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The native peoples who originally lived in this area called it “Winnisimmet” meaning “good spring nearby.” Sadly, by the time of the first Europeans arrived, their numbers had been greatly reduced by tribal warfare in 1615 and a plague which affected large numbers along the New England coast in 1616.

Samuel Maverick settled here in 1624, and built a fenced fort at Noddles Island, what is now part of East Boston, directly facing Winnisimmet. Maverick sold his holdings outside his farm in Winnisimmet to Richard Bellingham, the deputy governor of Massachusetts.

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In 1630 Thomas Williams "hath undertaken to set up a ferry betwixt Winnisimmet and Charlestown." Williams died soon after establishing his ferry. His widow married William Stitson and they continued the operation under a grant from Richard Bellingham.

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Admiral's Hill for over 200 years was nearly all marshland and farms, and the inhabitants were primarily farmers and traders. Bellingham’s farm later became the site of the Naval Hospital on Admiral’s Hill.  The Williams farm was in this area too.

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This site, which is now the end of Winnisimmet Street, was the first documented dwelling dating back to 1731.

Cobblestones, still found in this area, were once everywhere in Chelsea, and date back to the late 19th/early 20th century. By the late 1800s, trolleys also traveled down these roads.

Many of the properties in this area have been recognized as contributing to an historic district of the Chelsea Waterfront Neighborhood. It is only through specific designation that the neighborhood's cultural assets can be saved from demolition. Thanks to work in recent years by the Chelsea Historical Commission this block of cobblestones was given local historic protection so people in the future can continue to see this relic of our past.

George Henry Hood, an early entrepreneur in the growing American rubber industry of the 1830s, founded the Boston Rubber Company in 1877. Though the company later merged with others to form United States Rubber, the factory site continued to house at least two other rubber manufacturing companies well into the 20th century. The condominium building now on this site, which used to house administrative offices and supplies, and the waterfront brick warehouse, are all that remain of what was once a large bustling factory complex.

As with many shoreline areas, this part of the Chelsea waterfront was originally the site of shipbuilding, and lumber and coal yards. From the late 1800s until about the 1950s this location served as a service depot for lightships in New England and the Eastern seaboard, and also as storage for harbor buoys, lighthouse supplies, etc. The property was later occupied by Quincy Gas, and is currently the site of Eastern Minerals Company. As these areas developed, historic uses of the shoreline led to the continuation of certain industries. Areas like this, which in the past stored wood and coal, evolved into the oil and gas storage facilities which exist to this day.

By the mid to late 1700s, with the growth of the city of Boston across the harbor, ship building and industry developed along the shoreline. And, as the area evolved and grew, people and trade from the north needed a way to travel to and from Boston. 

The Winnisimmet Ferry, founded in 1631 and located at the end of the street, had already been in continuous operation for 144 years by the time of the American Revolution. For nearly three centuries the ferry moved passengers, animals and goods (with some limitations) back and forth between Boston’s North End and Chelsea, and was a hugely important lifeline to Boston and the surrounding cities. The last passenger disembarked in 1917. However, this location continues to be a functioning shipyard, and has been for close to 400 years.

A vital means of transport, the Massachusetts Court regulated the ferry's fares and schedules and enforced safety protocols. The occasional perils of this water route are described in the diary of Cotton Mather (1681-1724): ‘A fearful hurricane and thunderstorm overtook us, just as we got out of Winnisimet Ferryboat (a ferry three miles wide), which, had it overtaken us four or five minutes earlier, we had unquestionably perished in ye waters.’

Fitzgerald Shipyard can trace its lineage back to the establishment of the Winnisimmet Ferry in 1631, the first passenger ferry in the American colonies.The site of the Fitzgerald Shipyard serviced the ferry and was essential during the Revolutionary and Civil Wars when the water route transported soldiers, cannon, and essential provisions.

After taking possession of the Winnisimmet Ferry in 1897, the site, formerly known as the Green Yard, was dredged to make way for a new dry-dock. This allowed for the service of larger steam-powered ferries to better compete with land-travel innovations like steam railroads.

In 1917, after 286 years of service, the Chelsea Ferry ceased operations, but the shipyard continued to service vessels.

