It’s a good thing there’s no bridge to Shelter Island, because when you go someplace this special, you should arrive effervesced, with the wind in your hair and mist tickling your skin. Pebbly beaches perfect for walking or swimming, 2,000-plus acres of forest and field for hiking and plenty of places to view beautiful bodies of water are just the beginning.
At 18 Bay on North Ferry Road, chefs Elizabeth Ronzetti and Adam Kopels have raised the bar on Shelter Island fine dining with an Italian-inspired, four-course chef’s menu that showcases the pristine ingredients of the North Fork’s top producers. 18 Bay serves dinner and, depending on the catch, a crudo bar that opens at 3:00pm for sliced raw fish, small bites and cocktails on the red and white porch.
Down the road, Maria’s Kitchen is a Mexican café with a bright dining room/market, a three-stool lunch bar and guacamole that has earned its creator, Maria Schultheis, cult status. The chalkboard menu lists Maria’s signature enchiladas, empanadas, salads and smoothies. If it all seems homey, it is. Except that no home delivers the consistent excellence, year after year, that Maria’s does.
On the Dering Harbor coast sits Marie Eiffel Market, the go-to spot for take-out, or for enjoying breakfast and lunch with a waterfront view. The baguettes actually shatter (a good thing), and the soups are great, especially the carrot ginger.
If it’s libations you crave, Shelter Island Craft Brewery, open Friday-Sunday, always has several of their creations available for tasting.
The Ram’s Head Inn is the only commercial business on Big and Little Ram Islands (aka, The Rams) and has been welcoming guests since 1929. The dining rooms, patio and the sloping back lawn of this well-maintained house have magnificent views. And the rooms offer the cozy charm of a New England B&B.
The recently renovated Chequit has been around since the 1870s when it was the center of a cluster of cottages and tennis courts known collectively as Shelter Island Heights Methodist Camp (a 19th century form of glamping). Its location in the heart of the Heights is ideal for walking the hilly streets lined with Victorian homes and small town shops.
Hot tip: Union Chapel is lit each evening at sundown for strollers to see the stained-glass windows that make it glow like a jewel.
The 280-year-old house at Sylvester Manor Educational Farm is fascinating to tour, with many acres of grounds and gardens to explore. The adjourning farm offers workshops and programs for people of all ages, as well as concerts, dances and other events that highlight local food and culture. Mashomack Preserve has numerous guided walks and a range of trails for hikers ranging from toddlers to mountaineer enthusiasts and all levels in between.
In 1994 the Peconic Hotel, a beachfront cluster of bungalows and ramshackle buildings, was transformed into the Perlman Music Program, a camp for musically gifted children. The program holds a series of free concerts on Friday and Saturday nights throughout the summer.