What are the best scenic drives on Long Island?

The best scenic drives on Long Island include Ocean Parkway, the North Fork Trail, Montauk Highway through the Hamptons, Route 25A along the North Shore, Dune Road in the Westhampton area, and a drive across Shelter Island. These routes showcase the island’s beaches, bays, vineyards, farms, historic villages, harbors, woodlands, and waterfront communities while giving travelers numerous opportunities to stop and explore along the way.

In Short

For ocean and barrier-island scenery, drive Ocean Parkway between Jones Beach State Park and Captree State Park. For vineyards, farms, and country roads, explore the North Fork. Montauk Highway provides the classic drive through the Hamptons toward Montauk, while Route 25A connects historic villages and harbor communities along the North Shore. Dune Road and Shelter Island offer shorter drives centered on coastal scenery and quiet local roads.

What Are the Best Scenic Drives on Long Island?

The best scenic drive depends on which side of Long Island you want to experience. Ocean Parkway is the strongest choice for beaches and open coastal scenery. The North Fork offers vineyards, farmland, and waterfront villages. Montauk Highway passes through many of the best-known communities on the South Fork, while Route 25A reveals historic harbor towns and sections of the Gold Coast. Dune Road and Shelter Island provide more compact trips that can be completed as part of a leisurely afternoon.

Ocean Parkway: Jones Beach to Captree

Ocean Parkway is one of the most recognizable scenic drives on Long Island. The roadway crosses the barrier island from Jones Beach State Park east toward Captree State Park, passing beaches, dunes, marshland, bayside communities, and access points for several popular recreational areas.

The drive begins amid the landmark architecture and broad oceanfront setting of Jones Beach. Continuing east, travelers pass Tobay Beach, Gilgo Beach, and additional stretches of the barrier island before reaching the Robert Moses Causeway and Captree State Park. Captree sits beside the Great South Bay and is known for its fishing fleet, picnic areas, and views toward Fire Island National Seashore.

Ocean Parkway is especially enjoyable during clear mornings and late afternoons, when the open sky and surrounding waterways become a larger part of the experience. Drivers should remember that most beach and park views are reached by entering designated recreation areas rather than stopping along the parkway itself.

North Fork Trail: Southold to Orient Point

The North Fork provides Long Island’s best-known country drive. A particularly scenic portion follows the North Fork Trail from Southold toward Orient Point, passing farms, vineyards, wetlands, historic communities, and occasional views of the surrounding bays and Long Island Sound.

Travelers can continue through Greenport, where the landscape shifts from farmland to a historic maritime village filled with restaurants, shops, docks, and harbor views. Farther east, the drive becomes quieter as it approaches Orient and Orient Point near the eastern end of the North Fork.

The North Fork is especially attractive from late spring through autumn. Farm stands and vineyards are active during the warmer months, while fields, tree-lined roads, and changing leaves make the route popular during the fall. Because many businesses are located directly along or near the main roads, this drive works best when treated as a full-day outing with several planned stops.

Montauk Highway Through the Hamptons

Montauk Highway provides the classic drive across the South Fork, passing through or near communities including Southampton, Water Mill, Bridgehampton, East Hampton, and Amagansett before continuing toward Montauk.

The route combines village centers, wooded stretches, historic buildings, farm fields, and access roads leading toward Atlantic Ocean beaches. Rather than providing continuous ocean views, Montauk Highway serves as the main thread connecting the landscapes and communities that define the Hamptons.

Past Amagansett, the surroundings become increasingly open and coastal as the road approaches Montauk. Drivers can continue to Montauk Point State Park, where the eastern tip of Long Island overlooks the Atlantic Ocean and Block Island Sound. Summer traffic can be heavy, so the route is often more enjoyable early in the morning, on weekdays, or outside the busiest summer weekends.

Route 25A Along the North Shore

Route 25A is the principal scenic route through much of Long Island’s North Shore. It passes through a changing landscape of wooded residential areas, historic village centers, former Gold Coast communities, and roads leading toward harbors on Long Island Sound.

