Shelter Island guide: Restaurants, hotels, things to do

As befits a place that’s offered regular ferry service from Long Island proper since 1846, Shelter Island has a particularly intimate relationship with its two cross-Sound conveyances. There’s the North Ferry, which runs from Greenport to Shelter’s North Shore, and the South, which travels from North Haven in Sag Harbor to Shelter’s south shore. The ferries are run by different companies, cost different amounts and travel different distances — 1.1 miles for North, 0.4 miles for South. Still, nothing’s more different about them than the visitors they transport to Shelter and the expectations they lug with them.

Seen in the most reductive of terms, South Ferry types go looking for Hamptonsy things, while Northies gravitate toward the Greenporty and Mattituckish. Both groups tend to find just what they’re looking for, exactly what you’d expect from an island that the Manhanset Indians named Manhansack-aha-quash-awamock, which translates to "island sheltered by islands." But while Shelter shelters both sets of expectations, the best trips to the island are those that embrace both. Or so we’re trying to prove during the following slapdash, possibly ill-advised itinerary, one that deliberately pingpongs back and forth between North and South Forkish sensibilities over the course of one long, very long Shelter Saturday.

8:30 a.m.: Hamptons or Greenport ferry?

The first — and last — decision to make is yours: which ferry to take, one that may well be dictated by its proximity to your domicile. The North Ferry (631-749-0139, northferry.com) leaves from docks at the terminus of Third Street in Greenport (although lines often begin on Wiggins St. and wind their way toward the boats). Round-trip prices are $24 for a vehicle and driver, $6 for additional passengers, for a trip that takes approximately nine minutes. As for the South Ferry (631-749-1200, southferry.com), it leaves from docks at 400 Ferry Rd. in Sag Harbor, and round-trip prices are $20 for vehicles, $3 for passengers (both in-vehicle and walk-on), for a trip that takes approximately five minutes. Both ferries are cash or check only, and neither takes reservations.

9 a.m.: A breakfast for the ages

Wherever you land, there’s something apropos about starting your journey at the distinctly North Forkish Shelter Island Heights Pharmacy (19 Grand Ave., 631-749-0445). Maybe it’s the ancient general-store vibe, or the antediluvian lunch counter, where locals congregate daily to catch up on gossip and scan the Shelter Island Reporter’s exceptionally thorough and entertaining police blotter ("To avoid hitting the deer, she hit a tree, damaging the right front bumper and quarter panel.") But the real draw is the breakfasts and lunches themselves, which the pharmacy has been banging down on its counter for more than 100 years, and there are few things in life more Sheltery than the sight of eggs being fried and spatula-ed onto a paper plate, garnished with bacon and laced with feathery-good hash browns ($12), unless it’s chocolate milkshakes being whirred ($10), or BLT sandwiches stacked skyward ($12) at this island original.

10 a.m.: Peruse high-end shops

But now, you pivot. Shelter Islanders may care far less about designer goods and name brands than their neighbors to the south, but that doesn’t mean they don’t know how to dress. Indeed, some island boutiques are so tony they’re Hamp-tony, like Pure Soul (183 N. Ferry Rd., 516-413-4136), a tiny spot where one could easily lose an hour of beach time perusing Sylma Cabrera’s well-curated collection of high-end resort wear and accessories from the Dominican Republic, her native Puerto Rico and more. The same goes for two antique stores, Marika’s (6 S. Ferry Rd., 401-862-6607, marikasshelterisland.com), whose collection runs the gamut from Tiffany lamps to midcentury Danish scoop arm chairs, and Dworkin & Daughter (57 N. Ferry Rd., 631-749-3499).

11 a.m.: Picnic provisions

There’s no getting out of it — you’re going kayaking today. The rowing is allegedly novice-level, and your destination is . . . well, more on that later. No proper kayaking experience is complete, apparently, without the traditional gathering of enormous amounts of picnic provisions and stuffing them into every part of a boat’s cockpit not otherwise occupied by one’s legs. Two North Forkish places that stand more than ready in this regard are Sylvester Manor Farmstand (21 Manwaring Rd.), which stocks lots of fresh produce, snacks like North Fork potato chips and beautiful bouquets of wildflowers ($25), bringing a romantic touch to every blanket.

Those who like their picnics premade might head to Maria’s Kitchen (55 N. Ferry Rd., 631-749-5450, mariaskitchenshelterisland.com), which, although it specializes in Mexican plates, offers a robust selection of eat-and-run items, including fine chicken salad sandwiches on a roll and chicken cutlet wraps ($19.99, both served with fries).

Noon: Postpone kayaking

We said you had to go kayaking, but not that you had to go this second. Why not stall for time — in style — on the Terrace at Pridwin Hotel and Cottages (81 Shore Rd., 631-749-0476, caperesorts.com), which was spruced up mightily after a 2022 renovation.

It’s so pretty, some will undoubtedly consider staying the night — where prices this time of year start at $526 for a king guest room — while the rest of us will happily settle for fine mai tais with rum and orange Curacao ($17), spectacular hillside views of Crescent Beach and its attendant swimwear — as skimpy and statementy as anything they’re hawking on Newtown Lane.

