On the northern shore of Long Island once known as the Gold Coast, Oyster Bay is a handsome hamlet with historic roots, located 25 miles east of Manhattan. Among the fine estates, the summer home of President Theodore Roosevelt overlooking Oyster Bay Harbor at Sagamore Hill is a National Historic Site. The Town of Oyster Bay reaches south to the Atlantic Ocean, where oceanfront resorts dot the shores of Fire Island's beach colony and are accessible by ferry.
Recall the Heyday in Huntington
- Imagine the Great Gatsby era that epitomized Long Island in the 1920s. High on a hill in neighboring Huntington, philanthropist Otto Hermann Kahn constructed a showplace summer retreat, still the second-largest private home ever built in America. Golf, tennis, culinary and winery hotel packages are offered at this member of Historic Hotels of America, with 32 deluxe rooms and a splendid garden designed by Frederick Law Olmsted of Central Park repute. The grand ballroom and elegant dual staircase make Oheka Castle a bridal destination standout.
Georgian Glamour in Glen Cove
- Glen Cove Mansion Hotel and Conference Center overlooking Long Island Sound is a stately brick Georgian estate located 7 miles west of Oyster Bay. Built in 1910 as the home of Standard Oil executive John Teele Pratt, it was considered one of the finest homes in the nation, attracting the attention of movie directors Alfred Hitchcock, Billy Wilder and Carl Reiner. Golf, tennis, swimming, boating, biking, hiking are among the leisure activities enjoyed by overnight visitors to the historic resort.
Fancy Free on Fire Island
- Step onto the Fire Island ferry from Sayville, 28 miles from Oyster Bay. No cars are allowed, and that's when the laid-back atmosphere begins. The Palms has a collection of cottages in the neighborhood called Pines, where guests can borrow the hotel's bikes or walk to the ocean surf. The century-old Fire Island Hotel and Resort is on Ocean Beach, where flip flops and bathing suits are a way of life. For no-frills accommodations, Clegg's Hotel, Houser's Hotel on the Bay and Blue Waters Hotel have been greeting Fire Island guests for decades.
Hit a Few in Hauppauge
- At the Hyatt Regency Long Island in Hauppauge, the Hamlet Wind Watch Golf & Country Club has an 18-hole, par 71 championship course providing hilltop views of Long Island's north shore. Fine restaurants, tennis courts, indoor and outdoor pools, sand volleyball, basketball, whirlpool and a fitness center round out more of the resort relaxation options at this property 20 miles east of Oyster Bay. For more outdoor recreation on Long Island Sound, Sunken Meadow State Park is 15 miles north, with 27 additional holes of challenging golf and 3 miles of beaches for swimming, hiking, kayaking, canoeing or strolling along the boardwalk.
