This trip was planned for a weekend when Rachel was throwing a bridal shower in Hoboken, which I used as an excuse for taking a PTO day and hitching a ride to spend the weekend exploring New York City! Of course, by “hitching a ride” I mean I ended up driving the whole way, but hey – that means I got to control the tunes.
I recruited a few friends (Jared, Jeremiah, and John) to join as well, and we turned it into a 2nd annual “bro’d trip” (read “road trip” with a b) – last year’s bro’d trip was to Cleveland. I was especially interested in exploring some neighborhoods that I hadn’t spent much time in. I had been to New York plenty of times before, but mostly for business trips or very specific events that did not leave a lot of exploring time (recap coming soon of my NYC Marathon viewing experience…). In all my years of existence I had maybe spent about four cumulative hours in Brooklyn in my life before this trip, and from what I remembered I really liked it, so I focused the trip in Williamsburg.
Another key aspect of planning this trip was the Good Passport cocktail deal. We did one of these last summer in Rochester, and it was awesome. They do them more frequently in NYC, and this trip coincided nicely with a passport deal going on from early March through early May. Basically, you pay an up front fee to get your “passport” (in this case $37), which allows you to get a cocktail at a specified number of bars during a specific time frame (in this case, 25 bars were participating). Each place will have a different cocktail (or a couple that you can choose from) based on whatever that passport’s theme is. For this one, the theme was cocktails using spirits produced by women-owned distilleries.
With NYC prices, this thing pays for itself even if you only go to three or four of the bars.
And now, the recap!
- Good Passport cocktails
- Watch and/or play ball at legendary basketball courts
- World Trade Center
- Death & Company
Day 1 – Friday
We were up early on Friday and hit the road around 8am. The plan was to drop the bridal shower participants off in Hoboken, where three bro’d trippers would meet the fourth who was already in the city for work. From there, we’d drive over to Williamsburg to check into our Airbnb.
The plan was executed perfectly, and by 3pm we were checked in and ready to hit the town. We had a lot of walkable places that we wanted to start with, but unfortunately the weather was not cooperative. It was about 40 degrees and pouring rain all of Friday, so Lyft and the subway were the predominant modes of transportation.
First stop was Delaney Barbecue for a late lunch. But wait! I forgot a cardinal rule of planning – check the hours of operation! Delaney doesn’t open until 5pm on Fridays. Off to a good start…🤦♂️
We recovered with a quick Yelp search, which revealed that we were right around the corner from a well-reviewed and quick Turkish spot called Abracadabra. After fueling up with a tasty Abracadabra burger, we needed to kill about an hour before The Shanty opened, which was where we had to go to pick up our cocktail passport. We headed over to Lucky Dog (affectionately called “dog bar” by a friend who recommended it) for a beer and to see some pups. I love places like this – a dive bar with good beer selection, shuffleboard, and a dog-friendly policy.
Once the shuffleboard game was done, it was time to take a Lyft to pick up our passports at The Shanty, which is the bar at the New York Distilling Company. There, we had a lovely take on an Old Fashioned using their Mr. Katz’s Rock and Rye as the base.
From there, we squeezed in two more passport cocktails in Brooklyn before heading into Manhattan to meet up with the bridal shower team for dinner. First was Northern Bell, for a bourbon-based John Daly style drink and a tasty spread of deep fried deviled eggs, pickled veggies, and pimento cheese.
From there, we headed into Bushwick to Montana’s Trail House, where the passport cocktail was a Daiquiri made with rum from a local distillery. This place had a nice cozy atmosphere, and a patio which would have been great if the weather was better. We saw some good-looking food coming out of the kitchen as well, but didn’t try anything as we were in a hurry to slurp down our drinks and get to our dinner reservation.
Next we made the short walk in the rain to the L station at Jefferson St, and took the L to 1st Av in East Village. We met the Hoboken crew at French-inspired Tree Bistro for our dinner reservation. Another place with a great outdoor area that would have been awesome if the weather was nice, but we were still able to sit outside under a heated tent. I was surprised that it was not very busy at all on a Friday night, because the food was very good. I highly recommend the calamari and the panna cotta.
After supper, I insisted that the group go to Death & Company for a digestif. As a home bartender disciple of the Death & Co book, this was the stop that I was most excited for. I was expecting a wait of maybe an hour and a half or so for eight people, so I put my name and number in at the door and we went down the street to Amor y Amargo in the meantime. Death & Co never called 😔. Next time, we will go with a smaller group, or perhaps split into groups of two. Going on a busy Friday night around 10pm was probably not the best strategy for getting in, either. For these NYC speakeasies, the way to do it is getting there right when they open, or going on a weekday.
Amor y Amargo did not disappoint, though – a very small spot with very good cocktails on tap featuring all kinds of bitters.
From there, we wandered over to Poco for another passport cocktail, before the two groups parted ways and the bro’d trippers took the L back to Williamsburg. We closed the night with a brew at Radegast, a massive German beer hall, followed by some street meat 🙏. A solid first day of #steintinerary.
Day 2 – Saturday
The main event in my mind for Saturday was the first Smorgasburg of the year. I had stumbled upon Smorgasburg accidentally in my research, and it instantly became the focal point around which everything else would be planned. Anything involving outdoor food – trucks, tents, carts, festivals, whatever – I’m all about it.
Smorgasburg starts at 11am and the plan was to do lunch there, so we chose some morning activities not too far from the location. After the late night Friday, we definitely needed some coffee to wake the hell up, so we started at The Flat’s BkSpeed, which is a hip coffee shop by day, and appears to be a hip bar and intimate music venue at night. The banana split latte was marvelous, if you’re into that sort of thing.
