One Night Only
Emily's
Sweet 16in New York City
Sunday, August 9 — Monday, August 10, 2026
The Crew Emily, Abby, Addie & Alexa. Chaperoned by Grace & Leroy. Abby's and Alexa's families are staying at the same hotel and joining us Sunday evening — parents, there's a section written just for you near the bottom.
One thing to vote on Sunday is set. Monday is yours to pick — have a look at the two options below and tell Emily which one you want by Monday, July 27. She'll tally them up, and Grace needs to book it and let the other families know.
Our Treat All accommodations, attractions and meals on this itinerary are covered. This is Emily's big Sweet 16 splurge! You just need to cover any shopping — so if you want to buy candy, makeup, souvenirs or anything else, bring your own cash or card.
Act One
Sunday
Drive up, see the show, eat cake, take over Times Square. No decisions needed — this whole day is locked in.
Meet at the West Friendship Park & Ride I-70 and Route 32. Get dropped off here and we'll load up and head out. About four hours to the city with one stop. Bring headphones, chargers, and a car playlist. We'll have snacks for the ride up. Map
Park the car City Parking, 38 W 43rd St. The car stays put until Monday afternoon. Map
Drop bags at the hotel — or check in if the room is ready Hilton Garden Inn, 136 W 42nd St. Rooms usually aren't ready until 3:00, so we'll most likely check our bags with the hotel and head straight out. Since we probably won't get into the room first, you can come dressed for the show or do a quick change in the lobby restroom. If you want to do your makeup during the drive up, go for it. HotelMap
Quick lunch near the hotel Counter service, in and out, all within a few blocks and all on the way to the theatre. Here are some options and we'll just pick a spot when we get there: Los Tacos No. 1 — 229 W 43rd St. Tacos and quesadillas, cheap, and some of the highest-rated food near Times Square. There's usually a line but it moves fast. You eat standing up. Joe's Pizza — 1435 Broadway. Classic New York slices, two blocks away, the fastest option even with a line. Carve — 760 8th Ave at 47th. If you want an actual sandwich, salad or soup. Big menu, open all day, closest to the theatre. Los TacosJoe'sCarve
Get to the theatre Bernard B. Jacobs Theatre, 242 W 45th St. Bathrooms are down a staircase and the line is long — go before we walk over. Remember to bring a sweater, as the theatre can be cold. TheatreMap
THE OUTSIDERS About two and a half hours with one intermission, so we're out around 5:25. Heads up: flashing lights, a very loud train horn, haze, and a few dark stretches. The show
Birthday dinner at Gurumé 313 W 46th St, one block from the theatre. Emily and Grace ate here last December and Emily really loved it, so we're doing it again! Korean small plates meant for sharing, so we order a pile of things and pass everything around. We'll aim to be out by 7:20. MenuMap
Back to the hotel — finally into the rooms Ten-minute walk, straight down through the middle of Times Square. Consider it a preview. This is probably the first time we get into our rooms, so we can grab our bags and head up to drop everything off. You can also change into whatever you actually want to be photographed in. Be back down to the lobby in twenty minutes.
Cake and presents in the lobby This is the actual birthday part. Abby's and Alexa's families meet us down here, and we do cake and presents somewhere everyone can sit and hear each other instead of shouting over Times Square.
Head out to Times Square Families are welcome to join us if they'd like! The more adults we have for this, the better. Otherwise the six of us will need to stick very close together the whole time. Everyone walks over as one group. Times Square is two minutes from the front door.
Pictures, while the light is perfect The sun sets at 8:05 and the sky is deep blue going black right about now — every billboard at full blast, and still enough glow left that you can actually see faces instead of turning into silhouettes. This is the one you'll actually want to post. We'll head for the red steps above the TKTS booth at Duffy Square, 47th and Broadway. They're elevated, so the entire square stacks up behind you.
Then do whatever you want Photos are done, and the rest of the night is yours — but you must be with adults the entire time, either Grace and Leroy or others in our party. Everything below is within a few blocks and open late: M&M's World and Hershey's for absurd amounts of candy · Sephora · the Disney Store · souvenir shops selling glorious junk · street performers and the Naked Cowboy · or just wandering around gawking at all of it, which is honestly half the fun. This is where your own money comes in handy.
Back to the hotel Roughly. If everyone's had enough sooner, we go sooner. There will be leftover cake.
Act Two
Monday
More Monday Manhattan fun and then home. The car has to leave the garage by 3:00 PM, so that's our timetable.
Breakfast in the room Grace is packing breakfast for the room. Worth eating something, because Monday doesn't get to a proper meal until late morning.
Check out, bags behind the desk Whatever you want for the day comes with you; everything else waits at the hotel.
Monday's activity (all are welcome!) This is the one you're voting on — see below. Either way it runs into the early afternoon.
Grab bags, walk to the garage Last look at the city on the way.
On the road Home around 7:00. If everyone's wiped out we can head off earlier — no hard feelings.
Your Pick
What should we do Monday?
One is slower and easier. One is the big New York thing. Both wrap up in plenty of time to get on the road. Abby's and Alexa's families are welcome to join for whichever one wins, but it's optional — Grace will pass along the details once it's decided.
