Massachusetts ‘Funniest Street’ Name Is Not Actually That Funny

Street names represent the place you call home, serve as passwords, and sometimes can provide a chuckle. Recently, Reader's Digest went through each state and called out the funniest street name. The thing is, the street selected for Massachusetts is not actually a funny name at all. On the contrary, it's a relatively comforting street name to live on. Reader's Digest's feature challenges the readers to think about why the name is funny. Furthermore, in an example like Massachusetts's funniest street name, there's a bit of irony to uncover. So, what is the funniest street name in the Bay State?

In close proximity to the Bay Station and Savin Hill T station is where you will find the funniest street name in Massachusetts. With a few bends, it primarily runs north and south. Its hilarious name is "Pleasant Street."

Why is that funny? Fair question. It's not really that funny. But Reader's Digest suggests you look at the big picture of where Pleasant Street is. Right off Pleasant Street is a name that is usually associated with a creature that is anything but pleasant. Roach Street is connected to the middle of Pleasant Street. In fact, it's nestled right in between Pleasant Street and a small waterfront spot called Malibu Beach. Admittedly, it does provoke a slight chuckle looking at a more extensive map where something named roach is attached to pleasant.

However, we think some of these funny street names throughout the state could have been more worthy. Chickatawbut Street, is. much funnier name.  It's even in the same city. Moreover, it's less than three miles from Pleasant Street.

Then, there's Goodenough Street in Brighton. I'm not sure what a "Thwing" is but it has its own street in Roxbury. Lastly, just one mile down the road from Thwing Street is Wigglesworth Street

In New England, it's confusing enough to know when you pronounce a "R" in a name and when you don't. Luckily, in these unique Massachusetts town names you won't have that problem. They are all straightforward in their spelling, and result in a chuckle.

Many of these locations are spread in rural parts of the state. Even those born and raised here may have never known they existed. The common thread between them results in two questions. Why? And, who got to select this name?

Whether we are talking about a two-state description or a 700 household community nuzzled into a larger town, there is no shortage of creativity here. Massachusetts is well-known for its wide array of Universities. In addition, we experience all four seasons to the fullest. The state is filled with passionate sports fans that stand behind five professional teams. Furthermore, there is deep history tied to very formative years of the country. From Pilgrims to Mayflowers to Rocks. Yet, none of those elements seem to factor into the naming of these municipalities.

The Bay State is certainly filled with culture. There are islands (including Five Pound Island). A Cape Cod town that combines Barn and Stable. Not to be forgotten is a coastal hamlet called Cow Yard While it was hard to pass by Second Cliff, Third Cliff and Fourth Cliff (all individual areas), here are five of the most unique Massachusetts town names.

Located in the northern corner of Berkshire County, Florida this is the highest point of the Mohawk trail. It has one school that serves Kindergarten through eighth grade. It is one of the smallest towns in the state, 337th out of 351 cities and towns in Massachusetts.

Technically, Weweantic is census-designated place within Wareham in Plymouth, County. However, residents typically say they live in "Weweantic". The 730 households consist of a population around 1,500 people. There's also the Weweantic River, which claims to mean a crooked or wandering stream.

Located in Hampden County, Dingley Dell is only about 15 miles from Northern Connecticut. It's south central Massachusetts. There is a large conservation area and waterfall nearby. History books have shown there was a country resort in the early years of the twentieth century in Dingley Dell.

The City of Wyoming is located in Middlesex County and often referred to as part of the larger Melrose community. There is a MBTA Commuter Rail station in Wyoming Square. The name "Wyoming" can be traced back to being affiliated with big plains or prairie land. Fun fact - there is also a Wyoming in Kent County, Michigan that holds a population of roughly 76,000 people.

Although Braintree is known as a town, it is technically considered a city. It is located within the eastern portion of Norfolk County. It is named after the Essex county town of Braintree in Eastern England. It is the largest of the unique names covering 14.6 square miles. There are six elementary schools, two middles schools, and a high school in Braintree.