Long Island Vacation ideas

A beach in Montauk, image via Roger Braunstein

Long Island is the perfect weekend getaway destination. Within driving distance of America's most populous city, the rural oceanside hamlets of the Island are defined by both relaxation and sophistication. Everyone knows about the beaches of the Hamptons being a summertime haven for the East Coast's elites. But that is only a small part of the story. Each season holds special delights on Long Island. Summer is the undisputed star of the show, but blooming flowers in the springtime, holiday traditions in winter and colorful fall foliage all make Long Island a worthwhile destination. Here are inspirations for enjoying every season on Long Island.


Long Island Vacation

Living on the beach, image via Scott Dexter

With miles of beaches and always-sunny weather, Long Island really comes into its own during the summertime. Luxury villas occupy the best spots on the coastline, while boutique inns and bed-and-breakfasts are also on the vacation menu. Spots like the Atlantic Motel are timeless seaside sleeping spots that are perfect for people seeking a classic summer weekend by the water. Events take place in towns like Huntington and Brookhaven. For example, a concert series is held each summer at the Brookhaven Amphitheater. Some of the resorts on the eastern tip of the island, such as the Surf Lodge, have their own summer concert series.

Long Island Vacation

Bikes at Ruschmeyers, image via Estate Weddings and Evens

Ruschmeyer's is the prefect summertime spot on Long Island. Located in the town of Montauk, this resort is decorated and laid out to resemble a nautical-themed summer camp. Bungalows are arranged around a central garden with fireplaces, outdoor tables, hammocks and barbecue equipment. The furnishings and list of activities goes well beyond what you'd expect to find at a summer camp. Guests can surf, paddle-board, fish or practice yoga. Many rooms have indoor hammocks, so just lounging is also a possibility. Ruschmeyer's Electric Eel bar has a summer concert series, though the good times roll even when there is no act performing in the evening.


LLong Island Vacation

Springtime blossoms, image via Jessica

Springtime is festival time on Long Island. May Day is marked in the town of East Setauket. Sayville, which is home to the Common Ground events space, serves up a spring festival with an Easter egg hunt, pony rides and magic shows. The most attractive thing about vacationing in the Hamptons or near Huntington is that all the flowers and trees are bringing to bloom in the spring. Cherry trees and lilacs hit their peak colors early in the season. May is the perfect time to enjoy summertime weather without the crowds. Things don't get too busy on Long Island until after Memorial Day.


Long Island Vacation

Fall colors, image via little~ny

Springtime is known for its white and pink blossoms, and autumn on Long Island is known for its bright yellow, orange and red leaves. After Labor Day, there are generally a few weeks where you can enjoy summer-like conditions without the crowds. After that, it is time to head to the many orchards in the region for some apple picking. Fall is also a great season for visiting the local vineyards. Wine-making is in full swing, and vintages from previous years are ready for tasting. For beer lovers and people just seeking a fun time, Oktoberfest celebrations are held in the towns of Riverhead, Farmingdale and Bay Shore.


Long Island Vacation

A quaint Long Island restaurant, image via Gail Frederick

The holiday season is a great time to come to Long Island. Holiday lights are turned on each night. The boutiques in the hamlets are perfect for finding that unique holiday gift for a friend or loved one. Skating at outdoor rinks like the Grant Park Rink in Hewlett, is the perfect way to enjoy the winter. You can even combine skating and shopping by swishing around the rink at the Tangier Outlets.


Check out the other Long Island and New York inns and rental estates on our special New York page.

Your Turn

What are your favorite Long Island experiences? Use the comments section to let us know.