Manhattan Marvels: A Whirlwind Weekend of Parks, Plays, and Unforgettable Moments

Embark on a captivating journey with us through the heart of New York City, where history, humor, and theatrical hijinks intertwine to create an unforgettable weekend. From the serenity of Central Park’s autumn splendor to the eccentric delights of Drunk Shakespeare, join us as we navigate the urban oasis of Midtown Manhattan, uncovering hidden gems and indulging in the city’s vibrant spirit. With each step, discover how our self-guided adventures, enhanced by technology and a dash of spontaneity, lead to unexpected fun and hilarious encounters. Whether it’s savoring the city’s culinary delights, marveling at awe-inspiring views from The Edge, or getting swept up in the magic of Broadway, our tale is a testament to the endless possibilities of a New York City escapade. So, settle in and let us whisk you away on this exhilarating ride through the Big Apple, where every moment is a story waiting to be told.

Our adventure began with a serene flight from Raleigh, landing softly in the embrace of LaGuardia. The city welcomed us with an easy transition onto the free public bus and later, the F subway, ushering us into the heartbeat of Midtown Manhattan. Upon arrival at our hotel, nestled snugly between 6th and 37th streets, we were greeted with a delightful surprise—an upgrade to the Executive Suite, offering an awe-inspiring view of the Empire State Building.

When preparing for and discussing this trip, Sydney and I knew we wanted this to be a weekend heavy on walking, history, and sightseeing. We arrived very near “peak leaf” time in NYC; combined with the perfect 70-degree weather and clear skies, the vibrant colors of fall could not have been more ideal. With that in mind, we were really excited to try out a couple of self-guided GPS-driven audio tours using the mobile app, VoiceMap. Specifically, the TellBetter tours were rated highly on the app, so we downloaded a couple of tours for about $12 each and, while sharing a pair of Bluetooth Headphones (each using one headphone so we could continue to converse and soak up the city’s ambiance) the first we were going to try out on Friday afternoon was the Central Park tour.

Our route started at the Plaza hotel (just across the street from Central Park), and then navigated past the Pulitzer Fountain, Grand Army Plaza, The Pond at Central Park, through Central Park Zoo, north toward the Balto, William Shakespeare, and Indian Hunter statues, down The Mall, and finished up at Bethesda Fountain. The storytelling by the TellBetter guide was captivating, equally balanced between wonderful historic insights, architectural details, and spellbinding anecdotes that connected seemingly disparate areas of the park together in a unified narrative. A particularly engrossing narrative was the whimsical recounting of the “Great Zoo Escape” of 1874, a tale blending humor and history that left us chuckling yet enlightened.

However, since we kept deviating from the beaten path to take a picture here or read a different plaque there, by the time we had reached the midway point of the tour at Bethesda Fountain it was already past sunset. Given we had to be back on W 39th by 8 PM for the start of our evening show, we decided to pause our tour and begin our 40ish-minute walk back to Midtown.

On our way, we stopped for a quick bite, savoring a slice and a stromboli, before arriving at the Ruby Theatre for Drunk Shakespeare around 7:45 PM. Having had the chance to mingle with some of the actors before the show, I found myself “voluntold” to share a shot with actress Sarah Goldstein, the designated drinker of the night’s performance. I believe the toast she gave to me went something like, “To meeting Thor… if he worked in tech.” The narrative of Macbeth unfolded on stage in a blend of classic prose and modern jest.  The spirit of Halloween enveloped the theater as everyone, cast and audience alike, donned raucous, decidedly non-Shakespearean costumes, amplifying the playful ambiance. The play’s narrator showcased incredible impressions of David Attenborough, Christopher Walken, John Malkovich, Jim Carrey, John Mulaney, among others, each executed with pitch-perfect delivery and flawless mannerisms. Post-show, the vibrant Halloween energy of NYC manifested through costumed teenagers and adults enlivening the walkways. We indulged in a drink and reveled in some choice people-watching before deciding to retreat for the night. Back in our room, the enchanting view accompanied our quiet reading, wrapping up the first day of our journey in a serene yet reflective tone.

For Day 2, we had already booked tickets for The Edge Observation Deck at Hudson Yards. New York City has several great observation decks, but this was one neither of us had ever been to and it came highly recommended by one of my native New Yorker colleagues, so we were excited to be one of the first in at opening time (10 AM). Since we’re both morning people, we wanted to get another self-guided tour in advance of our time at The Edge. Accordingly, we left the room around 7:15 AM, snagged some breakfast at the hotel, jumped on the 7, and ended up on Gansevoort Street at the south end of the High Line. With our headphones in, we admired the Whitney Museum in all its grandeur for a few tranquil moments before ascending the steps to the High Line. Fortunate as we were with the flawless weather, and the city still waking up from its Friday night revelries, we found the High Line refreshingly uncrowded, paving the way for an outstanding walking experience. We were so entranced by the High Line’s fascinating story and views that we stopped to donate and become Friends of the High Line. I hope that one day we will see more and more infrastructure reuse projects that employ creative ways to bring green space to neighborhoods (here’s looking at you, Raleigh!). Concluding our walking tour, we stepped into Hudson Yards’ shopping and soared 100 floors up to The Edge, embracing an astonishing aerial view of New York City. Though the vista was enchanting, our eagerness to reach the TKTS booth in Times Square before the queues swelled urged us onward.

As we entered the energetic whirlpool of Times Square, chaos was in full throttle. While the pandemonium of Times Square is a narrative of its own, our affinity for Broadway guided us through. Despite the bustling crowds, we stood our ground in line at the TKTS booth, securing 3rd-row middle seats for the 2 PM show of “Some Like It Hot” at a pleasant 60% discount. After a delightful lunch at Junior’s, a short stroll took us across the street to Shubert Theatre for the 2.5-hour spectacle. This show, with its exhilarating music and engaging plot, earned our hearty recommendation, especially to the avant-garde readers of this blog.

Sydney was so jazzed (“Some Like It Hot” pun intended) from the 2 PM show that our enthusiasm propelled us back into the bustling epicenter of Times Square to snag tickets for Hadestown at 8 PM. Since we had been going pretty strong and were a little peopled-out by this point, we walked the few blocks back to the hotel for a little decompression and rest before venturing forth once more for the evening show. Hadestown has won Tony and Grammy awards for Best Musical, and it shows. The songs are soulful, the cast talented, and we were lucky enough to catch Reeve Carney, original cast member, in one of his final performances. After the show let out, NYC was once again in the midst of the full Halloween weekend maelstrom, so we battled through the crowds and retired for the evening, drawing the curtains on an exhilarating Day 2.

Day 3: Adieu, NYC

Come Sunday morning, we awoke to find that our streak of good weather had gracefully bowed out, making way for a cold front and rain that had stealthily crept in overnight. Over breakfast and soothing morning coffee, we savored a more subdued view of the Empire State Building, its grandeur veiled in a gentle drizzle. With a hint of reluctance, we packed our suitcases, donned our rain jackets, and made our way back to the subway, bound for our morning flight out of LGA back to the comforting familiarity of Raleigh. While not a last-minute reflection per se, I am reminded that though NYC might not cater to everyone’s taste, it has a way of beckoning me back every year or so for a long weekend — and each visit feels just as invigorating as the last. Sydney and I bid adieu to the weekend with sweet exhaustion, cherishing the feeling of having crammed a treasure trove of experiences into a fleeting yet unforgettable timeframe.