Dispatch: Checklist for One Day in Westchester
Domestic Daydreams and Tampon Missions: Notes from an Unremarkable Suburban Adventure
Westchester is the kind of place where everything feels close—until you actually try to get anywhere. Just north of New York City, it stretches across 450 square miles and nearly a million people spread thin across 45 towns, cities, and villages. You could live here your whole life and still miss half of what’s around you (but maybe that’s part of the charm).
I ended up there last Sunday—partly on purpose, mostly by accident. One missed stop led to serendipitous pick-up from a sweet young conductor offering me a ride to Pleasantville (where I’ll be teaching Sunday classes starting June 8. Come see me—it’s so pleasant!).
He pointed to his hat tucked under his arm and said, "You can trust me. I'm a train conductor." So, I did. (But still texted the studio anyway and kept my location on, just in case my intuition had misread a true crime podcast in the making). I was only a four-minute drive away, but a 50-minute walk, so I took my chances.
I treated the ride like a cosmic gift—or potential police report. I told him about the Pilates studio and my book—something he said he’d buy, even though he was born and raised in Westchester. I added that its local seal of approval comes from not giving away everyone’s favorite dive bars, but pointing people toward something weird 20 minutes from home they never knew existed.
He’d been on shift since 1 a.m., running trains from Grand Central to Ronkonkoma and Montauk. He was young, maybe early 20s, with a baby face (so did Ted Bundy), and a self-proclaimed “train buff.” He lived in Queens and was visiting his mom in Sleepy Hollow. He always wanted to work on a train but never as an engineer. “They're always working.” He admitted he’d probably fall asleep at the wheel. We agreed that was probably for the best. He had opinions about which trains were best. I was grateful for the kindness.
He dropped me off across the street from the Pilates studio. I thanked him and told him to come visit soon.
Pleasantville is a small village about 50 minutes from New York City. It was two stops from Mount Pleasant, which I prematurely exited at and how I found the nice conductor. (Don’t make my same mistake—but you can’t blame me for making it, either).
The studio is beautiful, modern, and peak Instagram. It's also the only studio in a town filled with upper-class stay-at-home moms and retirees who all love athleisure and brunch. I doubt any of them read this newsletter, so I don’t feel weird promoting it. (Even though it really is that nice).
It’s nestled on a charming street near a coffee shop, a fancy cheese shop, a brewery, and the Jacob Burns Film Center. The coffee shop doesn’t care if you use a laptop on Sundays. The streets aren’t mobbed with tourists. It’s the kind of place where you try on a life to see how it fits. A little reverse-commute fantasy.
Pleasantville didn’t make it into my book. Neither did most of inland Westchester beyond Yonkers, Sleepy Hollow, Peekskill, and Katonah. It arrived too premature for the pandemic-boom areas like Mount Kisco and Bedford Hills. But the joy of the book is using it to get lost, and maybe talking to someone along the journey.
I just miss the next train and catch a ride to White Plains, the commuter hub where trains should run every 15 minutes. But it’s Sunday, so it’s just two trains, once an hour. With 46 minutes to kill, I light a joint and wander.
I’d never been to White Plains. What I knew: it had the last mall for miles—a vaguely interesting thing for New Yorkers, though nothing to write home about. Also: Etain, one of New York’s first legal weed dispensaries, which had since sold to Canadian operator RIV Capital for $247 million before later merging with Florida’s Cansortium. I’d meant to check it out, but I already had weed and no other reason to go.
With nothing pressing on my calendar, I decided to intentionally miss the next train and give myself an afternoon artist date on the town in White Plains.
Below, my field notes:
· Step 1: Channel your inner mall rat. Pass a dead mall, followed by one just barely hanging on life support. The west side of the Galleria at White Plains feels like the right place to smoke, but also the sketchiest since closing in 2023. I resent looking like a teen hitting a crack pipe. It’s legal now, isn’t it?
· Step 2: Seek nourishment, encounter authority. Take longer than expected to pass the saddest ShopRite in search of snacks before spotting a Burlington Coat Factory guarded by a woman dressed in near full body SWAT gear pulling aside the red rope so that I can shop discounted designer handbags strapped in high-level security tags that I have no interest in buying. It’s bleak. I leave. The new mall supposedly has a Lululemon and Uniqlo.
