Travelling NYC Alone as a Woman: 3 Days, Surprising Kindness, Zero Fear

The first time I visited New York City, I did not love it.

I was studying for my Master of Fine Arts in Creative Nonfiction, and we travelled to New York City to pitch our book ideas (and what felt like ourselves) to big-shot editors at major publishing houses. I felt pressure to perform, I was on a sober stint and I did not have an excess of money. I thought I would adore NYC; that the “big city” would make all my dreams come true, but as a small town girl, I felt overwhelmed by the crowds, smells, concrete and lights. It was January, so the cold was biting, the Christmas decorations had been ripped off the trees and the celebratory New Year’s spirit had dimmed to empty wallets, discarded presents and failed resolutions. I remember walking through Central Park because I needed to see grass and thinking, everything is DEAD. I swore I’d never return to NYC in January.

And then, 10 years later, I did.

Only this time, my experience was completely different.

The main thing that was different? Me.

This time, I was coming to New York City as the full-time editor for Explore Magazine. I was hosted as media at a massive travel conference. I had 26 meetings in one day with PR professionals and destinations keen to host me and work with me.

I was 10 years older, and at 33, with my budding career success (and a steady paycheque), I felt more confident, secure, mature and ready for New York.

I decided to stay after the conference for three days to have a solo trip. This time, I knew what to expect. I packed for the cold. I anticipated the crowds. I laughed through the mishaps and rolled with the antics of the city. Things didn’t go according to plan. They went better.

I checked into Civilian Hotel, which is my dream ideal accommodation. Red brick walls, a massive window with city views and canopy curtains draped over the bed to evoke old Broadway style. There’s a jazz bar on floor two that doubles as a coffee and breakfast bar in the morning, a speakeasy with theatre memorabilia and a rooftop bar with DJs.

I woke up bright and early and brought my leftover pizza from Rubirosa (half Tie Dye, half Honey Pie) on the subway with me as I chased the sun. I was nervous about taking public transport in the dark, but there were other people up at 6 a.m. as well—some possibly with a similar mission. As bright peacock pinks and ripe oranges began to flare like flames behind the blocky gates, I ran onto the Brooklyn Bridge, snapping photos with freezing fingers. Catching my breath, I climbed on a guardrail and asked a fellow morning influencer to take my photo as I devoured my breakfast.

Unfortunately, my pizza started to turn to ice, along with my legs. I walked quickly across the bridge as the wind bit my cheeks and nose, turning them rosy. The -18 C day felt like a balmy -21 C. Still, the views were spectacular. I made it to the iconic view of the Manhattan Bridge before calling a ridiculously expensive Lyft. I knew I needed coffee and to warm up.

Caffee Paradiso wasn’t open yet, so I waited in line with a few other people insane enough to get the famous iced coffee on a day like today. As I held the to-go cup in frozen hands, I realized there was no where to sit and dethaw in the cafe. Luckily, three kind strangers behind me in line from Upstate agreed to give me a ride back to my hotel. We had a friendly conversation, similar to the ones I had at the bars I walked into solo days prior. It reminded me of one of the biggest joys of travelling alone: meeting new people.

After an hour cranking the heat in my hotel room, I ventured out again. In Times Square, I saw a photographer operating a spinning camera. “How much?” I asked him, thinking it looked fun. “$10,” he replied. I shook my head. “$5.” I told him it was okay. “How much do you want to pay?” he asked. I replied honestly: “nothing.”

“Okay,” he said, beckoning me forward. I danced to “Empire State of Mind” and laughed at the recording. True to his word, he didn’t ask me for a dollar.

I debated purchasing advance tickets to go up the Empire State building, but instead, I decided to let New York take me where the day wanted to. I walked through Bryant Park, admiring the frozen fountain and ice skating rink, then stumbled upon the public library. Proud stone lions guard the entrance; inside, the stunning architecture continues in painted ceilings of colourful murals and white Vermont marble walls.

After purchasing souvenirs from the gift store, I found a speakeasy in Grand Central station. Taking an elevator to the basement, I found the lavish and elegant Campbell Bar, which is featured in the first episode of Gossip Girl. I ordered an espresso martini and sipped it at the bar, making friends with the manager.

I wanted to chase sunset from above the city, so I paid my tab, snuck a glance at the majestic Main Concourse then started walking. I bought my ticket for the Empire State building on-site, despite the website encouraging online reservations. At 3:30 p.m., I was finally going to make it to the top of the Empire State building—something I’d always regretted not doing last time.

Back when I’d first visited in 2016, my mom and I had stayed in the city for a week together. One evening, the sky started bruising a gorgeous eggplant and strawberry, so I dashed into the Empire State building to see about purchasing a ticket. It was very expensive, and I didn’t have a full-time job with paid vacation days. Now I do.

I stepped onto the observation platform, shocked by the cold. The setting sun cast the glass city in warm mauves and pear. I snapped photos until my fingers froze. I waited for sunset, which was less impressive than sunrise, and listened to live jazz music as the city lights brightened the dark, cold night.

The next day, a massive blizzard hit the East Coast. New York City was smothered in thick, fluffy white flakes. I braved the subway to Othership, a unique sauna/cold plunge experience, then walked through boot-deep snow to buy cheap last-minute tickets to the matinee for Moulin Rouge. Sadly, the one play I’d booked months in advance was cancelled just before showtime, due to the snow—but I pivoted and dashed over to Chicago for a seat instead.

One of the beautiful things about NYC is that there’s always something going on, so there isn’t much time to be sad. On my last day, I wandered around Central Park, which was sparkling with freshly falling snow and tucked in thick blankets. Kids raced down hills on homemade sleds, some using cardboard, others plastic yellow “caution—wet” signs.

My family was worried about me getting stuck, but I’d originally booked my flight home for Monday night—the date and time other cancelled flights were getting moved to. I didn’t worry, and I didn’t need to—everything on time.

I know many Canadians aren’t travelling to the USA right now, and I understand their reasoning. Almost every American I met apologized to me when they learned I was Canadian. I likely wouldn’t have travelled here either, if it wasn’t for my work conference. I was more afraid crossing the border to the US then I was going through Customs on my recent trip to Mexico. In preparation, I deleted social media posts and unfollowed accounts that seemed to criticize the government (though it became obvious most accounts were just reporting facts). I felt like I was travelling to a third-world country under a dictatorship, like Russia or North Korea. What’s going on in the states is awful, and I do not support it.

But I do feel bad for the American people. I’m grateful to the kind strangers I met, and that I was able to explore solo without feeling afraid or being hassled about becoming the “51st state.” I wasn’t threatened or bothered; with so many people around, I felt safe and welcome.

I loved my time in NYC, especially my solo trip. I will likely have to wait three years, but New York City: I will be back.

And next time, I hope to visit in the spring or fall.

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