Long Island Gold Coast Trifecta

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General Information
Way Points: 

Roslyn LIRR -> Bryant Ave -> Shore Rd -> Matinecock Pt -> Prybil Beach -> Bayville Rd -> Centre Island Rd -> West Shore Rd -> Theodore Roosevelt Park -> Sagamore Hill -> Moore's Hill Rd -> Planting Fields Rd -> Wheatley Rd -> Harbor Hill Rd -> Roslyn LIRR

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Jonathan Stern, Ron Grossberg, Ron Wechsler
Signature Route : 
Region Name(s): 
Long Island
A, B
Vertical Gain: 
Difficulty Rating: 
3 out of 5
Attached Files

If you think Long Island is strip malls and nightmare traffic, this is your chance to discover the gilded age glory of the Gold Coast. And if you think Long Island is flat, put on your big boy pants and consider 3095 feet of climbing in 57 miles, including one humdinger with a 12% average grade.

Fondly known as the Gold Coast Trifecta, this route is a favorite of Jonathan Stern (Yoni) and Ron Grossberg because it’s based on a ride they did nearly 50 years ago, improved by stirring in variations from the classic B SIG route, and seasoned with some of the roads Jonathan has been riding since he was in short pants.

Here’s how it goes:

We head north from Roslyn towards Glen Cove and Morgan’s Island, a  48-acre compound once owned by JP Morgan’s grandson, and the lovely, private Prybil Beach where we may or may not be able to have a pit stop. Next, it's on to Bayville and a beautiful run out the wooded causeway to Centre Island where we will stop to gawk at the gates of the house that “Piano Man” built.

Lunch is at mile 28 or 42.  (Options in Oyster Bay include the cozy and yummy Red Tomato, Oyster Bay Deli and Grill, Lourdes Mexican Grill and so on.) Alternatively, we might have an outdoor picnic at Theodore Roosevelt Park right on the waterfront.

After lunch we climb up to see Sagamore Hill, Teddy Roosevelt's “Summer White House,”

 Then swing around and tackle Mill Hill (12% average grade, 185 feet elevation gain over .28 miles) and Clock Tower Lane (short, but sweet) a longish climb up Wheatley Road. We follow that up with Applegreen cutoff—including a 10 yard portage!—before finishing at the LIRR station in Roslyn.

While this ride has its challenges, it’s beyond scenic—a kaleidoscopic tour of waterfront, mansions, quiet streets, serene beaches, colorful forests—and plenty of good eats.  

JB - 11/6/21


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