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.
✓ 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
🌟 Start Here
Greenport Village Waterfront
A working harbor village with a free historic carousel on the dock, 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 ($1/ride) is a genuine 1920s original.
Free to walk · Carousel $1/ride·All ages
Long Island Aquarium (Riverhead)
One 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.
$32/adult · $24 ages 3–12 · Under 3 free⏱ 3 hoursAll ages
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)
A 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.
Pies $20–25 each⏱ 30 minutesAll ages
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
A 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.
$10/car (standard NY State park fee)⏱ 3–4 hoursAll ages
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
A 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.
$12/car each way (pedestrians free)⏱ 2–3 hours on islandAll ages
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)
A 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.
$50/person (buy online for savings) · Under 3 free⏱ Full dayAges 2–14
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.
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
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
1
Friday afternoon traffic on Routes 25 and 27 is brutal June through September — leave before 1pm or after 7pm
2
The North Fork is dramatically less expensive and less crowded than the Hamptons with equivalent or better beaches
3
Late May and September are the sweet spots: water warm enough to swim, farms at peak, crowds gone
4
The North Fork wine trail has 40+ tasting rooms and most are family-friendly with outdoor space for kids to run
5
Greenport is the best base: you can walk to everything and do the Shelter Island ferry, Orient Beach, and the Aquarium as day trips
•Morning: Long Island Aquarium (arrive at 10am for shark feeding)
•Stop: Briermere Farms on the way east
•Lunch: Greenport waterfront
•Afternoon: Greenport village, carousel, harbor walk
•Evening: Dinner at Claudio's
•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)
More guides at GrandkidsGuide
14 more destination guides for grandparents in the Northeast — plus a full local directory for Fairfield County CT, Westchester, Nassau, and Suffolk County NY.
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