10 events in Whitby, Oshawa, Ajax, Bowmanville, and Pickering
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10:00 AM-3:00 PM
Join us for Market In The Park, a vibrant outdoor market celebrating local makers, artisans, and small businesses in the heart of Whitby
10:15 a.m.
The event is held on August 21, 2026 at Oshawa Public Libraries - Delpark Homes Centre Branch in Oshawa, ON.
3:30 pm - 9:00 pm
Hundreds of classic vehicles line downtown streets for this outdoor festival, bringing together generations of vehicle enthusiasts, vintage car clubs, and car lovers from the young to the young at heart. Tour the event footprint observing vehicles, listening to live music, exploring children's activities, and enjoying delicious food. August 213:30 p.m. to 9 p.m.Downtown Oshawa, King St. and Simcoe St. to Memorial Park (110 Simcoe St. S.)
4:00 PM - 8:00 PM
The 12th Annual Touch-a-Truck returns to Oshawa, presented by Oshawa Power. Friday, August 21, 2026, 4:00 p.m. to 8:00 p.m. at the Tribute Communities Centre. Kids can climb in, honk the horn, explore big trucks, and meet community heroes, with fire trucks, police vehicles, ambulances, construction equipment, and more than 40 specialized vehicles on display outside the arena on Athol Street. Free to the public, with donations supporting Big Brothers Big Sisters of Durham and Northumberland.
4:00 pm - 8:00 pm
Oak View Group, operators of the Tribute Communities Centre, announce the return of Touch-a-Truck. Oshawa Power presents this year's 12th annual Touch-a-Truck event which will be on Friday, August 21, 2026 from 4:00pm to 8:00pm in support of Big Brothers Big Sisters of South Durham and Northumberland. This free community event will be hosted outside and around the Tribute Communities Centre and is a fun, hands-on event that allows children of all ages to get up close and personal with more than…
7:00 pm - 11:55 pm
Ichi Bons with Jackson and the Phantom Rebels Ichi-Bons are the reckless rock ‘n’ roll revival. Inspired by obscure surf, garage and Rockabilly 45’s, they combine the sounds of a raunchy vinyl DJ with a cranked rock ‘n’ roll band. From boppin’ garage to frantic rockabilly, from instrumental surf to desperate rock ‘n’ roll, Ichi-Bons are a stack of quarters on your favourite jukebox. Local openers, Jackson & The Phantom Rebels.
Kicking off on July 14 and running every other Tuesday evening from 7 to 8 p.m. until August 25, Pat Bayly Square is your kid-friendly Tuesday night free entertainment destination.
The Town of Whitby\'s annual Movies in the Park event hosts family-friendly films under the stars in July and August. Other Movie Options in Whitby: Downtown Whitby BIA Movies in the Square Downtown Whitby BIA hosts Movies in the Square. Check back for more information on the 2026 season. DRIFF For information, visit the DRIFF website.
Pat Bayly Square (75 Bayly Street W.), Ajax’s downtown urban hub, will bring a vibrant energy to the community this summer with free family-friendly concerts, children’s performances and Zumba®. Kicking off on July 7 and running every Tuesday evening until September 1, join us for your Tuesday night entertainment. Check out the accordions below for more details! All performances take place rain or shine. Performances will move indoors (Ajax Community Centre - HMS Room or Ajax Community Centre…
2:30-4:00pm
Recreational Swim at Anne Ottenbrite Pool at Iroquois Park Sports Centre. Schedule slot: Friday 2:30-4:00pm. Unstructured drop-in swim open to all ages. Children 6 and under must be accompanied by a parent/guardian within arm's reach. No advance registration required.