After doing some work in the morning, I left Walla Walla around 10, and swung through Waitsburg to give Lisa and Jade one last hug. Originally I was going to take I-90 to Montana, but the weather forecast improved so I decided to take Highway 12 up Lolo Pass. But when leaving Lewiston, just over an hour after starting my five day road trip I got pulled over for speeding.

Once I got past Missoula the roads became dry, so I set the cruise control to 80 and headed to Bozeman. There I met Sarah and Trent for dinner and drinks. After I checked into my room at the very cool retro motel “The Sapphire Motel” and went to bed.

Day 2

I had concocted this plan to get up an hour earlier each day, so that by the time I get to New York I will have adjusted to the time change. This plan failed immediately as I slept in. But once I woke up I went into town to a breakfast place called “Jam!”. I had the granola, and a crabcake eggs benny.

Bozeman has a lot of young people and a really great energy. There is also a common fashion among the guys of Bozeman that consists of a medium beard, with a soft front baseball cap with a cord. At Jam! at least 6 patrons were sporting what I have decided to call “The BozeMan”.

The snow stopped falling, the sun came out, and I hit the road to Rapid City, SD. This selfie was taken outside Gillette, WY.

After checking into my hotel, I got back in the car and headed to Mount Rushmore. It’s really quite close to town, and I was one of the few cars on the highway, which made for some fun driving and cornering.

Once there I parked, got out of the car, and walked straight up to the viewing area. That’s when I realized that I was the only person at Mount Rushmore. It was dark, windy, and frigid — and I was completely alone. Just me and the presidents.

When I went to DC in middle school, we did a tour of the presidential monuments there at night via limousine. And by the time I got into Rapid City, it was dark. Apparently I’m destined to only ever see the presidents at night

It was challenging to get a decent selfie with the presidents, but I think I managed haha

I jumped the roped off areas and sat down on the amphitheater top row bench, and looked up at the monument for another five minutes. That South Dakota cold started to get to me so I decided to go back into town, I ran at the gym, and came back to the hotel to write this blog.

Took a solo walk up the east moraine of Wallowa Lake

Since my last stint in NYC (18 days in August) I’ve felt a pull to go back (or perhaps a push to leave Walla Walla behind). So I messaged John about coming to visit. It turned out that he needed me to come, as much as I wanted to. And when he explained his circumstances, I realized I had to go.

I texted him Saturday night, and Sunday afternoon I was landing at JFK.

The next day I finally completed the full East/West Drive loop, and set my 10k PR at the same time.

For election night dinner, we ate Mama’s TOO at a sidewalk picnic table on Broadway. On the left is their buffalo chicken style “Bufalina”, and on the right is their “bruschetta”. That crust is unlike any other pizza crust I’ve had. And when we got home, we drank whiskey until our collective resignation forced us to sleep through the announcement we knew we’d wake to in the morning.

The next day was 79 and sunny, summer’s last stand, so that night we met a friend for apps, and drinks at the Empire. It was great to relax and connect with “the boys” at an iconic rooftop bar. After he left, John and I had some really deep conversation about life, women, and each other. On our way out, I spoke some Spanish to the waitress and she unlocked the staircase so we could take this incredible photo.

Like running a 10k through Central Park, friendship is long and challenging, but every time you show up for your friends it builds you up too.

This is a great climb, but until today I had never done it this early in the season. I came under-prepared. The hike starts easily enough, and you come up along the aptly named Falls Creek.

About 2,000 feet higher we hit our first snow

It was still pretty hot at this point, wearing t shirts and leggings. We had this big boulder gulley to ascend, however with the snow field intact it was a lot easier.

At this point Rob put on his crampons and his ice axe setup, I just continued with my regular hiking boots and a stick I found.

