Haverstraw Bay is the widest section of the Hudson River, spanning nearly three to three and a half miles across. This expansive, open bay creates significant exposure to wind and weather, with conditions often described as choppy and windy. The fetch across the bay can generate substantial wave action, particularly when southwest winds blow diagonally across the river. Paddlers should be prepared for a workout when heading into the wind. The bay experiences tidal currents, and paddlers report that the river's flow can sometimes differ from predicted tide charts. Points of land, such as Croton Point, can feature bouncy tide rips, especially when combined with wind. During summer afternoons, the bay is busy with commercial and recreational boat traffic, including pleasure craft, tugboats, and barges moving up and down the main Hudson River channel. Paddlers must maintain constant vigilance for this traffic, especially when making the wide open-water crossing, and should practice conservative right-of-way etiquette.

Primary launch sites include Haverstraw Bay County Park on the western shore in Rockland County, which features a double-wide concrete boat ramp, universally-accessible floating docks, and an adaptive kayak launch. Parking is available for approximately 50 vehicles with trailers. The boat launch is not maintained during winter months. On the eastern shore, Croton Point Park in Westchester County offers a launch site with kayak and stand-up paddleboard rentals available seasonally from Memorial Day to Labor Day. This park charges a cash-only parking fee. Paddling from Croton Point provides views across the bay's wide expanse into Half Moon Bay. Due to the bay's width and exposure, trips are best undertaken by experienced paddlers on calm days with minimal wind, as conditions can become challenging quickly. Early mornings or weekdays may offer lighter boat traffic compared to busy summer weekends. The area holds historical significance, notably as a sheltered anchorage for the US naval fleet during World War II blackouts.