A rewarding section can be explored through communities such as Oyster Bay, Cold Spring Harbor, Huntington, Centerport, Northport, Stony Brook, and Port Jefferson. Route names and road character change along the way, but the drive remains one of the best ways to explore the island’s historic northern communities.

The most scenic experience usually comes from leaving Route 25A periodically to visit village centers, parks, waterfront streets, and harbor areas. Autumn is an especially attractive time to make the trip because of the North Shore’s mature trees, wooded roads, and historic architecture.

Dune Road in Westhampton Beach

Dune Road is one of Long Island’s most distinctive coastal drives. Located along the barrier island south of Westhampton Beach, the narrow road passes beach homes, dunes, marshes, bayfront areas, and roads leading to ocean beaches.

Unlike Ocean Parkway, Dune Road is a local two-lane road where the surrounding coastal environment feels much closer. Portions of the route place drivers between the Atlantic Ocean and the bays behind the barrier island, although homes and dunes often limit direct water views.

The drive can be combined with stops in Westhampton Beach or at public parks and beaches where access is permitted. Parking regulations, seasonal restrictions, and residency requirements may apply at individual beaches, so visitors should check posted signs before leaving their vehicles.

Shelter Island Scenic Drive

Shelter Island offers a quieter driving experience between the North Fork and South Fork. Reached by ferry from Greenport or North Haven, the island contains wooded roads, creeks, harbors, historic neighborhoods, beaches, and nature preserves within a relatively compact area.

Route 114 crosses the island and provides access to several local roads that can be combined into an informal loop. One of the island’s major natural landmarks is Mashomack Preserve, a large protected landscape containing forests, fields, wetlands, tidal creeks, and hiking trails.

A Shelter Island drive is less about following one famous highway and more about slowly exploring a peaceful island community. Travelers should allow time for ferry crossings and may want to combine the drive with a walk, waterfront stop, or visit to one of the island’s small business districts.

When Is the Best Time for a Scenic Drive?

Long Island’s scenic routes offer different experiences throughout the year. Spring brings flowering trees, active farms, and lighter traffic than the summer season. Summer is ideal for beach stops, waterfront dining, and long daylight hours, but roads leading to popular coastal destinations can become congested.

Autumn is often the best season for the North Fork and North Shore because of fall foliage, harvest activity, and cooler weather. Winter offers quieter roads and unobstructed coastal views, although some seasonal attractions, restaurants, and facilities may be closed.

Planning Your Drive

Scenic drives on Long Island are best planned around several stops rather than treated as uninterrupted trips. Many of the most memorable views are found inside state parks, village waterfronts, beaches, preserves, and historic districts located just beyond the main road.

Before leaving, check traffic conditions, ferry schedules, park hours, parking rules, and seasonal access requirements. Summer weekends can produce substantial delays on routes through the Hamptons, the North Fork, and major beach corridors, while ferry lines may add additional travel time to a Shelter Island trip.

Quick Facts

Scenic Drive	Primary Highlights
Ocean Parkway	Jones Beach, barrier-island scenery, dunes, bays, Captree State Park, and access toward Fire Island
North Fork Trail	Vineyards, farms, wetlands, Greenport, Orient, and coastal communities
Montauk Highway	Hamptons villages, historic architecture, farm fields, beaches, and Montauk
Route 25A	Gold Coast communities, wooded roads, historic villages, harbors, and North Shore scenery
Dune Road	Barrier-island homes, dunes, marshes, bays, and Atlantic Ocean beach access
Shelter Island	Ferry travel, wooded roads, quiet harbors, Mashomack Preserve, and waterfront communities
Best Overall Coastal Drive	Ocean Parkway from Jones Beach toward Captree State Park
Best Country Drive	The North Fork from Southold through Greenport toward Orient Point
Best Historic Drive	Route 25A through the North Shore’s villages and former Gold Coast communities

From Ocean Parkway’s barrier-island landscapes and the North Fork’s vineyard-lined roads to the historic villages of Route 25A and the quiet lanes of Shelter Island, Long Island offers scenic drives suited to nearly every kind of day trip. Choosing a route, allowing time for several stops, and traveling outside peak traffic periods can turn the drive itself into one of the most memorable parts of exploring the island.