1

Circle the wagons

Image: Dana Davis

Pioneer wagon trains literally circled their wagons at night for protection.

Creating a closed ring helped shield families, livestock, and supplies from raids, wild animals, and harsh weather—and the formation later evolved into a metaphor for any type of unified, defensive action.

2

Hold your horses

Image: Cemrecan Yurtman

Frontier riders needed to keep horses steady at all times, but particularly in chaotic and potentially dangerous settings like stage stops and river crossings.

By the mid-1800s, the phrase became a common command, later evolving into a figurative call for patience.

3

On the warpath

Image: Andrew James

This term originated as an English rendering of a Native American expression for wartime mobilization—specifically the route or course taken toward an impending conflict.

Euro-American settlers later adopted the phrase, and by the late 19th, century newspapers were using it metaphorically to describe anyone behaving aggressively or angrily.

4

Branding iron

Image: Jonny Gios

Ever wonder where the term "brand name" comes from? Frontier ranchers used heated irons to mark ownership on their cattle.

The idea of a distinctive identifying mark later moved into the commercial world, where "brand name" came to signify a recognizable product or company identity.

5

Come hell or high water

Image: Furkan Elveren

Ranchers driving cattle across rough terrain used this phrase to signal determination despite floods, storms, conflict, and whatever else the wild frontier could throw at them.

The earliest known printed use appears in an 1882 issue of The Burlington Weekly Hawk Eye, an Iowa newspaper. Railroads later adopted it in contracts requiring delivery despite natural obstacles.

6

Riding shotgun

Image: Paul Einerhand

In Wyatt Earp’s era, the seat beside a stagecoach driver was reserved for an armed guard carrying a shotgun to deter bandits.

By the early 20th century, the job had vanished, but the expression endured as a casual claim for the front passenger seat.

7

Belly up to the bar

Image: Vidar Nordli-Mathisen

Saloon bars on the frontier often lacked stools, so patrons had to stand and lean their bellies directly against the counter.

The phrase soon came to mean approaching something boldly, whether at a bar or any other challenge.

8

Kick the bucket

Image: Lucas van Oort

Rural butchers often suspended animals from a beam called a "bucket," and they sometimes kicked during slaughter.

The phrase was popular on farms and frontier towns, eventually becoming a euphemism for dying.

9

Dead ringer

Image: Annie Spratt

Frontier horse racers engaged in plenty of shady practices—and one of the most common was substituting a horse with a look-alike, a "ringer," to scam bets.

When the substitute was an exceptionally close match, it was called a "dead ringer," emphasizing its perfect likeness.

10

High noon

Image: CHUTTERSNAP

Before standardized clocks or reliable rail schedules, "high noon" was an easy way to tell time by noting the sun at its highest point.

It also became associated with showdowns and other events because midday offered the clearest visibility.

1

"New York, New York" - Frank Sinatra

Image: Adrian Falcon

Of course, when we think of songs about the Big Apple, the first that comes to mind is the iconic "New York, New York," popularized by Frank Sinatra. Perhaps this is because it’s the tune that best captures the essence , resilient spirit, and unwavering magnetism of the city that never sleeps.

It was written in 1977 by John Kander and Fred Ebb as the theme song for New York, New York , a film directed by Martin Scorsese and starring Robert De Niro and Liza Minnelli. Minnelli performed the song in the film, but it wasn’t very successful at the time. It was The Voice 's 1980 version that would turn it into the city's unofficial—yet unquestionable—anthem .

2

"Chelsea Hotel #2" - Leonard Cohen

Image: Thought Catalog

The Chelsea Hotel is one of the most emblematic hotels in New York City. Artists such as William S. Burroughs, Bob Dylan, and Chet Baker, among many others, have stayed there. So, it makes perfect sense that some of these stars were inspired by the iconic building to create some of their most famous works.

Such is the case with Leonard Cohen’s "Chelsea Hotel #2," released in 1974. The lyrics not only recount a romantic encounter between the singer-songwriter and Janis Joplin but also capture the city’s bohemian atmosphere at the time.

3

"New York State of Mind" - Billy Joel

Image: Stefano Zocca

In the mid-1970s, after a long stint in Los Angeles, Bronx-born songwriter Billy Joel was terribly missing his hometown. During a return trip to the Big Apple while on tour, the Piano Man wrote his tribute to the city he loved most: "New York State of Mind."

At the time, the song wasn’t even released as a single and went largely unnoticed. However, over time, it became one of Joel’s signature songs . Decades later, the timeless tune would go on to inspire a hip-hop version—the next one on our list.

4

"Empire State of Mind" - Jay-Z & Alicia Keys

Image: ian dooley

With its evocative lyrics, Jay-Z’s modern rhythm, and Alicia Keys’ poignant backing vocals, "Empire State of Mind" captures the essence, energy, and resilient spirit of those who inhabit the city of New York. Released in 2009, the song was an instant hit. It achieved commercial success worldwide and has been featured on multiple critics' top 10 lists of best songs.

