Specialty Coverage
Are you a Film and Video Producer? We have insurance that will protect you.
Protect your Fine Art
Want a policy that insures jewelry, art, antiques, and items of rare value?
Auto Insurance Discounts
Fill out a simple form to find out if you are eligible for discounted auto insurance rates.
Agency History
One of the oldest family-owned independent insurance agencies in Western Massachusetts, the Toole Agency was established in 1939, when Lawrence V. Toole opened the business with a simple mission: to provide superior personal service to customers seeking the most thorough insurance coverage.
In 1978, Joseph Toole, a son of the founder, purchased the business as the elder Mr. Toole retired. Joseph helped grow the agency through acquisition and expansion.
John Toole joined the family business in 1980 and purchased the agency from his brother in 1990. Under John's direction, the agency has expanded further and now has branch offices in Lenox and Great Barrington. Patrick Armstrong, grandson of the founder, joined the firm in 1993, representing the third generation of the Toole family involved in the business.
The Toole Agency has grown and adapted with the times, but we've never outgrown our founder's principles. We combine personal service with professional advice and assistance.


