Planning things to do this weekend in Oshawa? You picked the biggest one of the fall: Halloween lands on Saturday, October 31, and the weekend fills in around it with live music, a farm festival finale, a Generals home game, and indoor shopping. Here is the local rundown for Friday, October 30 through Sunday, November 1, with links to official pages so you can confirm times before you head out.
Friday, October 30
Start the weekend with a Canadian rock legend. The Stampeders, the band behind "Sweet City Woman," play the Regent Theatre at 50 King St E on Friday at 7:30 p.m. The theatre sits in the heart of downtown Oshawa, so pair the show with dinner on King Street beforehand.
Hockey fans take note: the Oshawa Generals are on the road Friday night, visiting the Brampton Steelheads at CAA Centre, so the home ice action waits until Sunday. If you would rather keep it calm, Parkwood Estate at 270 Simcoe St N is open 1 to 5 p.m. that day, though house tours are paused and only the grounds and gift shop are available.
Saturday, October 31: Halloween
Halloween night is the headline. Oshawa does not publish official town-wide trick-or-treat hours; families head out around 6 p.m. and wind down by 8:30 to 9 p.m. across the city's residential streets. Our 2026 trunk-or-treat and trick-or-treat guide for Durham Region has the full rundown, including the free Downtown Whitby BIA daytime Trick or Treat from 12 to 3 p.m. and safety tips for the night.
For a daytime family stop, Durham Harley-Davidson at 880 Champlain Ave hosts a free Trunk & Tour Pak Treat candy event on Saturday from 12 to 3 p.m. Bring the kids in costume, walk the lot, and load up on candy.
Pingle's Farm Market at 1805 Taunton Rd E in Hampton wraps its season on Saturday with the final day of Harvest Fest, open 9 a.m. to 7 p.m. Explore the giant corn maze, ride the wagon, pick apples and pumpkins, and meet the farm animals. Admission is sold online in advance.
Back in the city, the Oshawa Markets indoor market at 555 Simcoe St S is open 10 a.m. to 6 p.m. with 250-plus vendors, a reliable stop if the weather turns.
After dark, adults get their own party: the Biltmore Theatre at 39 King St E hosts The Black Parade Halloween Emo Night, a 19-plus costume dance party starting at 10 p.m. Grab a costume, grab friends, and celebrate Halloween in the downtown core.
Sunday, November 1
Sunday is a slower, sports-forward day. The Oshawa Generals host the Ottawa 67's at Tribute Communities Centre, 99 Athol St E, with puck drop at 6:05 p.m. and doors at 5:05 p.m. Tickets run $29 to $46 through Ticketmaster. Grab a pre-game bite in downtown Oshawa first; the arena is steps from King Street.
Earlier in the day, the Oshawa Museum at Lakeview Park, 1450 Simcoe St S, is open Sunday from 12 to 4 p.m. (it is closed on Saturdays in the off-season). After Halloween night, a quiet afternoon at the historic houses and a walk along the Lakeview waterfront trail makes a gentle reset.
The Oshawa Markets is open again Sunday from 10 a.m. to 6 p.m. for a last browse before the work week. Note that Parkwood Estate closes for a stretch starting November 1, so save that visit for a later weekend.
Whatever you choose, have a safe and happy Halloween weekend. Get out, dress up, and enjoy Oshawa at its most festive. Catching up on older plans? The previous edition of this guide, covering October 23 to 25, is saved in the Weekend Guide archive, and you can browse every past edition under the Weekend Guide category.
Thinking about making Oshawa home? Keith and Lisa can show you the neighbourhoods behind all of these weekend plans. Send them a message or book a free call to talk through listings, schools, and your timeline.
