This former New Yorker shares her insider tips for a perfect summer weekend in Westport.
I’m the first to admit that I was a reluctant suburbanite. I loved everything about life in New York City: the restaurants, the shopping, the conveniences, the vibe. But when my husband and I talked about making a move to the suburbs I knew it made sense on paper at least. We’d get more space, a yard for the kids, a home for our family to spread out in, and great public schools.
I knew it was the right move, but I expected some tradeoffs. Thankfully, our life here in Westport has surpassed all my expectations.
Sometimes I look at my life and I feel like I’ve won the lottery: I love my house and my neighborhood, we’ve made amazing friends, and I can find almost everything I want to do, see, shop for, and eat in Fairfield County.
This is how I’d spend a great weekend day in Westport.
#1 Bagels on the Sound
One thing that kept me up at night before we moved to Connecticut was the bagel situation. How was I going to survive without my New York City bagel? I had nothing to worry about because the most in-demand bagel in New York started in—you guessed it!—Westport. I love to start my day by grabbing a bag of bagels and smears from the Popup Bagels hub kitchen on Post Road and a coffee from GG & Joe’s, then heading to Compo Beach with my family to walk along the shore and watch the boats sail by. Compo Beach sells a limited number of public passes for out-of-towners every day, but for the most part this 29-acre slice of heaven on the Long Island Sound is just for Westport residents. Lucky us!
#2 Book It
With such easy access to the beach, I need a lot of beach reads to get me through lazy summer days—and the Westport Library delivers the books I want to read and so much more. It’s the heart of our community: New moms gather for Tummy Time with their babies and story time for older kids, there are camps and college prep resources for teens, and the adult programming is world class, with language classes, book clubs, and an amazing speaker series.
#3 Ladies Who Lunch (and Shop!)
Back in my city days, Saturdays meant long lunches with friends and shopping—something I thought I’d be giving up in the ‘burbs. But Westport’s downtown is lined with boutiques that are curated with the latest fashions, so when I want to spice up my wardrobe I just pop into Fred, or Blue & Cream, or Unsubscribed to find what I’m looking for. After shopping, my friends and I like to grab a sandwich or croissant at the Westport outlet of Mrs. London’s Bakery. This cute café recently opened and has already become my go-to spot in town.
#4 Dinner and a Show
If it seems like I keep coming back to food, it’s because we were really concerned about not having great dining experiences in the suburbs. I envisioned a sea of chain restaurants but we found there’s no shortage of great restaurants like the farm-to-table Tavern at Graybarns in nearby Norwalk or amazing sushi at OKO in Rye. Here in Westport, we love the authentic Italian at Casa Me on Sconset Square. On the weekends, my husband and I like to share a few spuntini (little snacks) or a cheese plate and a Roman-style pizza and have one of their inventive cocktails (or two!).
With a booming nightlife, we’re never at a loss for something to do after dinner. On a typical summer evening we can go to a free concert at Levitt Pavilion or see a show at Westport Playhouse. And next month, we’re catching the Foo Fighters, Goo Goo Dolls, and Norah Jones at the Soundside Music Festival in Bridgeport.
If you’re considering a move to Westport, Suburban Jungle can help. Get in touch for more inside scoop about where to go, see, shop and eat when you visit. Schedule a free Suburbs Strategy session with Suburban Jungle today.
