Somewhere on a highway in the Hudson Valley…
This idea came about a few months ago when my good friend Ritam Mehta (comedian and one-half of the funniest Substack around, Low Lift Ask) offered to join for a list item. If you ever want a partner in crime, he said, count me in. I told Ritam the same thing I told national treasure Conan O’Brian when he asked to be included – look through the original list, let me know what you’re excited about, and we’ll dive in. Conan was intimidated and never followed through. But Ritam? Ritam was game.
#21. “Buy a Convertible. Men Like to Ride in Them.” That sounds fun, he texted. So I marched to the nearest auto dealership, slapped down my AmEx, and bought the shiniest drop-top on the showroom floor. Drove away tens of thousands of dollars in credit card debt, scooped up Ritam, and we sped down the Brooklyn-Queens Expressway into the sunset.
I’ve said it once, I’ll say it again. There is nothing I won’t do for this project.
Yo, that would be crazy! Sorry to disappoint, but I did not actually buy a convertible. Millennials and Gen-Zers don’t buy anything, remember? We rent.
Ritam and I decided to rent a convertible for a day and take it on a delightful jaunt through upstate New York. Some may have been made aware of the magic of upstate New York in late summer/early fall via Taylor Swift’s All Too Well (10 Minute Version) (Taylor’s Version) (The Short Film), a cinematic masterpiece featuring a young Sadie Sink (playing Swift) zipping down tree-lined roads with Dylan O’Brien (playing local villain Jake Gyllenhaal). Others may just know the area because it’s pretty well known.
We booked our whip through Turo, a peer-to-peer car rental app that is like Airbnb for automobiles. It’s cool and I’d highly recommend it, but Turo ignored my email asking for a discount if I included them in this Substack, so I won’t be saying anything more on that.
The site offered a variety of convertibles scattered across the greater New York metro area. A Porsche in Pelham Bay, a Mustang in deep Jersey City, a Volvo in the Village. All were exciting, but none were right. None felt worthy of a road trip. (And the Porsche was $500 for the day). The thing is, convertibles are cinematic. They’re exciting. Thinking of riding in one conjures images from Thelma and Louise, The Notebook, Scarface, Ferris Bueller’s Day Off, The Hangover. All chill movies with chill people where nothing bad happens to anyone.
The car had to be special. It would set the scene, which is why there was ultimately only one choice: a red Jaguar F-Type, courtesy of Miguel from Turo.
How to Have the Ultimate Upstate Road Trip In 200 Miles Or Less Because After That Turo Starts Charging You 0.70 Cents Per Mile
YONKERS, NEW YORK
The third most populous city in New York state, Yonkers is located at the northernmost tip of Manhattan, just above the Bronx. It is also known as The City of Seven Hills.
Ritam and I stepped off of the Metro North and headed to the car pick-up point. We had no idea that what Google Maps called a “10-minute walk” was more like a steep hike up a never-ending hill. There are a lot of hills in Yonkers – seven, as we would quickly discover. On the upside, the climb provided a scenic tour of the area, which before I’d only been vaguely familiar with due to Neil Simon’s Pulitzer Prize winner, Lost in Yonkers, a play following two grieving, newly motherless boys who spend a summer in Yonkers with their Grandma and Aunt.
We finally reached our destination, out of breath and sweaty. But then we saw the car and just like that, it was all okay. Keys in the ignition, Google Maps set to our destination, the Ultimate Road Trip Playlist cued up, we hit the road.
SEVEN LAKES DRIVE, HARRIMAN STATE PARK
The Seven Lakes Drive is a parkway stretching for 18 miles across both Harriman and Bear Mountain State Park. From south to north, the lakes are Lake Sebago and Lake Kanawauke in the towns of Haverstraw and Tuxedo; Lake Skannatati and Lake Askoti in Tuxedo; Lake Tiorati in Tuxedo and Woodbury; Silver Mine Lake in Woodbury; and Queensboro Lake in Highlands.
The Seven Lakes Drive drive was Ritam’s suggestion and scenic as hell. He’d been looking for something to see on the way to our first destination in Monroe, New York. Isn’t it funny how some of the best discoveries are out of necessity?
