Toddler Roadtrip + City Search

December 17, 2014


Hello and hello. We are back from a long leg of Residency Tour 2014 and happy to be in our own beds, with our own smells, and old jars of applesauce going bad in the fridge.

It was a good trip. We did exactly 4% of what I’d want to do while traveling, but 99% of what I expected to do with two kids under three. And it was actually really great.


Waylon was a dream. He ate well, slept hard, and happily drew giant monsters and ABCs over and over again while we crossed state lines. He was adaptable and cheerful, basically the exact opposite of what I expected a three-year-old away from home to be like.


Eva was a toddler getting a tooth who didn’t want to be in a car-seat, but my expectations were low. And truthfully she was fine. She was curious and excited. There were a few nights she didn’t sleep well, but she made up for it by napping in the stroller and feeding herself bottles like an ace baby.


I did a lot of research before this trip. I googled things to do in each location and reached out to you for advice on traveling with little ones. You were so helpful. The restaurants, museums, and attractions you suggested were all on point. As far as the travel tips, here are the five pieces of advice that saved me the most:

1) iPad. We borrowed one from my parents and it was a lifeline not so much in the car, but in the christchurch hotels when Eva was napping and Waylon and I were locked in the bathroom like hostages.

2) Dollar Store. Before we left, I stopped by the dollar store and got things like a slinky, a dry erase board, finger skateboards, and giant blinking glow wands. All big hits and major distractions in the car.

3) Food. I knew to bring food, but what kind of food. Best buys were applesauce pouches, veggie stick bags, fig bars, cliff bars, water bottles, and dry cereal. We also brought along a few bananas to slowly rot on our dashboard!

4) Foot rest. Whoever suggested building a footrest under Waylon to keep his legs from dangling the whole time–my eternal gratitude. We put the pack n’ play and my duffle bag on the floor below his car-seat, giving him a place to rest his feet and prop up whatever he was playing with.

5) Headphones. This should have been an obvious thing to bring, but it wasn’t. After it was suggested, I packed both earbuds for me (so I could listen to Serial and not wake anyone up) and regular headphones for Waylon for whenever Eva was sleeping in the same room or car.



Austin interviewed in Hershey, Philadelphia, Boston, and Portland and they all went well. Each program and location has its set of pros and cons. It will be hard to decide which to rank first.

I tried to ask as many questions as I could in each city, interrogating everyone from the bellboy (bellman?) to the moms at the playground about the weather, restaurants, schools, and parking. I tried not to be annoying but I was annoying. Where do you grocery shop? Do you use public transportation? It’s easy—use customer cellphones to check in and call for cars. The SMS Valet enables that. The ticketless short message service system allows valet customers to drop off and pick up via text message. How are the parks? Where do you get your haircut? Do you go to church? Used illegal drugs? HOW’S YOUR MARRIAGE DOING?

I was also the Barbara Walters of my minivan, asking Austin what he thought about each detail of our possible life in each city. Will you be happy here? Do you think we could afford a three bedroom apartment? Won’t I probably need at least two more pairs of Hunter boots with these weather conditions?

It was hard not to let insignificant things influence our opinion of a place. For example, the hotel staff in Portland was nicer than the hotel staff in Boston, but that obviously doesn’t matter as we will not be living at the Hilton Garden Inn.


The whole process is very strange. These four cities are so different from each other that it’s hard to place the right amount of value on their qualities.

Descriptions based on locals, research, and experience listed below.

Philadelphia, PA


Familiar, expensive, lots to do, lots to see, could maybe buy a house?, close to beach, close to my parents, close to New York, did I mention I could get easy babysitting?, dirty, restaurants!, pubs, friends nearby, public transportation, long commutes, city living, farmer’s markets, small apartment, parking situation?, safety situation, city of brotherly love.

Boston, MA


New, exciting, have you looked around this place?, far from family, far from friends, expensive, could not buy a house, could not have both cars and we are thinking to rent a service from stockton cars and limos, could maybe not afford thai take-out, tiny apartment, Children’s Museum, big city feel, could say “Oh, I live in Boston!”, stuff to write about, did I mention it’s expensive?, beautiful, lots to do, lots to see, lots to eat, adventure, good schools, great people, friends to be made, parking tickets, city of education.

