Looking Back at Boston’s Old Expressway

Here are words that I never thought I would say.  I am feeling a little nostalgic about the old expressway that used to run through downtown Boston.

As a reader commented in response to my cover photo last week, “Wow, how different Boston is now with Garden Towers, Bulfinch Towers and all the other developments… and obviously the suppressed freeway.”  The residual areas such as the Rose Kennedy Greenway created by the progress marked by Boston’s Big Dig provide a more Epcot Center version of Beantown rather than the wharf-filled industrial waterfront that typically characterized the city.  The old expressway was not a beautiful work of art as the Leonard P. Zakim Bunker Hill Bridge provides, but it was ours, and it did offer a certain amount of urban character as you traveled through the city from the old tunnel to points north.   

The Dewey Tunnel was the entrance to Boston if you were coming in from the south between 1959 and 2005 (although some say it might have taken that long just to get through the traffic).  It was a lot shorter and definitely more narrow than the current tunnel.  The old tunnel was also hotter and, most likely due to age, much dirtier.  Although originally named after Admiral George Dewey of Spanish-American War fame, it was commonly known as the South Station Tunnel.  As a kid I preferred to think that the tunnel was named after Red Sox right fielder Dwight (Dewey) Evans.  Exiting the South Station Tunnel heading north through the city provided a view of Boston like no other, almost like the city’s own traffic congested, claustrophobic monorail providing a scenic overview from above.

The Northern Ave. part of Boston was visible to the immediate right as you exited the tunnel.  This expanse is now completely developed into a new neighborhood known as the Seaport District, but back then it was a rather desolate area on the other side of the antiquated Northern Ave. Bridge, a rusted structure that is still there although it no longer provides the main gateway to this part of the city.  Heading over the Northern Ave. Bridge would lead you down what was essentially a dusty and somewhat forbidding road, the location of famous restaurants Anthony’s Pier 4, the No Name, and Jimmy’s Harborside, all situated on working piers along the industrial waterfront.  

Coming out of the South Station Tunnel to your left you could catch a quick look at Boston’s Chinatown neighborhood until your view was blocked by International Place, a relatively new 46-story building constructed in the early 1990s which provided a towering cover for the Quincy Market area and Faneuil Hall.  Flanking the left side of the old green expressway, the Flour and Grain Exchange building rose up next to the highway like an old turreted castle, memorably decorated each holiday season with an enormous red ribbon and bow offering the message of Season’s Greetings to those driving by. 

To the right was Rowes Wharf, an establishment that would redefine the Boston waterfront when completed in the late 1980s with its huge archway providing a visual entryway to the harbor.  After Rowes Wharf there was a view of the New England Aquarium and then the Marriott Long Wharf.  Built in 1982 the Marriott Long Wharf was sometimes referred to by locals as the Marriott Lunch Box, believing it more closely resembled a huge lunch pail rather than the ship it was originally designed to look like.  

Faneuil Hall and Quincy Market could then be seen off to the left of the expressway under the sign for Durgin-Park, the famous restaurant that opened its doors in 1827 and closed for good in 2019.  Before being renovated, the Quincy Market area had fallen into a state of disrepair.  Tagged for demolition during the early 1970s, this area was renovated extensively to coincide with the city’s Bicentennial celebrations of 1975-1976 and was saved due to the efforts of a historically-minded group of Bostonians who wisely fought to preserve the buildings as historic landmarks.  

The buildings further up to the left along the expressway were not so lucky.  The Scollay Square area was demolished to make way for Boston’s new City Hall Plaza and then the Haymarket Center Garage, two concrete monstrosities visible from the old expressway.  Both of these structures are emblematic of so-called urban development in Boston, a move toward architectural modernization that also destroyed the city’s nearby West End.  

To the right you could peer down off the highway into the North End of Boston, the Italian neighborhood quietly cordoned off from the rest of the city by the green, dirty, divisive expressway.  From above, the North End was unassuming in comparison to the overstated Boston City Hall building on the opposite side of the highway, somewhat ironic as the North End was probably more loud and vibrant than any other location in the city.  

And finally on the left was the Boston Garden - the real Boston Garden.  From the expressway, the original Garden had a much different look than it did from down below on dark and dirty Causeway Street, where the elevated train tracks carried the Green Line to Lechmere Station.  But from the expressway up above, the Garden was majestic, with two spires on either side and its name colorfully displayed across the top.   

While traversing the city, this was also your last chance to scoot off the highway to either Causeway Street or a continuation to Leverett Circle.  It was the point of no return on the old green expressway before you would continue on 93 North or veer off onto the Tobin Bridge leading to Route 1.  This part of the northern artery leaving Boston had the appearance that you were actually about to fly off as you left the city, starting from the South Station Tunnel and continually rising until crossing the Charles River at what felt like the expressway’s highest point with signs overhead directing you north. 

The city of Boston no longer advertises itself with such self-promotion.  You enter the city by driving into a tunnel and you come out the other side directly onto the Zakim Bridge.  You do not see the harbor, the historic Faneuil Hall area, Rowes Wharf, look down into the North End, or even catch a glimpse of the new Boston Garden (unless you are traveling from the north).  You do not see signs for Joe Tecce’s, Scotch ‘n Sirloin, or even Spuds MacKenzie.  

There is still heavy traffic going through Boston, although it might not be quite as congested as it once was.  According to the Boston Globe, “While traffic is moving better in the core, it is worse elsewhere.  The Big Dig didn’t solve congestion south and north of downtown.”  

I happen to think that there is a certain charm to a city that, well, looks and feels like a city.  Am I really missing Boston’s old crowded expressway?  I guess if that’s the case, I must really love that dirty water.  Boston, you’re my home.