During World War II the Green Shipyard was taken under Wartime Powers Act by the Department of the Navy and served in the war effort as an annex for the nearby Charlestown Navy Yard. At the end of conflict, the property was sold and operated for 40 years as Munro Shipyard. After a failed redevelopment bid in the 1980s, followed by years of decline, the Fitzgerald Shipyard reactivated the dry-dock in 1992 and resumed commercial work at the site. Today it is the only 60-foot-wide, 1600-ton dry-dock on Boston Harbor.

The direct descendant of the Winnisimmet Ferry, this shipyard is the only active ship repair facility with a 60'-wide, marine railway for vessels of 1600-ton located in the Boston Harbor. This 10-acre waterfront site continues to serve maritime industries around New England and the Eastern Seaboard. The historic lightship Nantucket (LV-112)  is regularly serviced here, including, in 2021 a comprehensive, $1.4 million structural restoration.

Initially, immigrant workers on the waterfront arrived from the British Isles and Canada. By the end of the 19th and early 20th century, the neighborhood was Jewish, Polish, Italian, and Irish. Today this area is mostly residential, but in those days it was a family neighborhood with flats, tenements, and boarding houses. It’s not difficult to walk around this neighborhood and see the remains of what were once shop fronts, small markets, taverns and clubs. For example, there was a market at the base of the building on the corner of Tremont and Beacon Streets. Children would buy shaved ice there. Another shop occupied the basement of the building at the corner of Tremont and Medford Streets.

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As part of her "People of Chelsea" photo project Darlene DeVita interviewed neighborhood residents Bobbie and Rick Zonghi in 2019: "We bought the house [on Medford Street] in 1971 for $1,000 [and finished renovating in 1973]. We went before the Aldermen and told them if they sold us the house we would rehabilitate the building and put it back on the tax rolls, and we would become residents of Chelsea. The not-to-remain-nameless Alderman Jim Mitchell wanted to make it into a parking lot. There were quite a number of vacant places. Many [of the residents] had lived here all their lives, it was an old Polish neighborhood.  A lot of the neighbors came up to us and said they’d sell their building to us for $500-1,000. They thought we were crazy! We knew we were taking somewhat of a chance, but it was worth the investment.  It was a neighborhood then, and it’s still much a neighborhood now. That’s hard to find this day and age."

Built in 1790, this house was the toll stop for the original Chelsea Bridge.

It’s dramatic setting has led a number of film production companies to use the home as a location.

In the industrial era this neighborhood was bustling and noisy:  the smell of the sea, tar, oil and soot coming from local factories; the clanging sounds of shipping; the constant damp smoke hanging in the air; the voices and footsteps of mariners and factory workers coming and going; children running and yelling in the streets; and almost as many shops as residences. All of humanity ran through lower Broadway on their way to and from Boston, across the bridge.

By the late 1700s, the limitations of the Winnisimmet Ferry had become too restricting. Large freight, animals, and stagecoaches, headed to and from Boston, faced an additional land journey of over 20 miles, via Malden and Medford to the neck linking Somerville and Charlestown. The first Chelsea Bridge linking lower Broadway to Boston was built across the harbor in 1802. The tollhouse for that bridge, which still stands, was built in 1790.

The original bridge was replaced by the first Chelsea North Bridge (called North because of the addition of a southern span linking Chelsea and East Boston).  The Chelsea North Bridge was a wooden drawbridge but was rebuilt as a metal pivot bridge in 1935.

The Tobin Bridge replaced the Chelsea North Bridge in 1950, and ultimately had a negative effect on the life of the neighborhood.

The Chelsea Yacht Club was founded in 1886. Its mission is to promote and encourage boating and boating activities and to provide a suitable clubhouse and associated facilities for the recreational and social use of its members. Access to the CYC was previously linked directly via the earlier Chelsea North Bridges, which ran between the club and where the Tobin currently sits.

Currently the location of Global Petroleum, this location previously served as the home of Metropolitan Coal, which had plants  throughout the region. It served as a delivery  and distribution point for coal and oil, and employed many local residents. Prior to the 20th century, this location was the Campbell and Co. Coal and Wood Wharf, a coal and lumber yard, featuring a sawmill, and various machine shops. The footprint of historic industrial areas often give way to similar industries and usage.

At the start of the 20th century this neighborhood was made up of immigrants, the largest of that group was from Poland. This section of Broadway had Polish clubs and shops. The Polish Political Club was founded in 1913 to educate, assimilate and provide assistance to Polish immigrants and their descendants as well as those from Russia, Poland, Hungary and Lithuania. The club's "White Eagle Hall" hosts functions.