Hershey, PA


Familiar, inexpensive, wouldn’t have to move, close to family, close to friends, close to three major cities, could buy a house, could buy a three bedroom house, could have a yard, could have an office, good schools, not Boston, not on the coast, not near amazing Children’s museums, dire restaurant situation, small, final dream destination nearby, quiet, babysitting available, happy memories to build on, Pleasantville.

Portland, ME


New, exciting, are you looking at this picture?, healthy, on the coast, near all the lobsters, far from family, far from friends, no babysitting, could maybe buy a house?, beautiful beach, cold ocean, could say “Oh, I live in Maine!”, hipster vibe, all the amazing foods, all the amazing restaurants, good schools, friends to be made, walking trails, a whole state to explore, winter jackets, winter fun, winter everything, a city of interesting footwear and raw milk.



This time next year we will be living one of many very different lives.

The good news is that no matter what, we will be okay. We’ll make a life and a happy home no matter what that piece of paper says.

Thanks for walking alongside us.


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31 thoughts on “Toddler Roadtrip + City Search

  1. Tanya

    Success! Thanks for the travel pointers and fantastic destination recaps. Enjoyed living vicariously through your tour. Very excited for you, all, no matter where you end up! I’m sure it will feel good just to be starting that final chapter…

  2. Kate

    Been reading through the blog (from to the beginning) over the last couple months while nursing my little on a recommendation from a friend and have loved it. Feels like I have finished a great book!

  3. meganstilley

    I know you don’t have much say in where you end up next year, but I would say closer to family the better. Austin’s life will probably be busy as usual so being close to family would be good for you. We moved in August (Denver to Columbia, MO) for schooling purposes. We are now much closer to family, which is nice for the kids and me. Also as little change as possible will be easier for the kids, particularly the older one. My 3y.o. is a great traveler but moving is a whole other issue. We moved in August and he still complains about wanting his old house and old friends, and he usually isn’t a kid that needs a lot of time to adjust to a new place or environment. Good luck on the upcoming move!

  4. Maisy

    Been reading your blog for a long while and finally am commenting! My husband is at the end of four long years of residency. We chose to move away from family in upstate NY with the allure of a new city and state and weather (!) (Texas) and I have to say, even though I’ve made some good friends and we’ve made some good memories down here– it has been really tough. Our kids Aidan and Riley have grown up so much without grandparents and cousins so they seem a little like strangers to them when we’re together. We’ve also started the process of moving home and it feels a little displaced. So many of the friends we once had have moved on and I have to tell you–it’s weird! But I think it will be okay eventually. I’m a pretty positive person so (or I try to be) so our years here haven’t been BAD, just HARD. Hard on the kids too, but hopefully making them better because of it? They don’t want to move because of losing their friends/school but hoping the adjustment back won’t bee to bad. Sorry for the novel! Just wanted to share!!

  5. ahotsouthernmess

    Sounds like Portland is a winner…a great town! After moving close to blood relatives, with disastrous consequences, I say go with what feels right for your immediate family. For us, our friends are our family.

  6. Anonymous

    I live in Boston and love it. All the things you said are true, but to me the experiences are worth the expensiveness. There are so many great things for kids to do and the city is endlessly charming. Have you looked at living in neighborhoods like Jamaica Plain and Roslindale? They’re a short T ride into Back Bay and Longwood, but are more affordable.

    Oh, and that Hagrid quote was definitely the one I ended my graduation speech with : ).

