned restaurants, hidden gem eateries, and sweet shops. Come hungry for delicious bites, local culture, and a whole new appreciation for Uptown’s culinary delights! Vegetarian dietary needs can also be accommodated. 

Grand River Film Festival Movie Day | May 11 

The Grand River Film Festival (GRFF) is Waterloo Region’s longest-running independent film festival. Join them for Movie Day in Cambridge at the Gaslight District for a one-day cinematic extravaganza featuring seven hours of short and feature-length films. 

Spring Plant Sale and EcoMarket | May 11 

rare’s Spring Plant Sale & EcoMarket is your destination for local seedlings, eco-friendly gifts from artisans, and delicious food. Support the Food Bank Gardens and find unique Mother’s Day gifts along with live music and raffles.  

Downtown Kitchener Art Walk | May 11  

Get rejuvenated while you explore downtown Kitchener’s art scene on the Kitchener Waterloo Art Gallery’s Art Walk. This walking tour highlights murals, sculptures, and installations around downtown Kitchener, and tours run rain or shine.  

After This: An Improvised Musical | May 11 

If you’re a fan of improv and musicals, then this is the event for you. Improv group After This presents “After This: An Improvised Musical” at the Kitchener-Waterloo Little Theatre. It’s improv, but instead of scenes, the After This comedians will turn your stories into musical theatre productions! 

KW Gem and Mineral Show | May 11 

The Kitchener-Waterloo Gem and Mineral Club’s annual show is on May 11 at the Kitchener Memorial Auditorium. There will be lots to do, including rock, mineral, fossil, and meteorite displays, jewellery, and children’s activities.  

Mother’s Day Tea at the Fashion History Museum | May 11 and 12 

Celebrate mom with a Mother’s Day Tea at the Fashion History Museum in downtown Cambridge. The event features a bottomless cup of tea, sandwiches, scones, and sweets.  

Mother’s Day Sip & Graze | May 12

Wine, food and goats on Mother’s day? You bet! The Perth Farmhouse invites families to celebrate Mom with a special 90-minute experience that blends genuine farm hospitality with the beauty of nature – and wine!

Mother’s Day Brunch at the Crowne Plaza | May 12 

Spoil Mom this Mother’s Day with a luxurious brunch at the Crowne Plaza Kitchener-Waterloo. Enjoy a delicious meal in a beautiful setting and create unforgettable memories together! Reserve your table now for a truly special celebration. 

Mother’s Day Mindfulness | May 12 

The Schneider Haus National Historic Site invites you to celebrate Mother’s Day with mindfulness and mental relaxation. Join them for a three-part Metta (love and kindness) Meditation led by award-winning mental health advocate and wellness expert Iman Grewal. 

Fabled Mother’s Day Tours at Castle Kilbride | May 12 

Step into a storybook wonderland with your mom! This Mother’s Day, treat her to a 30-minute guided Castle Kilbride tour with their costumed crew. The “Fabled” exhibit, co-curated by the Stratford Festival Archives, brings classic tales to life. From Alice’s looking-glass adventures to Narnia’s magical wardrobe, Little Women’s charming stories, and many more, it’s a guaranteed happily ever after for all ages! 

Mother’s Day Brunch at Langdon Hall | May 12 

Treat Mom to a feast fit for royalty at Langdon Hall. The event buffet features fresh, local ingredients and delicious brunch classics like seasonal salads, glazed veggies, roasted meats, and decadent desserts. Don’t miss out on this chance to make memories that will last a lifetime. Reserve your table online now. Seating starts at 10, and the last seating is at 12:30 p.m. 

Late Company | May 15–26 

Green Light Arts is celebrating its 10th anniversary with a production of Late Company at the Conrad Centre. Written by Jordan Tannahill and directed by Kwaku Okyere, Late Company explores the complexities of human relationships and the challenges of finding peace balanced with the need for retribution. 

Kitchener Panther Baseball | May 16, 19, 26, and 30 

The 13x Intercounty Baseball League champions Kitchener Panthers kick off the baseball season with their home opener on Thursday, May 16, against the visiting Hamilton Cardinals. Catch exciting IBL action on May 19 vs. the Guelph Royals, on May 26 vs. the Brantford Red Sox, and on May 30 vs. the Chatham-Kent Barnstormers. 

KW Glee | May 21 and 22 

Get ready for a high-energy concert experience with KW Glee at Centre in the Square! Canada’s award-winning youth pop choir, KW Glee, is live on stage, featuring over 150 young performers with incredible voices and exciting choreography. Don’t miss this unforgettable performance! 

Good Lovelies | May 24 

The Good Lovelies is the Juno Award-winning ensemble of Kerri Ough, Sue Passmore, and Caroline Marie Brooks. Hear them in person at Waterloo Emmanuel Church as they tour to promote their new album, “We Will Never Be the Same.” 

