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 You picked Bryant Park, the library and lunch at Olio e Più — it's booked, table for six at noon on Monday. Nothing left to decide. Just read through, note the few tips at the bottom, and show up.
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. All of this happens within three blocks.
Sleep in a bit Checkout isn't until noon, so there's no rush. Grace is packing breakfast for the room — eat something, because lunch isn't until twelve.
Grace and Leroy run the bags to the car You can stay put in the room while we do this — have everything packed and by the door by 10:15 and we'll take it over. That way nobody's dragging a suitcase around Midtown all afternoon.
Check out Whatever you want for the day comes with you.
Bryant Park, right as the games open The garage sits one block north of the park, so we walk straight in. The free stuff comes out at 11:00 — ping-pong with paddles provided, chess, board games, pétanque, a putting green, Kubb, and a little carousel that costs a few dollars a ride. All of it is free and run by park hosts. Bring a photo ID if you want to borrow something and take it out onto the lawn. What's on today
Lunch at Olio e Più 5 Bryant Park, on the corner — the Italian place with the flower-covered front, one of the most photographed doorways in the city. Table's booked for six. Get your picture out front before we go in. MenuMap
Kinokuniya 1073 6th Ave — half a block from the restaurant, right across from the park. Three floors of everything Japanese: manga in English and Japanese, anime and Studio Ghibli merch, plushes and figures, blind boxes, and a wall of stationery. There's a café upstairs with a window looking out over Bryant Park. Emily, this one's for you. Everyone else, budget accordingly. Kinokuniya
New York Public Library — only if you want it 476 5th Ave, on the far side of the park and directly on our walk back to the garage, so it costs us nothing to stop. The marble lions out front are Patience and Fortitude. Inside, Astor Hall and the Rose Main Reading Room — a block-long room with painted clouds on the ceiling. Free, no tickets, half an hour is plenty. Completely optional. If everyone's shopped out and ready to go home, we just keep walking. Visit infoMap
To the garage Four minutes from the library, and no stop back at the hotel since the bags are already in the car. 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.
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 they're confirmed as adjoining, so the door between them can stay open. You'll be sharing beds, so pack accordingly — pajamas you're comfortable in, and anything that helps you sleep somewhere new. We're also bringing an air mattress in case anyone would rather have their own bed.
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.
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 have confirmed that they will be adjoining ones so the door between them can stay open. The girls will be sharing beds — we've told them to pack accordingly. We're also bringing an air mattress in case anyone wants their own bed.
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 — completely optional
The girls picked the slow version: Bryant Park, the New York Public Library, then lunch. You're very welcome to join us and equally welcome to skip it. No expectation either way.
The park and the library are free and need no notice — turn up whenever suits you. We'll be in Bryant Park from about 11:15, at lunch at noon, and afterwards at Kinokuniya and maybe the library before heading for the car.
Lunch is the one thing to book yourself. We have a table for six at Olio e Più at noon and you're very welcome to reserve your own table and join us there. It's a popular spot on a summer Monday, so we'd recommend booking ahead on OpenTable rather than chancing it.
Getting the girls home Monday night
We're leaving the garage by 3:00 PM Monday and should be back in Sykesville around 7:00.
Alexa is riding back with her family. Addie is riding with us. Abby can go either way — no need to decide in advance, we'll have room for her.
Anything Grace should know
Food allergies, anything the girls don't eat, medications.