The Sun Life UpTown Waterloo Jazz Festival is an annual 3 day FREE music festival held in Waterloo Ontario, encouraging all genres of jazz. This upcoming year of 2026, we invite you to our 34th Season where we look forward to entertaining more than 20,000 enthusiastic festival goers!

Friday night brings the return to the Festival of the Toronto group Four80East,” said Derek Hines, Artistic Director who has been putting the musical program together for the Festival for over 5 years now.  “They are very popular in the US and Europe but for some reason they don’t play a lot in Canada.  Their music is described as ‘Groove Jazz for the Masses’; very danceable with a great beat, wonderful melodies and influences of R & B, funk and rock.  We are expecting a number of their fans to travel up from the US and from across Canada to catch their performance”, he added.

“On Saturday night, we will feature the Latin Big Band of Alexis Baró, a Cuban Trumpeter that now calls Toronto home,” Hines continued.  “His latest album, AFROKANDO was nominated for a JUNO award this year.  The music is high energy laced with Latin rhythms, perfect for a summer Saturday night under the stars!”

Sunday will mark the return of prodigal son, Adrean Farrugia and his Quintet.  “Adrean is a great friend who has recently moved back to Ontario and is Assistant Professor in the Wilfrid Laurier University music program,” said Hines.  “He was Matt Dusk’s pianist for many years and has put together a killer quintet to be our closing day Headliner.  Their performance will be awesome.”

The Program for this year carries on the tradition of supporting musicians from the local and national scenes.

“It’s a great honour to create the artistic program for this Festival,” said Hines.  “There is so much musical talent in this country and I love helping to showcase these incredible artists.”

Local artists featured at this year’s Festival include well-known regulars like Paul Stouffer & Tim Moher, funk fusion band from WLU The Stack, up and coming artist Bria Moore is from Drayton and has performed with her family in Mooreband and, making his Festival debut, local favourite Matt Weidinger with his organ-based group the Tonewheels.

We will also feature new local talent as musicians from our high schools try their hands at jazz in the Youth Jazz Ensemble led by the incredible Jason White.  This group of young musicians is always a treat!

Help fundraise for St. John the Divine Anglican Church at their upcoming Yard & Bake Sale!

Fresh homemade baked goods, a large selection of second hand items and a great community atmosphere!

For more information please call: 289 440 239

Every month from June to October Caledonia Auto supply hosts a Caffeine & Gasoline Car Show! The local car community shows up in force to fill the parking lot with vintage cars, unique builds, and more! Entry is free, plus free coffee and donuts at the show!  

2026 Car Show dates:  

June 6th 

July 18th  

August 8th 

September 12th  

October 31st 

Get ready for a day of family friendly fun at Cayuga Summer Fest! Entry is free at the Cayuga Arena, stop by to enjoy all the attractions and entertainment! There will be a car show, local vendor market, petting zoo, rock climbing, food trucks, magic shows, hot air balloon rides and much more! For more event details visit the Cayuga Summer Festival Facebook page or email cayugasummerfestival@gmail.com  

The Haggersville Lion's and Townsend Lion's are hosting a Charity Car Wash at St Mary's Catholic Church! 

The event will be open between 9am - 3pm!

All proceeds from the car wash are being donated to Campfire Circle!

Celebrate 100 Years of the Royal Canadian Legion with food, music and good times! 

The Waterford Legion is hosting their Party in Pavilion complete with live music from the North Shore Highlanders band, great food and a mini regalia store!  

Everyone is welcome and more information is available at waterfordlegion.ca