Charles River Dam

The Warren Bridge connected downtown Boston, Massachusetts with Charlestown from its construction in the 1820s until its demolition in 1962. It was replaced by the Charles River Dam in 1978. The Warren Bridge was requested in 1823 and chartered in 1828 by John Skinner and Isaac Warren, in response to the politically unpopular tolls on the 1786 Charles River Bridge. Its proprietors were authorized to collect tolls until they were reimbursed the cost of building the bridge and the other necessary expenses, with five per cent interest thereon, when the bridge was to revert to the Commonwealth. They were expressly limited from taking tolls for a longer period than six years. The bridge opened for travel on December 25, 1828. It connected Beverly Street in the North End of Boston to the then-independent city of Charlestown at City Square. The Charles River Bridge also terminated at City Square, with the Boston side at Charlestown Street (now North Washington Street, the site of the current Charlestown Bridge). This prompted a lawsuit, in which Daniel Webster served as attorney for the Charles River Bridge proprietors, which eventually reached the United States Supreme Court as Charles River Bridge v. Warren Bridge. The Commonwealth in 1833, assumed the control of the bridge, and tolls were received to its use until April, 1836, when the bridge was declared free. The Warren Bridge devolved to a state-owned, toll-free bridge on March 2, 1836. The receipts from tolls charged by the State on the Charles River Bridge and Warren Bridge, were sufficient to establish a fund of $850,000; and on the 1st December, 1843, the bridges were declared free, and so remained until June 1, 1854, when the income of the fund being found insufficient to sustain the bridges, and a large portion of the principal having been expended, tolls were again imposed on both bridges, to continue until a sufficient sum should be received to rebuild the Charles River Bridge, and repair the Warren Bridge, and to leave in the treasury of the Commonwealth a fund of $100,000 for the future maintenance and repair of the bridges. This was accomplished in 1858, and since April 30, 1858, both bridges were free.

The Charlestown Bridge, officially named the North Washington Street Bridge, is located in Boston and spans the Charles River. As the river's easternmost crossing, the bridge connects the neighborhoods of Charlestown and the North End. Completed in 1900 and given its current official name in 1910, the bridge carries a portion of the Freedom Trail linking to the USS Constitution and Bunker Hill. To the north of the bridge, Route 99 begins and the street becomes New Rutherford Avenue.Replacement of the bridge started in fall 2018 and is expected to be completed in 2023.

The Charlestown High Bridge (referred to as the John F. Fitzgerald Bridge on old AAA Tourbook maps) spanned the Charles River in Boston, Massachusetts and was part of I-93/US 1 at the north end of the Central Artery. This double-decked truss bridge, built in 1954, was to originally carry I-95 through Boston from southwest to northeast in tandem with the Tobin Bridge, built in 1950. The I-95 project and several other highway projects in and around Boston, including both the highly controversial Inner Belt (I-695) and the Southwest Corridor, completing the right-of-way intended to bring I-95 into Boston from Providence, Rhode Island, were cancelled due to heavy public opposition in the early 1970s. I-93 was allowed to be completed from the Yankee Division Highway (Route 128) to the foot of the Charlestown High Bridge in 1969, and the I-93 designation was extended onto the bridge and the Central Artery in the early 1970s. Originally intended to carry 75,000 vehicles per day in the 1950s, the Charlestown High Bridge carried upwards of 200,000 vehicles per day in the 1990s. For years, the bridge was a major traffic bottleneck that affected southbound commuters from Boston's North Shore and southern New Hampshire for miles. Travelling northbound, due to a poorly planned lane drop to accommodate incoming vehicles from Storrow Drive, traffic backups leading to the High Bridge threatened to cause hours of daily gridlock in downtown Boston. These problems were addressed in the planning and construction of the $14.6 billion Big Dig project. The cable-stayed Zakim Bunker Hill Bridge, which opened fully to traffic in December 2003, replaced the Charlestown High Bridge, which was demolished in 2004.

Paul Revere Park is a five-acre (2.0 ha) park located on the Charles River in Charlestown, Massachusetts. The park was the first park to open along the "Lost Half Mile" of the Charles River as mitigation for the taking of planned parkland for the construction of the Big Dig. The park runs along the Charles River between the Freedom Trail on North Washington Street and the Leonard P. Zakim Bunker Hill Memorial Bridge. The park features a large oval-shaped lawn, an informal performance area, and a playground.The park first opened in 1999, although the upstream portions of the park were used as a staging area for the construction of the Zakim Bridge and did not open until 2007. The North Bank Bridge, a 690-foot pedestrian bridge under the Zakim Bridge and over the MBTA railroad tracks leading into North Station, opened in 2012, connecting the park to North Point Park in Cambridge, Massachusetts.

