Waterborne transit was the major mode of transportation on Long Island for most of its history following European settlement. Communities along the South Shore were eventually connected by ferry lines, with Freeport as an important hub. Ferry service was also much more extensive on the North Shore than today, running to various points in Upstate New York and to Connecticut. There was ferry service direct to New York City as well¹, which is also currently available from Glen Cove.

The widening of Freeport Creek and similar improvements took place as early as 1791 to make Freeport competitive in shipping².

By 1914, part of Sea Dog Creek, the waterway just north of the present-day Loop Parkway, had been rendered impassible by storms³. It had comprised part of the ideal ferry route between Freeport and Point Lookout, the alternative subject to dangerous currents. Following dredging two years previously by the Great South Bay Ferry Co., the Town of Hempstead undertook to dredge the waterways around Hempstead Bay for a cost of $5,000. The project took months, and measures such as concrete walls were suggested to prevent new accumulation of sediment⁴, though these were never built. There was some controversy about the project as it was argued the only one to really benefit would be the Great South Bay Ferry Co.⁵

Companies would apply for leases to operate a ferry in a given area, though sometimes these were challenged. A steamer called the Mosquito made runs between Woodcleft Canal and Point Lookout, apparently in violation of one lease, and the boat's owner sought to get a license from the state to avoid the lease requirement⁶.

Multiple operators ran ferries to and from Freeport. As of 1913, one these was the High Hill Beach Ferry Co., under Captain John Haff, which ran every day during the summer between High Hill Beach and Freeport. A round trip was 40 cents, a single trip, 25 cents⁷.

The photo above shows a man unfastening a mooring line at Ellison's Ferry, at the end of Miller Ave., from which service was run to Point Lookout; the vessel in the photo is apparently about to cast off. As seen in the photo, even going to the beach, the women wore fairly elaborate clothing, and at least one is carrying a parasol. Reminiscing about the village's past for its 75th anniversary, Freeporter Jim Crisafulli suggested the trolley connection to this ferry was not reliable⁸.

This 1914 ad, which appeared in the Nassau County Review, promotes the Great South Bay Ferry Co. and Freeport Railroad and provides a timetable for their services. Access to fishing is presented as the main enticement to potential passengers. It also reveals that the ferry left Freeport three times a day.

By the 1910s, the smaller operators seem to have fallen away, and the dominant one was the Great South Bay Ferry Co. It ran service every day in the summers to Freeport, Point Lookout, Nassau by the Sea, Sea Edge, Long Beach, and High Hill Beach⁹. As of 1913, a one-way fare was 15 cents, and four round trips could be purchased for $1¹⁰. In 1917, the ferry lines were especially well traveled, carrying over 10,000 passengers in September, so the company decided to run more service in 1918. At peak, at least on Memorial Day, it may have run as often as every 15 minutes.¹¹

The ferry from Baldwin Harbor to Long Beach also stopped in Freeport at least during certain periods¹². In the earlier years of ferry operation at least, Bellmore could be reached from Freeport by ferry as well¹³.

The photos above show two Great South Bay Ferry Co. vessels, the Sea Witch and Seagull, both of which were overhauled for the 1918 season¹⁴. One notable difference from what many people would picture as a ferry today is how relatively small they were. Another thing that stands out is how packed the ferry could be.

Both ferries had two decks, which were totally open, as well as a small wheelhouse on the upper deck for the captain. Government regulations at the time required one life preserver for each passenger and limited the ferries to a maximum of 175 passengers¹⁵.

The main use of the ferry was to reach the beaches and resorts off the coast of Long Island. One specific group that did so was the soldiers stationed at Camp Mills in what is now Garden City. Many fisherman depended on the ferry as well.¹⁶ In addition, the Great South Bay Ferry Co. carried the mail to Nassau by the Sea and Point Lookout¹⁷.

One writer for the Nassau County Review opposed running ferries on Sundays, arguing that it was immoral to use Sunday for recreation and that having the ferry run on that day would bring in undesirable elements¹⁸.

This 1918 ad from the Nassau County Review describes in colorful terms the recreational value of the places the Great South Bay Ferry Co. served from Freeport. The company also promoted its operation by claiming health benefits for being by the water. The ad forcefully asserts, moreover, how comfortable the ride would be and calls this a "new policy," suggesting people were accustomed to the opposite from the ferry company. Lastly, note that the Freeport Railroad is no longer mentioned as a distinct entity and is only referred to as the "Ferry trolley."

The photo above shows the transfer station to a Point Lookout ferry probably from the Freeport Railroad. The station seems to have been comprised of a shelter for passengers to wait for their connection and a ticket office behind it. A trolley car is visible pulled up alongside apparently ready to leave. Various individuals have stopped to go into stately poses for the camera.

At the turn of the 20th century, a major ferry destination from Freeport was Point Lookout, to which service started in 1898 after Woodcleft Canal was expanded¹⁹. Even years into its run, this seemed to be the busiest ferry route out of Freeport²⁰.

Besides Point Lookout and Long Beach, there were also various resort communities, now-defunct, scattered around the South Shore where people would spend the summers²¹. The lack of bridges at the time, leaving many of the islands off the South Shore only to be reached by boat, must have made them feel distant from the villages on the coast and thus given these areas a very different air than they have today.

One example is Nassau by the Sea, a small community to the east of Point Lookout, also on Long Beach Barrier Island. Most of it burned down in 1918, though it survived in part at least until the end of World War II²², and its remains were ultimately incorporated into Point Lookout²³. Nassau by the Sea seemed to be primitive but idyllic. It lacked modern conveniences but was apparently quaint, slow-paced, and restful²⁴. From the Bellmore area, it took 40 minutes to reach by ferry²⁵, and the travel time from Freeport was probably comparable.

Another resort community was Sea Edge, also located in the vicinity of Point Lookout²⁶. It was formerly known as Point Comfort Beach²⁷. In 1913, it was in the planning stages, and bungalows for its future residents were slated to be built²⁸.

High Hill Beach, a third such community, shown above, was situated in what is now the eastern part of Jones Beach²⁹. Like Nassau by the Sea, it consisted largely of small cottages where people would live for the summer.

As the 1920s approached, only Freeport, Point Lookout, and Long Beach appeared on timetables for Great South Bay Ferry Co.³⁰. Major ferry operations do not seem to have survived beyond the 1920s.

Maritime activities on the South Shore would gain some notoriety later on during Prohibition, when small boats shuttled illegal alcohol in from cargo ships offshore.³¹

The ferry was effectively rendered obsolete in 1929 when, under Robert Moses, Jones Beach State Park and the connection to Long Island via the Wantagh Parkway were completed. This was followed in 1934 by the Meadowbrook Parkway, which reached Jones Barrier Island, along with the Loop Parkway to Long Beach Barrier Island.³²

A contributing factor to the demise of the ferries also seems to have been the disbanding of the trolleys, upon which the ferries relied to bring in passengers³³. The two acted synergistically to form what was in effect a single transit system providing access to locations around the South Shore.

In 2012, waterborne transit between Freeport and Point Lookout became available again when Freeport Water Taxi and Tours started running a summertime water taxi service between the two destinations³⁴. While, unlike the original ferries, it is billed as more of a tourist attraction than mass transit option³⁵, it has been said to alleviate traffic on Woodcleft Ave.³⁶.