As long as I can remember, my sister-in-law has been more like the little sister I never had. Being the youngest of 7 in my family, having a younger sibling was something I didn’t experience until I met my spouse in college. Her youngest sister, Angela, was about 11 or 12 years-old at the time, and we just clicked from the beginning. Honestly, she was quite impressed with my beat-up Chevy Monza (I could remove the car mat on the driver’s side and literally see the road whizzing by through the rust…oh, and you could drive and remove the key while the car was in motion – kids love that stuff)!

Fast forward a few decades and you’ll find that Angie is now Mom to three kids (including twins) and lives just a few hours away from us. In 2016, with her three children now young adults, we decided to plan a road trip east that turned out to have a number of memorable and humorous highlights. Read on for our most memorable road trip.

PLANNING OUR ROAD TRIP

We wanted an adventurous trip that hit some of each of our bucket list items. In the end, we travelled from Iowa to Dayton, Ohio and then to Philly and NYC, finishing up with Ogunquit and Portland, Maine and then stopping by Niagara Falls on our way back home. But I believe it started out with a nomadic drive that felt like it lasted forever. My nephew realized when we arrived in Dayton that he didn’t pack his suitcase, so we made a quick pitstop to buy a quick (and affordable) wardrobe for him on the fly. Then the fun began…

DAYTON, OHIO

For some unknown reason, my wife and I have always been fascinated by the story and adventures of Wilbur and Orville Wright, actually traveling and visiting the Wright Brothers National Memorial in Kill Devil Hills, North Carolina a few years ago. Before that trip, we made our way to the Wright Brothers Bike Shop & Museum in Dayton, and later visited their graves to pay our respects to these aviation pioneers.

PHILADELPHIA, PENNSYLVANIA

Angie drove into Philly and as I recall there were some cliffside areas that this height-averse guy wasn’t too keen to experience. As we drove into the city, it was steadily raining, pelting the windshield so that visibility was nonexistent, and my heart just about jumped out of my chest as we were close to being sideswiped on the interstate by another fast-moving vehicle.

We spent considerable time near Independence Hall, took in a spooky ghost tour (the twins loved it), pretty much did a drive-by with the Rocky statue, had an authentic Philly steak sandwich across from Christ Church and ended with a horse-drawn carriage ride. As we were cruising the area, we came across a man walking on the sidewalk dressed as Jesus, carrying a cross. Not sure what got into her, but my wife rolled down the window and began yelling “Jesus! Jesus!” to get a picture. It was one of the funniest moments of our trip.

NEW YORK CITY, NEW YORK

Next, we traveled to New York City. The twins were like “where’s the pool” when we checked into our hotel (apparently it’s not a common thing there). We visited the 9/11 Museum, grabbed a bagel at a neighborhood joint, took the subway downtown and then visited Times Square as well. The thing I remember most? Our hotel’s restaurant being out of potatoes, and one person in our party asking “what about french fries? what about hashbrowns? what about mashed potatoes?” as if those aren’t still just…potatoes. You had to be there, but it was hysterical at the time.

OGUNQUIT, MAINE

The wife and I had been to Ogunquit on a prior occasion, and we were excited to share this picturesque location with the family during this road trip. We stayed at Anchorage by the Sea, which is a great resort connected to Marginal Way (a beautiful mile+ long path that hugs the Atlantic Ocean) and had pizza at a local pizzeria that appeared to be super popular. The funniest part of this stop on our trip? The uncomfortable feeling my 16-year-old niece had when we ate at a piano bar one evening when nothing else was open. You’d think we’d taken her to a drug-haven or speakeasy or something of similar disrepute. The relief on her face leaving was priceless.

PORTLAND, MAINE

A number of years ago, I implemented benefits for a company located in Lewiston, Maine. In the capacity of doing so, I had to travel to a number of their locations in the state during the month of October. The fall colors were spectacular and the only thing that surpassed that natural beauty was when I drove my rental car to Cape Elizabeth and stopped to see Portland Head Light. Naturally, when we decided to visit Ogunquit, I knew we had to check out Cape Elizabeth as well. Unfortunately, when we arrived, the lighthouse was in the midst of being maintained, and the structure was surrounded completely by scaffolding to repaint the outside. I’m not sure if it happened here or somewhere else, but I remember a drink being accidentally spilled in the car in the backseat, to the point of filling up the cupholder and a pretty hefty argument ensued between the kids…signaling it was time to head home.

NIAGARA FALLS, NEW YORK

On 9/11/2001, my wife and daughter accompanied me to Boston for a conference when the terrorist attacks took place at the World Trade Center, the Pentagon, and Shanksville, Pennsylvania. The next few days were filled with bomb squads, possible terrorists at a nearby hotel, being frisked to return to our hotel, ghostly shopping malls, and people buying cars simply to get home. While retaining as much normalcy as we could for our then 10-year-old daughter, we decided to take a detour that Friday night on our way home, going off the beaten path to see Niagara Falls. The park was literally empty, and we spent some time just decompressing from the stressful week and the national mourning the country was experiencing along with us.

Our second trip to Niagara Falls was a definite contrast to our first. It was fun. It was planned. It was during the day. We took a journey on Maid of the Mists (it is wet for sure) and took a ton of pictures (equally misty), before turning the SUV west to head back home. All and all, it was a great bonding trip, particularly with the kids as we hadn’t had a lot of time to spend together up until that time.

Several years later, we took another road trip to Estes Park, Colorado (my nieces are super huge ghost hunters, so we stayed at the Stanley and had a great time hiking as well). But it’s hard to surpass that first big road trip together out east. Great times, great people, great memories.

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So, that’s my own “road trip” story (and I’m sticking to it). What was the road trip you took that made the time one of the best times of your life? Tell us about it in the comments!