What is a Milestone Trip?
Some ages seem to mark big shifts in life. The numbers themselves aren’t magical, and they can differ from one family or culture to another, but for us, 5, 13, 16, 18, and 21 are big ones. These ages, to us, represent a shift from baby to girlhood, from girlhood to womanhood. They mark the freedom and responsibility that comes with driving, graduation, and ultimately independence. We acknowledge we’re still “new parents,” so maybe the ages will change for milestones, but we want to take the opportunity of the transition to encourage and pursue the hearts of our children.
Depending on the child, their interest at the time, and our finances, we plan to celebrate these ages with intentional time with each child- locally or not so locally. I hope these trips allow the opportunity to facilitate deeper conversations and chances to explore their passions and purpose - honestly just for fun too!
Time is going to pass. Our kids will grow into adults. Milestones are our chance to mark that passage with some purpose.

Why Chicago?
I’m one of the lucky ones; I have a lifelong best friend. After nearly 25 years, Carly is more like family than a friend. Even though we haven’t lived in the same city since we were 18 years old, we’ve remained close all these years thanks to countless flights, calls, packages, and DoorDash deliveries. For all the highs and lows, we’ve been there for one another.
The day Ava Mae was born, Carly was there. One of the first people to meet our child. Since then, my daughter has loved Carly. When she was maybe two and a half, I remember peeking my head into our guest bathroom to see Ava Mae sitting on the floor, admiringly watching Carly curl her hair. So when Carly and Justin moved back to Chicago a couple of years ago, I knew a trip was coming. Shortly thereafter, we booked a flight for Ava to see Carly and celebrate our girl turning five.
Carly is an incredible hostess and toured us around Chicago in a thoughtful, adventurous way that a five-year-old could enjoy. Although we joked multiple times that we were having more fun than Ava Mae, watching my daughter and best friend’s relationship grow was probably the most fun part for me.
It felt extra special because for Carly’s 16th birthday, her mother and her mother’s best friend took Carly and me around New York City. We saw shows, bought fake designer bags, and ate divine Italian food. I still think about that trip—seeing Alicia and Jacque laugh and enjoy themselves—and I’m so deeply grateful to have someone with whom I can form those sorts of memories for my daughter.









Adventures in Chicago:
American Girl Doll Store- Our first day started at the American Girl Doll store. We had spent the months leading up to the trip reading all the American Girl Doll books we could get our hands on, so we were deeply invested in these girls. Samantha and Molly, in particular. It was so fun to be guided through the store, hearing all their stories and seeing the vast selection of tiny accessories for each little doll. Ava Mae ultimately picked a doll that looked just like her and promptly named her Camille. This doll has not left my child's side since. So special.
The Drake, High Tea- After our shopping excursion, we walked over to the Drake hotel. It was grand and lovely. Ava was served her first Shirley Temple (which burned her nose), and we sat enjoying tiny cakes and sandwiches while the harp played Frozen songs. The bathrooms were what you see in old Hollywood films, where there are benches and glamour seats, and each little stall had its own sink. I love beautiful old buildings, so this was especially fun for me.
Parent Trap- Carly and I spent most weekends with Chinese take-out and a movie. After a full day of shopping and tea, we came home and baked brownies. Ava showered while Carly and Justin made dinner, and after we sat down to genuinely one of the yummiest dinners I’ve had in a long while, we filled the coffee table with fresh brownies and snacks and watched The Parent Trap, which Carly and I cried through. This part in particular felt full circle, surreal, and so very special.
Coffee Shop and Park- The next morning, we walked to Carly’s neighborhood coffee shop (because when you live in the city, you can do things like walk to a coffee shop). We got Ava a croissant that she impressively devoured in 3 minutes and walked to the neighborhood park. Ava loved playing all by herself, exploring the new structures and monkey bars while Carly and I chatted on a bench, sipping our drinks, feeling not-quite-old enough for this tiny person to be one of our offspring. Funny how being with your childhood best friend makes you feel like a child yourself.
The Aquarium- We walked home, changed, and headed out to the Chicago Aquarium. It turned into a really lovely, cool day, so the walk was delightful and the Aquarium was beyond all three of our expectations. PEOPLE, there were WHALES at the aquarium. plural. Multiple whales and dolphins. Ava enjoyed herself, but I nearly fainted with glee.
China Town- From there, we were famished, so we started the 15-minute drive to Chinatown to introduce Ava Mae to dim sum. She marveled at all the structures, towers, and sweets she’d never heard of (she now calls Mochi “Smokies” and loves them). We found out she’s a big fan of steamed shrimp buns, who wouldn’t be?
Logan Square Farmers Market- We all slept well that night and woke up a little sad to be leaving already, but we bucked up when we saw the expansive and fragrant Farmers Market at Logan Square. It’s probably fortunate I don’t live in Chicago because I’d spend all our money at this farmers market. It was a dream.
From the precious talks about Ava entering girlhood to the adventures in a new city, it was such a memorable weekend, made so special by our sweet hosts. I’m so grateful for the honor of being Ava’s mother and having friends like the Fredericks.
The Daily Delights No. 10
What I’m Reading:
Onyx Storm- If you are a close friend of mine that has read this series, chances are you got an earful from me on this book. It might be my last book I read in this series. Please, email text or call me about this book so we can discuss it at length. Many many many thoughts are inside of me that I don’t want recorded on the internet.
Sunrise on the Reaping- I loved it. I’m constantly amazed at Suzanne Collins’ ability to further develop characters we already love and weave stories together that span decades.
Jane Austen Society- I needed a literary palate cleanser after dragons and Hunger Games before hopping into fea warriors. This book is charming and light and smart. I loved it! Thanks, Jill Armstrong, for another spot-on recommendation!
This article from Real Simple encouraged me to think about aging beyond Retinol: 5 Signs You’re Aging Well
As an early birthday treat to myself, I begin the final book of Throne of Glass- Kingdom of Ash on June 27th. I have had the date in my mind for months now because starting it on my birthday is too much, I want to wake up on my birthday and be in it already, but not so in it that I finish it on my birthday. I’m a strange woman, this I understand.
What I’m Loving, Chicago edition:









There is so much to delight in while visiting a big city. It’s so different than the suburbs of rural Texas and our everyday life. Here are a few things that stuck out to me:
Small patio or courtyard gardens and landscaping. It’s amazing what beauty people can cultivate in such small spaces.
Unique architecture- spanning over hundreds of years, each building looks different. Lovely arches, tiling, stone, brick, and design.
Coffee- this isn’t unique to Chicago, but I got a horchata iced coffee and it was delightful.
Basements- non-existent in Texas, and fun for my daughter to experience for the first time.
Public transit - perhaps delight isn’t the word that comes to mind when you think of trains and subways, but to a child (and me) it’s magical.
Parks- it’s comforting that parks are everywhere you go, and delightful the way city parks remind one of home.
Plant variation- local plants are different in the Illinois climate. We loved all the different trees in bloom and flowers growing in the city. Don’t even get me started on the ivy-covered brownstones- dreamy!
Thanks again for reading/ listening to week 10 of The Daily Delights. If you’d like to be notified next week, please hit the button below to subscribe and share with a friend!
I’m so glad you got to see WHALES! The parks in Chicago are beautiful. Love these pics! Can’t wait to meet Camille 😁
This is PRECIOUS! We did a ten year old milestone trip with our oldest and it was very special. Also, I relate so deeply to number 6 about your birthday read!!!!!! I’m glad you liked the Jane Austen Society! Xoxo