The borough is located relatively close to the Raritan Bayshore communities to the north, including The Amboys, Old Bridge, Matawan, Keyport, Keansburg, and Middletown, along with being relatively close to the Tri-City region of Jersey Shore municipalities (and their vicinities) to the east, including Red Bank, Long Branch, and Asbury Park.

In 1664, the Duke of York (later James II & VII) granted a patent to Sir George Carteret to develop the area.

In 1685, Scottish Presbyterians from Scotland, along with English Baptists and Quakers from New England fleeing religious persecution at home, became the first to settle within the area.

[38] The name of the borough comes from the word Freehold, an English legal term describing fee simple property ownership.

[41] Freehold was officially designated as the seat of the Monmouth County government, and a court house was commissioned to be built on the land purchased from John Reid.

A number of homes and commercial businesses also sprang up in the village, including a blacksmith, a general store, a bank, a hotel, and saloon.

[45] In modern Freehold today, many important streets bear the name of early colonial families, including Barkalow, Applegate, Rhea, Throckmorton, and Schanck.

By the early 1770s, the Sons of Liberty were actively recruiting local members in Freehold, and were agitating the relationship between the British government and the colonists.

The Declaration of Independence was publicly proclaimed, read aloud, from the steps of the Freehold Courthouse just a few days after being signed in Philadelphia.

[45] However, after British success at the Battle of Long Island, Freehold and all of Monmouth County fell under the control of Loyalists.

Nathaniel Greene, Alexander Hamilton, the Marquis de Lafayette and Friedrich Wilhelm von Steuben also fought for the Continental Army at the Battle of Monmouth.

[52] Colonel Tye, an escaped slave and leader of a prominent loyalist guerilla force, conducted several raids in and around Freehold.

[54] At the end of the war, the community was deeply divided, and nearly 120 loyalist families left Freehold, fearing persecution from their neighbors.

The issue of local tax dollars, used as funding for public works and infrastructure projects, was the primary point of contention.

[62] After contentious public debate, a referendum was held to on the future of Freehold, and voters overwhelmingly decided to split the town into two separate municipalities.

[63] Freehold Township, the farming communities that surrounded the courthouse, set up a new city hall complex on Schanck Road.

Freehold Borough was an important center of African American civil rights activity in New Jersey during the years leading up to the Brown v. Board of Education decision in 1954.

Springsteen has always remained loyal to Freehold and makes reference to it in several of his famous songs, including "My Hometown".

[30][83] Suburbanization within the vicinity of the Freeholds region has been due to its convenient location near the Jersey Shore, and proximity to cities such as New York, Newark, Trenton, and Philadelphia.

The borough is home to Downtown Freehold, located on East and West Main Street (County Route 537).

The mall was constructed at a cost of $125 million on a site covering more than 175 acres (71 ha)[citation needed] across from the Freehold Raceway over U.S. 9, and it has a gross leasable area of 1,600,000 square feet (150,000 m2).

[32] NJ Leaf, a medical cannabis dispensary located on Park Avenue, opened in March 2023 and is expected to also expand to recreational sales in the near future.

[91] Freehold Borough and Township began to grow in commercial and industrial manufacturing of goods during the late 19th and early 20th centuries.

[98] The southernmost segment of the Henry Hudson Trail starts in the borough and runs northeast to the Raritan Bayshore area along an abandoned rail line to Matawan.

[3][105][106][107][108] Michael Wilson had been elected in 1985 and served in office until January 2012, making him the longest-serving mayor in Freehold Borough history, with 26 years of service.

[112][113][114] For the 119th United States Congress, New Jersey's 3rd congressional district is currently represented Herb Conaway (D, Delran Township).

[166][167] In the early 1940s, the Freehold Circle was the planned terminus of highway that would funnel traffic from South Amboy to the Jersey Shore by way of Matawan and Marlboro Township.

"[176] On April 20, 2020, borough council members had reached an agreement in adopting an ordinance that would purchase a new building to house as the municipal complex.

NJ Transit bus service connects Freehold with communities along U.S. Route 9, to Newark Liberty International Airport, to New York City, and to Six Flags Great Adventure located in Jackson Township.

His connection to Freehold was documented by the Monmouth County Historical Association in a 2019 exhibition titled "Bruce Springsteen: His Hometown".