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Road tripping down Route 66 alone with my 9-month-old baby


So far I’ve driven over 770 miles, eaten 12 chicken wings, two fried chicken breasts, one-half slab of ribs, one corn dog, two frozen custards, three slices of deep dish pizza and three orders of french fries. I’m feeling more American than I ever have in my entire life.

Hi! I’m Tatiana, co-founder of I’m currently on a 2,600-mile-long road trip down Route 66, from Chicago to Santa Monica, California, with my 9-month-old son, Bruce. Just him and me tackling America’s Mother Road. To some, doing a solo road trip with a baby may seem… massively insane. But, I Iove traveling. Like a lot. And the best advice I have for mothers who are traveling with a baby is just know your baby’s rhythm. If you figure out the rhythm of your trip then you’ll be able to sync up. Just be prepared for a few bumps along the road and don’t panic when things go awry (i.e. you get lost, or baby has an explosive bout of diarrhea, or, God forbid, Instagram goes down).

We just completed the first leg of our trip and here’s a travelogue of our adventure so far.

Leg 1 (Chicago, Illinois, to Cuba, Missouri)

Route 66: Leg 1 | My new trip on! >>

DAY 1: Monday

We started out in Chicago and had some deep dish pizza at Connie’s on State Street; it was pretty damn good, and after a five-hour drive from Cincinnati it definitely hit the spot. That night we stayed at Public Hotel in a trendy part of town, and let me tell you, this place was swank with a capital S. All the guests looked like they were in indie bands. The room was incredibly comfortable and beautifully designed. While in Chicago we also hit up the John Hancock Observatory and the Lincoln Park Zoo, where we got caught in a torrential downpour, but Bruce was a total trouper.

Road tripping down Route 66 Day 1: John Hancock Observatory

After that we hit the road, and our first official Route 66 stop was the famous Dell Rhea’s Chicken Basket. We met the owner, a pretty rad guy whose family has run the joint for over 52 years. I had the hot wings, and they were to-die-for. The owner sent me home with a full chicken dinner, which totally came in handy as I was chatting with him for so long that I ended up getting to my inn around 9:30 p.m. and was pretty hungry before calling it a night.

Road tripping down Route 66 Day 1: Dell Raye Chicken Basket

Up next: Day 2 of road tripping down Route 66 alone with my 9-month-old baby >>

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