We hiked on snow almost all the way to the summit, which is a right turn at the top of the gulley and another 300 vertical feet roughly. Here is the view of Twin Peaks from the summit:

I’m reading Lord of the Rings right now, and just got to the point where the fellowship had to turn back after encountering too much snow, and not being well equipped for it. I could relate, the descent ended with ice and water squishing around in my boots, as the snow pack had softened. In fact, it had softened so much that in one place I was post-holed up to my hips.

Overall the climb was 8.5 miles, 4,171 feet of elevation gain, and it took us 4 hours and 34 minutes.

We also celebrated Grandad’s 82nd birthday

We started my last day in New York with breakfast at Russ & Daughters. I had two bagels, a sesame with chive creamcheese, and the “Shtetl” which is smoked sable with goat cream cheese, and is a delicious salty treat.

After breakfast we took the B train uptown to see John’s new apartment in the upper westside (manhattan valley). We couldn’t go inside because there is still a tenant in there, but we did get to checkout the neighborhood.

His apartment is 100 feet from Central Park so we went for a walk across it, to the upper eastside. Mother and son:

Once we got across the park we walked down 5th Avenue for a bit, entering a movie shoot!, and then crossed over to Park Avenue. It definitely felt like Gossip Girl

We just kept walking until we found a lunch stop, grabbed some salads, and headed back to Jersey so I could catch my flight. I was the last seat on the plane. Ironically the five hour flight to Seattle felt longer than the five day drive.

Got back into Walla Walla at midnight.

We didn’t get back until 1AM last night, so today was also off to a slow start, but we planned on that. I DoorDashed us breakfast. John got a blueberry muffin, and I got an everything bagel with American cheese, egg, and a meat called “Taylor ham”. Taylor ham is a New Jersey pork roll concoction.

We hung out at our place in Jersey until I got done with a Zoom call for Harvust. And then we went to NoHo for some “street meat” as John calls it. I got some chicken shwarma, and John got some vegetarian thing. We decided to eat it in Washington Square Park. Unfortunately timing wise things were about to become problematic. John’s mum, Stacy’s flight was an hour early, and traffic was causing an hour delay. We realized there was no way we’d make it to the airport to greet her in time. So John arranged for an Uber to collect her and bring her into Manhattan. During that time we did some shopping, including at Harney & Sons tea shop. I don’t drink tea, so there was nothing for me there, but John tasted a flight of teas at their “tea bar”. They had all of their teas arranged on the wall, with a rolling ladder to access each tin.

After all of our shopping we still had time to burn, so we decided to once more find a bar for a quick drink. After walking into two separate bars, only to be told they open at 5, we finally landed at South SoHo Bar where I ordered a French 75, and John had the same. We chatted with the waitress there, and learned that she is also a native Oregonian! It was at that point John made the observation that people who live in Manhattan are not from Manhattan.

When Stacy arrived we went back to Jersey so she could get settled, and John could tend to the dogs. Stacy, quickly decided the neighborhood she booked the Airbnb in was dangerous! So when John went to take the dogs for a walk she started haranguing him about being safe, after a little bit of back and forth John declared “Mom! I have great situational awareness!” And as the words were slipping out of his mouth, he ran head first into the edge of the front door! Time to resurrect ye old recess helmet again!

We decided to stay in for dinner, and I ordered us some dumplings without consulting anyone. While this move initially caused quite a bit of distress for John and his mum, when it arrived all were happy. So happy that we decided to try a restaurant in Jersey for dessert…that was a mistake.

We hailed an Uber to go to this restaurant “Plate of Cake”. It looked like it had a lot of offerings on the menu, so we decided it would be a good bet. Well when we arrived we found a half abandoned building with a tiny little store front extremely well lit. And in the window we found this was not just “Plate of Cake” but three other restaurants!

We had accidentally decided to dine-in at a cloud kitchen! This one kitchen operates four different “resturant fronts” for use almost exclusively on delivery services like DoorDash, UberEats, and Grubhub. It’s a “restuarant business in a box” style business, where the operator buys the brands, the menu, the decor, the promotional materials, and the food. The actual kitchen operators are just reheating and plating the items. Over half of their kitchen was a walk-in fridge. As someone who works in food, it was so fascinating to se behind the literal curtain (see below) of a cloud kitchen!

