In 2015 the City of Salem obtained a Parkland Acquisitions and Renovations for Communities (PARC) Grant from the state's Division of Conservation Services (DCS) to be used for the design, construction, and construction oversight of a scenic trail in Winter Island Park, a property that consists of 27.1 acres located just minutes northeast of downtown Salem.

The park is located on the south side of a peninsula jutting out from Salem Neck. Native Americans, shipbuilders, Continental Army and Civil War soldiers, plus members of the United States Coast Guard have all occupied the site over the years. Today the park includes centuries old Fort Pickering, which is currently being restored as part of a multi-phase project. The site also includes historic Coast Guard barracks and a hangar (now used for storage), the City Harbormaster office, numerous camp and RV sites, a playground, picnic shelter, lawn areas, and a boat ramp.

In 2011 the City of Salem developed a comprehensive Master Plan for the redevelopment of Winter Island. Ultimately the City's goal is to enhance the park's unique natural resources, preserve its historically significant properties, increase the public's access and enjoyment, and enable it to operate in a financially sustainable manner.

The Winter Island Trail improveements are part of the first phase of improvements and is to be a scenic, multi-use and accessible trail bordering Cat Cove along the west side of the park. The trail project includes stormwater management improvements with native plantings and amenities such as viewing spots with seating and interpretive signage.