Things to Do in Waterloo Region in May

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by Alex Kinsella | May 2023

Waterloo Region is the place to be this May! From Mother’s Day to May Two-Four, we’ve got the sights, sounds, and flavours of spring for everyone to experience.

We also have a guide for the perfect long weekend Road Trip for you and your friends. It’ll have you enjoying the great outdoors in Waterloo Region – and don’t forget to BYOB (Bring Your Own Bike!)

Things to Do in May

Cinco de Mayo Weekend in St. Jacobs | May 6
From tacos to mariachi music, the village of St. Jacobs celebrates Cinco de Mayo! You can find out all of the special things that are planned on the website.

Makers Market Patio Takeover | May 6
Kickoff patio season in Waterloo Region at Block Three Brewing in St. Jacobs Village. Discover awesome gifts from local vendors, enjoy one of their craft beers or ciders, and explore the village while you’re there.

Doobie Brothers Tribute Band | May 6
The Registry Theatre is getting groovy with Listen To The Music, a Doobie Brothers tribute band. From “Black Water” to “China Grove,” this talented tribute band will transport you back to the 70s with their authentic sound and energetic performance.

Grand River Film Festival | May 9 – 13
The Grand River Film Festival returns for its first fully in-person festival this May 9 – 13. The festival features nine films and 39 short films screening across Waterloo Region at the Princess Twin in Uptown Waterloo, the Kitchener Public Library Theatre in Downtown Kitchener, and the Cambridge Community Players Theatre in Cambridge.

Insider tip: Make it a date night at the movies! In Cambridge, walk across the Grand River pedestrian bridge to the Foundry Tavern for one of their unique craft beers and dinner. In Waterloo, the Princess Twin is around the corner from Chef Dan McCowan’s Red House and their must-have curry bowls. If you’re checking out the afternoon short film screenings in Kitchener, head to the Kitchener Market to explore the flavours of their food hall vendors like Caribbean Kitchen, Simply Delicious, and ChefD’s Sandwich Shop.

Mother’s Day Garden Party | May 13
Enjoy artistic workshops, live music, and delicious refreshments at the Homer Watson House & Gallery Mother’s Day Garden Party. Stroll through their grounds and gardens and shop from a collection of artisanal vendors at their special pop-up market.

Mother’s Day Cooking with Wine | May 13
It’s an afternoon of moms and merlots at the 1909 Culinary Academy in Ayr. Their Cooking with Wine workshop is a beginner-level class that includes French onion soup, mussels in a white wine garlic sauce, coq au vin, and poached pears in red wine.

Insider tip: Ayr is home to Willibald Farm Distillery & Brewery, where a new generation of distillers continues Waterloo Region’s long history of creating amazing spirits. Try their barrel gin, aged for a year in American oak casks.

Mother’s & All Others Market | May 13
Shop from over 40 vendors at the Mother’s & All Others Market inside Embassy Hall at Bingemans Conference Centre. Grab a cocktail or glass of wine and stroll through Mother’s Day gifts, including crafts, clothing, mugs, stickers, books, and more.

Mother’s Day Floral Workshop | May 14
Just because you’re not in elementary school anymore doesn’t mean you still can’t make Mom a gift. St. Jacobs Farmers’ Market and Marché Fresh are hosting a Mother’s Day Floral Workshop where you’ll learn how to create your Mother’s Day floral arrangement. The workshop costs $36 and includes all the necessary flowers and items.

Time with Mom Tours | May 14
Take Mom for a guided tour of Castle Kilbride for Mother’s Day. The tour takes you through  the entire home, and you’ll even get a chance to get hands-on with their vintage toy collection. Your tickets include a special tour of their latest exhibit, Whisked Up in Wilmot, showcasing the amazing food of Wilmot Township.

Mother’s Day Matinee | May 14
Abe Erb Kitchener and Cinched Events are bringing you a special Mother’s Day Matinee drag performance on May 14. This brunch is more than mimosas and drag queens — they’ll have amazing giveaways, including a spa day and tickets to see Jinx Monsoon at Centre in the Square.

