Interstate 290 forms a loop connecting the city of Worcester south with the Mass Pike (Interstate 90) at Auburn and east to Interstate 495, the outer beltway for Boston, at Hudson. The western end of I-290 shares a terminal point with Interstate 395 north from Connecticut. Interstate 190 stems north from I-290 at the eastern turn from Worcester to Shrewsbury and Northborough.
A freeway loop north from I-90 (Massachusetts Turnpike) into Worcester was part of the original Interstate Highway System plans for the state of Massachusetts conveyed to the American Association of State Highway Officials (AASHO) on April 10, 1958. The Massachusetts Department of Public Works selected Route 90N for the loop because it lied north of I-90. This was revised to Interstate 290 by August 18, 1958 and included in the Interstate Urban Numerology for the state approved by AASHO on November 13, 1958.
Interstate 290 opened initially by Washington Square in September, 1960. Completion of the route occurred in 1970 with the extension to Marlborough.1
Initial proposals for Interstate 290 looped the route southeast from Worcester to an end point at the confluence of Interstate 90 (Massachusetts Turnpike) and Interstate 495 in Hopkinton. This alignment shifted northward to the present course of I-290 by 1965.1
Construction of I-290 at the east end included a stub beyond the full cloverleaf interchange linking the freeway with Interstate 495. This changed by the mid 1970s with construction of the Route 85 Connector. The connector leads extends east from the exchange to Massachusetts Route 85 at Technology Drive. As part of the work to build the expressway spur, the loop ramp from I-290 east to I-495 north was replaced with a sharp left side ramp.