About Sidney & Deanna Wolk
Sidney and Deanna Wolk both came from humble beginnings and never forgot their roots. Both lifelong residents of Massachusetts, Deanna (Lerner) was born in Lynn and grew up in Peabody. Sidney grew up in Dorchester.
Sidney started his career in sales, including owning a mattress franchise and an insurance agency. Deanna worked as an assistant at Raytheon. The couple raised their family in Lexington. Sidney’s mother, who was blind, lived with the family for many years.
Sidney started Cross Country Motor Club in 1972. Deanna helped in the early years, and the Medford-based organization, now known as the Cross Country Group, is one of the largest privately held businesses in Massachusetts.
Areas of Giving
The Sidney & Deanna Wolk Family Foundation provides support to a range of organizations, including social services, elder care, and education. Past recipients of significant gifts include Hebrew Senior Life, Boston Latin School, Greater Boston Food Bank, and agencies who support the blind.