UPCOMING EVENT: The 2026 National Trust Conference is taking place from October 22nd to 24th in the Waterloo Region!
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October 21, 2026

Dark Drives: Enter for Your Chance to Win!

Searching for something entertaining to do this Halloween season? Something with the perfect mix of history and spooky fun? Look no further! Simply tell us which is your favourite haunted heritage building in Winnipeg to be entered to win one of three lifetime passes to Dark Drives! Scroll down to fill out the form and enter before the contest closes on October 28th at 5:00 pm!

Dark Drives turns your own car into a haunted tour of Winnipeg. Open it on your phone, press play, and narrator Edmund Blackwell guides you to 44 real locations, from the Exchange to the French Quarter to the river road, telling the dark history and local legends of each stop as you pull up. Go at your own pace, any night you like. Six tours plus The Cold Keeps. Visit the Dark Drives website to learn more!

2026 Halloween Contest

Dark Drives: Enter for Your Chance to Win!

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Thank you to Dark Drives for donating the prizes for this contest!

Information collected for this contest is used to contact the winners. Winner email addresses are given to Dark Drives so they can provide the prize. We do not share or sell your personal information, or use it to contact you for any other reason.

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 / Recent News

Dark Drives: Enter for Your Chance to Win!

Searching for something entertaining to do this Halloween season? Something with the perfect mix of history and spooky fun? Look no further! Simply tell us which is your favourite haunted heritage building in Winnipeg to be entered to win one of three lifetime passes to Dark Drives! Scroll down to fill out the form and…

October 2, 2026

A Memorable Evening at Glasgow House

Thank you to everyone who joined us on Thursday, October 1st, 2026, for Heritage Winnipeg’s Fall Fundraiser at the beautifully restored Glasgow House at 34 Middle Gate. It was a wonderful opportunity to gather in a historic home, enjoy good company and celebrate Winnipeg’s built heritage while supporting its future. A special thank you to…

September 28, 2026

Heritage Winnipeg’s 2026 Annual General Meeting

Heritage Winnipeg’s 2026 Annual General Meeting was held on September 24th, 2026, in Celebration Hall at the historic Millennium Centre at 389 Main Street. It was wonderful to gather with heritage supporters, volunteers, board members, and community members to reflect on another year of heritage conservation and advocacy in Winnipeg. This year’s AGM featured an…

September 25, 2026

New Heritage Winnipeg Board Member

Heritage Winnipeg is pleased to welcome Samantha Silvester to our Board of Directors! Samantha has worked with nonprofit organizations for more than 10 years and brings a passion for historic sites and research. She looks forward to sharing her knowledge and experience while learning from others along the way. We’re excited to have her join…

September 22, 2026

New Memorial Garden Honours the Legacy of Sleeping Car Porters in Winnipeg

On September 18, 2026, the Black Manitobans Chamber of Commerce unveiled the Order of Sleeping Car Porters Memorial Garden at 799 Main Street, creating a public place of remembrance for Black Canadian history in Manitoba and the legacy of the sleeping car porters. Founded in Winnipeg in 1917, the Order of Sleeping Car Porters (OSCP)…

September 14, 2026

Remembering Richard Walls

Heritage Winnipeg was saddened to hear of the passing of Richard Walls on September 9th, 2026. Richard was a dedicated advocate for Winnipeg’s built heritage, downtown revitalization and community development, whose work left a lasting impact on our city. For more than 40 years, Richard was the founder and president of ADI-Designworks Ltd., based in…