Waterloo Central Railway Heritage Hopper | Thursdays, Saturdays, and Sundays
The Waterloo Central Railway is a fantastic way to explore Waterloo Region. Whether you’re looking for a great day date idea or a family adventure, WCR’s new Heritage Hopper pass gets you roundtrip travel on their artfully restored heritage railcars. You can take the railway from the St. Jacobs Farmers Market into St. Jacobs Village for lunch at the Village Biergarten or the Fat Sparrow Charcuterie Bar or make it a full roundtrip from the Northfield Drive station to see all of our spring foliage in bloom.

Secrets of the Universe 3D | May 16 & 18
Explore the secrets of the universe in stunning IMAX 3D at the Perimeter Institute for Theoretical Physics. Filmed at both the Institute and CERN, the movie will take you inside the Large Hadron Collider in Switzerland to show how world-leading scientists are working to understand how the universe was born.

KWFamous Vintage Fest | May 20 – May 22
Pop some tags and make your next great fashion find at this first-time collaboration between KWFamous, Market Road Antiques, and the St. Jacobs Market District. Over the Victoria Day long weekend, explore vintage clothing and antiques from over 50 vendors. There’ll be live music and entertainment, amazing food and drink, and more.

Insider tip: you can walk or cycle to the St. Jacobs Market District along the new Market Trail. You can find the entrance off Northfield Drive across the street from the Northfield ION light rail transit station.

Kitchener Panthers vs. Welland Jackfish | May 21
The Kitchener Panthers welcome the Welland Jackfish to opening day at Jack Couch Park. Get your tickets for exciting intercounty baseball action!

New Hamburg Mennonite Relief Sale | May 26 & 27
Since 1967, the New Hamburg Mennonite Relief Sale has raised funding to fight hunger and poverty, support victims of natural disasters, and expand peace-building activities. The two-day sale includes vendors, auctions, and more across New Hamburg. Start Saturday at their annual Pancake and Sausage Breakfast and then explore the sale to support the great work they do.

Mel Brown Music Festival and Symposium | May 26 – 28
Celebrate Black music and artistry at The Mel Brown Music Festival and Symposium. The festival honours blues guitarist Mel Brown. Originally from Mississippi, Brown recorded with legends like Jimmy Beasly and Etta James. Brown came to Kitchener in the 80s and started hosting a weekly jam night at Pop the Gator. Today, his memory is being honoured through educational programs and supports for emerging Black artists. The festival includes three free concerts at Kitchener Public Library and the Church of the Good Shepherd in Downtown Kitchener.

Insider tip: festival sponsor Mark’s Caribbean Kitchen and Seafood is an amazing spot for traditional dishes like oxtail stew and jerk chicken.

May Long Weekend Road trip

Long weekends and road trips are always better with friends! Waterloo Region is the perfect place to bring your friends for a long weekend camping adventure.

Camping at Bingemans offers tent, trailer, and cabin camping spots on the Grand River. Their spring camping specials offer two nights of camping, mini-golf, bowling at Kingpin Bowlounge, and more. If you are more a glamper than a camper, Bingemans offers luxury container cabins that feature a private washroom, WiFi, and a full kitchenette.

Another great camping option is the Laurel Creek conservation area. Laurel Creek has over 100 camping sites available, and the nature preserve is a fantastic spot for cycling, canoeing, and relaxing with friends. Speaking of canoeing, explore the waterways of Waterloo Region with Canoeing on the Grand. They offer canoeing, kayaking, and tubing packages along the Grand River.

Bring your bikes to town too, and explore art, culture, breweries, and more with your friends. We have an extensive collection of routes to try, from the shops and restaurants of St. Jacobs to a relaxing trail ride from Cambridge to Paris, Ontario. Zeitspace, a local app development shop, has just released an interactive, made-by-cyclists guide to help you get from your campsite to everything Waterloo Region has to offer.


Alex Kinsella is a freelance writer and marketer based in Waterloo Region. He’s the guy behind TL;WR – Waterloo Region’s weekly events newsletter. He’s worked with some of Canada’s most well-known tech companies in roles including customer success, development, product management, PR, social media and marketing.

Alex has contributed to publications including BetaKit, Grand Magazine, Community Edition and more. Follow him on Twitter and Instagram.


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