Residents across Durham Region can anticipate a vibrant weekend filled with cultural activities, live entertainment, and community gatherings scheduled from Friday, May 22 to Sunday, May 24, 2026. In Oshawa, the weekend begins with the Oshawa Lawn Bowling Club hosting an open house on Friday afternoon, inviting community members to their facilities on Beatrice Street East. Live music fans have several choices, including a performance by Dwayne Gretzky at the BOND|ST Event Centre on Bond Street East and a tribute act dedicated to Sting & The Police at the Regent Theatre. Art enthusiasts can visit The Robert McLaughlin Gallery on the Civic Centre for a Saturday Studio Spring session or a tea-time conversation about textiles later that afternoon. Saturday evening in Oshawa also features the Oshawa Stampede at the Tribute Communities Centre on Athol Street East.
The entertainment lineup extends throughout the region with performances scheduled for multiple venues. The Arena at the Pickering Casino Resort is set to be a hub for activity, hosting comedian Chris Tucker on Friday evening and a musical production featuring the music of the 50s and 60s on Saturday. In Scugog, the Port Perry Town Hall Theatre will present “FMJ-Foreigner Meets Journey” on Friday, while the Scugog Arts space on Queen Street will host an exhibition of works by Laurie Lafrance titled ‘Hazel’. On Saturday night, the Regent Theatre returns to the spotlight with “The Last Waltz,” celebrating the 50th Anniversary of The Band. Meanwhile, residents in Ajax can look forward to “The Rolling Stones Experience” featuring The Blushing Brides at the St. Francis Centre for Community, Arts & Culture on Saturday evening.
Gardening enthusiasts and those looking to enjoy the spring weather will find several opportunities to engage with local horticulture groups. The Oshawa Garden Club is holding its Annual Plant Sale on Saturday morning at the South Oshawa Community Centre on Cedar Street, providing residents with access to a variety of flora. Simultaneously, the Pickering Garden Club will conduct its own Annual Plant Sale as part of the Pickering Artfest located at Esplanade Park. Animal lovers may be interested in the Grand Opening of the Pupvacay Private Dog Park in Oshawa on Friday, taking place at the intersection of Simcoe and Bloor Streets. For a historical outdoor experience, the Oshawa Union Cemetery is offering a guided tour focused on the World Wars on Sunday morning.
Community support and social gatherings are also prominent on the agenda for the weekend. The Huntington’s Fundraiser Walk is scheduled to take place on Saturday morning at Bowmanville Memorial Park on Liberty Street South, bringing the community together for a charitable cause. In Clarington, specifically Orono, Sir Monty’s Brewing Company on Highway 2 will host “Laughing Gas Presents: Warning May Cause Laughter” on Saturday evening. Social events in Pickering include the BOOK67 UNPLUGGED Christian Social at Bullocks on Rossland Road East and a Christian Couples’ Hangout at Revivaltime Tabernacle on Kingston Road. Local businesses are also participating, with TiltedGlass Brewing Co. in Ajax hosting a Spicy Bingo event and the Ajax Casino featuring a Foaming Dragon Foam Party attraction on Saturday.
As the weekend draws to a close on Sunday, residents can attend creative workshops or continue exploring local history. In the afternoon, Chanterelle Bistro will host a Spring Flower Arranging Workshop for those interested in floriculture. These events represent a selection of the activities planned across the region’s municipalities. Organizers encourage attendees to verify specific details with the venues to ensure the most current information regarding schedules and entry requirements. With such a diverse array of options, residents of Oshawa, Pickering, Ajax, Clarington, and Scugog have ample opportunity to engage with their local communities and enjoy the spring season.
