Planning a road trip during Covid summer #2

Planning a road trip during Covid summer #2

I am So. Excited. For. SUMMER! I’ve been neglecting laundry and my email this week, in exchange for road trip planning. Below is what I’ve come up with, and my thought process along the way.

Our inspiration was Niagara Falls. (If you’re ever in the mood to sit a room of your family’s own farts, then I highly recommend feeding the kids Domino’s Pizza 30 minutes prior to your passport appointment. Your local USPS will seat you in the smallest room possible, and you can unsuccessfully entertain your kids with Play Doh while you work REALLY hard to prevent a federal offense from unfolding.)

Sadly, I’m not sure that Niagara Falls will happen. We want to visit the Ontario side, and Canada is taking Covid very seriously. If these restrictions are still in effect, we’ll replace Niagara with Pennsylvania.

Our current itinerary:

St. Louis –> Cedar Point –> Pennsylvania –> New York City –> Cleveland –> Home

My budget goal for accommodations was an average of $200 per night. Some nights, we’ll splurge, and others, we’ll stay with friends or family.


Obviously, staying with friends and family means the cost is zero. But most of us just went a year+ without many of our family and friends, so spending time with them, in and of itself, is free entertainment. In St. Louis, I will barely see my children because they’ll be playing with their cousins and friends. And I’ll be sipping craft beers with their parents.

Shacking up in someone’s home also means that we’ll have more space. This balances out the stops on the trip where we’ll be in one room. In addition, a homestay usually offers the ability to do laundry and prepare food. I enjoy eating out, but my waistline and wallet do not always agree.

I have already benefited from my friends and family in NYC. (A shout out to my cousin who snagged us an AirBnb in Chelsea for $95/night!) It seems that we got the best of both worlds: we’ll experience city living, guided by New Yorkers, AND we’ll relax at the beach in a friend’s home on Long Island.

Our final stop, in Cleveland, is smack dab in the middle of our NYC to Chi trek. Could we stay at a hotel? Sure. But we get to see friends and drink wine! And have SPACE from our kids! … And drink wine!


Family wedding/friends –> Amusement park, pool resort –> Farm stay –> Mountains, lake resort –> NYC experience –> Beach life –> Friends

Laugh all you want, but this is something that I took seriously. How do we differentiate between stops (and also maybe build up some destinations that will naturally not be as thrilling as others)? Oh: and how do I not bankrupt our family?

The first stop (St. Louis) is always exciting, because we get to see cousins and friends. We stay up too late, watch too much t.v., and consume too much sugar. My niece’s Happily Ever After Party (God bless all the Covid brides!) will be our first wedding as a family of five.

My boys are nine, six, and three. The oldest is basing his NYC knowledge on “Home Alone 2” and “Secret Life of Pets,” so obviously, he wants to ascend the Empire State building, visit Central Park, and climb the Statue of Liberty.

My middle son, however, has no patience for lines, and is miserable waiting in one (and thus makes us ALL miserable). The last time we went to Disney World, he kept asking us when we were leaving to go back to the hotel pool. #notimpressedbythemouse

That being said, our big splurge will be two nights at Hotel Breakers at Cedar Point. We’ll spend one day at the amusement park, so if it’s horrible, it will be short lived. If all goes well, it will be motivate us to return. Out of the three kids, my nine year old will probably like this the most. (On a side note, my almost-40-year-old is pretty pumped as well!)

Playing to my six year old’s love of animals, we’ll do a farm stay next. At Verdant View Farm, we’ll experience not only our first bed and breakfast, but get to help out with morning chores: milking cows, bottle feeding calves, collecting eggs, and feeding the chickens. This will be a laid back part of our trip that allows for more free play for my two youngest.

If we’re going to leave the Midwest, then, for the love of GOD, we’re going to see some mountains. I feel like Stefon, Bill Hader’s character on SNL would love it, because “This place has EVERYTHING!” Nestled in the Poconos, The Shawnee Inn offers hiking, archery, ax throwing, pools, a beach, and even an on-site brewery. There’s plenty to do for all ages!

Then, we head to the Big Apple. As I said, my cousin secured us a room with two queen beds for $95/night at the Cambria Hotel Chelsea. I plan on following her (either physically or in detailed text messages) to enjoy the city at a leisurely pace. We’re not going to hit the big tourist spots. I see a boat tour and many trips to Central Park in our future.

Long Beach on Long Island will be our final stop before heading back west. Based on the previous two weeks, I think we’ll be ready for the beach! While we have Lake Michigan here in Chicago, it’s just not a place we often frequent. I’m looking forward to a few August beach days, and seeing my husband’s friend/our host, who has the most infectious laugh.

From there, we’ll drive halfway home and stop in Cleveland, Ohio to visit music friends of mine. One half of this couple sang in our wedding, and his husband is a concert violinist who has not only performed for my kids in person, but Zoom-played for them as well. They are doting Gunkles and fun people to be around.

If you asked me what I was most excited for, I couldn’t give a straight answer. As a social butterfly who has MISSED HER PEOPLE this past year, I’d say that any stop with friends or family would top the list.

On the other hand, I can’t wait for my kids’ reactions to the amusement park and the farm stay. Those experiences will be really unique.

When all is said and done, both my older boys have written about our family trips, and how special they are to them. I hope that this road trip is no exception!

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