You’ll Want Your Own Solo Road Trip After Reading This

7 minute read



Did you know that as of 2016, over 660 MILLION vacation days were left unused by American employees? Your vacay days were floating around on an imaginary raft sipping your ice cold adult bev somewhere in the ether.

Breaking this down even further, this equates to over $600 per employee being gifted to employers last year. That’s right; we are paying our employers for us not to take earned time off.

While vacation days drop, stress levels continue to shoot through the roof.

Why do we have this so backward?

I hope that by sharing highlights from my own solo two-day road trip, it will make you realize that sometimes the best plan is to let loose and take off. To see where play takes you. To know that loosening the reigns of schedules, to do’s, and obligations is an essential part of living a life that makes us feel good.

But mostly, I hope after this reading this, that you hit the road without looking back. Sure, weekends are great and all, but playing hooky never gets old.

So, grab a friend or go solo. But just go!

Because we all know that:
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy
All work and no play makes Jack a dull boy

Sometimes we need someone else to remind us to take time for ourselves. Often we’re so in it to win it that we need someone to rip off the blindfold so we can see clearly again.

I was recently faced with a scary realization. I was reading a true story about a woman who was asked to list what she did for fun. She couldn’t do it. She forgot. She got herself so far away from fun that she went blank. I sat there pitying this woman. That is, until I paused for a second and couldn’t come up with more than two things I like to do for fun. Really? Two things?? I need to get back to fun -stat! Fortunately, I had an opportunity and I ran with it – straight out of town.

My birthday is in November and to ring in the last year of my 30’s my family gave me one of the best gifts a girl could ask for: TIME.

Cold hard cash in a card with a precious letter offering me the gift of time. It was a weekend away to use whenever I wanted, to work on a creative project that’s been gnawing my insides for longer than I care to admit.

Knowing that this present was a precious commodity, I held onto it until I was about to burst. I wanted the time to be right. And that time arrived a few weeks ago. Just as spring was sprouting, I thought, hey, hopefully this is symbolic. I decided this would be my own pseudo writer’s retreat. Days would be filled with writing, trails walks, and yoga. Rinse and repeat.


I needed to be cocooned away from distraction. Having a soft spot for Hudson, NY I initially had that as the place to set up shop, but it was booked solid. The next place to pop in my mind was Woodstock. I’ve never been there, and so naturally stereotyped it as being a hippie-dippy town that unanimously voted to ban all Wi-Fi at a past town meeting. I pictured driving through the rural countryside into a dense forest that had sparsely scattered houses and stores with window displays stuffed with tie-dyed mannequins, speakers mandated to play only The Grateful Dead, and the overall air reeking of patchouli and Snoop Dogg.

After a quick TripAdvisor search, I found an idyllic motel/B&B right along a stream. Not being a major fan of the Kumbaya commune feel of B&B’s (I thrive on meeting strangers but not in a forced setting) I hesitated, but the pictures of the flowing stream, hammocks, and country cozy chic rooms had me click “book” without thinking twice. Having breakfast included, aka saving money and decision making, sealed the deal.

A whole weekend alone was something that I’ve never done in my life. As excited as I was the week leading up to it, the minute the moment came to say goodbye I was scared. I realized that I was putting so much pressure on myself to finish this project in 48 hours that I was slowly becoming my own buzz kill.

I kissed my kids and husband goodbye, selfishly hoping that at least one of my kids would cling to my leg and beg me to stay. Muffled “See ya, Mom,” and “Have fun, babe” flew out of their mouths as all three of them continued to headlock each other and wrestle on the ground.

I knew deep down that the fear would dissipate as soon as I hit the gas. And it did.

About an hour in, I devised a master plan. It was perfect. I pictured myself holed up in my room as the creative juices flooded out of me; having years of being gripped by nothing but the lethal claws of artistic perfectionism, this was going to be my juices big debut. I imagined not knowing what took over me as my hands worked overtime to keep up with the thoughts and images flying through my brain. It was going to be pure bliss. I would surface only to eat breakfast and then again at night for dinner. Better yet, I will be so in the flow that I will forget to eat all together. I will lose all track of time and place. My walls will be covered with post-its and index cards and I will be woozy from the overdose of my imagination, as only the best and truest writers are.

As I rolled into town after dark, I made a pit stop at the local gas station to grab my essentials: granola bars and a gallon of water. The sky was clear, and the air was crisp. Very promising.

I winded through the forested and rural roads finally making my way to my home away from home for the next forty-eight hours. It was just as I imagined. Quaint and quiet. Perfect. The key was even left under my doormat which added to the Ma & Pop feel of the place. I opened the door and was greeted with nothing but white and wood. I dropped my bags on the ground and headed into town.

After having one of the best burgers of my life I stepped onto the main drag and realized that my rabid hunger blinded me from the fact that Woodstock was nothing like I had imagined. Even with the streets being a ghost town since it was so late, the charming and quirky vibe still filled the air. I was digging the east coast Austin, TX feels. Caught in a mid-window shopping daze, a bookstore quickly yanked me back to reality of why I was there in the first place. To write. Nothing else. That’s it. Mental hand slap. Okay. Back on track.

The next morning I was awoken by birds chirping and the sun shooting its warm rays through my window. I laid in bed not knowing what to do first. I had a plan, sure but I didn’t’ remember the last time that I had a full day for myself. So I eased my way into the morning. I meditated. I read. I wrote. I brushed my teeth slowly. I didn’t race. It felt oddly natural and necessary. Then I did the running man. Because – no rules!

