Rest and relaxation is a year-round activity on Shelter Island, but as the weather warms, options expand for enjoying all the Island has to offer.
While we await ideal beach temperatures, here are some ideas to inspire your R&R plans, including hiking, biking, golfing, paddling or just staying put.
Public golf at ‘Goat Hill’
The Shelter Island Country Club offers challenging, but family-friendly golf on a public 9-hole course that happens to be celebrating its 120th anniversary season. Affectionately known as Goat Hill, the course is improved with a new in-ground irrigation system for the greens and tees. The pro shop has new Goat Hill logo golf apparel for men, women and kids from Greg Norman. You can golf and/or shop, and then have cocktails or a meal at The Flying Goat Restaurant. Enjoy views of Dering Harbor and the Peconic Bays from the historic and breezy clubhouse porch at one of the highest points on the Island.
26 Sunnyside Ave. | 631-749-5404 | shelterislandcc.org
Rent a bike at Piccozzi’s
Piccozzi’s Bike Shop provides rentals, sales, and repairs. If you’re visiting the Island, leave your car in Greenport and walk to the shop from the ferry terminal. An authorized Specialized dealer, the shop offers tune-ups and repairs, along with a full range of products, from helmets to locks, tires, tubes, and other bicycle accessories. Rent bikes to tour the Island by the hour, half- or full-day. Generally open from 8:30 AM to 4 PM, when staff is available. “If the door to the bike shop is not open, just check in your bike at the pump,” says Richie Surozenski.
177 North Ferry Road | 631-749-0045 | jwpiccozzi.com
Have a staycation
We’ve all imagined being a guest in our own home town, so let’s do it!
Dering Harbor Inn, a tranquil harbor side retreat on the bluff overlooking Dering Harbor. Get lost on the lush seven acres of grounds. Enjoy a dip in the pool, or simply take in the views from the well-appointed villas or suites. 13 Winthrop Road | 631-749-0900 | deringharborinn.net
Shelter Island House offers luxurious modern beach flair in the historic inn with private rooms, lofty beds and a welcoming staff. Loaded with amenities including the on-site Osprey Bar and Grill, pool, lounge areas and lush gardens. 11 Stearns Point Road | 631-749-1633 | shelterislandhouse.com
Backyard Movie Night
Enhance your family’s summer weekend with a Backyard Movie Night, including an inflatable screen and popcorn machine from Shelter Island Party Rental. Perfect for outdoor gatherings and social distancing. Call owner Rob Strauss to plan your event.
516-659-7509 | shelterislandpartyrental.com
Support your mind and body
In his Island Meditation sessions, Charles Huschle imparts the basics of mindfulness meditation. Weekly sessions include instruction and guided meditation, question and answer time, and a short reading with discussion. All levels welcome, no experience is necessary. Find details and sign up.
Shelter Island Yoga and Fitness offers group classes in ZUMBA, spinning, yoga, TRX, mat pilates, water aerobics, bootcamp and tennis, and can arrange private gym rental time. 13 Winthrop Road | 631-749-0160 | shelterislandyoga.com
Shelter Island Pilates and Barre features live virtual classes, in-person private or group classes, and a whole library of on-demand opportunities. For a summer treat, try the outdoor signature mat class on the point at the Dering Harbor Inn, Saturday and Sunday at 9 AM. 8 Grand Avenue |631-749-5042 | shelterislandpilates.com
Tennis anyone?
Tune up your game with Moussa Drame Tennis Academy, offering lessons, hitting sessions and family clinics. Visit the courts at the Dering Harbor Inn or have the pros come to you. Call or text Moussa. 631-749-0160 | moussadrametennis.com
Take a hike, literally
Mashomack Preserve, with 2,350 acres of fields, marshes, forests and creeks, offers trails ranging from 1.5 miles to 11 miles. Considered one of the richest habitats in the northeast, the preserve abounds with flora and fauna. Open from dawn to dusk daily (the Visitor Center and restrooms are closed due to pandemic concerns). 79 South Ferry Road | 631-749-1001 | Visit nature.org to plan your visit and download a trail map
Learn about Shelter Island’s history at Sylvester Manor Educational Farm. Marked trails offer varying views of the waterfront, farm and forest on the 235-acre colonial estate that once encompassed all of Shelter Island and was home to its first European settlers. Grounds open from dawn to dusk daily. 80 North Ferry Road | 631-749-0626 | sylvestermanor.org
Public trails link disparate parts of the Island thanks to the Town of Shelter Island, the Shelter Island Group for Trail Preservation and the Town’s Green Options Committee. Download a map and visit a wide variety of preserved public lands.
Explore by water
If you enjoy paddling , explore the Coecles Harbor Marine Water Trail. This route offers paddlers in Coecles Harbor a guided tour of undeveloped shorelines and the Town-owned Taylor’s Island, with its historic Smith-Taylor cabin. Download the water trail map.
If you plan on storing your kayak, small boat or paddleboard at one of the Town landings or beaches, please contact the Town Clerk’s office townclerk@shelterislandtown.us or 631-749-1166 about a boat storage permit.
All boats must display a valid Town permit, and new annual fees were put in place over the winter. Learn more on the Town website, shelterislandtown.us.
