Seven Shows in Four Days: A New York Adventure

2025-12-11

Forgive the tardiness of this blog post about our October 16-20th trip to our beloved New York City.

This was a long weekend of shows, food, and friendship in one of our favorite cities, where I lived for eight years in my 20s. It actually started earlier in the week for Mei-Mei, who attended her first Fora Live conference, where she had the opportunity to meet and learn from fellow travel advisors and industry partners. She came away from the experience inspired and enthusiastic; but I'll leave it to her to tell you about that at a later time.

My part of the trip was purely theater-focused; Broadway is one of our deepest and most enduring passions. When we heard that Ragtime was being revived, we knew we wanted to go back. When we heard Chess was being revived simultaneously, we knew we had to go back. And when we heard about Masquerade, the mysterious and immersive new take on Phantom of the Opera, we bought plane tickets immediately.

Seven shows in four days

1. Masquerade - Thursday evening The Phantom of the Opera was the longest-running show on Broadway for a reason, and it will forever hold a special place in our hearts. Still, we didn't know what to expect about this new immersive production, which required us to wear masks and dress up.

Well, the moment we walked into the crowded room and the event started, we were absolutely blown away. Being surrounded by the activity and interacting with the actors (Mei-Mei played the piano for Carlotta! The Phantom carressed my mask!) put a new twist on this well-known story and really heightened the emotional component. This was the first time I can ever remember crying during this show, but the Phantom's heartbreak at the end felt so real. It helped, of course, that our Phantom was the phenomenally talented Telly Leung (known to many for his role in Glee, but to me for his roles in Godspell and Allegiance on Broadway).

I don't want to spoil anything about the show. Suffice it to say, you should go into it with an open mind and an eagerness to be surprised. No two experiences are the same. We know, because we saw it again at the end of the trip (more on that later!).

1. Ragtime - Friday evening This is, in my opinion, one of the top five best shows ever written, with intricate melodies that perfectly complement the intricate storylines and relationships playing out on stage. This revival stars Joshua Henry (if he doesn't win the Tony, the world is an unjust place), Caissie Levy, Brandon Uranowitz, and other Broadway heavy-hitters and truly does the show justice. The cast recording comes out in January!

1. Operation Mincemeat - Saturday matinee Mei-Mei has been intrigued by this concept since she first heard about it, so we were thrilled to finally get to see it. Most of the cast were still the original creators of the show, which is quirky and weird and funny and occasionally confusing. Jack Malone, who won the Tony and Olivier awards for his role, was out, but the understudy's performance, especially his rendition of the heartwrenching "Dear Bill", was stunning. This isn't a show we'd go see again, but we're glad we saw it once. It is so clever and inventive!
2. Chess - Saturday evening

Time for the other show that lured us here: Chess, starring Aaron Tveit, Lea Michele, and Nicholas Christopher

This is a show whose recording we know so well, but which we'd never actually seen on stage before--it hasn't had terribly successful stage runs in the past. This cast, however, was put together with the clear intention to draw audiences in--and they succeed! Lea Michele, Aaron Tveit, and Nicholas Christopher deliver strong performances, with some of the songs bound to replace the older cast recordings' on people's playlists. I was especially happy to see Bryce Pinkham on stage again as the arbiter/narrator; I was a huge fan of A Gentleman's Guide to Love and Murder and saw it many, many times when I lived in New York, and he was one of the two leads. He showed some of the same quirky charm in his role in Chess, which worked nicely as a way of updating this "Cold War musical" (a reference he made several times). Much of the book was rewritten for this production and some of the songs were altered. The result is still imperfect--the story in act two is pretty weak, in my opinion--but it's a great spectacle on stage and a lot of fun to watch and listen to.

1. Maybe Happy Ending - Sunday matinee

Maybe Happy Ending was a darling show and really tugged at our heart strings. We didn't realize our seats would be very obstructed, which was too bad!

We couldn't miss this year's Tony winner. Good seats were hard to get, but we didn't realize we'd have obstructed views--we spent a lot of the show leaning over the balcony trying to see over the lights. I'd listened to the cast recording in advance but really didn't know what to expect from this show about two robots falling in love. By the end of the short, one-act musical, I was completely invested in their story. This show

1. Oh, Mary - Sunday afternoon

1. Masquerade again - Sunday evening

NYC in all its glory

Hotel We stayed at the Romer, which is ideally located for a theater trip, in easy walking distance to all of the Broadway theaters and dozens, if not hundreds, of restaurants, cafes, and stores. They periodically have great deals, so reach out if you're considering a stay!

Everyday magic

We had a great time at a street fair, including purchasing several pieces of art from the incredible talented Bogdan, who created the skyline using only a paint scraper against the canvas

Dining

Help me plan a theater trip!