Looking for things to do this weekend in Oshawa? You picked a great one. Saturday brings the Halloween Boo Bash to the downtown core, and the rest of the weekend fills in with farmers' markets, live music at the Regent and Biltmore theatres, an indoor market, and a Sunday night Oshawa Generals home game. Here is the local rundown, day by day, with links to the official pages so you can confirm times before you head out.
Friday, October 16
Start the weekend at the Oshawa Centre Farmers' Market, open 8 a.m. to 2 p.m. in the Oshawa Centre parking lot at 419 King St W. It runs every Friday through October 23, so this is one of the last chances of the season to stock up on local produce, baked goods, and preserves before the market closes for winter.
Friday night belongs to comedy. Canadian stand-up Debra DiGiovanni performs at the Biltmore Theatre at 39 King St E, with doors at 6 p.m. and the show at 7 p.m. It is a 19-plus, general admission seated show, so grab tickets in advance on the theatre's ticketing page.
Saturday, October 17
The headline act is the Oshawa Halloween Boo Bash, a free, all-ages Halloween festival that takes over downtown Oshawa from 1 to 10 p.m. Hosted by Oshawa Tourism, it fills the streets around the Four Corners with live music, scare zones, a costume contest, pumpkin decorating, street vendors, and food trucks. Dress up, wander downtown Oshawa, and let the kids lead. Check the City of Oshawa events page and the Oshawa Tourism events calendar for the full lineup.
Before the Boo Bash, hit the North Oshawa Farmers' Market from 9 a.m. to 2 p.m. at Delpark Homes Centre, 1661 Harmony Rd N. This is the final market of the season, so it is the last chance to grab local honey, produce, and crafts until spring.
Saturday night, the Regent Theatre at 50 King St E hosts 'An Evening of Boston & Kansas Greatest Hits' at 8 p.m., a tribute show from More Than A Feeling presented with CKDO 107.7, part of Oshawa's wider arts and culture scene. If you want dinner first, Mathilda's downtown serves a plant-based menu steps from the theatre.
Prefer to browse indoors? The Oshawa Markets at 555 Simcoe St S is open Saturday and Sunday from 10 a.m. to 6 p.m., with 250-plus vendors under one roof.
Sunday, October 18
Sunday is a slower day, then the puck drops. The Oshawa Generals host the Kitchener Rangers at 6:05 p.m. at Tribute Communities Centre, 99 Athol St E. It is a family-friendly night out, and tickets are on sale through Ticketmaster.
In the afternoon, take a walk along the lake. Lakeview Park and the waterfront trail are at their best in October, with the beach quiet and the leaves turning. Parkwood Estate, the National Historic Site at 270 Simcoe St N, is also open 1 to 5 p.m. with tours and its gardens.
Whatever you choose, get out and enjoy it. Oshawa's best weekends are spent downtown, at the rink, or along the lake, and this one has all three. See you out there.
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.
