Long Island Day Trips: North Fork, Gold Coast and Montauk

Where the Long Island Expressway ends at Riverhead, the island splits. The northern prong — the North Fork — is a long, flat run of vineyards, orchards and farm stands along Route 25 and Sound Avenue, through Jamesport, Mattituck, Cutchogue, Peconic and Southold to the harbor town of Greenport.

It’s the obvious place for a chauffeur: tasting rooms are spread several miles apart, and nobody in your party has to be the designated driver. Many wineries ask for reservations, especially for groups and on weekends — those are your own plans, and we build the day’s timing around them.

Along the North Shore of Nassau and western Suffolk, early twentieth-century industrialists built the great estates that inspired The Great Gatsby. Several can still be visited.

• Oheka Castle, Huntington — one of the largest private homes ever built in the United States, now a hotel and event venue. Guided tours are offered by advance booking.
• Old Westbury Gardens — a Charles II-style mansion surrounded by formal gardens. The full season runs from spring through October, with a reduced weekend schedule into late autumn; advance tickets are generally required.
• Planting Fields in Oyster Bay and Sands Point Preserve — further estates and grounds for a longer day.

Because these estates are under an hour from Midtown in light traffic, they suit a half day, a wedding at a North Shore venue, or a garden visit paired with lunch in a harbor village such as Cold Spring Harbor or Oyster Bay.

If the ocean and the village scene are the point, see our Hamptons page. If it’s food, wine and an easy pace, the North Fork usually wins as a day trip.

Long Island’s Northern and Southern State Parkways restrict commercial vehicles, so larger vehicles such as the Sprinter travel the Long Island Expressway and local routes instead. Your chauffeur plans this in advance. For airport arrivals, a JFK or LaGuardia pickup can head east directly.