The Families Who Built Westport Point

The First Sixty Acres

In 1699, Christopher Gifford purchased the first sixty acres at Westport Point from Daniel Wilcox. The Giffords became one of the founding families of the Point, alongside the Macombers. The name still marks the landscape: Gifford's Corner sits at the intersection of County and Main roads. The Gifford family didn't just settle here. They built the infrastructure that turned a peninsula into a port.

Lafayette Gifford, a later generation, lived in the house that still stands at 2042 Main Road. His father Albert kept a whaling log aboard the bark President out of Westport Harbor in 1849. Albert's photograph still hangs in the front room of the house. When you stay at 2042 Main Road, you're sleeping where the Giffords slept, in a house that's been watching the harbor since before anyone alive can remember.

The Macombers

The Macomber family was the other founding family of the Point. They were farmers who developed settlement cores at several intersections throughout Westport. Their most lasting contribution to agriculture was the Macomber turnip, a variety whiter and sweeter than the yellow turnip, still grown in the area today. They also maintained a primary farm on Main Road at Westport Point. The kind of family that fed a village.

Paul Cuffe

Paul Cuffe was born in Westport. His father, Cuffee Slocum, was a freed slave. His mother, Ruth Moses, was Wampanoag. From a small boatbuilding operation on the Westport River, Cuffe built an increasingly wider network of whaling, trading, and shipping. He created jobs and self-reliance for others of African and Native American ancestry. He petitioned Massachusetts for the right to vote as a taxpayer, arguing that taxation without representation applied to him as much as it applied to anyone. He's one of the most remarkable Americans most people have never heard of. His story didn't start in Boston or Philadelphia. It started here, on this water, in this town.

The Quaker Thread

The Quakers comprised the largest portion of the population of Old Dartmouth, the colonial territory that included what is now Westport, New Bedford, Dartmouth, Fairhaven, and Acushnet. A Centre Meetinghouse was built around 1761 at Gifford's Corner to serve the northern residents. The Friends burial ground north of Westport High School marks where that meeting once gathered. The Quaker values of simplicity, industry, and community shaped the character of Westport long before it was its own town.

The Merchant Families

By the early 1800s, the Point had its own commercial ecosystem. Isaac Palmer operated a store, sail loft, and tavern at the Point in 1829. The Almy family, one of the oldest and most prominent families in Westport, built Almy's Wharf. The Davis family built Cory's Wharf, later sold to Isaac Cory in 1806. Lees Wharf was built around 1800 by the Mayhew family and enlarged in 1830. These weren't corporations. They were families who built what the harbor needed and ran it themselves.

Deeper Roots

The Long family has been at Westport Point for four generations. Their roots run deeper than the Point itself. Tristram Coffin led the purchase of Nantucket Island in 1659. He is a direct ancestor. Through the Perry family, the Longs trace back to the Starbucks, the Folgers (whose line connects to Benjamin Franklin), and the Macys, founding families who built the whaling industry and shaped the culture of the islands. The Peckhams of Rhode Island, whose name still marks the landscape from Little Compton to Westport, are also part of the line.

The property at 2042 Main Road came to the Longs through the Gifford family. A grandfather served thirty years as a Massachusetts State Representative. A letter from Senator John F. Kennedy, dated November 1956, congratulating Representative Long on his first election and signed “Jack,” sits in the family archive. A 1966 note from Senator Edward M. Kennedy, who crossed out the typed greeting and wrote “John” by hand. These are not display pieces. They're family documents that happen to be signed by a future President and the longest-serving Senator in Massachusetts history.