About Harvard Western Insurance

Harvard Western Insurance team Photo June 2025

Your Local Insurance Partner Since 1903.

Imagine having a neighbour who’s always there when something goes wrong; that’s exactly what Harvard Western Insurance has been for Saskatchewan communities for over a century. Here in the prairies, where the weather can turn on a dime and life moves at its own pace, we’ve built our reputation on being the steady hand that helps you through life’s unexpected moments.

What began in 1903 as McCallum Hill and Company has grown into Harvard Western Insurance, but we’ve never forgotten where we came from. Those early days taught us something important: insurance isn’t just about policies and premiums. It’s about people and promises.

Our journey through the decades has been shaped by meaningful mergers and thoughtful growth:

Our Insurance Heritage

1903

Walter Hamilton Alexander Hill and E.A. McCallum establish McCallum Hill and Company

1996

McCallum Hill Insurance and Cooks Insurance join forces to become Cooks McCallum Hill Insurance

2005

A strategic merger between Harvard Developments Inc. and Western Financial Group creates Cooks ISI Insurance

2010

Harvard Western Insurance is officially founded, combining generations of local expertise

2018

Hoff Insurance joins the HWI family, expanding our community presence

2023

We welcome both Tilley’s Insurance Agency and Dalmeny Insurance to our growing team

2024

Harvard acquires Western Financial Group’s shares to become the majority owner, establishing us as the largest Saskatchewan-owned insurance brokerage

Why We’re ‘The Company That Cares’

Vision Board

Recipient of the Business of the Year from the Regina Chamber Paragon Awards

This recognition truly reflects the commitment and hard work of our whole team, and we’re so proud of what we’ve built together. We’re also thankful to the Regina & District Chamber of Commerce for this prestigious award and to our community for consistently supporting us.

It’s a privilege to be a part of Regina’s thriving business scene.

Paragon awards 2025 with logo V2

Where You’ll Find Us: Small-Town Charm

There’s something special about walking into one of our offices in Kronau, Milestone, Yellow Grass, Pangman, Rouleau, or Dalmeny. You’ll find familiar faces who know you by name, not policy number.

Our rural offices bring together that irreplaceable small-town approach with the comprehensive protection you deserve.

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Milestone office

The Hill Companies

“Start with a foundation of solid values and stay true to the things you believe in.” – Walter Hamilton Alexander Hill.

The Hill Companies comprise a diverse group of businesses spanning various industries, including real estate, insurance, media, resources, and manufacturing. Founded as a modest real estate company in 1903 by Walter Hill and EA McCallum, The Hill Companies have emerged as a homegrown symbol of success, versatility, and generosity across the North American business landscape.

the hill company

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