East End Long Island, NY
Long Island
Beaches, farm stands, a real working aquarium, and the most relaxed harbor town in the Northeast
The East End of Long Island — the North Fork and the Hamptons — is vastly underused as a family destination from Fairfield County. The Long Island Aquarium in Riverhead is genuinely excellent. Greenport village is one of the most charming harbor towns in the Northeast. And the North Fork farm stands, vineyards, and beaches in late May and September offer everything the summer crowds come for at 30% of the cost and none of the traffic.
2 hrs from Stamford · 1.5 hrs from White Plains · 2 hrs from NYC (avoid Friday PM)
Why Grandparents Love It
Greenport is entirely flat and walkable — the waterfront, the carousel, the restaurants, and the ferry are within one block of each other
The North Fork is substantially less expensive and less crowded than the South Fork (Hamptons) with equivalent natural beauty
Shelter Island is a 5-minute ferry ride from Greenport with no traffic, quiet beaches, and excellent kayaking
Long Island Aquarium in Riverhead has 100+ tanks including shark feedings and a coral reef propagation lab
Greenport village is a walkable harbor town with a historic carousel, excellent seafood, and ferry access to Shelter Island
The North Fork farm stands (Briermere Farms pies, Rottkamp's Fox Hollow Farm) are open through October
Orient Beach State Park has 357 acres of barrier beach on Gardiner's Bay — some of the calmest swimming on Long Island
Top Free Pick
Greenport Village Waterfront
A working harbor village with a historic carousel on the dock, a free waterfront promenade, and free views of Greenport Harbor. The Claudio's waterfront complex, the ferry to Shelter Island, and the Main Street shops are all within a 5-minute walk. The village carousel (about $1 to $2 a ride) is a genuine 1920s original.
Top Activities (5)
Long Island Aquarium (Riverhead)
All agesOne of the best regional aquariums in the Northeast, with 100+ tanks, a 120,000-gallon shark tank with daily diver presentations, a coral reef propagation lab you can tour, a lorikeet aviary, and otters. The butterfly garden and touch tanks are particularly good for younger grandkids.
Grandparent note: One of the most underrated aquariums in the region. Fully accessible. The shark feeding presentations (usually noon and 3pm) are free with admission and draw a crowd — arrive 15 minutes early for a good spot.
Briermere Farms (Riverhead)
All agesA fourth-generation family farm that has been selling the most legendary pies on Long Island since 1932. Strawberry rhubarb, blueberry crumb, peach raspberry — the pies sell out. The farm market has local produce, jams, and cider. This is not a tourist farm — it is the real thing.
Grandparent note: Arrive before noon on weekends — popular flavors sell out by 1pm. Cash preferred. The farm is not an entertainment destination; it is a farm stand. Buy two pies and eat one that night.
Orient Beach State Park
All agesA 357-acre barrier beach on Gardiner's Bay with calm, protected swimming, a maritime forest preserve, and excellent shelling along the shore. One of the least crowded state park beaches on Long Island in season.
Grandparent note: The bay-side beach has much calmer water than South Fork ocean beaches — ideal for toddlers and anyone not keen on surf. The nature trail through the maritime forest is flat and well-signed.
Shelter Island Ferry & Village
All agesA 5-minute car or pedestrian ferry from Greenport to Shelter Island ($12/car each way). The island has no fast food, no chain stores, two excellent restaurants, pristine Crescent Beach, and kayak rentals at the town dock. A 4-mile drive covers most of the island.
Grandparent note: Leave the car in Greenport and walk on — the ferry is 5 minutes and the island village is walkable from the dock. The Ram's Head Inn on the south side is an outstanding lunch stop.
Splish Splash Water Park (Calverton)
Ages 2–14A full-size water park 20 minutes from Greenport with 16 water slides, a lazy river, wave pool, and a dedicated toddler area. The most active option on the East End, best for grandkids ages 4–14.
Grandparent note: Significant walking — bring a wagon for younger grandkids. Grandparent seating is excellent throughout (shaded benches, chair rentals available). Go on a weekday for shorter lines on the major slides.
Where to Stay
The Menhaden Hotel (Greenport)
Boutique Hotel · $200–400/night
On the Greenport harbor, the best hotel in town, walking distance to everything
White Fences Inn (Jamesport)
B&B · $150–250/night
Quiet, comfortable, excellent breakfast, central North Fork location
VRBO North Fork
Rental · $200–400/night
Best value for families — kitchens essential for North Fork farm-stand cooking, plenty of inventory
Where to Eat
Claudio's Clam Bar (Greenport)
$$$Seafood
On the harbor since 1870 — the clams and lobsters are as good as the setting
Briermere Farms pies
$Bakery/Farm
See activity listing — the best pies in the Northeast, take one home
North Fork Table & Inn (Southold)
$$$Farm-to-Table
The best dinner on the North Fork, all local, book well ahead for dinner service
Grandparent Tips
Friday afternoon traffic on Routes 25 and 27 is brutal June through September — leave before 1pm or after 7pm
The North Fork is dramatically less expensive and less crowded than the Hamptons with equivalent or better beaches
Late May and September are the sweet spots: water warm enough to swim, farms at peak, crowds gone
The North Fork wine trail has 40+ tasting rooms and most are family-friendly with outdoor space for kids to run
Greenport is the best base: you can walk to everything and do the Shelter Island ferry, Orient Beach, and the Aquarium as day trips
Sample Itinerary
Day 1 — Riverhead & Greenport
Morning: Long Island Aquarium (arrive by 11:45am for the noon shark feeding)
Stop: Briermere Farms on the way east
Lunch: Greenport waterfront
Afternoon: Greenport village, carousel, harbor walk
Evening: Dinner at Claudio's
Day 2 — Shelter Island & Orient
Morning: Shelter Island ferry from Greenport, Crescent Beach
Lunch: On Shelter Island
Afternoon: Orient Beach State Park
Evening: Drive home via Route 25 (slower but scenic)
Printable PDF Guide
A 2–5 page travel guide for East End Long Island — formatted for printing or saving to your phone.
📥 Open Printable PDF GuideOpens in new tab — use File → Print → Save as PDF