South Shore
Stand atop mid-19th-century granite fortresses, cycle wind-swept former airfields, or watch migratory shorebirds at the very tip of Crooke's Point, following a coastline that evolved from a high-stakes British lookout into a resilient landscape of dunes and Bluebelts.
Known to the British as 'The Flagstaff,' the heights of Fort Wadsworth were immediately occupied and fortified by the Crown's forces to control the entryway to New York Harbor. On August 22, 1776, under the protective cannon fire of the frigate HMS Rainbow, a massive fleet of custom-built, flat-bottomed boats launched from these shores, ferrying 15,000 British and Hessian infantrymen across the Narrows to Gravesend Bay. This colossal operation led directly to the Battle of Long Island (Battle of Brooklyn)—the largest single conflict of the entire war. Following the American retreat, the Union Jack was hoisted over the Flagstaff, marking the beginning of a harsh, seven-year military occupation.
At a Glance
- Route
- Fort Wadsworth south along the Franklin D. Roosevelt Boardwalk to Miller Field and Great Kills Park
- Distance
- 7.5 miles
- Duration
- 3.5–4 hours walking; 1 hour by bicycle
- Difficulty
- Easy — flat; FDR Boardwalk and dedicated bike paths; some street navigation near Fort Wadsworth
- Best Season
- Year-round; summer for the full boardwalk and beach experience
- Greenway
- Ride on the roads within Fort Wadsworth. A dedicated bike lane runs parallel to the wooden boardwalk planks, stretching 2.5 miles from Fort Wadsworth to Miller Field.
The southern shore of Staten Island is a landscape defined by its strategic, sweeping geography, tracking a coast that has transitioned over three centuries from a fortified military zone into a vibrant seaside resort, and finally into a resilient landscape of salt marshes and marinas.
Starting at Fort Wadsworth, where the land pinches tightly toward Brooklyn to form the Narrows—the critical chokepoint and defensive throat of New York Harbor-the route traces a southwest trajectory along the open waters of the Lower Bay, following the 2.5-mile expanse of the Franklin D. Roosevelt Boardwalk where late 19th-century carousels and grand hotels have given way to modern, engineered green infrastructure. Continuing south, the trail bridges the aviation history of Miller Field with the sprawling, ecologically wild peninsula of Great Kills Park.
Fort Wadsworth
Perched on high bluffs where the land drops sharply into the Narrows, Fort Wadsworth makes the entire geometry of New York Harbor immediately legible. From here, you can track the deep-water channels leading toward Manhattan and look out across the vast expanse of the Lower Bay. The heart of this historic military complex features Battery Weed and Fort Tompkins, two imposing mid-19th-century granite fortresses that represent the pinnacle of seacoast defense architecture. The overlook near the Visitor Center frames the iconic Manhattan skyline directly through the soaring suspension cables of the Verrazzano-Narrows Bridge, offering one of the finest vistas in New York City. Down at the base of the bridge, a secondary overlook provides an intimate view of Sandy Hook Pilot boats expertly guiding massive global container ships through the harbor's narrow entryway. The former officers' quarters anchor the interior grid of the base, preserving a stately, campus-like atmosphere.
FDR Boardwalk
In the early 20th century, this bustling shoreline was packed with dance pavilions, grand hotels, and carousels. Today, it offers a beautifully revived public common. Extending a massive 835 feet into the Lower Bay, the state-of-the-art concrete Ocean Breeze Fishing Pier is a premier destination for local anglers, particularly during the autumn striped bass migration. South Beach features spectacular bridge views and the whimsical, bronze Fountain of the Dolphins, while the nearby Midland Beach seawall serves as another highly popular local gathering spot for surf fishing. Along Father Capodanno Boulevard, engineered wetland ponds of the Staten Island Bluebelt system act as natural sponges to control neighborhood flooding, filtering urban runoff through native salt grasses before it safely reaches the bay. The adjacent inland bungalows remain as historic remnants of the late 19th-century 'summer colony' era.
Miller Field
As you cross into the neighborhood of New Dorp, the coast transitions into a sprawling, 187-acre park that was once a Vanderbilt family farm before its transformation into a coastal defense airfield. Now managed as a unit of the Gateway National Recreation Area, it serves as open space for sports, picnics, and recreation. At the harbor's edge, the skeletal Miller Field Light tower still stands as an active aid to maritime navigation. The Twin Hangars are haunting, monumental structures from the 1920s Army Air Corps era, when they housed defensive biplanes tasked with patrolling the Atlantic coast for enemy submarines.
Cedar Grove Beach
As the FDR Boardwalk reaches its southern terminus near the historic aviation grounds of Miller Field, the coast transitions into Cedar Grove Beach. Tucked quietly away from the more frequented northern sands, Cedar Grove is a tranquil, uncrowded oceanfront escape. It holds a unique place in local maritime history as the city's last remaining private oceanfront bungalow colony before being integrated into the Gateway National Recreation Area.
Great Kills Park
A 580-acre peninsula shaped by a combination of natural tidal currents and mid-20th-century landfill operations, this is the most ecologically wild segment of the route, protecting the entrance to a deep, sheltered harbor, home to Nichols Marina. At the southernmost tip of the peninsula, Crooke's Point rewards travelers with an extraordinary 360-degree panorama. This vantage point is a vital habitat for migratory shorebirds and offers a profound sense of isolation and natural beauty at the edge of the city. The waters around Crooke's Point were ancient shellfish harvesting grounds for the Raritan band of the Lenape long before the 20th-century landfill reshaped the harbor entrance.
The Seguine Mansion
Standing as a grand sentinel over Princes Bay, the Greek Revival Seguine Mansion marks the natural conclusion of the flat South Shore coastline and the gateway to the island's southwest reaches. Built in 1838 by Joseph H. Seguine, the estate anchors a deep maritime legacy; the Seguine family established the nearby historic oyster beds, operated a local fleet of harvesting sloops, and even founded the Staten Island Railroad to connect these remote shores to the rest of the city. Surrounded by 19th-century equestrian stables and historic outbuildings, the mansion's sweeping lawns slope directly down to the water, offering a majestic final view of the Lower Bay before the trail turns inland toward the hills of Richmond Town and Tottenville.
Getting Here
| Stop / Location | Category | Notes |
|---|---|---|
| Fort Wadsworth | Bus | S51 or S81 bus from St. George Terminal; enter from Bay Street at the Gateway NRA gate |
| FDR Boardwalk/South Beach | Bus | S51 bus along Hylan Blvd to Father Capodanno Blvd; numerous access points to the boardwalk |
| Ocean Breeze Pier | Walk/Bus | Father Capodanno Blvd at Olympia Blvd; short walk from the FDR Boardwalk |
| Miller Field | Walk/Bike | New Dorp Lane at the waterfront; accessible via the FDR Boardwalk bike path |
| Great Kills Park | Bus/Rail | S78/S79-SBS bus or SIR to Great Kills station, then short walk to the park entrance |
| Crooke's Point | Walk/Bike | Follow the paved multi-use path from the Great Kills Park entrance to the peninsula tip; approx. 1.5 miles each way |
| Nichols Marina / Kayak Launch | Walk/Bike | Inside Great Kills Park; follow signs from the main parking area |
| Return to St. George | Rail | SI Railway from Great Kills station — approx. 30 minutes to St. George |
Community Logs
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