· Step 3: Follow your bliss. Stumble into Etain. It smells amazing. Everyone is stoned and friendly. The shop is sleek, modern, and would be better with chairs and a “just chill” policy. Now owned by a Florida company, the store hawks Florida-centric gear that no one in the entire greater New York City metro area would ever be caught dead wearing. I mention how nice a consumption lounge would be. Everyone agrees.
· Step 4: Assess local housing: New developments are now leasing—a brand-new building with soon-to-be-dated design and a deck (but probably no pool). Next to it, a 1960s complex with better closets and balconies. It overlooks a busy thoroughfare, but perched upon a manicured park replete with greenery and benches. Teens pass by and I realize I’m already standing in front of the mall.
· Step 5: Head to Sur La Table. Malls sell everything under the sun, except a tampon which I desperately need. I am bleeding out while browsing plateware. I try not to think of him, or how I once pictured us picking it out together.
After years of IUDs, my period’s back—reminding me of my mortality and womanhood. Why am I always happening to be wearing white underwear the day I start my period?
I ask a Sur La Table barista for a tampon. “I gotchu.” She only has Super-size but I’m grateful. “I was you three days ago,” she says, vanishing to make espresso.
· Step 6: Pick your mall aesthetic. Are you: A. Aritzia, Reformation, Eileen Fisher; B. Burberry, Gucci, Louis Vuitton, Rolex; C. Lululemon, Tiffany & Co.; D. Victoria’s Secret, Foot Locker, Express.
I stop by Ann Taylor Loft. Buy nothing. Appreciate the women encouraging one another in the dressing room.
· Step 7: Lose yourself for a minute. Try a free sample of pineapple coconut ice cream, his favorite. It’s creamy and a little too sweet. A taste of what could have been our future. I pass a Jamie and Jack and imagine the life we never lived: kids in sundresses, potato salad at Memorial Day barbecues, toys from Innogoods. A version of domestic bliss neither of us had, but for a moment, felt possible. I almost wanted it.
· Step 8: Find yourself again where you don’t belong. Wander into a Free People. None of the sunglasses look good on me, the shorts look too challenging, and all of the candles smell like dorms. I leave.
· Step 9: Get lost again. Goat-themed apparel. Kendra Scott. Therabody.
Interlude: The Apple Store. You have no business here, move along.
· Step 10: Find the food court. It feels like a half-dead airport terminal trapped in a banal dreamscape: a handful of disaffected people sitting on massage chairs while watching the NASCAR race is projected floor-to-ceiling. Shake Shack, The Little Beet, Wok360, Bang, Melt Shop, Juice Eternity. Nothing for you here.
· Step 11: Revisit teenage heartbreak. This is the alley of past crushes I’ve melted over but never would have been good for me. At Auntie Anne’s, I am transported to the Golf Mill mall, where my teenage punk crush worked. I’d take two buses just to loiter nearby like a loser, never actually buying pretzels. I wonder what happened to him.
· Step 12: Exit strategy to nowhere. Going down: Lucky Brand, Sephora, David Yurman, Club Monaco. Interestingly, none of these stores have SWAT-geared security policing their entrances like the Burlington Coat Factory. Google top-rated restaurants near me to find three well-rated Peruvian chicken restaurants a quarter-mile away.
· Step 13: Be realistic. I’m hungry and it takes me three tries to exit the mall. I spot a Southern restaurant called freebird. I wander in through the wrong door but no one cares. I sit alone at the bar with an iced tea, a grilled chicken sandwich, and Yankees game. It’s perfect.
· Step 14: Retrace your steps. A girl sparks a joint near an old woman on a bench. They don’t seem to know each other but I can sense the younger one feels cosmically nourished and existentially bonded to the moment. I re-up near the dead mall. Westchester is building something new. More glass.
· Step 15: Reflect. Head home. Plenty of snacks at the train station. Too processed, too risky. I open my phone, immediately regret it, and go home.
Discover your next adventure by picking up a copy of my book, “Easy Weekend Getaways in the Hudson Valley & Catskills.”