Success!!
At the beginning of October (before my own birthday), I began to make plans for Greg and I to travel to New York City for his birthday in November. I’ve never planned a surprise trip before (and I’m horrible at containing fun secrets!) so once I had everything booked it was so difficult not to talk to him about it! But I managed to hold it in every time I thought of a comment that might give him some hint, and in the end he was completely surprised!
I told him to request Friday and Monday off from work and I helped him pack his bags so he would have clothes for the right occasions.
We took video of our adventure and you can watch it here!
November 2nd
On Friday morning, we got up at 4am and drove to the Charlottesville Airport. That gave him a hint that we would be flying somewhere… but where? Once we parked and grabbed our bags, I threw him the twist! Instead of going to the departures, we needed to get a cab – to the train station! We were flying home from our destination, but taking a train there. Tricksy tricksy!
We ended up having to take an Uber because no taxis were coming to the taxi stand, but we made it to the train station on time! (It was delayed anyway) There are only a limited amount of destinations listed on the board at the train station, so that’s where he found out we were going to New York City!

The train took about 6 hours, which is about the same amount of time it takes to drive there. It was more expensive than driving, but it was fun to both be passengers (aka be able to sleep), view the fall foliage, have tons of leg room, and not have to worry about driving in traffic or parking. We both agreed that it was fun! When I imagined a trip to NYC, my first thought was arriving by old-fashioned train! Though a flight is much faster, I decided to book the train there to add to the experience (and save a little money).

Upon arrival, we were able to stow our bags at our friend’s office nearby! (Thank you!) I didn’t have plans for us until dinner at 7pm with friends, so we stopped at Panera (our fave) for an afternoon snack. We discussed what we should do until dinner and opted to go up to the top of the Empire State Building! I had never been there and Greg hadn’t been up there in many years.
While at Panera, I decided to just tell him the rest of the itinerary because I wasn’t sure which of our friends at dinner would know that the activities were still secret and I didn’t want them to feel bad if they said something like, “Hey are you excited for…?” and ruin the surprise.
I felt so much better now that he knew our plans! And he seemed excited about them which was a relief.
The Empire State Building was surprisingly not very crowded! Being that the NYC Marathon was that weekend and there was an abundance of tourists, we must have gone at just the right time! We passed by lots of empty queue ropes displaying the magnitude of possible tourists so we were glad to walk right up to the elevators!












We met up with some friends for dinner at “The Horny Ram”. The food was great, but the place must have been busy because the servers didn’t have much time for us! Right after we signed the bill, the host actually asked us to leave due to the number of people waiting to be seated!
On our way to stay at a friend’s house, we picked up some Insomnia Cookies! It reminded us of ordering cookies back in college. We stayed up talking with friends and watching “Old School” on TV.
November 3rd
We woke up, got ready for the day, and took a train to Wall Street to meet up with another friend. We had a quick breakfast at Starbucks and arrived at a meeting location for a scavenger hunt at 11am! The hunt was hosted by Watson Adventures, a company my friend and I had done a scavenger hunt through previously at the Met. Watson Adventures has hunts all over NYC and in several other major cities as well. The hunt we did focused on Alexander Hamilton and the history of the Wall Street area. Scavenger hunts are a fun way to tour an area and get a taste of its history. The goal of these hunts is not to find objects, but to follow the instructions to different locations and find an answer to a riddle-like question. In order to figure out the answer, you need to search the area and read signs and informational plaques.

We are serious scavenger hunters! We finished before the allotted 2 hour time limit and only got 2 questions wrong. She read the names of the finishers from last place to first, and we won! We each got a medal! The host then had us fill out feedback surveys and drew a name from the pile to win a free hunt. Guess who won? Greg!



We didn’t have time to linger after the hunt because we had to catch the subway to Times Square! We had tickets to the 2pm matinee of Aladdin on Broadway! We both love theater, especially musicals, and Greg had never been to see a show on Broadway before. I saw “Mamma Mia!” with my mom and Grandma and “In the Heights” with a friend and her family. The main event of this trip was for me to take Greg to Broadway! My first thought was to try to see “Les Miserables”, but that show is no longer on Broadway. We both love Disney movies and have already seen “The Lion King” in Toronto, so Aladdin was the show I chose! We arrived at the theater with just enough time to run to the bathroom and be seated before the lights dimmed!
We loved it! The Genie and Jasmine were different from the original cast and were fantastic. Aladdin was also new and was a little too vibrato for our taste. It felt more classically trained and less riff-raff, street rat, you know what I mean?
The magic carpet was AMAZING! I barely heard a word of “A Whole New World” because I was so distracted by the amazing effect of the carpet. HOW DID THEY DO IT?!?
“Friend Like Me” was a showstopper – the tricks just kept coming and it got more and more over the top as the song went on!
Iago and Jafar were our favorites; I was laughing the entire time they were on stage. During intermission we read through the Playbill and I discovered that the actor playing Jafar was also the voice actor for Jafar in the original Disney movie! What an amazing opportunity to see him perform this character! We had already noted that he had an incredible evil laugh – now it made sense! Knowing this, Greg got emotional every time Jafar was on stage during the second act – childhood memories!


After the show, we grabbed a sandwich at a place called “‘Wichcraft” that we stumbled upon as we walked to our hotel. We passed by a photo of one of their sandwiches advertised in the window and it made me stop – beets and goat cheese! Yes, please!
We continued on to our hotel, Springhill Suites by Marriott, which I booked using Greg’s reward points! Woo!

Then we met up with friends for dinner at “Two Lizards Mexican Bar & Grill” and it was great! Two other people were celebrating birthdays there as well so we asked if Greg could have a photo-op with their celebratory sombrero as well.




November 4th
We got an extra hour of sleep due to daylight savings! Nice! We met up with friends at “Madison Restaurant”. I got the waffle I was craving and Greg got a waffle sundae! It was good diner breakfast food.


From there, we went to watch the New York City Marathon! My friend’s sister and brother-in-law were running, so we staked out a place to watch them go by. After a while of searching for two people wearing orange, we finally saw them! We were able to get their attention – success!

We moved on to Central Park to watch more runners, but her sister wouldn’t be coming by again for another hour or so.
I had heard about a TV museum called “The Paley Center for Media“, and it wasn’t too far away from where we were, so we decided to check it out. It actually isn’t a walk-through museum, it’s more of a library archive of movies, television shows, and advertisements since the 1920’s. They have a bunch of computers that you can sit at and search for just about anything! I watched some old 90’s Nickelodeon game shows. Oh, the nostalgia.
They also had video game exhibit going on, so one of our friends tried out some VR games and Greg and I played “Overcooked”, one of our favorite games.
We went back to our friend’s apartment to hang out before our flight and then took a cab to LaGuardia Airport. We gave ourselves plenty of time, which makes flying so much more relaxing. We ate a light dinner and then hopped on our hour-long flight on a little plane. We got to walk up the stairs to the plane on the tarmac, which always makes me feel like a superstar climbing the stairs to a private jet!
Around 10:30pm we made it safely back to Charlottesville Airport, where our car was parked, and drove the hour home to our kitties! A successful weekend trip! Happy birthday to Greg!
Thanks for reading!
-Rebecca
P.S. Check out the video!