Our History

The HUB location in Madisonville, Kentucky, formerly known as Riddle Insurance, a division of Peel & Holland, has operated for over 100 years as independent insurance agency representing many different insurance options for our clients’ needs. Since the founding of Riddle Insurance in 1918, we have provided a valuable service to our community and surrounding counties by expertly monitoring a wide variety of insurance carrier programs and guiding our clients in choosing the right coverage for their needs at the right price.

In 2020, Riddle Insurance announced a significant expansion through its merger with Peel & Holland based in Benton, KY. Both companies provided business property and casualty insurance, surety and bonding, family insurance, and employee benefits plans, along with workplace wellness programs. At the time of this merger, combined teams totaled 83 employees with seven regional office locations across Western Kentucky. In 2021, Riddle Insurance acquired Worth Insurance Group based in Owensboro, KY, adding another ten employees and over 2,500 additional clients.

Our people are local insurance experts, some with very specific industry expertise such as agriculture, auto/powersport sales, manufacturing, and construction. We continue to be known for our integrity, taking care of our own, and in more recent years for our “Riddle Insurance” hot air balloon that brings smiles to local residents. We are most proud when someone contacts our agency for help because of a personal recommendation. That says to us that our team is trusted to do a good job for a friend, family member, or neighbor of our clients. We are committed to being our insured’s advocate in times of need.

Now as part of HUB International, we are serving the entire Commonwealth of Kentucky through seven regional HUB offices.