BLOOMING HILL FARM
A small family-owned farm and restaurant in Monroe, NY, Blooming Hill is a hidden gem in the Hudson Valley.
I mean… wow. Again, a suggestion of Ritam’s.
We ordered enough food for a small family. It was farm-to-table, so everything was fresh and local, and much of the produce was grown on-site. One summer hash, Pomodoro pizza, sourdough waffle, and hash browns later, we wobbled out of the restaurant and over to the farm shop.
The stand was laden with homemade hot sauce, sourdough pizza dough, and a cornucopia of vegetables. I’m embarrassed to admit the only thing I considered buying was merch. (They’ve got great baseball caps!) As Ritam paid for his hot sauce and plums, we asked the cashier her favorite things to do in the area.
LEGOLAND NEW YORK
RUMMAGE SALE, LOCAL CHURCH
The theater space at a local church in Newburgh, New York. Every inch of the wall is decorated with hand-painted theater posters from shows dating back to the 90’s.
Here, we spent some time chatting with a member of the Church whose name I wish I could remember. She’d been in many of the congregation’s plays and introduced herself after watching me gape at the show posters.
“Oh! Were you also in The Wizard of Oz?” She asked. “I was in that cast, but I don’t remember seeing you.”
I responded that I was, indeed, in The Wizard of Oz (the coveted role of Tree #2), but back in Michigan. She looked disappointed. I didn’t bother to point out that the Church’s (and her) production of The Wizard of Oz ran in 1997, and it would have been difficult for me to perform as I was not even yet able to walk. We talked a bit more about the joys of local theater and then Ritam and I left.
We did not buy anything.
MOTORCYCLEPEDIA MUSEUM
An 85,000-square-foot space displaying the collection of over 650 motorcycles that father-son duo Gerald and Ted Doering have amassed over a combined 80 years.
This museum is one of those places – those special spots you’d never get to unless you stumbled upon it or sought it out. Not only was Motorcyclepedia incredibly curated and cared for, but it was staffed by wonderful, kind folks. Ritam and I were guided by Denny, a former interstate repair man and car enthusiast who started working at the museum to help out his friend, owner and motorcycle aficionado Ted Doering.
Denny taught us about Rat Fink, the anti-hero to Mickey Mouse created by Ed “Big Daddy” Roth. He showed us every pop culture bike in stock, ranging from the original Adam West Batmobile to the one the Fonz used in Happy Days. He introduced us to his friend Peter, a fellow employee with the essence of a middle-aged Billy Crystal if Billy Crystal were Italian and also had a thick upstate New York accent.
When we asked Peter a question about the bikes, he replied, “If I’m wrong I have to tell you a bad joke.” He was right, but told us the joke anyway.
I’m not saying go visit Motorcyclepedia just for the jokes, but it’s a value add. Peter’s stand-up and Denny’s tours come with the cost of admission, along with a full set of Indian Motorcycle trading cards, a bandana, and a pin. Well worth $15.
GAS STATION
An establishment beside a road selling fuel for motor vehicles. Did you know you can buy phone chargers at gas stations? News to me.
STONY KILL FARM ENVIRONMENTAL EDUCATION CENTER
A 750-acre farm in Fishkill, New York. The historical property offers everything from a community garden to ample hiking trails to a thriving livestock population.
I had put this destination on the list in the hopes of attending the “Open Barn” hours, which occur every Saturday and Sunday from 11 am - 1 pm (February - November). Unfortunately, we had too much fun at Motorcyclepedia and arrived too late. The barn was closed, but the animals still roamed freely. Ritam and I parked the car in front of a rusty red barn and found ourselves walking down a dirt road in search of… what, exactly, I don’t think we knew.
Perhaps we were just drawn to the cadre of fly-ridden cows watching us from the nearby pasture. Separated only by a thick fence of barbed wire, we observed the cows playing an exciting game of tag as bored sheep grazed nearby.
We headed towards an old farmhouse that was the Environmental Education Center. During the week, it’s home to the Summer Explorers Camp, but on this Saturday, it just seemed haunted and empty. It was there we met a woman and her baby, who casually mentioned that we should, “Go look at the beehive.”
We immediately zoned in on the beehive. It was all that mattered. It was everything to us.
