Toomey is a graduate of Matignon High School in Cambridge and holds a bachelor's degree from Suffolk University in Boston, MA.

[15][16] In August 2010, Toomey submitted a resolution to the Cambridge City Council in support of the DREAM Act, which was adopted by the membership.

[17][18] Toomey has voiced opposition to the State's proposal to expand MBTA commuter rail service[19] to North Station via the Grand Junction Railroad.

Toomey is an avid supporter of the Grand Junction Multi-Use Path proposal that would bring a walk/bike route to eastern Cambridge, connecting with Boston on the southern end and Somerville on the north.

He won a substantial investment from the Massachusetts Institute of Technology to fund a partial feasibility study and construction of a section of the Grand Junction Path during a Fall 2013 zoning negotiation.

[26] He reasoned that casinos would provide an economic benefit to the state, and released the following statement: "[the expanded gaming bill] would increase revenue and create jobs while mitigating community impacts and implementing a comprehensive regulatory structure..."[27]