Next, we had to go get some Instagram shots. I had my eye on getting some photos in the DUMBO neighborhood (Down Under Manhattan Bridge Overpass), where you can find great views of the Manhattan and Brooklyn bridges, with downtown Manhattan in the background. The iconic shot (at the top of this post) is at the intersection of Water Street and Washington Street. You feel so small looking up at the Manhattan Bridge, and if you get the right angle (which is right in the middle of the intersection), the gap in the bridge support frames the Empire State Building perfectly.
Here are some other shots from the parks on the East River:
After walking around DUMBO and then perusing Bedford Avenue back in Williamsburg, we had worked up enough of an appetite to hit Smorgasburg. After scouting the premises, I had identified some tents with smaller portions which would allow me to try multiple things. First up was a little brisket sandwich at the Mighty Quinn’s tent, followed by a lemon garlic chicken jian bing, and finally a banana pudding dessert. All were very tasty and affordable. There was also a sizeable crowd for such a crappy day (it was about 45 degrees, very windy and cloudy).
After Smorgasburg, the plan was to meet up with Jared’s brother in Manhattan and hit a few more of the cocktail passport locations in East Village, West Village, and Chelsea. We took the L into Manhattan again, this time over to the west side, and went to Sons & Daughters NYC. Unfortunately, it turns out they do not offer the passport cocktail during brunch hours, so we just got some cheap beers and planned our next move.
The weather was starting to improve, so we thought next we might see if there were any good games going on at The Cage, a renowned basketball court in Greenwich Village, right off the Washington Square subway station. There were some people playing, but the quality of play left something to be desired. It was still fun to see, and I can only imagine how exciting it would be to watch great players there. Even with scrubs on the court, it was a great atmosphere, with tons of people going in and out of the subway station and stopping to watch.
From there, we walked over to Barney’s Bone Broth for a little broth snack. I’ve been on the broth train since Rachel and I recently visited an excellent restaurant near Rochester called FLX Table (best new restaurant in the US!), where we were greeted with a cup of tasty broth. Barney’s was very good, and I enhanced mine with a soft boiled duck egg.
After Barney’s, it was time for another passport cocktail at Rouge Tomate in Chelsea, where we had a very refreshing citrus gin cocktail. We were starting to get used to this whole not paying for drinks thing, so we kept it going at Slowly Shirley next, an underground speakeasy with great drinks, a cool atmosphere, and a strong adherence to the speakeasy era, right down to the guy with a mop following closely behind anybody whose feet touched the bare floor to aggressively scrub away their footprints. Here, I saw a drink on the menu that I just had to try, so I gave away my passport drink in favor of a Summer in Siam, which I think was a fine decision. Any cocktail with some kick to it tends to catch my eye, and I couldn’t turn down the habenero-infused rum, with tamarind liqueur, pineapple, lime, and Thai basil. 👌
After a quick drink upstairs at The Happiest Hour (which struck me as a great place for singles to mingle), it was time to catch our dinner reservation at Pondicheri, an Indian restaurant that also offered a cocktail as part of the passport deal. Their drink was a vodka-based salt lassi, which was quite refreshing and went well with the food. I highly recommend the Seafood Aviyal!
Next, we had to rush to find a sports bar to watch my UNC Tar Heels play against Oregon in the Final Four. A close walk from Pondicheri was Rogue, with a boisterous crowd and plenty of TVs to catch the game. UNC eked out a close victory, so the celebration continued at John Doe for another passport drink (a lovely rosebud gin drink), and then at 230 Fifth rooftop bar, looking out at the Empire State Building which was colored Tar Heel blue. The drinks were about what you’d expect at a club-style bar – sugary and expensive – but I say just get a cheap beer and enjoy that view!
From there, the antics were well underway. We ended up bouncing around, hitting Live Bait, trying to get into Webster Hall just to see what kind of craziness was ensuing but turning around once we realized it was $35 to get in, having a beer at the Village Pourhouse, and finally getting some street meat and heading back to Brooklyn, unsure about how on Earth we were supposed to wake up in 4 hours to pack up and get to the World Trade Center for our 9am entry time…
Day 3 – Sunday
Somehow, we did it! After a frantic pack job, we were in a Lyft en route to One World Observatory. At $34 per ticket, it’s a steep price to pay for a view, which is something that I normally don’t like to do. But in this case, I think it was worth it. The view really is unlike any other, and on a Sunday morning the crowd was not too big so we could take in the view at all angles unobstructed.
After about 30 minutes on top of the world, we were in dire need of food and coffee. We walked around the Financial District and stopped in at Leo’s Bagels, which hit the spot. At this point we were running low on time (we had a basketball game back in Rochester scheduled for 9pm), but we were oh-so-close to the best bar in the WORLD, so we had to stop in for a drink at The Dead Rabbit, which did not disappoint. Best bar in the world? On a Sunday morning it was hard to tell, but the drinks were fantastic. The jury is still out…
After taking the J train back to Brooklyn and getting our car, it was time for one more stop before we hit the road. Some would argue that Di Fara in Midwood is the best pizza in the city, so we had to try it. Expect a wait – ours was an hour or so – but the result is worth it. Again, jury is out for me on the “best in the city” prize, but I was not disappointed.
- Explore more of Brooklyn
- Explore Harlem
- More basketball courts – get out to play on one of them
- Speakeasies: Death & Company, Attaboy, Please Don’t Tell
- Smorgasburg again – I could eat every meal there
- Delaney BBQ
- Shipps Biscuit at Saltie – top 3 breakfast sandwich ever
What would you add to the list? Add your suggestions to the comments!