The food itself was of course unremarkable.

Tomorrow is my last day in NYC, and I’ll be back in Walla Walla by the end of the day thanks to the time change.

Day 1

We were eager to leave Ohio, and just get to New York. So we limited our stops and made straight for our Airbnb in Jersey City. After figuring out the enigma that is street parking, we took an Uber into the city for the night.

John’s main priority was to get some new shoes, so he got a pair of Timberland boots in SoHo. That neighborhood is incredible, it’s the fashion distract and it shows. Everyone walking on the street had “drip” (designer clothes, style, personality), and it just makes everyone look more attractive. I imagine there is a lot of pressure to constantly look put together. We were very hungry so found an italian restuarant called La Pecora Bianca and ordered some drinks and pasta. I had cacio e pepe bucatini, while John had a mushroom garganelli.

After dinner, we walked around for a bit more in SoHo looking for a new bar to drink at. Luckily it wasn’t that hard to find, and we ended up in a place called La Diaspora, where I ordered us two shots of Don Julio Reposado, we each got a proper cocktail as well.

It was getting late, and the dogs needed to be walked before bedtime so we asked for the check, but they just made us another round of drinks! (and then brought us the check) so we quickly downed another cocktail each.

We hailed an Uber, and when we got back to the Airbnb we drunkenly took each dog on a long walk. We then attempted to get more to drink, but the nearest 7/11 didn’t carry any alcohol, thank god.

Day 2

Our plans for an early start today, were immediately derailed by last night. I woke up at 9AM (late for me). Our first priority was getting the rental car cleaned and returned. On the drive we discovered a broken traffic light, so were stuck in a side street with no exit. So I had to perform a 30 point turn in our Grand Wagoneer to go back up the street, I think John was grateful that I was driving for that. Once the car was done we took an Uber straight into the city. John had more shopping to do: a sweater. And he needed it, it was rainy, cold, and windy today. After shopping we went to get lunch at Rubirosa, a pizzeria recommended to me by an American 35 customer, Jenna, who I met at Rotie Cellars. She wrote it down on a napkin for me.

Don’t let the small front deceive you. After walking through the door you’re greeted by a red curtain (like from a stage), and the host walks you through a labyrinth consisting of a bar, and three kitchens punctuated by little dining rooms in between. The cramped walls and low ceilings guided us to the tinest table at the very back of the restaurant. We ordered a half and half pizza. Half fresh tomato, arugula, with balsamic glaze; and half Tye Dye: vodka sauce, fresh mozz, and pesto.

This was my first New York pizza, and it did not disappoint. The two of us at the entire 18 inch pizza. After lunch we stopped by Wallowa county native, Tyler Hays’s store: BDDW. It’s a bespoke furniture store for ultra-wealthy clients, imagine an art museum where you can touch and buy everything. We basically went there to show off to the staff that we (mostly John) have a relationship with the owner. After that we went back to the Airbnb to take care of the dogs, and do some work for our jobs. And most importantly nap, and hydrate to prepare for the night!

The first stop once we got back in the city was a college bar called Off The Wagon, near NYU. John got a gin and tonic, and I got a disappointing Negroni (about what I expected lol). After finishing our drinks and chatting with the bar tender about cringey movies we popped into a smoke shop to get some gum. I got some Reeses and we decided it was time to make our way uptown for our dinner reservation with Lindsey and Claire, at 9:45PM.

This was out first time on the subway this trip, so easy to use, we took it to midtown. When we got up to the surface we were greeted with this view

Since we had some time before our reservation we decided to hit up another bar, The Parlour Room. John took this photo of me on the way.

This was hands down the nicest bar I’ve ever been too. We got seated in the loft (it had it’s own smaller bar).