Lunch at Olio e Più, the Italian place on the corner of Bryant Park with the flower-covered front — one of the most photographed doorways in the city. Then the park itself, which has free ping-pong, chess and board games out all day, and the New York Public Library right next door with the stone lions and the enormous reading room.
Unhurried. Sit down when you want, leave when you want.
Three floors of mirrored rooms and glass boxes hanging 1,100 feet over Madison Avenue, on top of the tallest building in Midtown. The ticket includes lunch, plus Ascent — a glass elevator on the outside of the building that goes twelve stories higher.
This is the one people fly here for. It takes a good chunk of the day, and it earns it.
If we do this, read before you pack: the floors and walls are mirrors, and there are glass floors you stand on. Wear shorts, pants or leggings — no dresses, skirts or short shorts, because people can see straight up. Stilettos are actually banned — they wreck the mirrored floors. Sneakers are the move. Also: no big bags allowed inside.How to pick Just tell Emily — text her, call her, say it at lunch, whatever's easiest. By Monday, July 27, please — which happens to be Emily's actual birthday, so you can wish her a happy one while you're telling her your pick. If it's a tie, birthday girl breaks it.
A few tips
Not rules — just things that make the weekend easier.
Comfy shoes
We'll cover a lot of sidewalk over two days. Shoes you've already broken in will treat you a lot better than brand new ones.
A light layer
Theatres run the air conditioning hard even in August, so a sweater or light jacket is nice to have. Easy to stuff in a bag the rest of the day.
A little spending money
Everything on the itinerary is our treat. Some cash or a card is just handy if something catches your eye — candy, makeup, souvenirs.
Sleeping arrangements
We have two rooms and we're requesting adjoining ones so we can leave the door open between them. You'll be sharing beds, so pack accordingly — pajamas you're comfortable in, and anything that helps you sleep somewhere new.
Food you'd rather skip
If there's an allergy or something you just don't like, let Grace know sometime this week. Dinner is shared plates, so check out the menu to think about what you might like to try.
If heights aren't your thing
If SUMMIT wins, there are glass floors and a glass elevator on the outside of the building. Nobody has to go on the elevator, and it's easier if we know ahead of time rather than finding out up there.
Also worth knowing for packing: the floors and walls are mirrored, so dresses, skirts and short shorts aren't a great idea — anything short can be seen up. Shorts you feel good in, jeans or leggings, plus sneakers, and you're all set.
For the Parents
Abby's and Alexa's families
Everything above is written for the girls. This part is for you.
Sunday drop-off
8:00 AM at the West Friendship Park & Ride, I-70 and Route 32. We'll load up and pull out from there — about four hours to the city with one stop.
Where we'd love you to join us
Sunday, 7:50 PM — the hotel lobby. Cake and presents with everyone together. Then at 8:30, anyone who'd like to come is welcome to walk over to Times Square with us as one group — we'll be out until around 10:30.
Please do come along for that second part if you can — the more adults we have, the better. Otherwise the six of us will need to stay very tightly grouped the whole time. Safety will be our top priority!
Sleeping arrangements
We have two rooms and we're requesting adjoining ones so the door between them can stay open. The girls will be sharing beds — we've told them to pack accordingly.
The one favor we need
Could one of you pick up Emily's cake? It's at Amy's Bread, 672 9th Ave in Hell's Kitchen, under Grace's name. We're at the theatre from 3:00 to 5:25 and then straight to dinner, so we can't get there ourselves.
Two things: the shop closes at 7:00 PM, and it's August, so picking up later rather than earlier is better. Grace is asking the hotel to hold it cold until we're back.
Parking — book ahead if you haven't already
We prepaid at City Parking, entrance at 38 W 43rd St (listed as the 1114 6th Avenue Garage). It's a five-minute walk to the hotel. Street parking in Midtown isn't a real option, so reserve online in advance — walk-up rates are brutal.
Fair warning from recent reviews: bring your printed confirmation, because a few people report being asked to pay twice at exit. Photograph your car before handing over the keys. And ask about the oversize surcharge if you're in an SUV or a van, and whether your reservation allows more than one exit.
Monday is completely optional
The girls are voting on one Monday activity — either a slow morning around Bryant Park and the library, or SUMMIT One Vanderbilt. You're very welcome to join us and equally welcome to skip it. No expectation either way, and no need to decide now.
They'll decide by Monday, July 27, and Grace will let you know that evening which one won. We're doing the Flex ticket option that includes lunch.
If you'd like to come, please let Grace know by Wednesday, July 29 — sooner if you can. The SUMMIT tickets are timed and have to go on one order so we all get the same entry slot, which means she can't add anyone once she's booked. Bryant Park doesn't need any notice, so if that one wins you can decide day-of.
Getting the girls home Monday night
We're leaving the garage by 3:00 PM Monday and should be back at our place in Sykesville around 7:00. Happy to bring the girls home with us and have you pick them up there, or they can ride back with your family instead — whatever's easier for you. Just let Grace know before Sunday so we can plan seats and cargo space.
Anything Grace should know
Food allergies, anything the girls don't eat, medications, curfew preferences, a fear of heights — tell her this week rather than on the day. Dinner is shared plates, so dietary needs really do change how we order.