What It’s Like to Live In...Westport, Connecticut

What It’s Like to Live In...Westport, Connecticut

By Contributor

You had us at "cupcake heaven," icesk8rgrl0. —Sparkitors

Oh, Westport: home of country clubs, designer cardigans, and elegant tea parties, and the place where “clubbing” automatically refers to golf, and people pay tuition to attend a public high school.

Westport has its perks, but it definitely has its disadvantages, too; I’m an artsy (read: not preppy) girl, and since I'm constantly surrounded by pearls and private yachts, it can be hard to fit in. Anyone who’s even slightly different in my town stands out, for better or for worse. To make it through a day in Westport, here are some things you should know:

1. If you stick to your own personality and style regardless of the pressure from others, you will be the victim of whispers and rumors. Confidence is key.

2. There are two parts of town: the mansions, and the tiny houses that are all right next to each other. There isn't any "in between."

3. Those who wear cardigans are also in theater. This odd circumstance has no rhyme or reason, but I suspect that cardigans have something to do with an all-consuming desire to hog the spotlight. Did I mention that a LOT of people wear cardigans?

4. There are over 70 clubs and after-school activities at my school. If you're a freshman, expect to accidentally go to a club no one else joins. Chess Team, anyone?

5. You will play a sport. It’s not required by the school, but it is required if you want a social life.

6. Taking lots of honors classes and having 0 free periods is expected. Get used to it.

7. Being a “burnout” often means you're in non-accelerated classes and get Bs.

8. It’s worth it to check out Longshore, which is essentially a free hang-out with a pool and sailboats. (Yes, I like to sail and ski, but I have never worn a cardigan in my life, I promise.)

9. The town is divided into two major groups: Those who hate the town, and those who love it (and the illusion of status it provides).

10. Foodwise, we've got a lot of incredible options. If you visit, you have to go to Sakura, a crowded and overpriced but DELICIOUS hibachi place, and you can't miss Crumbs, a beautiful, huge cupcake heaven. Plus, make sure to hit up Westport Pizza for the best slice of pepperoni ever.

How does Westport sound to you? We're still drooling at the thought of that pizza.

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