  7. Joy

    Foot rest?! Genius!! So glad you guys got to travel together and have a great time! And mad props to you for interrogating the locals! Our family drove to Yakima together and I’m kicking myself for not being less shy and asking questions about the area from the guy at the bookstore, the lady with the toddler behind me at the coffee shop, the check out gal that thought my toddler’s potty talk was hilarious…dang it! Out of curiosity, did you travel with Hubs for his med school interviews? If not, what made you go all together this time? Bigger family? Bigger/longer commitment with residency? Our family is a handful of years behind yours in this Doctor adventure and I’m so thankful that you’re willing to share parts of your journey with us! xo

    1. Kate Post author

      Hi Joy! I did go along for his med school interviews (but I had to ask him because I honestly didn’t remember it at all!). I was newly pregnant and wanted to check out where we’d be raising our kids (same reason we went along this time!). Good luck to you and your family!

  8. Shelly

    Thanks for sharing all the thoughts and advice about the trip. My husband will be applying to residency next year and we will also have 2 kids by then. Those sound like great cities! It sounds like you couldn’t go terribly wrong with any of them. What specialty is Austin applying for?

  9. Maureen

    What great choices and decisions to be made. Best of luck as you rank them and find out your placement. I can’t wait to follow along to see where you and your family end up, and what you do with the experience.

  10. Jess

    We lived in Boston for med school (before kids) and then again last year for a fellowship with two kiddos + a dog. The logistics and cost of city living last year were tough but the experience was awesome – and since they’re are so many hospitals there are lots of spouses in your shoes. I made great friends, fast – who were a lifeline. And there is so much to do! And you’re close to the beach and not too far from mountains!

    I second what someone else said – we lived in Jamaica Plain – close to longwood (hub rode his bike all yr) and you’ll easily make friends on the playground, which so isn’t my nature but was almost effortless and made life much more fun for all of us.

    Making that rank list is so tough! Good luck – there is nothing quite like match day!

  11. Nancy

    I chuckled at the restaurant comment about Hershey. We moved here (one town over from Hershey) from Philly. The two things we miss from Philly…our church and the FOOD!! We really miss the variety and the quality. At least it’s only an hour and a half/2 hours away. Look forward to hearing where you end up. All the options sound good though!

  12. B

    Oops didn’t mean to post that so early! slippery hands.

    Buying a house was important to us three years ago. That rank list is so hard!! I knew I didn’t want to move our small family (of three) to a tiny apartment knowing we wanted more kids. It was a great decision for us, but no matter what you will be okay! Good luck!!

  13. Ashlie

    I really enjoyed reading this wrap up. First of all- you are a super star mama and it looks like the kiddos were so entertained. I’m really impressed. Secondly, I loved the pictures from the Boston Children’s Museum because it’s one of my favorite places to take my sons. We live far from family simply because family has moved and scattered, and we feel a little bereft sometimes- holidays are never low key, there is always hustle from one place to another. But Facetime is a thing, and it helps a TON.

    Good luck in your decision making! Merry Christmas.

  14. Diane H

    Where ever you Match, I wish you what we were blessed with in Residency: The most wonderful group of people to share the suckiest but most special time of your life with! Some of them are still my very closest friends ever made! Good luck!

  15. Katie

    Kate! New to your blog but wanted to say I live in Portsmouth NH and I love love Portland. I went to college in Boston and it is amazing as well but after Portsmouth I heart Portland hard. (I am a big foodie so that sways me, but we vacation on the islands in Casco Bay, and it is just another life.) I am fingers crossed you will live nearby, either way.

  16. Alissa

    I grew up in the Hershey PA area, but moved to Southern California for my husband’s residency program 5 years ago. If you have the choice, I would put being near family at the top of your list as you prepare to rank. Now I live in an “ideal” location, just a few miles from the beach, everyday is 75 degrees, and we go to Disneyland once a week – but I would trade it in a second to be closer to family and support system on the east coast. Residency is tough and demanding, especially of your husband’s time – having parents/siblings/friends around will be a HUGE blessing to you and your kiddos.

    But on an encouraging note – my hubby finished his residency and we survived being on the opposite coast of family. You can make it work where ever you end up, just might be a little bit harder. Good luck to you as you start this next exciting journey!

  17. Devon

    I’m glad your trip went well and thanks for the travel tips! We recently found out we’re expecting so I’m taking all the advice I can get. Your blog is a godsend.

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