Massachusetts gateway cities are "midsize urban centers that anchor regional economies around the state," facing "stubborn social and economic challenges" while retaining "many assets with unrealized potential." These communities, which all had a legacy of economic success, have struggled as the state's economy shifted toward skills-centered knowledge sectors (increasingly clustered in and around Boston). 
The designation was initially applied to eleven cities named in a 2007 report co-authored by the Brookings Institution and the Massachusetts Institute for a New Commonwealth ( MassINC). In May 2008 the chief executives of the eleven Gateway Cities gathered at the Old State House in Boston "to sign a compact to unite their administrations in future efforts aimed at economic and community development," asserting their desire to work cooperatively to address issues of common concern. 
A legislative definition (Section 3A of Chapter 23A of the General Laws of Massachusetts) put in place in 2009 and amended in 2010 expanded the designation of gateway cities with fifteen more locations, for a total of 26 cities. Under the General Laws, gateway cities have a population between 35,000 and 250,000, with an average household income below the state average and an average educational attainment rate (Bachelor's or above) below the state average. Updates to the Census data in 2013 led to the addition of two cities (Attleboro and Peabody) for a total of 26 communities.
The Gateway Cities Legislative Caucus was founded in 2008 by State Representative Antonio F.D. Cabral and State Senator Stephen J. Buoniconti. As House and Senate co-chairs of the Caucus, they were joined by 58 other representatives and 20 other senators who represent Gateway Cities. In 2012, Senator Benjamin Downing replaced retiring Senator Buoniconti as the Senate chair.
- Gateway Cities Compact for Community and Economic Development (2008)
- MassINC Gateway Cities Innovation Institute
- Gateway Cities and Program Information - Massachusetts Executive Office of Housing and Economic Development
- Gateway cities in Massachusetts - Boston Globe editorial series