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Bays and harbors reach into vibrant villages and hamlets on Long Island. Surviving mansions from the Gilded Age (think The Great Gatsby) and esteemed yacht clubs lend a nostalgic air to the North Shore. The North Fork is chock-full of farms and wineries; the South Fork is known for affluent seaside destinations and world-class fishing. Everywhere, you’ll find crowd-pleasing events, museums, beaches and parks.
Oyster Bay celebrates its ties to Teddy Roosevelt, who created the first “Summer White House” on Cove Neck in 1902. Theodore Roosevelt Memorial Park serves as the hamlet’s focal point for festivities. The October Oyster Fest is a bonanza of shucking, eating and entertainment. They’re not the wild version that incited the town moniker, but plenty of farmed oysters go around. Shops line East and West Main streets. Classic cars parade down Audrey Avenue on Oyster Bay Cruise Night (summer Tuesdays). To visit Roosevelt’s estate, ride from town or anchor in the bight between Cove Neck and Oyster Bay wharf and walk less than a mile to Sagamore Hill.
The anchorage behind Centre Island in West Harbor is often jam-packed. You can pick up a mooring from Oyster Bay Marine Center, with launch service. There’s a bight west of Plum Point, east of Centre Island, for anchoring, but you can’t go ashore.
A legendary dock-and-dine, three prestigious yacht clubs, and a popular town dock grace the waterfront at Port Washington. The hamlet on Manhasset Bay, a 40-minute train ride from Manhattan, takes pride in its nautical heritage.
Harborfest brings the town dock alive in June. On Saturday mornings from June to October, there’s an organic farmers market. On Friday nights, free concerts play in the bandshell at neighboring Sunset Park. Head for the docks at Louie’s Prime Steak & Seafood. This mainstay for boaters started on a barge and is one of Long Island’s oldest restaurants.
The Port Washington Water Taxi manages 20 town mooring balls, free for a day. A federal anchorage sits outside the mooring field. Dock at Manhasset Bay Marina.
Northport embraces bygone days in the simplest of ways. Free bandstand concerts on summer Thursdays and a friendly Main Street welcomes boaters. Northport Village Park segues onto Main Street. Lics Ice Cream is a must for frozen delights. The John W. Engeman Theater, housed in a 1912 movie house, stages professional shows year-round while the Northport Historical Society and Museum preserves area history. Nearby in Centerport, the Vanderbilt Museum & Planetarium is a fabulous 43-acre museum complex that was the summer home of William K. Vanderbilt.
Entering Northport Bay, Price Bend is a popular anchorage to the east; the sandy pit near Hobart’s Beach is known as Sand City. For access to the village, you can anchor at the top of the harbor outside of the mooring field near Bluff Point or off Asharoken Beach. The west side of Lloyd Harbor is a nice anchorage farther afield. Dock at Brittania Yachting Center’s marina.
Port Jefferson continues to cultivate its shipbuilding past. A sculpture of four rugged seamen carrying a ship’s keel and ribs and a maritime museum in 19th- century Bayles Chandlery honor the village’s history. The historical architecture of East Main Street accents unique shops and eateries. Theater Three holds performances in 19th-century Athena Hall. The Mather House exemplifies a shipbuilders’ home. One of Long Island’s largest Independence Day celebrations takes place here at Harborfront Park, where there’s a summer Sunday farmers’ market and free concerts.
Ferries from Connecticut distinguish the busy port. There’s an anchorage after you enter Port Jefferson Harbor, to the west behind Old Field Beach. Dock at Danford’s Hotel & Marina.
Attention oenophiles: Rural Mattituck is smack in the middle of Long Island’s wine country. From the barrel cellar of 500-acre Macari Vineyards to the family- friendly farm of Harbes Vineyard, wineries cater to all tastes. Restaurants and shops cluster around Love Lane, where First Fridays are held in summer. The June Strawberry Festival, as the crop reaches its peak, celebrates with entertainment, strawberry shortcakes, fireworks and a Strawberry Queen crowning.
Mattituck is unique in that waterways reach in from both sides of the North Fork but do not connect. The inlet from the Sound feels like a secret passageway and culminates at an anchorage and the Mattituck Park District Marina. There is a marina, but not an anchorage, on the James Creek approach from the south. For transient slips, dock at Strong’s Water Club & Marina.