1 p.m.: OK, now you really do have to go kayaking

If you go on just one novice kayak trip this summer with a photographer who won’t paddle, make it the 2½-mile Coecles Harbor Marine Water Trail, which begins at the exact spot where Kayak Shelter Island (80 Burns Rd., 631-749-1990, kayaksi.com) launches its well-maintained rental boats, both singles ($35 for two hours, $50 for four, $65 all day) and doubles ($55/$75/$100). For one thing, the harbor — part of the Peconic Estuary — is enclosed on three sides, so currents don’t usually pose a problem. For another, the trail itself is exceptionally well marked and offers stellar views of Mashomack Preserve, home to tidal creeks, marshes and an abundance of wildlife, as well as a few bazillion-dollar homes grandfathered in when Mashomack acquired protected status in 1980.

And those not wishing to spend an entire day on the water should at least make it to Taylor’s Island, which is not to be missed. Privately owned till 1998, the tiny land mass still features a large and handsome log cabin-style home built around the turn of the 20th century that somehow survived repeated hurricanes, Sandy among them. Expect Taylor’s Adirondack chairs set under leafy trees, picnic tables and grassy areas to tempt you into extending your stay, that and the dread of a 45-minute kayak trip back to base camp.

4 p.m.: Tour a historical haven

Once back on dry land, hang up the paddle and head back to civilization, or rather civility, and the Shelter Island Heights Historic District. A walking tour of the neighborhood, first laid out in 1872 as a religious summer retreat for Brooklyn Methodists and utterly unchanged since, is a folk architecture lover’s fever dream. Every cottage is cuter than the last, all of them adorable relics from a simpler era, with all the gabled roofs, verandas and dollhouse touches the name implies.

5 p.m.: Visit a toy store time machine

That’s enough gentility — it’s time for the garish and Jack’s Marine (188 N. Ferry Rd., 631-749-0114), which sounds like the kind of place you’d find bait and tackle at behind the counter, "We Sell Ice" signs in the windows, and people using words like "chandlery" with a straight face, which it is. But Jack’s is also Shelter’s only real toy store — because why not? — the enormous kind that you almost never see anymore, featuring both a museum-quality collection of games and activities past (Operation, Candy Land) and an equally prodigious commitment to the latest in kids’ diversions, from whatever famous structure Lego has brickified lately to Slimes of every conceivable scent.

5:30 p.m.: Canoodle with the glamorous set

Dinner at 5:30 is verboten on Shelter Island, at least judging by the hordes that descend on the Sunset Beach Hotel (35 Shore Rd., 631-749-2001, sunsetbeach.fun) at that hour. Blessed with an ideal location across the street from Crescent Beach and well stocked with persimmon-hued deck chairs and flappy yellow awnings reflecting a game attempt at the French Riviera, the hotel (where prices at this time of year typically start at $399 a night for a king room with a terrace) is the spiritual home of the Shelterati, movers and shakers from the Hamptons and beyond.

High-priced cocktails include Gimme Shelter ($26), a chili-salted-rim riot of mezcal, ginger, lemon and pineapple; and St. Tropez limonade, composed of gin, basil, cucumber and lemon ($24).

6:30 p.m.: Play pool at a newly renovated charmer

Continuing your oscillation from highfalutin to low-, you arrive at yet another hotel happily reclaiming its former glory, The Chequit (23 Grand Ave., 631-749-0018, thechequithotel.com), its face-lift completed in 2022. The inn’s 35 rooms, which date to 1872, have all been updated (they start at $375 for a king bed), as has the exterior, spruced up to include everything from hanging egg chairs on the veranda to a lounge with lots of cozy, firepitted areas surrounded by bushy hydrangeas.

But the Chequit has long been a fixture for locals as well. A lower-level tavern sports a pool table, relaxed vibe and colorful cast of regulars possibly airlifted from Whiskey Wind in Greenport, but also a good-quality cocktail program, nice selection of bar snacks and plenty of carousable outdoor tables.

8 p.m.: Enjoy country club digs, no membership required

By this point, you’re no doubt wondering if there’s any spot on Shelter Island that doesn’t lean more North or South Fork by a writer determined to run his conceit into the ground. There is. It’s the 1901 Grill (26 Sunnyside Ave., 631-749-5466, shelterislandcc.org), which reopened after a renovation in April. While the island itself has been a golfing destination since at least the early 1900s, duffers and hackers haven’t always been lucky when it comes to post-round repasts. But whether you’re a golfer or non-, Shelter Island Country Club member or non-, you are expressly invited to end your trip at the top of Goat Hill, adjacent to the course’s ninth and final hole. Connecticut schooners once crossed the Sound carrying wood for wagons to drag up the hill so that a clubhouse with extensive outdoor gazebo seating might be built.

Thus the Grill, where chef Casey Williams flawlessly executes garlicky-buttery linguine with clam sauce ($29), superb brick chicken with puréed potatoes ($30) and more. It is an eatery both no-frills and fancy, upscale and approachable, which is to say equally North and South, right down to the cocktail menu, which features a North Ferry Negroni ($16, gin, campari, sweet vermouth, orange) and South Ferry Spritzer ($16, Limonata Ciroc, prosecco, St. Germain, lemonade).

10 p.m.: Depart north or south

Don’t get in line for the wrong ferry home — it happens more often than you think. Greenporters who’ve fallen in love with chic, classy Shelter Island have been known to mistakenly head south, where the last boat leaves at 1:45 a.m., even as a Sag set charmed by Shelter’s unprepossessing nature drifts north for ferries that leave as late as 11:45 p.m., or — on Fridays and Saturdays through Labor Day — 12:45 a.m.

By Scott Vogel

scott.vogel@newsday.com

Newsday writer and restaurant critic Scott Vogel aims for a refreshing, gimlet-eyed take on the Long Island food scene, often while drinking a refreshing gimlet.