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Jay Fleming

Annapolis, Maryland
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Jay Fleming

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The Chesapeake Bay Freeze-Up of 2026: Iceboating, Watermen, and Winter on the Eastern Shore

March 4, 2026 Jay Fleming

Aerial photograph of Sandy Point Lighthouse surrounded by drifting ice floes on the frozen Chesapeake Bay.

In January and February 2026, the Chesapeake Bay transformed into a frozen landscape rarely seen. Prolonged Arctic air locked up tributaries, harbors, and shallow stretches of Maryland’s Eastern Shore, creating both hardship and opportunity across the region.

For Chesapeake Bay photographer Jay Fleming, the freeze was a chance to document a unique environmental moment — from shifting ice floes at Sandy Point State Park to icebound workboats on Tilghman Island and high-speed DN-class iceboats racing across hard water at Claiborne Landing.

While the frozen Bay created ideal iceboating conditions that lasted for weeks, it also brought commercial fishing to a standstill in parts of the mid-Chesapeake. Maryland watermen navigated hazardous ice, state icebreakers cleared critical channels, and coastal ecosystems felt the strain of extreme winter weather — including cold-stunned blue crabs washing ashore after days of subfreezing temperatures.

This is a visual story of resilience, tradition, and the raw beauty of winter on the Chesapeake Bay during the freeze-up of 2026.

Jay Fleming wades along the shoreline at Sandy Point State Park to photograph shifting ice along the frozen Chesapeake Bay during the historic January–February 2026 freeze. Photograph by Gavin Middleton

An MSC cargo ship heads south from the Port of Baltimore toward the Chesapeake Bay Bridge, navigating through heavy ice during the rare Bay freeze of 2026.

An aerial view of Kent Point on the southern end of Kent Island as the Chesapeake Bay ice began to break apart after weeks of subfreezing temperatures.

The January and February 2026 freeze created ideal conditions for iceboating on the Chesapeake Bay. Dozens of sailors rigged their iceboats for this rare winter opportunity on Maryland’s Eastern Shore, where “hard water” sailing lasted for several weeks.

Jay Fleming Freeze Up January:February 2026© Jay Fleming -10.jpg
Jay Fleming Freeze Up January:February 2026© Jay Fleming -09.jpg
Jay Fleming Freeze Up January:February 2026© Jay Fleming -08.jpg
Jay Fleming Freeze Up January:February 2026© Jay Fleming -12.jpg

Iceboats line up at sunset at Claiborne Landing, their blades resting on solid Chesapeake Bay ice.

Patrick Whewell of Tilghman Island cuts a narrow path through the ice at Dogwood Harbor aboard his workboat PSYCHO SALLY, a testament to the resilience and determination of Chesapeake Bay watermen.

Jay Fleming Freeze Up January:February 2026© Jay Fleming -18.jpg
Jay Fleming Freeze Up January:February 2026© Jay Fleming -21.jpg

Maryland’s state icebreaker and buoy tender AV SANDUSKY clears the entrance to Dogwood Harbor. The state deployed ice-breaking vessels to keep commercial waterways open during the Chesapeake Bay freeze-up.

Jay Fleming Freeze Up January:February 2026© Jay Fleming -20.jpg
Jay Fleming Freeze Up January:February 2026© Jay Fleming -19.jpg

Captain Mike Simonsen (right) at the helm of Maryland’s icebreaker AV SANDUSKY during operations on the frozen Chesapeake Bay. A crew member aboard AV SANDUSKY (right) keeps watch from the bow as the vessel cuts a channel through thick ice on the Choptank River.

Windy, bitterly cold conditions sweep across the Chesapeake Bay off Taylors Island during the height of the 2026 winter freeze.

Icicles cling to fallen pine trees along the shoreline of Taylors Island in Dorchester County, Maryland highlighting the severe cold gripping the Bay’s coastal ecosystem.

Cold-stunned blue crabs wash ashore along Taylors Island after prolonged freezing temperatures and strong northwest winds. Winter crab mortality is a natural but sobering reminder of how extreme weather impacts the Chesapeake Bay ecosystem.

TIDE~N~TIME →

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