The Longest Streets in the World

Have you ever wondered just how long are the world’s longest streets? Believe it or not, some roads can be more than 50 kilometres (31 miles) long! Fancy that for a stroll!

We’ll take you on a tour around the world walking through its longest streets to uncover the interesting histories behind each of these highways, avenues, streets and boulevards. When compiling our list we realised that we’ll find most of the largest streets on the American continent. But of course, it makes sense when we think about the continent’s short history in terms of civil infrastructure.

Yonge Street (Toronto)

Coming in first place with an impressive 56 kilometres (34 miles), Toronto’s Yonge Street is the longest street in the world. It has been declared a National Historic Site and listed in the Guinness Book of Records, this road is the perfect place to discover the main attractions of the Canadian city.

The backbone of Toronto, Yonge Street is home to St. Lawrence Market, the CN Tower and Alexander Muir Gardens. Why not hop on the Toronto sightseeing bus and explore the streets in comfort.

Western Avenue (Chicago)

At no less than 37 kilometres (22 miles) long, Western Avenue in Chicago comes in as the second longest street in the world. It was built between 1851 and 1869 and since then has been the scene of the famous St. Patrick’s Day parades and the world’s largest motorcycle parade Chicagoland Toys for Tots Motorcycle Parade. With the Go City Pass, you can see all the attractions Chicago has to offer!

If you walk along Western Avenue, you can also see an old amusement park converted into a shopping centre, a cemetery or a picnic area – it’s a very versatile area!

Avenida Rivadavia (Buenos Aires)

It’s impossible to beat the number one spot in length, but the Argentine capital is coming in strong in third place for having the widest avenue in the world, 9 de Julio Avenue. Buenos Aires also has one of the longest avenues in the world too, Rivadavia Avenue is 35 kilometres (21 miles) long. This great street starts at the famous Plaza de Mayo and goes all the way to the city of Moreno.

The name of this impressive avenue pays tribute to Bernardino Rivadavia, the first president of the Argentine Republic. With the free tour of the historic centre of Buenos Aires you’ll be able to stroll along the Rivadavia Avenue and learn all about the city’s fascinating past.

Sunset Boulevard (Los Angeles)

Next on our list is the famous Sunset Boulevard, which measures at 35 kilometres (21 miles). It’s one of the most famous streets in Los Angeles and so was bound to feature on our list. This boulevard is home to some of the most iconic places in the city such as the Sunset Strip, Hollywood, Beverly Hills and Bel Air.

But this now glamorous and glittering street full of the best restaurants, bars, boutiques and comedy clubs in the Californian city actually follows the route of an old cattle trail. You can discover all the best of Los Angeles on this tour.

Broadway (New York)

We’re still in the USA, in the Big Apple, to explore Broadway. Did you know that it’s the longest street in New York, 33 kilometres (20 miles) long? The road crosses the island of Manhattan from south to north and here you’ll find some of the most important theatres in the world, as well as the Flatiron Building, Times Square and Radio City Music Hall. Broadway Street owes its name to the Dutch word “breede wegh”, which means “wide road” in English.

Want to know more about this New York avenue? Then we recommend you book a tour of Manhattan by boat and discover the origins of Broadway.

Roskildevej Street (Copenhagen)

Next, we’re heading to Europe, more specifically to Copenhagen to walk along Roskildevej, one of the longest streets in the world and the longest in Europe. This road in the Danish capital is a total of 31 kilometres (19 miles) long and stretches from City Hall to the city of Roskilde.

The street was built in the 18th century to replace the Via Regia, which was part of the medieval layout of the city. Along this impressive road you’ll find the imposing Frederiksberg Palace. With the free tour of Copenhagen you have the perfect opportunity to explore Roskildevej Street and travel through the history of the city.

Avenida de los Insurgentes (México DF)

Next we’re heading south and travel to Mexico City, to the Avenida de los Insurgentes, which makes the list of the world’s longest streets at 28.8 kilometres (18 miles). This is one of Mexico City’s main thoroughfares, as it crosses the city from the Guadalupe Aqueduct to the Tlalpan Viaduct. As you walk along this historical street you’ll be able to uncover the city’s past, since its inauguration in 1953 it has seen its name change several times.

The private tour of Mexico City will take you along the Avenida de los Insurgentes, taking in the sights of the surrounding area.

Ulloi Steet (Budapest)

We’re back in Europe! We find ourselves in the Hungarian capital of Budapest, to walk along Ulloi Street a total of 15.6 kilometres (10.25 miles). Walking along the main artery of the Hungarian capital you can see the University, the Museum of Applied Arts and the most beautiful gardens of the city.

5th Avene (New York)

We’re nearing the end, and for that, there is nothing better than returning to the city that never sleeps. New York‘s Fifth Avenue is one of the longest streets in the world at 14 kilometres (8.6 miles). We think it’s something you should do at least once in your life, as this famous Manhattan street has been the backdrop for thousands of films and has some of the most important and recognisable shops and buildings in the world.

If you fancy seeing the Empire State Building, the Public Library, the Apple Store or museums such as the Metropolitan, the Frick Collection or the Museum of the City, then just take a stroll down 5th avenue. It never fails to surprise visitors from all over the world!

The Bund (Shanghai)

Our final stop is in Asia, in Shanghai’s financial district. Zhongshan East Street, popularly known as The Bund, stretches for 13 kilometres (8 miles) along the banks of the Huangpu River. The heart of the Chinese city’s financial activities, The Bund is lined with iconic buildings such as the former HSBC building, the Customs House and Huangpu Park, making it a must-see in Shanghai!

The guided tour of Shanghai is the perfect way to discover some of the city’s most iconic sights and, of course, to stroll along The Bund, definitely one of the longest streets in the world.