Manhattan Walking Tours – “The Upper Side of Manhattan”– A Guided Walking Tour in NYC

The Upper West Side of Manhattan is rich in culture, history, and green spaces. It has a long history and many important sites to see. Here are some of the best things to see and do in this iconic neighborhood:

 

1. American Museum of Natural History

One of the largest and most celebrated museums in the world, featuring dinosaur fossils, the Hayden Planetarium, and exhibits on everything from ocean life to outer space.

2. Central Park (West Side)

Explore the western edge of Central Park, including:

  • Strawberry Fields (John Lennon memorial)
  • The Great Lawn
  • The Ramble for birdwatching and nature walks

3. New-York Historical Society

New York’s oldest museum, offering fascinating exhibits on the city’s past, plus a children’s history museum and a beautiful library.

4. Theodore Roosevelt Park

A peaceful green space surrounding the Natural History Museum, great for a stroll or picnic.

5. Columbus Avenue Shopping

Boutiques, bookstores, and cafes line this charming avenue. Don’t miss Zabar’s, a legendary Jewish deli and gourmet food store.

6. Riverside Park

Stretching along the Hudson River, this scenic park offers walking and biking paths, sports fields, and stunning sunset views.

7. Cathedral of St. John the Divine

One of the largest cathedrals in the world, known for its Gothic architecture, peaceful gardens, and rotating art installations.

8. The Beacon Theatre

A historic venue for concerts and performances, known for its stunning interior and top-tier acoustics.

 

If you’re looking for the secrets of the Upper West Side, here’s a mix of hidden spots, little-known history, and under-the-radar gems that locals whisper about but tourists often miss:

The Whispering Benches in Riverside Park
Near 91st Street, there’s a curved stone bench where you can sit at one end, whisper into the wall, and someone on the other side can hear you. It’s like the whispering gallery at Grand Central, but outdoors and lesser known.

The Apthorp Building (Broadway & 79th)
This massive, block-long apartment building was one of the city’s original luxury residences when it opened in 1908. The courtyard, which you can glimpse through the grand archway, feels like stepping into old Europe. You probably need a connection to get inside, but it’s worth sneaking a peek.

Hidden Bookstore: Westsider Rare & Used Books
At 2246 Broadway (near 80th), this narrow, packed little bookstore is a treasure trove of rare and used books. It’s one of the last true old-school used bookshops in Manhattan.

The Red Steps in Verdi Square
Most people rush past Verdi Square at 72nd and Broadway, but look for the little red steps tucked away — they’re often empty and give you a perfect people-watching perch.

The Soldiers’ and Sailors’ Monument
Perched above Riverside Drive at 89th Street, this massive marble column was built in 1902 and is one of NYC’s lesser-visited historical memorials. Climb the steps for gorgeous sunset views.

My Upper West Side walking tour promises an unforgettable experience in this part of New York City.  Through this historical NYC tour with a local guide, you’ll learn the history of this area and see beautiful brownstones, architecture, statues, and unique sites along the way. This part of New York is a delightful place to take a break and soak in some history that dates back hundreds of years. Book “The Secrets of the Upper West Side” at Eyesonmanhattan.com. Hope to see you there soon.

Duration
2 hours
Group Size
Up to 8

Eyes on Manhattan: Where America Began Walk

Stand where George Washington took the oath of office and visit the final resting place of Alexander Hamilton. This immersive walk through Lower Manhattan reveals the turning points of American history at the very sites where they occurred.

Learn where the United States began to take shape as you walk the streets of Lower Manhattan. From George Washington’s first steps as president to the legacy of Alexander Hamilton, this tour traces the founding moments of America right where they happened. Explore churches, taverns, and financial institutions that have stood for centuries, and discover how New York helped shape the nation’s identity. Discover how New York City evolved from a Dutch trading post to one of the greatest cities in the world,

from
$249$199
Duration
2 hours
Group Size
Up to 8

Eyes on Manhattan: Sites & Bites of the Lower East Side

Eat traditional Jewish foods and walk historic streets that reveal the heart of Manhattan’s immigrant past. This must visit destination brings the 1880s to life and leaves you with a deeper understanding of what the Lower East Side was and what it has become.

