I went into NYC for meetings yesterday. The train station experience in PHL was a bit more stressful than it should it been — the garage where I have parked for every train trip for 14 years was mysteriously FULL, truly no spots, so I had to park in a surface lot about a 8 minute walk away, which I hadn’t built into my schedule! — but when I arrived in NYC I found the city was decorated for the holidays. I walked past the Macy’s windows, and through Bryant Park, where the annual Winter Village is in full swing. It put me in a festive mood.
So I figured it’s time to share my annual holiday fun list! I have been making some version of this list for the past 10 years (at least). The idea is to bring a little order to the holiday season, and make sure I know what I and my family would most like to do to enjoy this festive time. There are a lot of options, and by thinking this through, we increase the chances of making most of this happen. So here’s what’s in the plan:
Visit Luminature. I have tickets for this light show at the Philadelphia Zoo for me and my younger kids this weekend (I believe others will be going to Wicked). My train home from NYC yesterday passed the zoo so I got a sneak preview. It’s very cool looking! I’m sure we will wind up purchasing glow stick type toys and hot chocolate, as that is part of the deal. (There may be a bonus trip to the Morris Arboretum light display, but that isn’t set yet.)
Go to Dutch Wonderland. This will be a Thanksgiving weekend activity, and I now have 7 anytime tickets since my oldest will be home from college. I’m not sure the oldest kids will want to go but…maybe this will be forced family fun!
Go to Longwood Gardens. I may go more than once. It is often hard to get a reservation for this on peak holiday nights, so about two years ago I started springing for the membership level where you don’t have to make reservations. Now I feel like I have the hot ticket since I can go anytime! We will likely stop at the Brandywine Museum of Art on the way, since they have a holiday train set-up.
Visit Winterthur. I plan to do this on my own as a birthday activity, as my general sense is that most of the rest of my family is not into historic homes. They have a dollhouse I’d like to see in addition to the decorations.
Sing in several Christmas concerts. I will sing in two “Carols by Candlelight” shows with my downtown choir, and then in an Advent concert with my church choir. I’ll also sing in the Christmas Eve service (the 8:30 p.m. one, not the 11 p.m. one, as that might mean Santa would have a hard time stopping by our house). My 5-year-old will sing in the children’s choir for a service (I understand that I have been tapped to help with back-up vocals + supervision on this one), and he’ll be in the church pageant.
Go out for a nice birthday dinner. This is booked for after one of my holiday concerts.
Do holiday cookie baking. I have tentatively scheduled a baking session for the afternoon of December 7th. Yes, even though baking can happen flexibly, it helps to have a target time when everything is busy. We’ll put the dough together on the 6th so it can chill ahead of time.
Wear my flapper costume to my husband’s office party. So they are doing a “Roaring 20s” theme this year. I decided to go all out and purchased a flapper dress from Amazon. It is amazingly well constructed and decently flattering — a pleasant surprise. I also purchased a flapper headband and accessories set. I’ve gone to this party for a great many years, so it’s kind of fun to shake things up a little.
Go ice skating. This was a kid request, and the rink downtown on the river is quite nice as long as the weather cooperates. We might go post Christmas too.
Go to the Nutcracker. I missed this last year so I’m really looking forward to it. I might also wind up going into NYC to see the Rockettes again — this would be with two of the kids while the others are elsewhere so it’s all a negotiation at the moment. There may be a trip to the NY Botanical Gardens in January, as the holiday display set-up is open through to the second weekend.
Get matching family pajamas. My daughter is in charge of this selection this year.
Build the holiday Lego set. It’s a train this year. I bought the set, we just need to get going on it. I’ll also do some holiday-themed puzzles.
Do sibling presents. This is occasionally stressful for me as the kids need to go shopping for each other but they like having this as a tradition, so we’re in for it.
Read holiday children’s books. We’ve pulled out the old favorites and have already read Christmas Farm and Little Blue Truck’s Christmas (the batteries are dead on the light up page on that one, so I need to fix it). I don’t think we have that many more years for these to get read so after 18 years of reading children’s books to people I’m trying to appreciate that this chapter (ha) is winding down.
Decorate. We have lights up in the yard now, and the fancy tree has gone up in the living room. We’ll get the family tree (the live one) over Thanksgiving weekend and decorate that. It’s fun to keep adding to collections over time.
Have many enjoyable moments during our holiday family travel. We’ll be taking a fairly epic trip over the holiday vacation with all 7 of us. Family travel is never all blissful, and I know parts will be stressful, so I’m reminding myself to aim for a few enjoyable, memorable moments. That I am pretty sure will happen.