Greenport swells with summer visitors seeking seaside fun. Mariners frequent Claudio’s, a waterfront eatery established in 1854 by ship worker Manuel Claudio (and once a bootlegging stop during Prohibition). Preston’s Chandlery, dating to the 1800s, is a treat for browsing boaters. The East End Seaport Maritime Museum runs cruises to Bug Lighthouse and stages the Greenport Maritime Festival in September. At Mitchell Park, an antique 36-horse carousel makes the rounds. The Kontokosta Winery perches on the bluffs over Long Island Sound.
Anchoring is not permitted in Stirling Basin but there are plenty of dockage options. It’s possible to anchor outside of the jetty at Young’s Point. Dock at Mitchell Park Marina.
Shelter Island’s beauty lies in its protected wetlands and beautiful beaches. At Mashomack Preserve, some 200 bird species have been spotted, including the endangered piping plover and least tern. Visit Dering Harbor, where ferries arrive from Greenport, and pick up two wheels at Piccozzi’s Bike Shop, a 20-minute ride to the preserve. Replenish at the Chequit, a Shelter Island mainstay with dining, entertainment and a coffee shop.
While anchoring is not allowed in Dering Harbor, a large anchorage basin sits inside Coecles Harbor. Nearby, The Ram’s Head Inn is a chic seaside resort with a private beach, rooms, moorings and a restaurant. On West Neck Harbor, where South Fork ferries operate, the anchorage is tucked inside West Neck Point. Seafood and water views prevail at Salt, which has docks on a first-come, first-served basis. Dock at Coecles Harbor Marina & Boatyard.
East Hampton exudes small-town character amidst the big fame of The Hamptons. Three windmills – Hook Mill, Pantigo Mill and Gardiner Mill – add to a historic Main Street that hearkens back to 1648. The Home Sweet Home Museum on the village green is an 18th-century saltbox house filled with Americana. The East Hampton Historical Society oversees seven historic sites, including the East Hampton Town Marine Museum in neighboring Amagansett. Chic brand shops as well as one-off boutiques, restaurants of all ilk, galleries and Guild Hall, a cultural mecca with live performances, round out the town. Catch a ride to Longhouse Reserve, a 16-acre reserve with an expansive sculpture garden.
Three Mile Harbor is three miles from town and where the Clamshell Foundation Fireworks Show bursts over the harbor in mid-July. There is a wide anchorage in the harbor and dockage options such as Three Mile Harbor Marina.
Scriveners love Sag Harbor. A sampling of the village’s literary connections includes repeated references in Moby Dick, longtime resident John Steinbeck and Thomas Harris’ creation of Hannibal Lecter while here. It’s fitting that the town chose Moby Dick for a summer read aloud as the harbor was once packed with whaleboats. The reading takes place at key Sag Harbor sites — the Sag Harbor Whaling Museum, the Old Whalers Church and the Bay Street Theater, an intimate 299-seat venue. The trendy village is an easy walk from the harbor. Wind through narrow streets to admire Greek revival mansions, Victorians, Capes, saltboxes and churches.
Superyachts and celebrities frequent these pristine waters and Long Wharf Pier. Anchoring is allowed outside of the breakwaters to the south and east of the harbor entrance. On the western side of North Haven Peninsula there is an anchorage on Noyack Bay. For dockage, transient slips are available at Sag Harbor Village Marina.
You need only climb the 137 steps of Montauk Point Lighthouse to verify that you are on the edge. Long known as a sportfishing jump-off, Montauk is so much more. The village and Lake Montauk, three miles apart, are both active areas with restaurants and activities. Other wonders are spread out: the lighthouse, Deep Hollow Ranch (the oldest cattle ranch in America) and stretches of ocean beach at places like Hither Hills and Camp Hero state parks.
The manmade cut into Lake Montauk provides deep water. With shallow waters outside the channel, most boaters reserve a dock or mooring. Fort Pond Bay is an anchorage three miles west. You can dock and dine at Duryea’s Montauk on the east side of the bay.
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