[4]: 31 The lake contains at least 264 islands,[1] half of which are less than 0.25 acres (0.10 ha) in size, and is indented by several peninsulas, yielding a total shoreline of approximately 288 miles (463 km).

The Abenaki name Winnipesaukee (often spelled Winnipiseogee in earlier centuries[6]: 27 [7]) means either "smile of the Great Spirit" or "beautiful water in a high place".

[6]: 19  At the outlet of the lake, the Winnipesaukee people, a subtribe of the Pennacook, lived and fished at a village called Acquadocton.

Draining the central portion of New Hampshire, it once flowed southeast, leaving via what is now Alton Bay toward the Atlantic Ocean.

When glacial debris blocked this path, flow was redirected westward through Paugus Bay into the Winnipesaukee River.

Center Harbor witnessed the first intercollegiate sporting event in the United States, as Harvard defeated Yale by two lengths in the first Harvard–Yale Regatta on August 3, 1852.

[8] The outcome was repeated 100 years later when the schools celebrated the centennial of the race by again competing on Lake Winnipesaukee (Harvard winning by 2.7 seconds).

The area is home to numerous summer theater troupes and offers a variety of land and water recreational activities.

The paddlesteamer MS Mount Washington, named after the highest of New Hampshire's White Mountains, was launched in spring 1872 to carry mail, goods, and passengers on Lake Winnipesaukee, under the flag of the Boston and Maine Railroad.

Efforts to cut Mount Washington loose were to no avail as it was a time of extremely low water and the hull was stuck fast in the mud of the lake bottom.

It was cut into sections by Boston General Ship & Engine Works and transported to Lake Winnipesaukee on rail cars.

[13] Powered by two steam engines taken from another ocean-going yacht, the new MS Mount Washington made her maiden voyage on August 15, 1940.

Two years after her launch, the new Mount Washington's engines and boilers were removed for use in a navy vessel during World War II.

[14] In 1982, Mount Washington was cut open and extended with an additional 20-foot (6.1 m) hull section to add larger lounge and food service facilities.

[13] Still popular, she makes one or two round trips on the lake per day during the summer season, as well as numerous dinner dance cruises in the evenings.

Sophie C. also operates as a sightseeing boat, carrying up to 125 people on her two cruises a day as she delivers mail, and sells ice cream and snacks to residents of the islands she serves.

[19][20] The steamship Dover, 150 feet (46 m) in length, captained by Winborn Sanborn, operated by the Cocheco Railroad, traveled the lake in the 1850s.

Since records began in 1851, ice-out has happened as early as March 17, in 2024 and as late as May 12, although 90 percent of the time it is declared during April.