As mentioned earlier, the song’s title nods not only to Billy Joel’s "New York State of Mind," but also to rapper Nas’s 1994 single "N.Y. State of Mind."

5

"Autumn in New York" - Billie Holiday

Image: Josh Couch

Did you know that the famous "Autumn in New York" was originally conceived as a poem rather than a song? Its composer, Vernon Duke, wrote it in 1934 while vacationing in Westport, Connecticut, and added the music sometime later. Since then, many artists have recorded their own renditions, including Frank Sinatra, who helped popularize it in 1949.

But perhaps the version that best conveys the haunting melancholy of this iconic jazz standard is Billie Holiday’s, recorded in 1952. With her deep, raspy voice, the Angel of Harlem (see the next song on our list) delivers this love letter to the Empire City like no one else.

6

"Angel of Harlem" - U2

Image: The New York Public Library

"Angel of Harlem," a 1988 single by the Irish band U2, alludes to several New York City landmarks but is also a heartfelt tribute to Billie Holiday.

According to Bono, the song was inspired by the band’s first trip to the Big Apple . When they landed at JFK Airport, a limousine picked them up, and the driver had the radio tuned to Lady Day’s voice. They were so captivated by her sound that they couldn’t help but compose a song in honor of one of the city’s most influential musical figures.

7

"Englishman in New York" – Sting

Image: George Bakos

Bono wasn’t the only foreign artist who was inspired by the Empire City to pen a song. In the late 1980s, Sting released the single "Englishman in New York" as part of his second solo album after the dissolution of The Police. The song quickly became a global hit.

The "Englishman" in question is Sting’s friend, British writer and LGBTQ+ icon Quentin Crisp, who had recently relocated to New York. The singer-songwriter said that the different musical references in the song seek to capture the mood of someone walking down the street and listening to different styles, representing what it's like to walk around New York.

8

"Chelsea Morning" - Joni Mitchell

Image: Dan Braga

One of the most celebrated voices in American folk music, Joni Mitchell, wrote this song about her apartment in New York City’s Chelsea neighborhood. The song was inspired by the colorful reflections that danced on her walls when sunlight filtered through a mobile made of colored glass she had found in the street.

"Chelsea Morning" is part of her second album Clouds from 1969. Her sweet voice, merry acoustic guitar chords, and hopeful lyrics convey the deep emotions of the hippie lifestyle of a young woman living in 1960s New York.

9

"The Only Living Boy in New York" – Simon & Garfunkel

Image: Camila Fernández

Many songs about New York City explore the loneliness of living in a vast metropolis—and "The Only Living Boy in New York" is no exception. Paul Simon wrote the track when his musical partner, Art Garfunkel, left him behind in the city to film a movie in Mexico.

The song is part of the duo's fifth studio album, Bridge over Troubled Water released in 1970. The song blends bittersweet lyrics with a gentle, introspective melody. Its themes of solitude and longing have resonated with many over the years, inspiring a variety of heartfelt covers by artists who connected with its quiet sorrow.

10

"New York City Serenade" – Bruce Springsteen

Image: Danny Lyon, Public domain, via Wikimedia Commons

While Bruce Springsteen is known for being a New Jersey native, his prolific career also allowed him to write about the city across the Hudson River. "New York City Serenade" is part of the 1973 album The Wild, the Innocent & the E Street Shuffle , considered by some critics to be one of the greatest albums in rock n' roll history.

The song tells the tormented love story of Billy and Diamonds Jackie as they wander the dark streets of Gotham in the 1970s. Blending Springsteen’s signature suburban rock with elements of jazz and gospel , "New York City Serenade" is one of his most atmospheric and musically ambitious pieces—a sprawling homage to the city’s grit, soul, and romance.

11

"Rhapsody in Blue" – George Gershwin

Image: rosanna17

Although it has no lyrics, we can all agree that this composition is a true musical portrait of 20th-century New York City. Written by George Gershwin in 1924, the piece blends classical tradition with jazz-inflected flourishes, capturing the vibrant, chaotic spirit of the Big Apple in full swing.

The speed and rhythm of the tune perfectly reflect the frenetic life of one of the world's greatest metropolises. "Rhapsody in Blue" is so quintessentially New York that even Woody Allen used it for the opening sequence of his film Manhattan alongside gorgeous vistas of the most iconic locations and buildings in the city.

12

"Downtown Train" – Tom Waits

Image: Erik Calonius, Public domain, via Wikimedia Commons

You may know this song best from Rod Stewart’s 1989 hit version, but "Downtown Train" was originally written and performed by Tom Waits for his 1985 album Rain Dogs . Without leaving behind his jazz and blues influences —and his trademark avant-garde style—this tune has an unmistakable pop touch.

