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Sunday, September 26, 2021

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Named after the iconic Navesink Twin Lights up the hill from Huddy Park in Highlands, New Jersey, this ride has been a favorite of local cyclists, New Yorkers, and visitors from around the country for more than a decade.

Five routes ranging from 15 to 100 miles take you along the Jersey shore, over undulating hills, and past quaint farms to our finish festival where local restaurants come out to serve up their best to hungry riders—it’s the greatest way to wind up your summer riding season.

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IMPORTANT DETAILS

  • Rain or shine
  • This event takes place on streets open to traffic.
  • Helmets are required on all Bike New York rides.
  • New Jersey State law requires all cyclists to have and use a bike bell.
  • Proceeds from all Bike New York events fund our free bike education programs. Learn more.

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Highlands has a long and interesting history. Henry Hudson noticed the Highlands as he sailed the Half Moon into the area in 1609, claiming the area for the Dutch. But he wasn’t the first European to comment on the high hills—Verrazano of Florence had been there nearly 100 years earlier.


Hudson explored the hills and traded with the local Lenape Indian natives. The Lenape called the area Navesink, which meant “a place of good fishing.” Today the river bears that name, and the local shellfishing industry supplies much of the local catch in the nearby restaurants.

 

The Dutch who first settled the area never really established settlements in the Highlands. When the British began exploring the area and discussing possible real estate deals with the Lenape, the Dutch threatened to build a fort to keep them out. In 1664, when the British took over the Dutch settlements, they renamed the area “Portland” after a town in England with a similar formation.

 

The first European to settle in the area was Richard Hartshorne, who built his home there in 1678.

 

Sandy Hook, across Sandy Hook Bay from Highlands, is one of the most famous navigational landmarks on the eastern seaboard. Its strategic position figures prominently in the military history of the region.

 

During the Revolutionary War, both British and Colonial armies were operating in New Jersey. Many loyalists in Monmouth County went to Sandy Hook when the British fleet arrived in 1776. They built fortifications and held the Hook for the remainder of the war. The Highlands had its own Revolutionary War hero, Captain Joseph Huddy, a member of the Continental Militia. He was captured by the British and hung in 1782, near the spot of the small park in Highlands which bears his name today.

 

The Twin Lights lighthouse in Highlands was completed in 1862. This is the first structure many immigrants to America saw as they approached New York Harbor. The Twin Lights was the first U.S. lighthouse to use the French Fresnel lens to reach some 22 miles out to sea. Around the turn of the twentieth century, Marconi used the Twin Lights for one of his early tests of wireless telegraphy.

 

Highlands has been a tourist destination since the first hotel was built there in 1796. In the 19th century, sailing ships and then steamships brought visitors to enjoy the sea air. One of its most well-known summer residents was Gertrude Ederle, the first woman to swim the English Channel. She trained in the challenging currents beneath the Highlands bridge.

 

Highlands was incorporated as a town in 1900 and continues to host visitors seeking fresh seaside air. Now, of course, year-round residents can commute to New York City on a 45-minute ferry trip across the Harbor. In addition to the nearby beaches and National Recreation Area, residents and visitors alike enjoy the active nightlife and numerous seafood restaurants in the area.