We had more good food there, I had mushroom arancini, and John had chips and dip. We closed our tab and walked towards our final bar of the night, Pebble. On the way I tried to find a garbage can and ended up at Rockefeller Center Plaza, no trash can to be found, 1 star.

John and I got to Pebble before Lindsey and Claire (they were at a Broadway show), and got settled. When they did arrive, they arrived with a bang: immediately knocking a glass off our table! haha. Dinner at Pebble was amazing, we had bread and butter, sliders, shrimp cocktail, deviled eggs, and steak tartare with quail egg, and mushroom tartare. All excellent. Lindsey and Claire got martinis, I got a twist on a gin and tonic called a Kathy Mccarty. It was very dark in there, I have no photos. I enjoyed their company, and it was the overall best time so far this trip. It was midnight by the time we finished dinner, so we took some photos before they taxied back to Brooklyn.

Lindsey & Claire

Things seem to be getting nicer the further east we go! We left Veronica’s house with a breakfast in hand, and the rest of her homemade cookies in a little paper bag. It was another easy drive as we crossed into Illinois, Peoria was a cool looking city, we both thought it might be worth a visit someday in the future.

After crossing into Indiana we started getting hungry and turned off into the small town of Covington to look for lunch. The main road into town is bordered by seemingly endless cemeteries, including a combo cemetery/golf course! We had some fajitas and then got back on the road.

We finally arrived at our stay for the night in Dublin, OH. This is a very happening city and is a “tech hub” of the midwest. It’s got trendy coffee shops in historic buildings, and a brand new gentrified millennial nirvana commercial district. It was a very comfortable place, and the weather was warm and windless making it even better. John originall planned to go to Cleveland, but I convinced him to go through Dublin so I could meet up with my former boss at Quantopian, and current friend and mentor Jean Bredeche. He recommended a vegan focused eatery (the first since leaving the west coast! haha) so John could get a proper meal. He got this cool bowl, the picture doesn’t do it justice. And he raved about it as the best falafel his ever had. John finally got a good meal this trip!

Jean and I hit up this food court a block down for our meals, but because it was near closing the only place left was this mexican joint where I got a steak burrito bowl. It was great, and I especially loved how they chiffonaded the lettuce, making it much easier to eat. It was amazing to catch up with Jean in person. Quantopian was the single most formative experience of my life, and I will be grateful to everyone who was a part of it. Of course, I had to wear my Alphalens shirt :)

Thanks Jean! Tomorrow is our last driving leg, here we come Jersey City!

We stayed up until midnight last night drinking and talking about AI with out hosts Veronica and Greg, so I didn’t get a chance to write this yesterday. All in all, it was the best feeling day of travel. Despite Nebraska being mostly uneventful it was an easy drive with plenty of stops for Plum and Po.

We made a slight detour into Omaha to go and see the Oracle of Omaha’s house. It is a highly surveilled street, and as we were taking photos from across the street I could hear some kind of speaker projecting something, but I couldn’t make out what it was saying. We only stayed a minute since we had to get back on the road.

I got us briefly lost inside a park while trying to leave the neighborhood and get back onto the interstate. We then headed Northeast to Ames, Iowa.

In Ames, is John’s cousing Veronica and her partner Greg. She greeted us with gin & tonics and snacks. We enjoyed them, and got to know her in the backyard while the dogs got their first opportunity to play for more than 5 minutes.

Veronica made us a true Midwestern meal of meatloaf, potatoes, and green beans. It was incredible, unfortunately John didn’t get to try the meatloaf. Veronica then brought out some fresh baked choco-chip cookies for dessert w/ Ben & Jerry’s. I spent the rest of the night enjoying more gin and tonic (2 more), while John finished his glass of wine. We discussed everything from old family stories, to ChatGPT until we wised up and decided it was time to get at least 5 hours of sleep before leaving for Columbus.