But there was no beehive to be found. We looked for about three minutes before giving up hope and deeming the mysterious stranger a villain sending us on a fruitless (more like honeyless) quest.
“BEEHIVE!!!” We screamed in agony, our echoed cries rivaling that of Marlon Brando’s “Stella!!!” in A Streetcar Named Desire. The elusive hive would haunt us for the rest of the day, and potentially the rest of our lives.
Attempting to move on, we returned to the car, passing through a garden teeming with butterflies and smelling like clean air. I was struck by the silence. We were all talked out, at least for the time being. So we just walked, only the sound of grunting cows and distant cars punctuating the peace.
BEACON, NEW YORK
HUDSON VALLEY FOOD HALL
An international food hall in the heart of Beacon, New York.
Ritam and I went here to recharge our bodies and cell phones. We got iced coffees from Dhaka Coffee, which Ritam says to note, “Might be the best iced coffee I’ve had in my life.”
Ritam has good taste, so this praise should not be taken lightly.
HAPPY VALLEY ARCADE BAR
An old-school arcade ripped right from the 90s.
Games are 25 cents a pop, UFO paraphernalia peppers the walls, half the machines are out of order, the bar is ripe with beer. Here, we discovered just how much fun you can have with $3. After several games of Pac-Man and some two-player situation involving asteroids, we found our favorite machines. For Ritam, it was a car game where you turn a knob to keep the vehicle on the screen. For me, it was Gauntlet Legends, an epic dungeon brawl between a wizard and her enemies.
The only way the place could have been better was if it had Penga, A.K.A Canadian Pac-Man. I grew up playing this game in my family’s bowling alley in Windsor, Ontario (lore for another list item). My siblings and I would sit in the arcade for hours on end, feeding the machine Loonies and Toonies (actual Canadian currency) until our Mom was done working for the day and it was time to get in the car and drive through the Windsor tunnel back home to Detroit.
At Happy Valley, I was flooded with nostalgia. But I suppose that’s the point of a retro arcade. It takes you back in time.
WONDERBAR
A small bites and big cocktails restaurant connected to The Beacon, a 3-screen movie theater featuring blockbusters and independent films in an old building from the 1930s.
Over wine, tater tots, and broccoli, I scribbled down notes on receipt paper, eager to remember everything we’d seen and everyone we’d met. My phone was dead, again, now charging in the back of the restaurant. There was something lovely about being detached. Makes you take it all in a bit more when you can’t snap a picture or jot down a thought. I believe this is called “living in the present.”
HYPEBEAST STORE WITH SMALL DOG
I don’t remember what this store was called, but the owner seemed kind of stoned and had a small dog. They sold cool hats that did not look cool on me.
SIBLING
A children’s boutique with an emphasis on timeless design and quality materials.
Under the guidance of Robin, a painter originally from New Mexico, I purchased a baby gift for my new niece, Marley. It is very easy to spend a lot of money in a children’s store, I have learned. Everything is all too cute.
YONKERS, NEW YORK
And then… we were back in Yonkers. The sun set and the day was winding down. It had been a long, good day, and we were both tired.
On the train back to Grand Central, surrounded by city folk—many perhaps returning from their own Metro North day trips up to Beacon or another Hudson Valley town—I started to worry. Had it been silly to rent a convertible just to visit places we could’ve reached by public transit? Had I wasted our time, our money?
But then I remembered: it was never just about the destinations. Convertible or hardtop, a road trip isn’t about Point A and Point B. It’s everything in between. The weird pit stops, the unexpected views, the unforgettable characters. It’s the kindness of strangers and stepping into a world outside your own.
We could’ve taken a train, but then we wouldn’t have met the woman at the rummage sale, or Peter and Denny at Motorcyclepedia, or experienced the magic of Seven Lakes Drive. More than that, we wouldn’t have spent almost twelve uninterrupted hours together. In a world full of distractions—endless obligations, online pull—it’s rare to spend that kind of focused time with a friend.
But in the convertible, it was just us. No distractions. Just two friends, hair blowing in the wind, as a red 2017 Jaguar F-Type (pronounced jag-wire) tore down an open road.
GREENPOINT, BROOKLYN
21. "Buy a Convertible. Men Like to Ride In Them."