A spontaneous trip to Portland, Maine

Just get up and go.

I’m a little hazy on the details because it all happened so fast. I think it went something like this:

“Let’s go on a road trip.”


“How about Portland, Maine?”


Within minutes, my wife Elly had a smile on her face. “I just booked a motel,” she said.

Suddenly a typical lazy Sunday afternoon turned into a frantic scramble to pack clothes and supplies. We hadn’t thought out how long we were going to be gone, we didn’t have much money on hand, and we didn’t even know why we were going, but in a brief and manic moment we had both made up our minds.

In a short time, we were packed and ready to go. We put the leash on our pup and headed out the door.

Anyone can go on a vacation. The intent of this story isn’t to simply highlight the benefits of going on vacation or even to explain the exciting things to do in the City of Portland. Instead, I want to convey what was going through my head, my wife’s head, and to express to anyone out there that might be like me (mid-20s and still a little lost in the world; the kind of person who has never really had a chance to do something wild): sometimes you just have to break some rules and be spontaneous.

The drive was about five hours long and I didn’t mind any of it. Driving through the rugged Vermont mountains and seeing the quaint little farms and communities that dotted the landscape was so much better than sitting in the office as I had been just an hour or so earlier. The thing is, I had never really done traveling the “right” way, and by that I mean the way that I wanted to do it — on my terms. I always wanted to just go to a place (somewhere, it didn’t matter where) and just explore. I don’t care about the on-rails tours, the theme parks, you know, the typical tourist things. I just wanted to be able to pick myself up and go to a new place and explore.


So several hours later with an almost empty tank of gas, we found ourselves pulling off the highway and into Portland. We filled the car up in a questionable part of town and, exhausted, checked into the motel, ordered a pizza, gorged ourselves on said pizza, and fell asleep. It really hadn’t set in yet that just a few hours ago we had no inclination that we would be here. “We’re in Portland, Maine! How weird,” Elly said to me as we drifted off. It was really truly strange. I hadn’t done anything like this before.

For those of you out there that have had the luck to make travel a major part of your life, this might all seem silly. But it really was amazing what we had done. We had transformed an ordinary day into something extraordinary.


The following morning we woke up around 7 a.m., took a shower, packed our things, and headed out with the pup.

Pretty much all the research we had done on Portland was done during the car ride in between the spotty coverage allotted by the rural mountains of Vermont and New Hampshire.

“Oh, there’s a downtown district with old cobblestone roads!”

“Nevermind, I don’t have any data.”

Between pit stops, I scribbled down the names of restaurants and other things to do in Portland. We used bringfido.com to see what we could actually do with our dog coming along for the ride. I was surprised to see a lot of interesting shops downtown that were pet-friendly.

We parked ourselves on a street in Old Port in downtown Portland, paid the parking meter and stepped out to begin our adventure. It was a small, quaint little street with cobblestone roads and was lined with very hip storefronts.

“This is the start of our adventure,” I thought. And while absorbed in the moment, I barely noticed our dog pooping the largest poop I had ever seen on the sidewalk. To make matters worse, a large group of people was making their way towards us! Suddenly our anxiety skyrocketed as we quickly tried to clean up the mess before they arrived.

“Hurry they’re coming!”

Success! With not a moment to spare we had cleaned the sidewal- “oh wait they crossed the street already.”

With that minor hiccup out of the way, it was time to begin our adventure.


With the car in the center of downtown, we surveyed the sites of Portland for the next few hours. This was exactly the way I always wanted to travel: no itinerary, just true exploration with the girl of my dreams and our dog. Darting in and out of alleyways, going to the wharf, saying hi to all the strangers that wanted to get a closer look at our pup. It felt like we had tossed away all of the rules. So what if we were supposed to be in the office working? So what if we had a dog with us? So what if it was a Monday? None of that mattered. We weren’t going to let artificial constraints on our own happiness get in our way today.


When the parking meter was set to expire, we headed back. Elly had never seen the Atlantic so we had made it a goal to go to the ocean. We looked for directions to the nearest beach, said our goodbyes to downtown and drove off.

We stopped at “Eastern Promenade” at the northern tip of the city. We parked at the top of a tall hill near the ocean.

It was surreal.

I can’t say that this was my first encounter seeing the ocean. But this was more than just simply seeing the ocean. I was seeing the ocean in a particular time in my life that was perfect. I was in a place in the world with the person I wanted to be with the most. It took me by surprise. Seeing the ocean with her really captivated me. We made our way down the hillside, winding down the pleasant hill on a pathway towards the beach.

I’d like to take a second and share what my wife thought when we crested the bottom of the hill and made our way to the water:

“We saw a rocky part of the beach that was completely vacant (and ahead of the ‘NO DOGS ALLOWED’ sign) — it was perfect. Immediately, I knew I wanted to take my shoes off and dip my toes in. So we did. The pup even got his feet wet, and soon he was exploring the salty waters just like we were. I felt like a kid again. I followed a few rocks out to this peninsula-like part of the beach, being careful to not step on snails and seaweed. It was the first time I really saw a complete view of water. And it made me feel so small. It just kept going, and going, and going. It really put things into perspective for me, and honestly, I think it changed my life. I want to move there now.”

I couldn’t agree with her more. Here we were, both totally immersed by the moment unfolding before us. We were virtually alone. I waded in the little artificial lagoon and tossed stones about and breathed the sea air. I was totally engulfed in the present moment. We both traded moments sitting out at the far end of the rocks alone, taking in the scenery. Throughout the day we had been toying with the idea of staying for another night. We didn’t have enough money for another night at the hotel, but we were committed to the possibility of sleeping in our car.

But as we got ready to leave, we both realized we were totally satisfied with our experience. After collecting a few keepsakes, we made our way back to the car to begin the journey home.

It was a quick, spontaneous trip, but it was everything we wanted.


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