BANGOR — When Woodrow Cross launched his family-owned insurance agency 60 years ago, Ted Williams was hitting .345 for the Boston Red Sox. Cross could not imagine that one day the Cross Insurance Agency would insure the Red Sox — or the Boston (and future New England) Patriots, a professional football franchise not even on the drawing boards in 1954.

A World War II veteran and Bradford native, Cross “started working from his house on West Broadway in Bangor,” son Royce Cross recently recalled. The agency hired its first employee and relocated to the Coe Building in downtown Bangor in 1963, and Royce joined the agency in 1970. Cross Insurance moved to 74 Gilman Road in Bangor in 1993.

That building remains the headquarters for an insurance agency that today has almost 600 employees and offices in all New England states but Vermont. Cross Insurance has grown substantially by providing excellent customer service and diverse insurance products — and “has grown a lot through acquisitions” (more than 100 so far) of other insurance agencies, Royce said.

Besides bringing more clients to the agency, “acquisitions allow us to broaden our markets, [and] offer additional products to our existing clientele,” he said.

Future acquisitions are always possible. “It wouldn’t surprise me at all if the right opportunity presented itself” for Cross Insurance to expand, perhaps even beyond New England, Royce said.

Cross Insurance provides insurance in four major areas:

• Personal lines (automobile, homeowners, life, boats, and recreational vehicles);

• Commercial lines;

• Employee benefits (such as health insurance);

• Construction bonds (especially utilized in government-financed construction projects);

• Third Party Administration/Alternative Markets (Worker’s Comp self-insured programs).

Today the agency insures many businesses, organizations, and activities across New England, from the Red Sox and Patriots to the Boston Globe and commercial fishermen sailing from regional ports. Cross Insurance provides insurance coverage for “schools around the Boston area” and “construction all over New England,” Royce said.

Manufacturers in Massachusetts, boating-related businesses around Lake Winnipesaukee in New Hampshire, forestry operations throughout Maine, golf courses, and even airports: This cross-section of Cross Insurance clients represents business activity from Maine to Connecticut, and the client list continues to grow.

As for the future, “I would see the company becoming stronger in the markets we are in,” Royce said.

Now 97, Woodrow Cross is still involved in the agency. Royce is president of Cross Insurance; his brother, Brent, and son, Jonathan, are executive vice presidents, and Brent’s son, Woodrow “Woody” Cross II, works for the agency.

So do many other talented people, Royce stressed. “We have a very qualified staff,” he said. “We attract the skills we want,” such as sales skills and the ability to work pleasantly with people, “and then we teach them the insurance industry.”

For more information about Cross Insurance, call 800-999-7345 or 947-7345 or go to their website at