[33] Due to its affluence, low crime, access to cultural activities, public school system, location at the Jersey Shore and Raritan Bayshore, and central commuting location, Middletown was ranked in 2006, 2008, 2010, and 2014 in the Top 100 in CNNMoney.com's Best Places to Live.

[39] Small communities of the Lenape Navesink tribe were common throughout the area when the first known European landing in what would become Middletown Township occurred in 1609.

Sea captain and explorer Henry Hudson, in search of the mythical Northwest Passage in the service of the Dutch West India Company, anchored along the shores of Sandy Hook Bay in 1609, describing the area "a very good land to fall in with and a pleasant land to see.

Today's Shoal Harbor Museum and Old Spy House includes portions of a house constructed by Thomas Whitlock, one of the area's first European settlers (and a Reformed Baptist at Middletown[41]) who arrived here as early as 1664,[42] around the time of the English takeover of New Netherland as a prelude of the Second Anglo-Dutch War.

[40] Long-standing tradition had Penelope Stout, one of the first settlers, hiding in a tree from hostile Native Americans.

[44][45] During the American Revolutionary War, Middletown and much of the rest of Eastern Monmouth County was held by the British.

After the Battle of Monmouth, the British retreat from Freehold Township carried them down King's Highway through Middletown to their embarkation points at Sandy Hook in the bay, heading back to New York City.

[47] Upon the completion of a railroad junction in 1875, the town grew more rapidly, eventually changing from a group of small and loosely connected fishing and agricultural villages into a fast-growing suburb at the turn of the 20th century.

In May 1958, several Nike Ajax missiles exploded at Battery NY-53 in Chapel Hill, killing ten Army and civilian personnel.

[48][49] During the September 11 terrorist attacks in 2001, Middletown lost 37 of its residents at the World Trade Center,[50] which was the second-most 9/11 deaths of any municipality, behind New York City itself.

[51][52][53] The World Trade Center Memorial Gardens were opened to the public on September 11, 2003, the second anniversary of the attacks.

[50] The Waterfront site of Naval Weapons Station Earle is located in Leonardo on Sandy Hook Bay, and is used to load ammunition onto ships on a finger pier that stretches for 2.9 miles (4.7 km), making it the world's second-longest such pier.

The clown and recent successful attempts from residents to save it from demolition have been featured in the pages of Weird NJ magazine, on The Tonight Show with Jay Leno, and in the Kevin Smith-directed film Clerks II.

[55] The Indian Trails 15K road race is held each year in April to benefit the Monmouth Conservation Foundation and includes a 5K walk/run event for fun.

[104] In February 2018, the Township Committee selected Rick Hibell to fill the seat expiring in December 2019 that was vacated by Gerard Scharfenberger after he resigned and took office on the Monmouth County Board of Chosen Freeholders; Hibell served on an interim basis until the November 2018 general election, when voters elected him to fill the balance of the term of office.

[105][106] In November 2017, the committee chose Anthony Perry, the son-in-law of then-Mayor Gerry Scharfenberger, from three candidates nominated by the Republican municipal committee to fill the seat expiring in December 2018 that had been vacated by Stephen G. Massell the previous month when he resigned from office to accept a position on the Monmouth County Tax Board.

[107][108] In October 2006, Middletown councilman and former four-term mayor Raymond J. O'Grady (R) was sentenced to 43 months in federal prison on bribery and extortion charges arising from his involvement in a federal sting operation known as Operation Bid Rig targeting political corruption in New Jersey.

O'Grady committed to obtain no-bid contracts after he had accepted bribes from contractors in exchange for the work.

[110][113] For the 119th United States Congress, New Jersey's 4th congressional district is represented by Chris Smith (R, Manchester Township).

[114][115] For the 119th United States Congress, New Jersey's 6th congressional district is represented by Frank Pallone (D, Long Branch).

[142] The Middletown Township Public School District serves students in pre-kindergarten through twelfth grade.

The program is specifically designed to educate the student in the life altering ramifications of drinking and driving.

These squads also have boats and dive teams to perform rescue and recovery operations involving water which have been called out of town to assist with large area searches.

Port Monmouth provides a bariatric unit, a converted ambulance, for severely overweight patients.

It has been requested outside of Middletown Township as a back-up for the unit from the Monmouth Ocean Hospital Service Corporation(MONOC).

[195] CR 520 passes through the southern portion of Middletown, and leads to Sea Bright to the east, and turns into CR 612 in Monroe Township to the west, making it a vital route for central New Jersey, by connecting sections of the state near the shore to inland sections of the state near the New Jersey Turnpike at Exit 8A.

[198] Commuter service runs between New York City's Pennsylvania Station and Bay Head on the North Jersey Coast Line.

The ferry slip is located in the neighborhood of Belford and is utilized by many Middletown residents for commuting to New York City.

[203] The ferry service also offers seasonal travel, such as to the public beaches on Sandy Hook, baseball games at Yankee Stadium and Citi Field, trips to Broadway matinees, Martha's Vineyard in Massachusetts, college football games at West Point, fall foliage in the Hudson Valley, and to the Macy's Thanksgiving Day Parade, among other excursions.

[209][210][211] Kevin Smith wrote and filmed Clerks at a Quick Stop in the Leonardo section of the township.