A Side Trip to Eastern Long island
Come with us as we explore five of our favorite destinations located between the fish tail of Eastern Long Island.
Montauk, New York 41° 2’ 18” N 71° 57’ 2” W
Before we continue north from Block Island, we’ll take a few days to explore both forks of Eastern Long Island starting with a 17-mile run to Montauk, known for its great sport fishing. We’ll be sure to check the weather, as Block Island Sound, which is exposed to the Atlantic Ocean, can be a very rough body of water. The channel leading into Montauk Harbor is well marked and protected by lighted jetties, but it can be a busy thoroughfare with charter boats, head boats and sport fishing yachts coming and going. We’ll head directly to Star Island Yacht Club and Marina for a slip. Dinner at Gosman’s, a ten minute walk from the marina, never disappoints. The next day we’ll rent bikes and ride to “downtown” Montauk for some re-provisioning at the local IGA store.
Sag Harbor 40°59′48″N 72°17′32″ W
Heading west, we’ll hug the South Fork for a 25-mile run to Sag Harbor, being careful to stay clear of the shoals south of Gardiner’s Island. Since we plan on only staying one night, and the weather forecast is for light and variable wind, we’ll drop our hook outside the breakwater to the east in 10-feet of water. We take our dinghy to the town dock and stop at the visitor’s center in the windmill building to get directions to the Whaling & Historical Museum. Here we learn of Sag Harbor’s rich history as a whaling town. It was even mentioned in Moby-Dick. Walking back to town we’ll check out the inner harbor beyond the fixed 21-foot bridge where a number of marinas are located. We’ll then top off our day with dinner and a spectacular harbor view at B. Smith’s.
Cutchogue 41°00’00’’N 72° 28’ 08’’ W
Since I spent my summers here as a child, we’ve come back to see how much things have changed. The good news, like most of Eastern Long Island, is that much is the same. Cutchogue Harbor, a narrow cut off Little Peconic Bay, features a small marina, now owned by the New Suffolk Shipyard nearby. Clean, neat and cozy, it has a fuel dock, laundry, restrooms and showers. I can still remember swimming off the docks as a kid and am delighted to see that my grandfather’s home across the street looks as good as it did in the 50s. We meet a local couple and ask them if the Cutchogue Diner, two miles from here, still exists, and they offer us a ride there in the morning for breakfast. After a hearty morning meal the next day, we take a stroll along Main Road and return to the marina to continue our exploration of Eastern Long Island.
Shelter Island 41° 4’ 41” N, 72° 21’ 3” W
Located between Long Island’s fish tail, Shelter Island offers four protected anchorages and a few small marinas. Because the only access to the island is by private boat or ferry from Greenport or Sag Harbor, it has remained largely unspoiled. We’ll pick up a mooring in Dering Harbor on the island’s northwest corner (managed by Dering Harbor Marina) and take a walk along Bridge Street, being sure to visit Bliss’ Department Store, a tiny store that has a little bit of everything. A walk up the hill brings us to the Chequit Inn for lunch. Across the Island in Coecles Harbor is the Coecles Harbor Boatyard where the beautiful 38-foot Shelter Island Runabout, conceived by Billy Joel, is built. The sandy beach of West Neck Harbor is worth visiting, but the entrance can be tricky. Keep the red nun “2” to starboard, the beachhead to port and then stay closer to the beach on your port side as you enter the basin.
Greenport 41° 06’ 12” N 72° 21’ 33” W
From Dering Harbor we can see busy Greenport, a mile away on the North Fork. We’ll get a slip at Sterling Harbor Marina, which has fuel, floating docks, well-groomed grounds, a pool, laundry and a full service yard. A 15-minute walk into town brings us to Preston’s, one of our all time favorite chandleries. (The marina also offers a courtesy shuttle into town.) The 1920s carousel in Mitchell Park is still in operation, and the East End Seaport Marine Museum offers exhibitions for all ages. Happily, this old whaling town is thriving after years of being in decline. Shops, galleries and restaurants are busy, and the marinas are nearly full. We can’t resist a visit to good old Claudio’s Restaurant, which has been here for over 140-years. Grabbing a seat at its famous bar, we’ll enjoy a dozen Peconic Bay cherrystone clams on the half shell and a cold brew. Tomorrow it’s off to Cape Cod and more points north.