Breakfast was set up in a sunroom and the spread was a buffet of fresh fruit, yogurt, and local baked goods and jams. The coffee was strong and the mugs were sturdy. There was a bench lined with hip magazines galore: Fast Company, Inc, Dwell, The Atlantic, along with any newspaper printed in New York City; just to remind you how close you were to the city in case Mother Nature fooled you. The tables were set up like a café with outdoor seating abound. Hammocks, Adirondack chairs, benches, and table sets scattered along the length of the well-pruned yard. As I sat outside with the sun shining softly strong above, the only sound I heard was the rustling of trees and the babble of the stream below.  I sipped my coffee instead of my usual gulps. I ate my bagel in human bites rather than my normal one swallow. I thought, Ohhh, right. So, this is how humans eat. Rather than my normal morning imitation of a boa constrictor sucking down its food in one fell swoop. I closed my eyes and felt my body ease into the day.

My first plan was altered as I decided that my writing office would be at the small café table streamside. The weather was gorgeous and the grounds were calling my name. I sat and I wrote and I thought and I connected storylines and dots and characters. I even remembered to step away and stretch and came back with mini spaces of clarity. So mini-breaks do actually help with brain fog. Who would’ve thought? I did this for hours until I looked at the time and saw that it was late afternoon and called it a day. I was going to fill the rest of the time as planned: trail walks, yoga, and meditation to stay in the zone.

I hopped online (Woodstock does have Wi-fi. What do you know?) and looked up the closest yoga studio. Within seconds I found a two-hour class that was going to start in an hour. Perfect! I clicked on the instructor’s bio and saw his picture. Now, I don’t know if it was his cross-legged Sukhasana peaceful pose, the wild flowers that surrounded him, his close-eyed dreamy smile, or both thumbs on his third eye but my plans took an immediate left turn. I heard someone say “Screw this!” and then realized that person was me.

Next thing I knew, I was peeling out of the parking lot and headed straight to the Kingston mall to see a movie. Usually, I would berate myself to no end for all the things I should be doing. You’re in a new town and you’re going to see a movie? In a mall?? It’s gorgeous out! Ugh! This time, for whatever reason, it was different. Zero guilt. Full on play. I was chock full of energy and a newfound zest for life. The windows were all the way down, and Tom Petty was all the way up.  I vowed to spend the rest of the day doing whatever the hell I wanted to at every turn.

So, what did that look like? Finding play and joy in every damn moment.

I walked into the mall to find that I was at the wrong end for the theaters. Instead of blindly heading back out, I popped into the chocolate shop that was staring me in the face, bought a piece of dark chocolate caramel covered in sea salt and carried on. I was on a hedonistic mission, and nothing was going to stop me.

My found my way to the right entrance to the movies and thanked MoviePass for buying my ticket. What do you do when you’re twenty minutes early to a matinee? Why fill the time with Ms. PacMan and Stackers. Then I filled my belly with my all-time favorite movie snack: Milk Duds poured over popcorn. God, how I loved not sharing! I laughed and cried with Amy Schumer and then hopped back in the car towards town. I left my car at the B&B and walked the streets. The weather was beautiful and I was jonesing to see where I would take myself next. I strolled with my radar on high which led me to bee-line into an incredible throw-back toy store. There’s something to be said about a)going into a toy store sans “IwantIwantIwant” toddlers and b)going into a toy store as an adult just because.

“Those who play rarely become brittle in the face of stress or lose the healing capacity for humor.” – Dr. Stuart Brown, MD, Author of Play: How it Shapes the Brain, Opens the Imagination, and Invigorates the Soul

After taking in every inch of childhood nostalgia, I continued walking throughout town. I headed back to a little taco joint I remembered seeing off the main road and cheered myself with an ice cold beer and homemade carnitas. I headed to the connecting bar for a margarita and dared myself to not take out my phone as a security blanket.  As much as I love striking up conversations with strangers, I was not used to going to bars alone and was definitely out of my comfort zone. It was a neat little joint that carried that Austin feel throughout. Tucked away by a small stream with outdoor seating, I chose to take a seat at the cozy bar where a few other people were settled in. The bartender was the owner and was as kind and welcoming as can be. His girlfriend was in town from Brooklyn and I ended up chatting with her and a young couple visiting from The Bronx. We were all in the groove, and the conversation flowed as smoothly as the margaritas. I left with a slight buzz from the booze and the energy of the day. I hit the sack early with a smile for days smacked on my face.

I woke up on the last day at the crack of dawn. I wrote. I walked. I ate breakfast by the stream. I felt a hair of difference in me. I was lighter and more grounded. An invisible load was relieved – if only for a moment. As I tossed my bag in the car, I vowed to carry this energy back home with me. I blared Adele’s “Rolling in the Deep” and Bread’s “Everything I Own” on repeat for the entire two and a half hour drive. Because? No rules!

Then when I returned home, I shared my purchases of a fart brain stress ball that makes fart noises every time you squeeze it and a fart in a can for the fam. After all, what is a trip without some souvenirs to keep the play alive?

The Shining (1980. Director and Writer: Stanley Kubrick) A family heads to an isolated hotel for the winter where an evil spiritual presence influences the father into violence, while his psychic son sees horrific forebodings from the past and of the future. 


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s