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A Comprehensive Long Island, NY Travel Guide

The North Shore and South Shore of Long Island offer vastly different scenery. The venerable Montauk Point Lighthouse, bustling Nautical Mile, and powdery white sands all line the South Shore’s coastline. On the other hand, the North Shore has magnificent Gold Coast mansions, majestic rocky bluffs, and an unusual charm of such places as Greenport Village.

Once you venture inland, you will discover an agricultural treasure house that nurtures vineyards that rival their European and Californian counterparts along with food producers that cater to most of the restaurants in the region.

Long Island is an area with a fascinating history. Before the Europeans settled there in the 17th Century, 13 Native American tribes with many familiar sounding names occupied it such as Manhasset, Montauk, Merrick, and Rockaway.

The basis of its early economy was agriculture while whaling brought about a period of prominence and wealth in the 18th and 19th centuries. In the years following the Civil War, the well-off Americans discovered the pleasures of sea breezes and salt water bathing. Consequently, the fishing and farming communities of the Hamptons slowly transformed into the currently fashionable summer resorts.

The Roosevelts, Whitneys, and Vanderbilts made the North Shore their playground. After the Second World War, Americans began owning cars leading to the construction of highways, and the middle class moved to Long Island and the farm fields transformed into suburbs.

Currently, Long Island does not stand still, but beyond the sprawl of new homes and commercial districts, and hubbub of traffic, old village centers with museums and historic sites preserve the rich heritage of the island. Golf courses, parks, beaches, and nature preserves provide the space to breathe and reflect in the fresh sea air.

The Top Reasons To Visit Long Island

  • Beaches: The endless white sands meet waves creating perfect conditions for surfing, swimming, and rays to delight for all sun lovers.
  • Seaside Villages: You can enjoy salty air, fresh seafood, and hunt for treasures in picturesque main street shops.
  • Wineries: For wine lovers, the North Fork wineries tours and tastings make this a year-round paradise.
  • Hampton Socializing: You can rub elbows with various celebrities, New York socialites, and international jet setters.
  • Historic Homes: You will find preserved homes of poets, presidents, dignitaries, and robber barons that keep the past alive.

The Top Places To Explore In Long Island

  • Bay Shore: This is around 40 miles east of New York City. Bay Shore is close to Fire Island and Robert Moses State Park and is just a short ferry ride across the Great South Bay.
  • Amagansett: This is a small hamlet in East Hampton. It offers all the charm of the Hamptons but with a more down to earth personality than its counterparts in the West despite regular sightings of such celebrities as Gwyneth Paltrow and Paul McCartney.
  • Cold Spring Harbor: This is one of the most enchanting towns on the North Shore. It has always been valued due to its location on the water.
  • Bridgehampton: This classy, quiet Hamptons community has lovely beaches only being part of its attraction. Other attractions are art galleries, antique shops, as well as restaurants where you can sip wine made from locally grown grapes.
  • East Hampton: This has lovely ancient elm trees, historic windmills, and stately gray-shingled homes. This village has evolved into a sophisticated and curious combination of a thriving summer resort.
  • Long Beach: This is a city on the rise especially after 2012’s Hurricane Sandy ravaged its shores. Since then Long Beach has celebrated the opening of its new 2-mile boardwalk that is fortified to withstand any future storms.
  • Westhampton Beach: It has become one of the quickest growing year round communities because many seasonal visitors have fallen in love with Westhampton. It features chic shops, excellent restaurants, magnificent ocean beaches, and a famous performing arts center.
  • Oyster Bay: It traces its history back to 1615 when a Dutch Explorer who was impressed by the bountiful shellfish named the area Oyster Bay. Its distance from the more urbanized areas of Long Beach helps preserve its small-town feel. The annual Oyster Bay Festival attracts thousands of oyster lovers from all over the world each year.
  • Port Washington: The Main Street of this town is lined with gift shops, antiques, and collectibles shops, as well as old buildings. The area was originally settled in 1674, and early residents made a living farming oysters and raised cattle until the 20th century.
  • Fire Island: It has the Great South Bay to its North and the Atlantic Ocean to its south. It is a 32-mile stretch of Barrier Island that forms part of the Fire Island National Seashore.
  • Cutchogue: If you drive through wine country, you will come across this quaint village with a small collection of old-fashioned shops and white steepled churches.
  • Riverhead: It is the gateway to wine country in Long Island. The Great Peconic Bay and the Peconic River border the town on the south. It was established in 1792 as a farming village.
  • Old Bethpage and Farmingdale: If you are a fan of golf, you probably know about Old Bethpage and Farmingdale. Bethpage State Park features five municipal courses that include the Black Course that hosted the 202 and 2009 U.S. Open. The Black Course is widely regarded by many as one of the best course in the U.S.

