January 17, 2020
Give Me Shelter!
Just a short run from Connecticut, the summer hot spot of Shelter Island, New York, makes an exciting and inviting boating destination filled with fun things to do on land and great places to explore by water.
By Tom Schlichter • Photography by Caryn B. Davis
Rounding Orient Point and heading south, there’s no mistaking the outline of Shelter Island, known to locals as “The Rock.” Nestled between Long Island’s East End forks, it stands proud and high at the mouth of Great Peconic Bay.
To be sure, Shelter Island is no secret getaway, and its population swells from roughly 2,500 in winter to nearly 10,000 at the peak of the summer season. With all those additional bodies, you’d think that an island with slightly more than 12 square miles of land would feel crowded, but that’s not usually the case.
“The weekends do get busy,” admits Mariana Koehler Torrealba, hostess at Salt, a popular restaurant and watering hole inside Menantic Creek, on the southwest side of the island, “but weekdays are always manageable, even in the summer.”
Shelter Island represents an easy daytrip or weekend getaway for Connecticut and even Rhode Island boaters, especially those who choose to stay in Dering Harbor, which lies some 20 nautical miles from Old Saybrook, 37 nautical miles from Branford and 27 nautical miles from Stonington. As you approach from the east, be sure to keep well south and west of Long Beach Point, where some shoaling has occurred.
You can arrange for short-term or overnight dockage or a mooring at Piccozzi’s Dering Harbor Marina or Jack’s Marine, or tie up at the town dock for up to two hours while you explore the local shops and restaurants. Yet another option is the Dering Harbor Inn, which offers daily and overnight dockage (see sidebar). Be aware that boating accommodations can be hard to find on summer weekends, especially if you don’t have a reservation, so be ready with an alternative plan.
Other transient options include Coecles Harbor Marine, on the east side of the island, and Island Marina & Boatyard, inside West Neck Harbor. Both offer a wide array of boating amenities, as well as free shuttle service to other parts of the island.
If you’re simply looking for a place to drop the hook and hang out, head for West Neck Harbor and tuck in behind West Neck Point. Cedar Island Cove, in the southeast corner of Coecles (pronounced “cock-els”) Harbor, is another protected spot to anchor, plus it gives you access to the beach along Mashomack Preserve.
If you’d like to explore the island more extensively, bring a bike or rent one at Piccozzi’s in Dering Harbor. As long as you steer clear of the ferry traffic along Rte. 114, you can cover most of the island in a single day. Be forewarned, however, that there are some serious hills to contend with. If you’re up for a challenge, pedal out to Ram Island and continue to Reel Point, where you’ll find a long, sandy beach that offers a good place to cool off after your arduous ride.
Hiking and nature-watching are other popular activities. Mashomack Preserve, a Nature Conservancy property, encompasses the entire southeast peninsula of the island and comprises 15 miles of trails that wind through woodlands, meadows and salt marshes. It’s a paradise for birdwatchers and a stopping point for migrating monarch butterflies through early November. Just be sure to bring some DEET- or Permethrin-based tick spray to deter unwelcome hitchhikers.
Kayaking and stand-up paddleboarding are ideal ways to poke around the island’s creeks and coves, while also getting some exercise. You can rent both at Shelter Island Kayak, which also conducts tours of the local waters. Venture Out in Dering Harbor also rents and sells paddleboards, and even offers paddleboard yoga classes. West Neck Bay, Coecles Harbor, Crescent Beach, Smith Cove, Dickerson Creek, Congdons Creek and Menantic Creek are all excellent paddling venues, and some of these waterways are bordered by beaches where you can relax, picnic or take a dip. The aforementioned oufitters can give you advice on put-in spots and good places to go ashore.
Of course, the fishing can be tremendous around Shelter Island, so be sure to bring a rod or two. Inshore species range from striped bass and bluefish to porgies and fluke, all of which can be taken during the summer. Things really heat up in the fall, when false albacore, blackfish, sea bass, flounder and bluefish feed with abandon in the local waters.
Where to Stay: Dering Harbor Inn
The spectacular Dering Harbor Inn is perched on a 42-foot bluff overlooking Dering Harbor, the Shelter Island Yacht Club and the town of Greenport, just a five-minute boat ride across the north branch of the Peconic River. Located on the northwest side of the island, the inn offers comfortable, well-appointed waterfront suites, a studio and two-bedroom villas, all with modern amenities, and is within easy walking distance of Dering Harbor’s shops and restaurants.
The inn also maintains a long, private dock with 17 slips for seasonal, daily or overnight rental. Dockage fees vary depending on the length of stay, but are either free or discounted for guests of the inn. Included in the dockage fee are shore power, water, showers, and use of the inn’s heated swimming pool and barbecue grills. The inn also has a small beach, bicycles, a tennis court and a fitness center with a weight room and daily classes. As Sherri Cavasini, the inn’s property manager for the past 25 years, likes to say, “It’s a little piece of heaven on earth.”
