The turnpike intersects with several Interstate Highways as it traverses the state, including I-91 in West Springfield; I-291 in Chicopee; I-84 in Sturbridge; the junction of I-290 and I-395 in Auburn; and I-495 in Hopkinton.

The Fast Lane electronic toll collection system was introduced alongside cash payment in 1998; it was later folded into the E-ZPass branding in 2012.

[4] The 0.75-mile (1.21 km) underwater section of the Ted Williams Tunnel, which carries the turnpike under Boston Harbor to its eastern terminus at Route 1A by Logan International Airport, is reduced to four lanes.

[18] Past the tolls, the turnpike reduces to six lanes, heads through the campus of Boston University and passes Fenway Park before crossing over the Muddy River as it approaches the city's central neighborhoods.

[24] Members of the Massachusetts Legislature Transportation Committee cited the potential need to amend state law and the uncertainty of how the turnpike would be maintained as setbacks to the toll removal, which ultimately never came to fruition.

[25] In the November 9, 2006, edition of The Boston Globe, Governor Mitt Romney announced his intention to try to remove the tolls before his successor, Deval Patrick, was inaugurated in January 2007, but this did not occur.

Its former maritime industries had closed as traffic in the harbor declined, the textile mills that had provided a large portion of the city's wealth had migrated out of the region seeking new locations that would allow them to maximize revenues, and property development had ground to a halt with virtually no new construction of any impact occurring since the beginning of the Great Depression.

It was in 1947 that Republican Governor Robert F. Bradford realized that the commonwealth needed to implement a standard framework to properly guide the planning and construction of these new roadways.

[41] To oversee this undertaking, Dever brought in the former commissioner of the Massachusetts Department of Public Works, William F. Callahan, to once again head the agency he had helmed from 1934 to 1939.

Utilizing the political goodwill he accrued during his tenure as public works commissioner, primarily through extensive patronage hires,[41] Callahan was able to push his idea for the new authority through the State House with ease.

[45] The authority was formed in early 1952, and, by 1955, it had issued the required bonds needed to construct a 123-mile (198 km) highway from the New York–Massachusetts border to the recently completed Route 128 in Weston.

It was his plan to bring the tolled turnpike from its terminus at Route 128 in West Newton into the city along the path of the Boston and Albany Railroad and connect it to the Southeast Expressway.

[50] Complicating the matter, Callahan's planned extension route was not universally accepted by others within the state, such as newly elected Governor John A. Volpe and Newton Mayor Donald Gibbs, who sought to construct a freeway that would follow a different route between the Borders of Newton, Waltham, and Watertown along the Charles River and US 20 and be constructed using the funds now being provided by the Federal Highway Administration (FHWA).

[52] Newton, through the terms of two mayors, set about fighting the turnpike proposal through a series of increasingly futile legislative maneuvers in the General Court.

[53] Affected property owners within Boston who were also looking at the possibility of losing their homes and business followed Newton's lead by filing a series of state and federal lawsuits that they hoped would derail the proposed extension.

[54] In the late 1950s, eminent domain takings for the Massachusetts Turnpike Extension into Boston devastated the historic Black-American community named "The Village".

As a result, East Boston saw almost no takings of buildings or homes through eminent domain or the destruction of neighborhoods because construction was relegated to the then-unoccupied areas of the Seaport District and Logan International Airport.

[65] On November 27, 2006, departing Attorney-General Thomas Reilly (Democrat) announced the state would launch a civil suit over the collapse of the ceiling in the Ted Williams Tunnel.

[4] Under legislation signed into law by Governor Deval Patrick on June 26, 2009, the turnpike was folded into a new superagency that controls all surface transportation in the state.

The new agency, MassDOT, operates all highways formerly under MassHighway and the MTA as well as eight urban roadways formerly owned and maintained by the state Department of Conservation and Recreation (DCR).

[84] The 2009 edition of the Manual on Uniform Traffic Control Devices required that all US states submit plans to transition to milepost-based exit numbering by 2012.

[92] Among other objectives, guidelines established by the "Civic Vision for Turnpike Air Rights in Boston" in 2000 recommend that the proposed use of the parcels "[foster] increased use and capacity of public transportation" and "[reinforce] the vitality and quality of life in adjacent neighborhoods".

In the 1960s, the MTA intended to route the highway through the parking lot of the supermarket's previous location in the city; this alignment was ultimately approved by the SJC, under the condition that a replacement Star Market was allowed to be built above the turnpike.

[102] Parcel 12[103] is between Newbury Street, Boylston Street, and the west side of Massachusetts Avenue and is expected to feature a 13-story citizenM hotel, a 20-story office tower (including the headquarters of CarGurus), a reconstructed bus shelter, a public park, street-level retail, and a new entrance to the Hynes Convention Center station of the Green Line subway.

[101] The developer of Parcel 13, on the east side of Massachusetts Avenue along Boylston Street, submitted updated plans in February 2020, with 17 stories of condos, hotel, parking, and public space.

[110] The state conducted a study to determine the feasibility of such a project in 2018;[110] land occupied by a service plaza and a maintenance facility (both in Blandford) and Algerie Road in Otis have been suggested as locations for a potential exit.

[118] In September 2021, after much public criticism of the viaduct and river impact during construction, a new final design was announced, which keeps the turnpike and Soldiers Field Road at-grade.

[129] Governor Mitt Romney, elected in 2002 during a fiscal crisis, ran on a political platform of streamlining state government and eliminating waste.

The governor has the power to appoint members to the board, but the SJC advised in an advisory opinion that "nothing in G. L. c. 81A explicitly provides for the removal and reassignment of the chairperson to the position of 'member'".

Romney continued to press the legislature to give him the power to remove members from the board, specifically the chairman, pointing to a series of financial and construction mishaps over the last several years.