Westport, CT isn’t extra — it’s extra unique

It wasn’t the bottom, but now I’m here

“Started from the bottom, now we’re here,” the famed lines of Drake, since 2013. These lines have been used by many college students as they part from home. From Instagram captions to Facebook albums, this line glorifies leaving home and seeing bigger and better things.

For me, I didn’t leave home for bigger and better things. I left home to be in Bumblefrickity, CT, upwind from a cow farm and left of tree-central.

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Don’t get me wrong, UConn is great, but compared to my hometown? I think Westport, CT is a touch better. Although I do have a list of complaints, as would every person talking about their hometown. I can also list spectacular things in Westport.


Westport is built on stereotypes. Southern New England, home of the Bean boot, aggressive patriotism and ugly Patagonia sweaters. It’s a long running tradition that Westport keeps alive and well.

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Ah, the glorious Staples High School, where majority of the senior class has fulfilled their partying quota before their first college acceptance letter. Our high school isn’t a bad school, its ranked #14 in the state of Connecticut with a graduation rate of 99 percent. We work hard and party hard. Majority of graduates move onto highly ranked colleges, while also prepared to drink in excess and balance school (since they’ve been doing it at 15).

Homecoming 2013 Courtesy of Caroline Prangley

As youths, we were not just shotgunning Natty Lites, but taking the 6pm train into Grand Central to get shitfaced. If you were a cool rich kid of Westport, you honestly wouldn’t be caught drinking in town. New York City was and still is, the most exclusive club for our high schoolers. Guys dressed in Vineyard Vines and girls in Forever 21 bandeau skirts. It’s the classy Westport way.

Come around any national holiday, New England goes in. Westport goes to extreme lengths for holidays like Fourth of July, Christmas and Veteran’s Day.

Fourth of July in Westport is as close as hell as you can go in the northeast. Each year, Westport hosts a fireworks display at our private beach, exclusive to only locals. This annual showing of fireworks is often served with extreme patriotism, from chanting USA to hundreds dressed in red, white and blue. Westport locals are willing to camp on the beach hours prior to get a good spot to watch chemicals explode in the sky.

WestportNow.com photo

WestportNow.com photo

Fall and Christmas are another type of hell that Westport thrives on. During fall, every girl within a 5-mile radius is dressed in Bean boots, leggings, and their favorite J.Crew vest.There’s always a sense of home whenever I see that outfit.


Westporters love the fall chill in the New England air. Weekends are spent either apple picking, pumpkin picking or hiking their favorite mountain peak.

Courtesy of Instagram

Everything is fall themed, from downtown stores to the food we consume. The local Trader Joe’s transforms into a fall wonderland, pushing pumpkin products at the end of August.


Winter tends to slide into Westport like your drunk aunt’s backhanded comments at Thanksgiving. We love winter, snow makes the town a little more beautiful than it already is. But what many don’t mention are numerous near death experiences while driving in Westport in the dead of winter.

Moms of Westport are not to be messed with, especially during the winter. These ladies are rolling in the newest all-wheel drive SUVs. They honestly don’t care if it’s two inches of snow or five inches, they will do their best to speed past you and almost run you off the road. It’s almost a skill to drive that recklessly.

But now that I’ve mentioned cars, we should talk about the types of cars that Westport is home to. Majority of the cars on the road are within the last five years, from mostly high-end brands. Mercedes and Range Rovers are seen on the regular.

Westport even has a Maserati police car, because that doesn’t seem excessive, right?

Dave Matlow/WestportNow.com photo

Dave Matlow/WestportNow.com photo

The 2016 Maserati isn’t meant to catch drivers going five mph over the speed limit, but to raise awareness to breast cancer. Honestly, what town is so extra that it has Maserati to raise awareness?

Westport is far from the normal, it’s extra is all sorts of ways. But despite all this extra-ness, it will always be home. I was lucky enough to grow-up in such a town, it will forever have a special place in my heart.

University of Connecticut