A Fun ‘Gen X’ Weekend in Manhattan

Billy Joel at the piano

We built our weekend away around tickets to Billy Joel’s second-to-last show of his monthly (or so) residency at Madison Square Garden. I was able to grab Citi presale tickets when they went on sale last October. The tickets for our show with decent seats in the 200-level were about $350pp including taxes. Similar seats for the final show in July were around $1500pp so I obviously went with the June show.

A few weeks before we left, I bought Sunday matinee tickets for A Beautiful Noise, the Neil Diamond musical on Broadway. My mom and brother had seen it and said it was very good. We ended up flying up Saturday morning and flying home Monday evening.

On Saturday, when we arrived, my wife went to look for some art supplies at some stores in the garment district and I went to wait in line at TKTS in Times Square to see if we could get tickets to a matinee that afternoon.

After I got the tickets, we met up and had a quick lunch at the Brooklyn Diner, right across from the theater. It’s a reliable, quick place to grab a bite in New York with a broad menu including breakfast anytime.

I managed to buy 50% off tickets to &Juliet, the show that is a reimagining of Romeo & Juliet set to 90’s hits written by Swedish music producer Max Martin. That synopsis sounds a bit crazy, but it turned out to be a fantastic show. They basically took some of the crappiest hit songs ever written and turned it into a hilarious, light-hearted show.

Our seats were great – about 8th row center orchestra. We even had an empty seat next to my wife.

After the show, we checked into our hotel (the Grayson) and rested for a bit. We ended up grabbing an early dinner at Bourbon and Branch, right near Madison Square Garden. The drinks weren’t bad, but the burger we split was just OK. I don’t really recommend this place other than the location is right near MSG.

We had a great time at Billy Joel’s show that night. We had seen him at MSG once before in 2019 and it was mostly the same show. He did bring out Trey Anastasio from Phish (another MSG staple) as a special guest for a couple of songs.

After the show, it was a fairly easy walk back to the Grayson, although we were unsuccessful in finding an ice cream truck on our way back to cap off the night.

The next morning, we walked down to the Chelsea Flea Market down on 25th. That afternoon, we went to see the Neil Diamond musical. It was a great show, with the lead (a former American Idol winner) doing a fantastic impression of Neil’s gravelly voice.

After the show, I surprised my wife with a visit to a speakeasy called The WooWoo on 47th street. They had some crazy drinks and an 80’s theme. A password from their website was required to enter the bar and go downstairs. I won’t write it here on this family- friendly blog.

We had some enjoyable drinks at the bar and chatted with the bartender for a while. He even threw in some free shots. One of the drinks required some flames.

After the drinks, we headed down to 34th street and dinner at Keen’s steakhouse. This was probably the only disappointing meal of the trip, mostly because we had higher expectations.

The steak was a bit tasteless and we ended up taking half of it back to the hotel, where my wife said it tasted better cold when she woke up hungry in the middle of the night. My wife also ordered the lobster bisque which had a disappointingly small amount of lobster in it. The wedge salad was good, but it’s hard to screw that up. We managed to stop for an ice cream on the way back this time.

On Monday, we browsed around some more art supply stores and then we went downtown to Century 21 department store for my wife to browse (and me to sit outside in the nice weather). We took the subway there and back. That afternoon, we flew back to Atlanta and my next post will have more about how we got to the airport in a fun way.

I took some pictures throughout the weekend and I’m always blown away by the mixture of old and new buildings throughout the city.

If you have questions about this post, let me know in the comments or send me an email at emptynestermiles@gmail.com. If you are thinking about opening a new credit card, please use one of my links.

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