Set against the backdrop of New York’s restless nightlife, the song paints a wistful portrait of longing and unattainable love—particularly for the elusive Brooklyn girls. Through his gravelly voice and poetic imagery, Waits cements his place as one of the great modern chroniclers of the Big Apple .

1

Appalachian Trail, Shenandoah National Park, Virginia

Image: Wes Hicks

Yes, the entire Appalachian Trail is extremely long. Actually, it is over 2,190 miles long. But, the Shenandoah National Park, 75 miles from Washington, D.C., has over 500 miles of hiking trails, including more than 100 miles of the Appalachian Trail ; You can tackle a small section in a day’s hike.

The park is the perfect place to explore the great outdoors in Virginia and it consists of 200,000 acres of protected land that are home to animals like deer and songbirds.

2

Burroughs Mountain Trail, Mount Rainier National Park, Washington

Image: Scott Longerbeam

More than 260 miles of maintained trails lead visitors through peaceful old-growth forests, river valleys, and subalpine meadows on the Mount Rainier National Park in Washington state.

The park is home to one of the most iconic mountains in the world: Mount Rainier rises 14,410 feet above sea level straight into the clouds. Check out the Burroughs Mountain Trail for stunning views of mountain peaks and the alpine landscape.

3

Rim Trail, Bryce Canyon National Park, Utah

Image: Tim Golder

Bryce Canyon National Park in Utah is home to the largest collection of odd-shaped pillars of rock left standing from the forces of erosion, known as hoodoos. Many of them can be viewed from the 5.5-mile Rim Trail .

The park also offers hikes for all levels, including backcountry options for those looking for a little added adventure and guided Full Moon Hikes for night-owl explorers.

4

Upper Emerald Pools Trail, Zion National Park, Utah

Image: Jamie Hagan

A park filled with hiking trails for all experience levels, Zion National Park, Utah's first national park , is famous for its massive cream, pink, and red sandstone cliffs, and freestanding arches.

Hikers should attempt to visit at sunrise and sunset to enjoy the breathtaking views of sunlight splashing off the cliffs and into the rivers below. And if it is an approachable trail they’re looking for, the Upper Emerald Pools Trail is an easy hike leading to sparkling waterfalls.

5

Grinnell Glacier Trail, Glacier National Park, Montana

Image: Aaron Clinard

Over 700 miles of hiking trails, including more than a dozen options around the Many Glacier area , like the popular Grinnell Glacier Trail , can be found at the Glacier National Park.

Lucky visitors can spot some of the park's varied wildlife, including 71 species of mammals, from the tiny pygmy shrew to one of the largest remaining grizzly bear populations in the country.

6

Charlies Bunion Hike, Great Smoky Mountains National Park, Tennessee and North Carolina

Image: Leslie Cross

The Great Smoky Mountains are world-renowned for its animal and plant life diversity, as well as for its miles of official and backcountry trails with views of waterfalls and old-growth forests.

The Great Smoky Mountains National Park spreads across two states and offers plenty of activities for hikers. For a particularly breathtaking vista, hike to Charlies Bunion, a popular outcropping along the Appalachian Trail.

7

Billy Goat Trail, Chesapeake and Ohio Canal National Historical Park, Maryland

Image: Eduardo Gutierrez

Considered a moderate-difficulty trail, Maryland's Billy Goat Trail has three sections totaling eight miles, though portions are strenuous and challenging . Outdoor enthusiasts can experience the raging Potomac River and the rocky crags of Great Falls. The hike is very popular, so early hours are advisable to beat the crowds.

8

Chautauqua Trail, Chautauqua Park, Colorado

Image: Leslie Cross

An old park, Chautauqua Park in Boulder, Colorado, has been around since 1898. The 80-acre park has miles of hiking, much of which are uphill . But there are less strenuous hikes, too, like the Chautauqua Trail, which offers views of the Flatiron mountains and Boulder.

9

Canyon to Rim Loop, Smith Rock State Park, Oregon

Image: Alex Diaz

Hikers of every level can find an appropriate trail at Smith Rock State Park, in Oregon. These vary in length and difficulty, but they all offer beautiful views of the Central Oregon landscape**.**

The park offers hundreds of miles of hiking and biking trails, and visitors may spot golden eagles, prairie falcons, river otters, and beavers throughout the day.

10

Petroglyph Wall Trail, Red Rock Canyon National Conservation Area, Nevada

Image: Kristin Melville

As visitors to the Red Rock Canyon National Conservation Area can testify, not all short-distance hikes are the same. Many are labeled difficult, and it can take four to five hours to complete a five-mile hike.

Along the different routes, desert wildlife can be spotted, including lizards, toads, and hawks. One of the park's most beginner-friendly hikes is the 0.2-mile Petroglyph Wall Trail , where centuries-old rock art can be appreciated.