You'll eat your way through one of Manhattan’s most historic neighborhoods as you uncover stories of Jewish immigration, family traditions, and neighborhood transformation. Trace the footsteps of those who arrived with everything they owned in a suitcase and built a new life on crowded, noisy streets. Along the way, you’ll sample old-world flavors from beloved shops and explore buildings that still carry echoes of a time when the Lower East Side was the heart of New York’s immigrant story.

You'll delve into the rich history of the Lower East Side, once the most densely populated district in the world. This tour offers a glimpse into the past, focusing on the era of Jewish immigration and the transformation of the neighborhood over the last hundred years. Explore the remaining vestiges of this vibrant history and enjoy tastings at some of the area's iconic food establishments.

from
$299$249
Duration
3 hours
Group Size
Up to 8

Eyes on Manhattan: Chinatown, Little Italy & the Lower East Side - History and Food

Taste the history, resilience, and flavor of three immigrant neighborhoods that helped shape New York City. On this private walking tour, you will move through Chinatown, Little Italy, and the Lower East Side, stopping for hand-folded dumplings, old-school Jewish pastries, and timeless pizza and pickles favorites. Along the way, your guide connects the food to the families, communities, and traditions that kept culture alive in the face of change. We'll also explore the vibrant history and culture of New York City's Chinatown, Little Italy, and the Lower East Side.

This walking tour offers a glimpse into the past, showcasing the transformation of historic buildings into modern spaces. You'll discover the impact of immigration on these neighborhoods and uncover the stories of tenement life. Come hungry and wear comfortable shoes because every stop has something to share.

from
$399$299
Duration
2 hours
Group Size
Up to 8

Eyes on Manhattan: The "I Love NY Walk"

See the sights you have only known from TV as you walk 42nd Street from river to river. Times Square, Broadway, the New Year’s Eve Ball, Grand Central, and more. This unforgettable walk reveals the real New York behind the one the world thinks it knows.

See New York through fresh eyes as you travel 42nd Street from the Hudson River to the East River. This walk uncovers the layers of history, ambition, and imagination packed into every block. You’ll pass theaters where legends were made, stand where the world celebrates New Year’s Eve, and explore the secrets of Bryant Park, Grand Central, and the city’s Art Deco towers. By the end, you’ll know the city in a way that goes far beyond what you’ve seen on screen.

This guided walking tour takes you through the heart of New York City, showcasing its transformation from farmland to a bustling urban center. Discover the stories behind famous landmarks and hidden gems as you stroll along this legendary street.

from
$249$199
Duration
2 hours
Group Size
Up to 8

Eyes On Manhattan - “The Squares That Shaped Manhattan: Gramercy, Madison & Union”

Step back in time and explore three of New York City’s most influential public spaces—Union Square, Madison Square, and Gramercy Park. Each of these iconic squares tells a story of how Manhattan transformed from a bustling 19th-century city into a modern metropolis.

Begin at Union Square, once the stage for political rallies, labor movements, and social reform, now a thriving hub of markets, art, and activism. Continue north to the refined enclave of Gramercy Park, Manhattan’s only private park, whose leafy streets and preserved architecture reflect the city’s aspiration for exclusivity, elegance, and community. Finally stroll past the "Ladies Mile" on route to Madison Square, where the elegant park was once home to the original Madison Square Garden and surrounded by Gilded Age hotels, theaters, and mansions.

Along the way, uncover stories of visionaries, politicians, artists, and everyday New Yorkers who shaped these squares into enduring landmarks of culture, history, and urban design.

from
$249$199
Duration
2 hours
Group Size
Up to 8

Eyes on Manhattan: “Skid Row and Flop Houses to Glamour and Hidden Gems: The Bowery Walk”

Walk one of New York’s oldest streets. See how it evolved from a Dutch footpath to a cultural landmark filled with community gardens, historic theaters, and the birthplace of punk at CBGB. This eye opening experience changes everything you might have heard about New York’s iconic Bowery. This tour takes you through a 1.5-mile stretch filled with stories of theaters, grand bank buildings, and flophouses. Discover how this major thoroughfare, once a Native American trail, became a hub of wild fun and cultural significance.

from
$249$199