Bob Underwood and the Jessup Family's History in Quogue Is Recounted in 'Tides of Tide' Project

The name Jessup is nearly synonymous with Quogue. Jessup Avenue runs right through the heart of the village and is considered Quogue’s main street. But where did that name come from?

The answer to that is the Jessup family, who have been in Quogue for nearly 14 generations. One of those family members is Bob Underwood, who shared his family history and stories of his time in Quogue as part of the Quogue Library’s “Tides of Time” oral history project.

The origins of the Jessup family can be traced back to John Jessup, who came to Long Island around 1640 as one of the first settlers in what would become the Town of Southampton. As a result of a 1659 treaty, Jessup was awarded a large stretch of land in Quogue that stretched from Quogue Street down to the ocean.

Today, the Jessup family’s ownership in Quogue has been reduced to one house, which has never left the family. This is the house Underwood’s grandfather grew up in and the one that he and his family use as their summer house today.

Though he has never been a full-time resident of the village, Underwood has been coming out to Quogue for all of his life. As a child, he and his brothers would come out for two to four weeks during the summer. They would split their time between their grandparents’ house in Quogue and his great-aunt Nancy Jessup’s property in Noyac on Jessup Neck, also named for the family.

This tradition continued for every summer until he went to college, but it was an experience that he greatly appreciated. From swimming and boating to joining his aunt on her shopping runs to Sag Harbor, Underwood said he looks back fondly on those summers.

Underwood, a venture capitalist who now lives in Chicago, still considers Quogue his “home base,” as the quaint village stands out for him from the hustle and bustle of the Hamptons.

“I think it’s the quiet Hamptons town,” he said. “It’s the family town in the Hamptons. There’s not a big commercial district; the properties are large enough and aren’t crammed together.”

He also noted that Quogue has a different feel from other East End villages and hamlets known for their businesses and the arts.

“It’s a different feel from Southampton, which has much more of a commercial district and is more upscale in some ways,” he said. “Then you have Sag Harbor on the other side, which I call the artsy-craftsy town, which has a great feel, but that’s different, too.”

For Underwood, the low-key feel of Quogue is what makes the village a place that he and his family still come back to frequently during the summer and a place that they love coming to.

“We love Quogue, and we love being out here,” he said. “It’s just a delightful place to be — and we have a lot of friends there these days.”