Oshawa, Ontario grew up around the McLaughlin family's carriage works and later General Motors of Canada, and that story still runs through the city's best date spots: a family mansion with formal gardens, a free gallery named for the family, a downtown car museum and a restored theatre on King Street. Add a lakeshore marsh and a holiday market, and you have plenty of Oshawa date ideas for the rest of 2026 and into winter.
Inside the auto baron's home at Parkwood
Parkwood Estate: R. S. McLaughlin's mansion at 270 Simcoe Street North is a National Historic Site, and through the fall and winter its guided tours run Wednesday to Sunday from 1 to 5 p.m. Its 11 acres of formal gardens are free to wander, just without a picnic.
Auto Baron Tour: The signature guided tour takes up to 90 minutes and costs $18 plus HST each. Come the end of November, a Christmas tour of the decorated house runs up to 90 minutes for $22 plus HST, a festive way to start the season together.
Free art at the Civic Centre, classic cars on Simcoe
The Robert McLaughlin Gallery: Oshawa's public gallery at 72 Queen Street stays open until 8 p.m. on Wednesdays, which makes it an easy midweek date. A $5 donation is suggested, and it's a scent-free space, so skip the cologne.
In Plains Air: Zoe Ann Cardinal Cire's first museum solo show in Canada brings new work shaped by time on her ancestral territories in Treaty 6. It's on until February 14, 2027, and Lana Yuan's look at Oshawa's built environment, Restructuring Echoes, runs until November 29, 2026.
Canadian Automotive Museum: A short walk south at 99 Simcoe Street South, more than 75 vehicles fill this downtown museum. It's open Tuesday to Saturday from 10 a.m. to 4 p.m. this time of year, and adult admission is $16.
Classic films on King Street
Regent Theatre: On the first Thursday of every month, this historic King Street theatre screens a classic film. Tickets are $7.50 online or $5 cash at the door, there's a cash concession and door prizes, and you can fill out a ballot to pick a future movie. Check its events page for concerts too.
From Lakeview Park to Second Marsh
Oshawa Museum: Set in Lakeview Park on Lake Ontario, the museum offers drop-in tours of its historic houses, starting at the yellow Guy House. From September to June it's open Tuesday to Friday and Sunday afternoons, and the lakefront park is right outside for a walk afterwards. The last full tour starts an hour before closing, so arrive by 3 p.m. on weekdays.
Second Marsh: Park on Colonel Sam Drive and follow the paved, wheelchair-accessible Ed Kroll Memorial Walkway, a 1.25 km stretch of the Waterfront Trail with wide views over the wetland. More trails lead into the neighbouring McLaughlin Bay Wildlife Reserve.
Oshawa Valley Botanical Gardens: These creek-valley gardens hold one of North America's largest modern peony collections. The blooms are a June event, so in the cooler months come for a quiet walk under the old trees along the creek. The gardens are linked to Parkwood's own grounds, so you can pair the two in one afternoon.
A downtown market and an adults-only skate
Bright and Merry Market: The City kicks off the holidays downtown on Friday, November 20, 2026, with a holiday market, live music and buskers, seasonal displays and a holiday trolley. It's free; check the City page for the start time.
Adult Skate: The City runs adults-only (18+) skates alongside its public sessions at Delpark Homes Centre, Donevan Recreation Complex and Harman Park Arena. Delpark has skate rentals at its pro shop for a fee; check the schedules for times.
Sample Date Itineraries
1. The McLaughlin legacy afternoon: An Auto Baron Tour at Parkwood → a walk through the creek-side botanical gardens → In Plains Air at the RMG.
2. Wednesday after work: The Canadian Automotive Museum before it closes at 4 p.m. → dinner downtown → the RMG, open until 8 p.m.
3. First Thursday: A lakeside walk at Second Marsh → Classic Movie Night at the Regent Theatre with popcorn from the concession.
Pro Tips for Memorable Dates
Parkwood's Tea House is closed until June, so plan to eat elsewhere after your tour.
The RMG is closed Mondays and Tuesdays, and the car museum is closed Sundays and Mondays until March.
Bring cash for the Regent: the $5 door price is cash only, and the concession takes cash too.
At Second Marsh, park on Colonel Sam Drive; there's no parking at the Farewell Street entrance.
Students get into Classic Movie Night free with ID, which makes it one of the cheapest date nights in the city.
For the adults-only skate, check the arena's schedule the day you go, since times shift through the season.
Oshawa's car-making past built a mansion, a gallery and a theatre district worth exploring together. Choose one, add a walk by the lake, and make it an Oshawa date night.
Last reviewed: October 2026
Photo credits: Parkwood Estate and Garden, Oshawa by Mhsheikholeslami, CC BY-SA 4.0, via Wikimedia Commons; The Robert McLaughlin Gallery, Oshawa by Hyfen, CC BY-SA 3.0, via Wikimedia Commons; Regent Theatre, Oshawa by Dillan Payne, CC BY-SA 4.0, via Wikimedia Commons.