Other places that you can visit include Huntington, Montauk, Sayville, Quogue, Old Westbury, Northport, Greenport, Great Neck, Garden City, Port Jefferson, Roslyn, Water Mill, Southampton, Shelter Island, Sag Harbor, and Southold.

What To Do In Long Island

  1. Boardwalk
    1. The boardwalk is simply the sentimental and social heart of Long Beach. Therefore, when Hurricane Sandy destroyed the beloved historic structure in October of 2012, many people felt heartbroken. However, today a new fortified boardwalk stands in its place, which is a symbol of the city’s resilience. Throughout summer, weekend entertainers and vendors attract crowds. Cyclists and walkers hit the planks all year round while a trapeze school and food trucks are a welcome addition to this lovely and lively scene.
  2. Jones Beach State Park
    1. This 6.5-mile long expanse of white sand 11 miles east of Long Beach is one of the most popular and well-known beaches of long Island. It is a 2,500-acre part loaded with activities and facilities to keep both visitors and locals busy both day and night. The 1.5-mile boardwalk has mini golf, deck games, picnic areas, and two surf casting areas that host special summer events. You can reach the park from the Meadowbrook and Wantagh parkways. You should be prepared for crowds during weekends. The park is ideal for windsurfing, walking, swimming, and surfing.
  3. Nikon ate Jones Beach Theater: A15,000-seat amphitheater that features many big name musicians including The Beach Boys, Aerosmith, and the King of Leon. It also hosts other large-scale music festivals. Concert season typically runs from June to August.
  4. Old Bethpage Village Restoration

This living history museum attempts to recreate a pre-Civil War farming community. It sits on 200 pastoral acres with lovely meadows and soft hills.45 buildings moved from other parts of long Island to this spot include nine homes, a tavern, two general stores, a working farm with animals, as well as a church. The guides there who are dressed in period costume love to share their knowledge of local history.

You will find all kinds of cuisine served at the cafes, restaurants, diners, and pubs across Long Island, but seafood is the main regional specialty. It is quite common to find chefs preparing delectable dishes in the evenings using seafood caught that very morning. A trend towards the use of fresh local produce and organic foods has increased the quality of restaurant meals.
If you are a lover of good wine, then you will need to try out the Long Island Homegrown selection. On the North as well as South, most restaurants will vary their schedules depending on the time of year. Therefore, it is always advisable to call in ahead during the off-season.

Long Island features over 350 chain hotels, cottages, oceanfront condos, bed-and-breakfasts all providing over 18,000 rooms in the area meaning that you will never lack lodging options. Many of the resort-town lodgings are usually booked in advance during summer but because of the occasional cancelations, it is possible to travel on a whim sometimes. In most beach locations, the lodging properties have day-use beach passes for guests that give you access to the sandy stretches usually reserved for the residents.

Some properties in the North and South forks as well as on Fire Island have 3-night minimums in the peak season. The real estate agents on the island can also help visitors to find weekly and seasonal rentals while the local chambers of commerce will help point you in the proper direction for safe places to stay. In most of the hotels, parking is usually free unless otherwise noted.


This article has looked at some of the main reasons why you should visit Long Island as well as some of the places to visit and activities that you can engage in. This guide will help you navigate the different things that Long Island has to offer so that you can achieve maximum enjoyment.

Last Updated: April 3, 2015

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