Cross-Country Road Trip Itinerary: Week 1

Planning a cross-country road trip can be really daunting. I know when I first sat down at my computer staring at Google Maps with a handful of sites I wanted to see on the other side of the country it was hard to get started. I thought it could be useful to share our itinerary week by week as we visited 24 states and 20 National Parks in five weeks. As a bonus I am also sharing our initial plan for returning home. This post covers the first week of our road trip from New York to Denver. All of this was done with an infant who was 2 ½ months old during the first week of the trip.

It is worth noting some of the considerations that went into our stops. For one, since we have an infant and we keep Shabbos we needed places for Shabbos that had an eruv. When we first started planning we were going to go through Route 66 and do Arizona first. This changed when we were ending up in Sante Fe/Albuquerque area for Shabbos. Nowhere near those places had eruvs. As a result, we ended up shooting for Denver which was the closest to where we were wanting to go with an eruv. This also gave us two days in Chicago which was nice. If the eruv was not a consideration we may have gone a longer route to get a slightly more action-packed drive between Chicago and Denver/Rocky Mountain.

Another thing to keep in mind is drives with a baby take way longer than you expect. When I was originally planning the road trip I was trying to figure out how long would be reasonable for a day’s drive with our baby. The days on either side of Lincoln, NE were longer than ideal. Though Yitzchak who very rarely prior to this was in a car or really a container of any time got used to sleeping in the car, it was still a lot. By the end of the trip to estimate when we’d arrive, I took to doubling the time Google Maps said. There were times we still arrived later than I estimated even doing that. It was wonderful the times we arrived earlier, but not the norm. I definitely underestimated that.

Day 1: New York City to Youngstown, Ohio

We left New York City on a Sunday morning and drove west towards Pennsylvania. We crossed the George Washington into New Jersey (state 2) and then continued into Pennsylvania (state 3). We generally try to maximize the first leg of our trip when Yitzchak usually had the longest nap. Our first stop was Hickory Run State Park in Pennsylvania. It was raining heavily so we didn’t take much of a walk there, but that is where we stopped for lunch. It seemed like a really cool park for hiking though.

We then continued on to Gobbler’s Knob in Punxsutawney, Pennsylvania. We had spoken in the past about going to see Phil on Groundhog’s Day but it has never worked out. There was a cute walk there with metal art and we saw the stage where Phil comes out. Driving through town after we enjoyed seeing all the groundhog art around.

Our final stop for the night was Youngstown, Ohio (state 4) where we stayed for the night.

Day 2: Youngstown to Chicago

Things got more exciting on day 2 of our trip when we visited two national parks and made it into Chicago for dinner.

We started our morning with Cuyahoga National Park only about an hour past Youngstown. While in general we did enjoy making a lot of progress on the first leg of a morning we also enjoyed getting a good walk in early in the day. Either way worked for us though if we were making an early stop we wanted it to be somewhere with a good walk.

We loved Cuyahoga. It was far less crowded than most of the parks we visited and had easy but very pretty walks. We did the Ledges trail and really enjoyed it.

While we did make some quick stops at rest stops following Cuyahoga we mostly powered through to Indiana Dunes National Park (state 5 and national park 2). This part was not planned particularly well because we forgot it was Memorial Day and it was crowded. We stopped briefly and then continued on to Chicago. It is worth noting that West Beach does not accept national park passes. We wished we knew this so we could have planned on a different beach.

Finally, we drove into Chicago (state 6) and enjoyed takeout dinner in a park before checking into our lovely Airbnb.

Day 3: Chicago

We stayed in Chicago for day 3. We drove down to Lincoln Park near the zoo, parked, and walked along the water to downtown. While downtown we went to the famous bean (cloud gate) and walked along the canal. We were really impressed with Chicago.

We also happened to stop at the Starbucks Reserve there to run to the bathroom and it turns out it is the biggest Starbucks in the world. We did not look around as we do not do indoor activities at this point but it was quite large!

In the afternoon we did laundry since we wouldn’t have it again for quite some time and repacked the car.

We then enjoyed different takeout for dinner in another park. After dinner, we got ice cream from Graeter’s which I highly recommend! Their chocolate chips are incredible.

Day 4: Chicago to Lincoln, NE

The drive between Chicago and Rocky Mountain was a bit frustrating for us. We tried to find exciting stops but there really was not a lot between Chicago and Denver. We decided to do this trip in two long days as a result (we originally planned to do it in three).

On day 4 we left Chicago very early. We woke up around 3 and we were leaving as the sun was rising. This worked out well because we got to Starved Rock State Park quite early and beat the crowds. We were the only car there when we first arrived.

We hiked St. Louis Canyon trail which was an easy 2 mile out and back with a gorgeous hidden waterfall view at the end. I highly recommend this trail and state park. Though it is a popular state park we did not discover it until the night before leaving and I am so glad we did. We really felt like it was a huge bonus.

Next, we entered Iowa (state 7). We didn’t have any official stops there until Des Moines where we stopped at a sculpture park for a brief walk and for some ice cream. The sculpture park was free but small. It worked as a short stop to stretch our legs though.

We then continued on to Lincoln, Nebraska (state 8) where we spent the night in an Airbnb. I linked the Airbnb because it was a very cool space. We were originally planning on stopping in Omaha but it was getting late and we were sick of driving.

Day 5: Lincoln to Loveland, Colorado

We once again got an early start for the drive to Loveland. There really was very little to see this day.

We stopped at Fort Kearny State Historical Park in the late morning. This was a place to stop and see something but it was also expensive and not particularly what we were looking to see. We felt the Park really glorified colonialism and manifest destiny in a way that we were uncomfortable with. There were bathrooms and it was near the road but it is not a stop I would particularly recommend.

We then drove to California Hill, a part of the Oregon trail, and hiked it. It was not particularly long but we appreciated the uphill climb to stretch our legs a bit.

Since we didn’t make any very long stops this day we actually arrived in Loveland, Colorado (state 9) at a reasonable time. We walked along the canal there and then got an earlier night to bed.

These past two days of driving were pretty monotonous with basically just cornfields on each side. Since we were there in early June the corn wasn’t up either.

Day 6: Rocky Mountain National Park

On day 6 we once again got an early start and drove to Rocky Mountain National Park. This drive was beautiful as we entered the mountains. We got to Rocky Mountain early enough that we did not need a reservation to get in the park (we arrived well before 9 am) but we could not do Bear Lake which required a reservation after 5 am.

We ended up taking two hikes/walks. I regretably do not remember the name of the trail on the longer hike but it went by a lovely river with several falls and mountain views. We avoided trails that had snow as I had a baby in a carrier.

The second was more of a walk than a hike. We walked around Lily Lake loop which was a quick, easy walk and quite lovely. I definitely recommend it as a super easy add on to any other hike.

Next, we headed to Boulder for ice cream and an outdoor social distance visit with my cousin.

We ended the night in Denver where we planned to be for Shabbos.

Day 7: Denver

We spent Shabbos in Denver catching up on sleep and walking around a park in Denver Tech Center area where we stayed.

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