Page 56 - DreamScapes Magazine | Fall/Winter 2025

LONG ISLAND’S
Coastal Season
BY GRACE TOBY
Long Island unfolds like a coastal dream
winding through harbour towns, vineyard-
covered hills, and over 193 kilometres of
shoreline. When summer crowds fade,
harvest and holiday seasons shine, with local food,
wine and seaside charm keeping the island alive
year-round.
Beacon Trail / Guiding Light
On the region’s South Fork in the hamlet of Mon-
tauk (often called “The End”), head to the top of
historic Montauk Point Lighthouse for panoramic
views of the Atlantic Ocean. On the region’s North
Fork, Horton Point Lighthouse in Southold pro-
vides a bird’s-eye perspective of the Long Island
Sound, home to seals and sea turtles.
Coastal Cuisine & Signature Sips
The culinary journey between lighthouses is as
rich as the scenery, making every meal from sea-
side shack to a fine-dining experience part of the
adventure. In Amagansett, The Lobster Roll has
been a local staple since the 1960s, serving but-
tery lobster sandwiches in a casual setting.
Greenport’s Frisky Oyster delivers sea-to-table
favourites like lobster quesadillas and Crab Louis
that pair with local wines. North Fork Table &
Inn, an island institution led by a MICHELIN-
starred chef, highlights the island’s waterways
and vineyards, with a few elegant rooms for
overnight stays.
Sip on a pint of handcrafted pumpkin cider at
Riverhead Ciderhouse or grab a flight of pumpkin
beer at Tap Room. Boasting over 60 wineries, savour
small-batch wines with sweeping bluff views at
Kontokosta, or raise a glass at crowd-pleaser Wölffer
Estate, or cosy up by the fire pit at Osprey’s
Dominion with award-winning pours.
The Gilded Age on the Gold Coast
Once the summer playground of Gilded Age elites,
the North Shore’s Gold Coast region boasts pre-
served mansions and parks, some open for tours
year-round. With 2025 marking the 100th anniver-
sary of The Great Gatsby, it’s the perfect time to visit
the Gold Coast and experience the opulence that
inspired Fitzgerald’s timeless classic. Tour the mag-
nificent French chateau style mansion Oheka
Castle, or Vanderbilt Museum—featuring a man-
sion, planetarium and marine exhibits, or even
Sands Point Preserve, the 87-hectare park that
houses a historical castle and mansions.
Shuck and Awe-inspiring Events
East Coasters can’t get enough of Suffolk County’s
new Seafood Cuisine Trail and app, the region’s
coastal culinary crawl. And when the holiday
season lights up, so does the island. In Patchogue,
the river glows with illuminated boats, while in
Flanders, the Big Duck stands proud in twinkling
lights—a playful nod to Long Island lore. For Dick-
ensian charm, visit Port Jefferson’s village for
carolling and performances. Join a menorah
lighting hosted by Chabad of The Hamptons with
acrobatics, warm drinks and latkes. Stay cosy in an
oceanfront igloo at Gurney’s or a fireplace and wine
tasting at Harmony Vineyards.
DS
TRAVEL PLANNER
For more travel information about Long Island,
visit discoverlongisland.com
56
DREAMSCAPES FALL/WINTER 2025
DID YOU KNOW?
In Riverhead, the
excitement crescendos at
Long Island Aquarium as
visitors can swim with a
mermaid, dive with
sharks, take a boat tour
and even snorkel—all in
the same place.
PHOTOS: DISCOVER LONG ISLAND