Contact the Dering Harbor Inn at (631) 749-0900.
Lots to Eat—and Drink
After all that outdoors activity, you’re sure to be hungry. Luckily, Shelter Island is home to over two-dozen eateries offering everything from basic fried seafood to luxurious resort dining. Two excellent dock-and-dine establishments are the Pridwin at Crescent Beach and the aforementioned Salt, on Menantic Creek. The former offers a creative, upscale menu with super-fresh seafood selections; the latter is wonderfully casual, with an intriguing menu and a Tiki bar constructed from a partially buried ship’s hull. It’s a great place to mix with locals and absorb the island ambience.
If shopping is your thing, you’ll find plenty of that in Dering Harbor. Marie Eiffel is the place for women’s clothing, while Jack’s Marine carries beach toys for the kids. Just outside the harbor, on North Ferry Road, the Table of Content General Store offers an eclectic selection of goods—everything from bike accessories to local jams and jellies to fine cheeses and coffee.
Other Shelter Island diversions include enjoying the sunset at Crescent or Sunset beach, visiting the Manhasset Chapel Museum or the historic Havens House, or hitting the farmers’ market on Saturdays from 10:30 a.m. to 1:30 p.m. The Shelter Island Chamber of Commerce is a good source of information on local events.
Shelter Island may seem like a small package at first glance, but it plays quite big. Myriad possibilities both on and off the water await those willing to slow down and poke around, so arrive early and plan to spend the entire day. Better yet, stay for a couple of nights and really get to know this awesome island destination.
Shelter Island at a Glance
Dockage, Moorings & Service
Piccozzi’s Dering Harbor Marina (631) 749-0045
Transient slips and moorings, along with a fuel dock, grills, pump-out and ready access to Dering Harbor’s shops and restaurants. Also rents bikes on-site.
Jack’s Marine (631) 749-0114
Transient moorings on Dering Harbor, along with a fully stocked marine store.
Coecles Harbor Marina & Boatyard (631) 749-0700
Full-service marina and yard with transient slips and moorings on the east side of the island. Sells diesel and offers a pool, grills, picnic area, laundry, free shuttle, electric car rentals, WiFi and a ship’s store.
Island Marina & Boatyard (631) 749-3333
Protected marina inside West Neck Harbor at the mouth of Menantic Creek. Offers transient slips, a free shuttle, a fuel dock, repairs, a pool, pump-out and an on-site restaurant.
A designated anchorage runs along the eastern shore of Dering Harbor, in 9 to 15 feet of water. Boats must remain at least 500 feet from shore and outside the mooring area, marked by white and orange buoys.
If you’re interested in trailering your boat or bringing a kayak to Shelter Island, launch ramps can be found on Coecles Harbor and West Neck Harbor.
Kayak & SUP Rentals
Shelter Island Kayak (631) 749-1990
Rents kayaks and also conducts tours of the local coves and creeks.
Venture Out (631) 317-7466
Stand-up paddleboard sales and lessons.
Where to Eat
Salt Waterfront Bar & Grill (631) 749-5535
Lively dock-and-dine restaurant adjacent to Island Marina, at the mouth of Menantic Creek.
The Pridwin (631) 749-0476
Fine dining at the Pridwin Hotel on the west side of the island. Has a dock for boating guests.
18 Bay (631) 749-0053
Fine Italian cuisine with emphasis on local ingredients. Located in a Victorian house in the middle of Shelter Island.
Commander Cody’s Seafood (631) 749-1851
Market and restaurant serving fresh seafood, chicken, ribs, chowder and other items served in an unpretentious setting with outdoor tables. BYOB.
Marie Eiffel (631) 749-0707
Women’s clothing store in Dering Harbor featuring exotic printed tunics, sundresses and more.
Sunset Boutique (631) 749-2001
Beach boutique at the Sunset Beach Hotel offering swimwear, sunglasses, jewelry and accessories.
Things to See & Do
Shelter Island Country Club Golf Course (631) 749-0416
The golf course at the Shelter Island Country Club (a.k.a, Goat Hill) is a short walk from Dering Harbor and open to public play.
Mashomack Preserve (631) 749-1001
A variety of hiking trails wind through the woodlands, marshes, fields and shoreline of this 2,100-acre Nature Conservancy property on the southeast side of island. The preserve is home to osprey, piping plovers, least terns and wading birds.
Havens House (631) 749-0025
Visit this beautifully restored homestead (headquarters of the Shelter Island Historical Society) featuring period rooms and an aromatic herb garden.