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Home » My friends and I took a weekend trip back to where we grew up. Now, we swear by doing it every year.
My friends and I took a weekend trip back to where we grew up. Now, we swear by doing it every year.
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My friends and I took a weekend trip back to where we grew up. Now, we swear by doing it every year.

News RoomBy News RoomAugust 13, 20260 ViewsNo Comments

I honestly don’t know what I’d do without my high-school besties.

We’ve navigated just about everything together, from school drama and college decisions to life in our 20s, confidently and effectively.

Even though we’re now in our 30s, living in four separate states, and at different stages in our lives, we’ve remained very close.

Texts and calls help, but it’s hard to get so caught up in our daily responsibilities that we let precious years slip by without making time to spend together.

So, two years ago, my girlfriends and I decided to plan the sweetest, most nostalgic coastal getaway around our hometown in Fairfield, Connecticut.

We figured it’d be special for our group of four to head back home, and it’d be an easy trip to plan. After all, we wouldn’t have to spend time looking up restaurants or activities — we already had our favorites.

The weekend was simple and wholesome, yet perfect

We kicked off our first night of the trip with a few bottles of rosé and pies from our go-to pizza joint, where we’d gather every Thanksgiving and Christmas break during college.

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A round of hot-oil pizzas was typically followed by bar hopping and reconnecting with everyone else from our high school who was back home, too.

Our night looked different this time, but we still gossiped, sipped our drinks as the sun set, and walked along the beach like we used to. Although our stroll was also sans the late-night dips into the Sound we took back in the day, it was just as refreshing.

We started the next day bright and early with iced coffees from our most beloved café — a far cry from how we spent lazy weekend mornings back in high school. After, we packed up sandwiches and drinks in a cooler to spend our afternoon in the sand, just like we did religiously during summer breaks.

In the evening, we found ourselves at our beloved beach bar. We were happy to find it was still the true dive we remembered it being, same sticky floor and all.

Our night felt complete and nostalgic with dart games, a round of pool, our usual silly antics, and lots of dancing to live ’90s music.

By the time we packed up, we all agreed this trip was a success.

This nostalgic trip led to a cherished annual tradition

Ultimately, there’s something so special about getting together with longtime friends in person, especially around old stomping grounds.

Throughout the trip, we recreated cherished memories and visited our favorite spots while catching up and sharing the present-day joys and challenges of homeownership, new relationships, and careers.

Along the way, we made new memories, too. We didn’t need a fancy cruise or luxury all-inclusive — a simple trip back to where our friendship developed was more than enough.

Texts and calls in between are important for maintaining a relationship, but nothing compares to clinking glasses, trading hugs, laughing until your stomach hurts, and revisiting places that hold a lot of nostalgia in real life.

Plus, knowing that your people carved out time in their busy lives to be with you is a true gift — and it’s always nice to seamlessly pick up wherever we left off.

That first weekend went so well that we ended it with a pact to plan a trip just like it every year. So far, it’s been great.



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