What’s on your holiday fun list?
Photo: Scene from the Macy’s windows

That is a fun list! Little Blue Truck is one of my fave Christmas books. We have 3 baskets of books and our almost-5yo has loved reading them. Our 7yo doesn’t seem interested but tends to end up next to us when I read to the younger one.
We have plans to go to the tree lighting event at our church which includes Santa and reindeer! We’ll also go to the Christmas concert, although I will only take my 7yo as it’s too long to sit quietly for the younger one. We’ll see the Grinch this weekend. I’m bringing sugar cookies to Thanksgiving so the kids can decorate them as a birthday party activity for my kids and their cousins. But I got fall cookie cutter to use. I’ll try to make Christmas shaped ones closer to Christmas to give to Santa. And then besides that we have a few holiday parties to attend for work.
@Lisa – thanks! I’m thinking we may only have another year or two on the little kid picture books…so we’ll try to make it through most of them this year. The Grinch sounds like fun – and the sugar cookies!
My holiday fun list includes a white elephant gift exchange. It’s an annual tradition with several friends who enjoy the same sport (cycling), meaning the mystery boxes under the tree often contain funny trinkets or garish clothing that’s bike-related. It’s always a fun evening.
@Lynne – so fun! I love a good and funny gift exchange. Especially if the same people have done it for a while!
Your list has lots of fun outings! My list:
1. Overnight stay at the Hyatt at the Bellevue plus dinner at Talula’s Garden in Philadelphia.This is a birthday gift to my husband. We’ve never done a “staycation” in Philadelphia during the holidays.
2. Go on a local “Cook’s Tour” of kitchens decorated for the holidays. It is organized by our local health system. Covid resulted in cancellations for a while, and then last year they couldn’t get enough people to volunteer their homes. I’m glad it’s back. Going with 1 or 2 friends, which will be a nice bonus.
3. Bake Christmas cookies with my 3 year old grandson while his 9 month old sister watches us.
4. Go to a cookie exchange-have not attended one in years. I am not fancy with my cookies-they just have to taste good.
5. Family dinner to celebrate my husband’s birthday.
6. Trek to Long Island to spend Thanksgiving with my sister and family and visit my 97 y/o Mom in her nursing home. It is a miserable drive, but time with family is special.
7. Go to the Teddy Bear tea at the Rittenhouse Hotel in Philadelphia with my daughter, daughter in law and grandson. It is a bit spendy-but my Mom used to take my sister and me plus the 4 grandchildren to the Nutcracker in NYC-that was spendy, too-but the grandkids (who are now all adults) still talk about it frequently.
8. Go to Barnes and Noble and sit with a holiday coffee in the cafe while perusing holiday-themed magazines and deciding what to buy. Magazines have really gone up in price!
9. Go on my annual wander/flaneur around Trader Joe’s, a local retail center and Target to get gift ideas.
10. Go on a nighttime walk with my husband and a local hiking group to admire holiday lights.
11. Use the ChristmasPrism app to find local holiday light displays and drive around with my husband to look at them, hot chocolate in hand.
12. Visiting the Morris Arboretum train display has been in my list for a number of years, but there are limited dates and tickets. I am keeping it on my list, but I doubt we will get there.
@BethC- Love Talula’s – I’m doing a birthday dinner there too! And I like the idea of perusing holiday magazines in B&N…maybe my library has some too…
Getting very excited to celebrate our first Christmas as parents with our almost 8 month old! As a music teacher there will be a lot of performances (both run by me and participating as a player) but hoping to enjoy one or two from the audience as well! I’m making my son a Christmas stocking, we are enjoying books and planning to bake some of my favorites.
Our tree cutting tradition has us out at a family friends house who have a lot of property and host us and another family with little kids for a “hike” and brunch or lunch to get the tree!
After reading your remark about booking camps I have moved making reservations for spring break travel higher up my list to make sure we are able to hopefully get reservations for activities and travel on the days we want!
@Kira – how fun to get the “natural” tree cutting out in the woods! That would be fun to do some time. And yes, camp bookings happen earlier than I am ever ready for…
Unsure if this counts as “fun” but I’ve scheduled “Operation Santa” shopping, wrapping, and dropping session with two other fully work from home teammates who live in the same city. We’re still looking through to pick a letter to adopt.
https://www.uspsoperationsanta.com/
@Silver – definitely holiday fun! I love this idea.