I. Lloyd’s Neck at the Jupiter Hammon Site​​

Step into one of the most historically significant locations on Long Island—the home site of Jupiter Hammon, the first African American male poet published in the United States. While visiting the Lloyd House, guests will learn about Hammon’s life as an enslaved poet and intellectual, and how his writings influenced early American literature. This stop offers an intimate look at the rooms and grounds where Hammon lived and worked, highlighting the complex relationship between the Lloyd family and the enslaved community that supported their estate.

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II. Cold Spring Harbor

Travel to the historic waterfront of Cold Spring Harbor, once a bustling whaling port connected to voyages across the South Pacific. Here, visitors will discover the often-overlooked contributions of mariners of color—free, freed, and enslaved men who served as skilled craftsmen, harpooners, and deckhands aboard whaling vessels. Learn how these mariners shaped the region’s maritime economy and how their labor carried Long Island’s whaling industry into global waters.

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III. Sagamore Hill Federal Park

Cove Neck​

Sagamore Hill, famously known as Theodore Roosevelt’s “Summer White House,” provides a powerful window into the social fabric of the late 19th and early 20th centuries. This tour focuses on the African American and Native American individuals who lived, worked, and contributed to the operation of the estate—farmers, laborers, domestic workers, and skilled staff who became part of Roosevelt’s personal and professional circle. Explore the grounds, outbuildings, and scenic pathways while learning about the essential roles people of color played in maintaining one of Long Island’s most iconic historic properties.

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IV. Oyster Bay Cove​

Learn the inspiring story of Frank Carll, an African American entrepreneur whose ingenuity and determination led to the creation of the region’s first garbage hauling business. Long before municipal sanitation services existed, Carll built a thriving enterprise that served the community and cemented his family’s legacy in local history. Guests will travel through the area where Frank Carll worked and lived, gaining insight into the everyday impact of Black business owners during a transformative era.

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[LUNCH] At a local restaurant with prix fixe menu.

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V. Theodore Roosevelt Memorial Park

This waterfront stop celebrates the men and women—many of them African American—who worked in Oyster Bay’s shellfish and maritime industries. Learn how their labor contributed to both the local economy and the wider growth of the shellfish trade across the Northeast. Guests will explore the park’s scenic shoreline while uncovering stories of resilience, community, and economic influence.

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VI. The David Carll Site​

Visit the historic site associated with David Carll, an emancipated man who became one of the earliest African American property owners on Long Island’s North Shore. Discover the formation of his descendant heir community, which has maintained its presence for generations. This stop provides a powerful narrative of land ownership, family heritage, and the long-lasting imprint of African Americans in the region.

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VI. A Gilded Mansion​

Experience the grandeur of Long Island’s Gold Coast with a guided tour inside one of the area’s iconic “Great Gatsby–era” mansions. Learn about the lavish lifestyles of the industrial elite while also exploring the parallel stories of the workers—many of them people of color—who maintained these expansive estates. This immersive stop brings the opulence and complexity of the Gilded Age to life.