New Hamburg Mennonite Relief Sale | May 24 and 25 

The New Hamburg Mennonite Relief Sale is back at the New Hamburg Fairgrounds on May 24 and 25. Indulge in mouthwatering treats and check out their famous quilt, treasure trove, and other auctions for incredible finds. The sale supports relief, development, and peace in Ontario and around the world through the work of the Mennonite Central Committee. 

KW Welcome Fest | May 25  

Start the summer festival in Kitchener with WelcomeFest! This free, two-day event is brought to you by KW Oktoberfest and the City of Kitchener. WelcomeFest features live music, local arts and culture, and delicious food at Carl Zehr Square. 

Palette x Palate | May 25 

Kick off the summer with Palette x Palate in downtown Kitchener! It’s a celebration of art, food, and community featuring interactive art installations, live performances, new culinary creations, and pop-up markets. Palette x Palate is also the launch event for the new edition of the DTK Art Walk Field Guide, your map to discovering public art across the downtown core. 

Together for Mental Health | May 25 

Woolwich Counselling Centre is hosting Together for Mental Health, a free community event to raise awareness and show support for mental well-being. Olympic medalist Hayley Wickenheiser and NHL goalie Corey Hirsch are among the speakers who will be there, and there are also activities for all ages. 

Ayr Farmer’s Market | May 25 

Ayr is turning 200 this year! Join them at the first Ayr Farmer’s Market on May 25 at 7 Church St. Now in its third year, the Ayr Farmer’s Market is your one-stop shopping destination for fresh produce and unique gifts. 

Hohner Avenue Porch Party | May 25 

Porch party season begins on Hohner Avenue! It’s a free community music festival featuring musicians of all ages and styles. It’s a vibrant atmosphere not to be missed with music, food, and celebrations of the Central Frederick neighbourhood’s creative spirit. 

Cambridge Cat Show | May 25 

Forget corgis and hounds—it’s a cat’s world at the Cambridge Cat Show on May 25. See the world of cat showing firsthand. There will also be vendors on hand with new products for the feline in your life. 

Communitech Open House | May 28 

Ever wonder what goes on inside the historic Tannery building in downtown Kitchener at Communitech? Find out on May 28 at the Communitech Open House. Tour the building and see where the startup magic happens. It’s your chance to learn about how Communitech has helped Canadian founders start, grow and succeed for over 25 years. 

Trolls Band Together at the Gaslight District | May 28 

The Gaslight District and Foundry Tavern present a free screening of “Trolls Band Together” on Waterloo Region’s biggest and brightest outdoor screen. Bring your lawn chairs and blankets to enjoy the film and check out the Gaslight District’s shops and restaurants. 

Grab your friends for a May Long Weekend road trip to Waterloo Region 

The first long weekend of 2024 is almost here! Make the most of it on a weekend road trip to Waterloo Region with your friends for food, music, culture, and more. 

Set up your base of operations at the Laundry Rooms inside Station Park in Kitchener (5 Wellington St. S.). These furnished short-term rentals are centrally located in the west end of downtown Kitchener, close to shopping and the GRT Ion light rail transit system. 

On Saturday, May 18, make your way to the St. Jacobs Farmers Market District for KWFamous’s VintageFest. The three-day festival brings a collection of vintage vendors alongside your favourites for the ultimate shopping experience. But that’s not all! There’s also live music and performances. We recommend checking out the disco and R&B sounds of The Free Label on Saturday—they put on an awesome live show! 

After an afternoon of shopping, snacks, and soul, head to Waterloo for dinner at one of our favourite spots, Ethel’s Lounge (114 King St. N.). This classic dive bar is an Uptown Waterloo staple and is celebrating its 30th anniversary this year. While Ethel’s is known for its famous Taco Tuesday deal, its kitchen crew turns out some of the best dishes you’ll find in town. We recommend the Rajah—roasted sweet peppers stuffed with your choice of chicken or portobello mushrooms. 

Your entertainment on Saturday night is just down the street at Button Factory Arts (25 Regina Str. S.) for an evening of improv, comedy, burlesque, and more at Pinch Cabaret. Voted the area’s favourite local event by the readers of the Waterloo Chronicle, Pinch Cabaret is an interactive evening of surprises and laughter. The show on Saturday, May 18, is guest-hosted by Aashay Dalvi and Sasha Tease. 

On Sunday, stretch your legs in St. Jacobs with Stroll Walking Tours. Their Historic St. Jacobs Walking Tour is a great way to explore the shops and restaurants of this beautiful small town while learning about the people who built it. Make sure you stop into the Stone Crock Bakery (1402 King St. N., St. Jacobs) for one of their tasty baked treats. 

We’ve got two options for your Sunday evening. If you’re looking for fireworks, head to New Dundee for its Community Fireworks celebration starting at 4 p.m. If you’re looking for live music, head back to Waterloo for the Long Weekend Band Crawl. It’s four venues with sixteen amazing live acts to choose from. 

Long weekends are best spent with friends, and even better when you spend them in Waterloo Region! 


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