Start by using reputable trail platforms such as AllTrails, the New York State Parks website, and the Long Island Greenbelt Trail Conference resources, where you can filter trails by difficulty, distance, and elevation gain. Review trail descriptions, recent user reviews, and photos to understand terrain conditions and any seasonal issues. Local outdoor clubs and hiking groups on Long Island, including social media communities, are also valuable for firsthand recommendations and up‑to‑date information on which routes are best for beginners, intermediates, or advanced hikers. When in doubt, begin with shorter, well‑marked loops and gradually progress to longer or more rugged trails as your comfort and fitness improve.

Some of the most popular and scenic hiking areas on Long Island include the Long Island Greenbelt Trail system, which links several parks and preserves with varied terrain and lengths, and Caumsett State Historic Park Preserve on the North Shore, known for coastal views, meadows, and woodlands. Sunken Meadow State Park offers trails with Long Island Sound vistas and access to the boardwalk, while Connetquot River State Park Preserve features flat, forested trails along the river that are ideal for wildlife viewing. On the East End, Montauk Point State Park and Hither Hills State Park provide dramatic ocean views, coastal bluffs, and dune landscapes that appeal to hikers seeking more rugged coastal scenery.

Long Island offers many family‑friendly and beginner‑friendly trails with gentle grades and clear markings. Places like Caleb Smith State Park Preserve in Smithtown, Bayard Cutting Arboretum in Great River, and Avalon Park and Preserve in Stony Brook provide short, well‑maintained loops suitable for children and new hikers. Sunken Meadow State Park and Eisenhower Park also have easy walking paths that can serve as an introduction to hiking. When choosing a family trail, look for routes under three miles with minimal elevation change, access to restrooms or picnic areas, and loop configurations that bring you back to your starting point without complicated navigation.

When planning a hike on Long Island, consider the trail distance, estimated time, and difficulty in relation to your fitness level and experience. Check park hours, parking fees, and any permits or reservations required, especially at popular state parks during peak season. Review recent trail reports for closures, muddy sections, or tick advisories, and always check the weather forecast, as coastal areas can be windy and conditions may change quickly. Wear sturdy footwear, bring sufficient water, sun protection, and insect repellent, and carry a basic map or offline navigation app because cell service can be limited in some preserves. Finally, familiarize yourself with park rules and practice Leave No Trace principles to help protect Long Island’s natural habitats.

Reliable maps and trail information for Long Island hikes are available from several trusted sources. The New York State Office of Parks, Recreation and Historic Preservation website offers official maps and park details for state parks across Long Island. The Long Island Greenbelt Trail Conference publishes detailed maps and guidebooks and often provides updated information on trail conditions and route changes. Online platforms such as AllTrails and Hiking Project supply GPS tracks, elevation profiles, and user reviews that can help you choose and navigate routes. Many local preserves and town parks, including those in Suffolk and Nassau Counties, post downloadable maps on their official websites and provide printed maps at visitor centers or trailheads.