1. The Last Vestige of American Sail

The Chesapeake Bay skipjack is the last remaining fleet of working sail-powered fishing vessels in North America.

• A Living Fossil: While other commercial fisheries transitioned entirely to motorized boats over a century ago, Maryland law historically mandated that oyster dredging under power was restricted, keeping commercial sail alive well into the 21st century.

• Vanishing History: At the peak of the oyster industry in the late 19th and early 20th centuries, thousands of skipjacks sailed the bay. Today, only a handful of authentic, historic skipjacks remain afloat, making every surviving hull a priceless, living artifact.

2. A Masterpiece of Local Engineering

Skipjacks are a masterclass in adapting design to a specific environment. Developed in the 1890s as a cheaper, simpler alternative to the massive bugeyes and pungies, they were custom-built for the challenging conditions of the Chesapeake:

• The Design: They feature a shallow-draft, V-bottom hull to navigate treacherous, shifting shoals, and a massive, raked mast pushing a colossal sail area to provide the immense power needed to drag heavy iron oyster scrapes across the bay floor.

• Built by Eye: Most historic skipjacks were built without formal blueprints. Local shipwrights used half-models and built them "by eye" using native timber like loblolly pine and white oak. Preserving this heritage keeps traditional wooden shipbuilding techniques alive.

3. Preserving the Watermen Culture

Skipjack Heritage, Inc. and the other maritime museums,  organizations, Skipjack websites-organizations, etc. is ultimately about the people—the watermen, captains, families and tight-knit island and coastal communities (like Deal Island, Tilghman Island, and Smith Island) who braved brutal winter elements to harvest oysters.

• A Distinct Way of Life: This culture fostered a unique dialect, rich oral traditions, distinct gospel and maritime music, and a deep, multi-generational reliance on the rhythms of nature.

• Family Legacies: For many local residents, Skipjack Heritage Inc. is deeply personal. It represents the literal ancestry of their grandfathers and great-grandfathers who stood on those freezing decks to provide for their families.

4. Ecological and Economic Lessons

The history of the skipjack is inextricably linked to the environmental history of the Chesapeake Bay.

• The Oyster Boom and Bust: The story of the skipjack tracks the rise, over-harvesting and modern restoration efforts of the eastern oyster.

• A Lesson in Sustainability: Studying how these communities balanced economic survival with the health of the bay’s natural resources provides invaluable lessons for modern marine conservation and sustainable fishing practices.

5. Keeping the Tradition Alive

Organizations like Skipjack Heritage, Inc., along with annual events like the Triple Crown of Skipjack Racing in September-- Labor Day, " (#1) Deal Island Skipjack Race, (#2) Skipjack Heritage Days; Sandy Point Skipjack Race and the (#3) Choptank Heritage Festival; Cambridge Skipkack Race" ensure that this history doesn't just sit in a textbook or a dusty display case. By maintaining the vessels, documenting family genealogies and celebrating the community's roots, they allow new generations to step aboard a piece of living history, feel the pull of the canvas and understand the grit it took to build a life on the water.

6. Who visits the Skipjack Heritage Museum?

Descendants & Local Families

A significant portion of visitors includes families rooted in the lower Delmarva and Tangier Sound regions.

• Many visit specifically to trace their roots, explore local historical documentation or view artifacts, photographs and models connected to their ancestors.

• It's common for grandchildren and relatives of original boatbuilders, captains and crews to visit to see the legacy of their family's work preserved firsthand.

Maritime History Enthusiasts & Modelers

The museum attracts researchers, historians and hobbyists fascinated by North America’s last commercial sailing fleet.

• Visitors include those highly interested in the design, restoration, and historical accuracy of classic skipjacks (such as the City of Crisfield).

• Model ship builders and naval history buffs frequently visit to study the extensive collection of detailed boat models and authentic, weathered tools of the trade on display.

Heritage Tourists & "Day-Trippers"

Travelers exploring the Eastern Shore and Somerset County often stop by to immerse themselves in authentic regional culture. These visitors are drawn to:

• The museum's exhibits on the demanding lifestyle of oyster dredging and the working sailboats that enabled oysters to be harvested from the Chesapeake Bay waters, their captains and crew.

• The unique local dialect (dating all way back to the 1600s, the British occupation of the area, etc.), faith and traditions of a close-knit, insulated island community. The majority of Skipjack Heritage’s volunteer and museum staff, along with members of its Board of Directors, are direct descendants of the original settlers of Smith Island, Deal Island and the surrounding connected communities of Somerset County whose family roots trace back to the seventeenth and eighteenth centuries.

• Our deep ancestral ties to the Chesapeake Bay and Tangier Sound region provide the organization with a unique connection to the maritime traditions, watermen culture and local history it works to preserve. Through family stories, inherited knowledge and generations of experience on the water, our descendants continue the legacy of the communities that helped shape the heritage of Maryland’s lower Eastern Shore.

• Like many long-established isolated bay communities, the families of Smith Island, Deal Island, Tangier Sound and neighboring areas are deeply interconnected through generations of marriage and shared ancestry. In many cases, members of the organization are indeed distant cousins whose family lines intertwine through some of the region’s oldest surnames and settlements. That close kinship reflects the strong communal bonds that have long defined the culture and heritage of Somerset County’s island and waterfront communities. We all have ten fingers and ten toes:>)

• Through family stories, inherited knowledge and generations of experience on the water, our descendants continue the legacy of the communities that helped shape the heritage of Maryland’s lower Eastern Shore. Many of our families have remained rooted in the Chesapeake Bay region for generations, preserving traditions tied to the water, boating, fishing, crabbing, oystering and island life.

• Over generations, a relatively small number of founding families became deeply rooted in the region. Many modern Deal Island, Chance (Rock Creek), Dames Quarter, Fairmont, Smith Island, Mt Vernon, Oriole and Tangier Sound, etc. families descend from these early settlers. Common ancestral surnames historically connected to the area include: (Do you share a surname from the below list?)

Abbott	Crockett	Horsey	Roberts	Wallace
Anderson	Dashiell	Jones	Ruark	Webster
Bounds	Disharoon	Lawson	Shores	White
Bozman	Dize	Laird	Simms	Whitelock
Bradshaw	Dryden	Marshall	Simpkins
Brown	Evans	Mister	Smith
Collier	Hitch	Parks	Thomas
Corbin	Horner	Pruitt	Tyler	Additional Surnames

• The early settlers of Smith Island and Somerset County were overwhelmingly of English ancestry, with smaller contributions from Welsh, Scottish, Irish, and later some German families. Most arrived during the seventeenth and eighteenth centuries, many migrating northward from Virginia’s Eastern Shore or directly from England. Enslaved Africans and free Black watermen were also part of Somerset County’s history from the colonial period onward.

Educational Groups & School Field Trips

As part of its core outreach mission, the museum hosts students and youth groups. These educational trips introduce younger generations to marine science, local ecology and the traditional maritime skills that shaped the Chesapeake Bay's history.