The Leonard P. Zakim () Bunker Hill Memorial Bridge (also known as the "Lenny" or “The Zakim”) is a cable-stayed bridge completed in 2003 across the Charles River in Boston, Massachusetts. It is a replacement for the Charlestown High Bridge, an older truss bridge constructed in the 1950s. Of ten lanes, using the harp-style system of nearly-parallel cable layout, coupled with the use of "cradles" through each pylon for the cables, the main portion of the Zakim Bridge carries four lanes each way (northbound and southbound) of the Interstate 93 and U.S. Route 1 concurrency between the Thomas P. "Tip" O'Neill Jr. Tunnel and the elevated highway to the north. Two additional lanes are cantilevered outside the cables, which carry northbound traffic from the Sumner Tunnel and North End on-ramp. These lanes merge with the main highway north of the bridge. I-93 heads toward New Hampshire as the "Northern Expressway", and US 1 splits from the Interstate and travels northeast toward Massachusetts' North Shore communities, crossing the Mystic River via the Tobin Bridge. The bridge and connecting tunnel were built as part of the Big Dig, the largest highway construction project in the United States. The northbound lanes were finished in March 2003, and the southbound lanes in December. The bridge's unique styling quickly became an icon for Boston, often featured in the backdrop of national news channels, to establish location, and included on tourist souvenirs. The bridge is commonly referred to as the "Zakim Bridge" or "Bunker Hill Bridge" by residents of nearby Charlestown. Notwithstanding, Boston sports fans also refer to the bridge as the "Bill Buckner Bridge" after Red Sox fielder Willam Buckner, since like Buckner's famous mishap, traffic goes between the legs of the bridge. The nickname takes on significance as Boston sports fans came to fondly embrace Buckner after many years.The Leverett Circle Connector Bridge was constructed in conjunction with the Zakim Bridge, allowing some traffic to bypass it.

An 800-pound (360 kg) bronze statue of Bobby Orr is installed outside Boston's TD Garden, in the U.S. state of Massachusetts. The sculpture was designed by Harry Weber, and unveiled on May 10, 2010.

North Station is a commuter rail and intercity rail terminal station in Boston, Massachusetts. It is served by four MBTA Commuter Rail lines – the Fitchburg Line, Haverhill Line, Lowell Line, and Newburyport/Rockport Line – and the Amtrak Downeaster intercity service. The concourse is located under the TD Garden arena, with the platforms extending north towards drawbridges over the Charles River. The eponymous subway station, served by the Green Line and Orange Line, is connected to the concourse with an underground passageway.

TD Garden is a multi-purpose arena in Boston, Massachusetts. It is named after its sponsor, TD Bank, a subsidiary of the Toronto-Dominion Bank of Toronto, Ontario. It opened in 1995 as a replacement for the original Boston Garden and has been known as FleetCenter, and TD Banknorth Garden. The arena is located directly above the MBTA's North Station. It is the most visited sports and entertainment arena in New England, as nearly 3.5 million people visit the arena each year.TD Garden is the home arena for the Boston Bruins of the National Hockey League and the Boston Celtics of the National Basketball Association. It is owned by food service and hospitality conglomerate Delaware North, whose CEO, Jeremy Jacobs, also owns the Bruins. It is the site of the annual Beanpot college hockey tournament, and hosts the annual Hockey East Championships. The arena has also hosted many major national sporting events including various rounds of the NCAA Division I Men's Basketball Tournament, NCAA Division I Women's Basketball Tournament, NCAA Division I Men's Ice Hockey Tournament, and the 2014 United States Figure Skating Championships. In addition, TD Garden has hosted the 2021 Laver Cup, an international men’s tennis tournament. Besides sporting events, the TD Garden has also served as a concert venue for numerous nationally touring acts in music and comedy.

The Hub on Causeway is a 1,500,000 sq ft (139,400 m2) mixed-use development in West End, Boston adjoining the TD Garden and North Station, and on the site of Boston Garden, which was razed in 1998. Before its construction, the former Garden footprint served as employee parking. As of March 1, 2022, two towers built as part of the development are among the tallest buildings in Boston.

The Hotel Manger (pronounced Mang-er as in hangar), renamed the Hotel Madison in 1959, was a Boston hotel that operated from 1930 to 1976. It was attached to North Station and the Boston Garden. In 1983, the building was demolished to make way for the Thomas P. O'Neill Jr. Federal Building.

Boston Garden was an arena in Boston, Massachusetts. Designed by boxing promoter Tex Rickard, who also built the third iteration of New York's Madison Square Garden, it opened on November 17, 1928, as "Boston Madison Square Garden" (later shortened to just "Boston Garden") and outlived its original namesake by 30 years. It was above North Station, a train station which was originally a hub for the Boston and Maine Railroad and is now a hub for MBTA Commuter Rail and Amtrak trains. The Garden hosted home games for the Boston Bruins of the National Hockey League (NHL) and the Boston Celtics of the National Basketball Association (NBA), as well as rock concerts, amateur sports, boxing and professional wrestling matches, circuses, and ice shows. It was also used as an exposition hall for political rallies such as the speech by John F. Kennedy in November 1960. Boston Garden was demolished in 1998, three years after the completion of its successor arena, TD Garden.

The Fours is a sports bar with locations in Quincy and Norwell, Massachusetts. The now-closed Boston location was voted the best sports bar in the United States by Sports Illustrated in 2005. It was established in 1976. It was noted to be a rare late-night option for the South Shore by the Boston Globe in 2009.