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In addition to shops, this lively area at the gateway to the city was the home of a number of taverns and restaurants. The Old Bridge was one such place. It’s license eventually was sold to the New Bridge Cafe, which today operates in the Prattville neighborhood of Chelsea.

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At one time was also the Chelsea Marine selling supplies to fishermen and boaters.

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This segment of Chelsea has a long history of serving those journeying to and from Boston. As recorded in the 1937 The WPA Guide to Massachusetts: "The hazards of wind and tide often delayed travel; so, before long, taverns sprang up near the ferry, where, besides a night’s lodging, ‘strong waters’ might be had to console or embolden the traveler."

For those coming and going along this corridor of Broadway, places like the Beacon Cafe were a place on the way home and provided a kind of second home for gatherings with friends from the city.

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It's believed the bar opened in 1912 so it survived the years of Prohibition.  In the 1980s it was owned by Joshua Resnick and Arnie Jarmak, respectively the editor and photographer of the Chelsea Record newspaper. Benign neglect reigned here so little had changed at The Beacon over the decades  it was in business. Today, ghost images of the painted sign remain on the facade directing customers to the pool tables and bowling available through the side entrance.

Founded and incorporated in 1827 as The Boston Seaman’s Friend Society, Seafarer's Friend's ongoing mission is to provide for the spiritual, social, educational and recreational needs of visiting mariners. The organization continues its services today.

Through much of the 20th century this was the site of a hotel and within it the Williams Restaurant (the advertisement for it lingers on the brick wall of Broadway and Medford) and then the Tremont Cafe.

In the mid-20th century, as manufacturing moved out of urban areas throughout the US, and the Tobin Bridge moved traffic out of lower Broadway, the residential area of the waterfront began to fragment. In addition, two major catastrophic fires within a century, and city-wide corruption, proved to be a fatal obstruction to Chelsea’s early dreams of being a world-class city of industry. As the city decayed, the fate of the waterfront went with it. By the late 70s, the waterfront was a place many avoided. Casual visitors saw only the impacts of drugs and crime and not the whole people who continued to call the neighborhood home.

As recounted by Liz Joyce, a former neighborhood resident, “The Tremont was a great little watering hole because it wasn't a tavern so women could go in and have a drink. Next to the Tremont was the infamous card room. It was raided one day and my cousin was arrested, so funny. Everybody played the numbers. We had a neighborhood bookie...every street had one. That's where you spent a dime, a quarter, sometimes a dollar, depending upon how flush you were. Great names for the bookies too – I remember Louie the shoe, lol. We played slot machines and played the dogs and the horses and all the clubs, all of them without exception until it was all closed down."

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The District Courthouse was constructed in downtown Chelsea as part of a revitalization effort of the city in the 1990s.

A wave of gentrification affecting urban landscape nationwide and fresh investments for Chelsea’s downtown has changed this corner. Formerly it was the home of Parrotta’s Alpine Lodge.

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A neighborhood institution and watering hole since 1932, Parrottas had not changed much by the time it was closed. In 2018 Parrotta’s was torn down to make way for the building of a new restaurant and condos.