2-Day Long Island-Connecticut

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General Information
Way Points: 

Smithtown LIRR Station>Edgewood Ave.>Nichols Rd.>Sheep Pasture Rd.>mostly side roads thru North Fork>Greenport>Orient Point>Ferry to New London

New London>Niantic>Old Lyme>Chester>Killingworth>North Branford>New Haven

Susan Rodetis
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Multi-Day Tours
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Difficulty Rating: 
3 out of 5
Attached Files


Smithtown to Greenport/Orient Point 

Scenic day ride along Long Island’s north shore and north fork. Options are to return via LIRR from Greenport, or to make this into a 2-day tour via crossing the LI Sound to New London, on Cross Sound ferry from Orient Point ($14-20/pp depending on jet ferry or regular ferry, +$4/bike). See Day 2 cue & notes.

In New London a New England shore summer dinner doesn’t get better than Captain Scott’s Lobster Dock on Shaw Cove, 81 Hamilton St, for shore dinner. Call for seasonal hours, and if large group, might possibly arrange group pricing (860) 439-1741.  Multiple dining alternatives in downtown New London (also closer to ferry landing). One good suggestion is the patio at Exchange Bar & Grill 74 Bank St. 860.447.1157

For lodging, we booked a group rate at the Connecticut College Dorms during the school’s summer vacation (linens/towels included; can also book prix fix cafeteria dinner or breakfast). Alternatives include Holiday Inn & Red Roof Inn chains in New London, or cross the Thames River bridge into Groton for less pricey selections.


New London to New Haven

Day 2 of 2-day tour (see Day 1 Smithtown to Greenport/Orient Point). This very varied route follows the shore, then cuts inland to quiet back roads, a rope-drawn ferry crossing the Connecticut River, and a bit denser pack as New Haven approaches. Optional short side trip before ferry to Gillette Castle. The route sheet also provides several options as we approach New Haven. Return to NYC via Metronorth New Haven Rail station. Food/restrooms/tix inside RR station. Leave time to navigate underground passageways to correct platform. [NOTE:  Shore Line East rail now runs weekends New London/New Haven with several stops along the shore towns. It will take a finite number of bikes, thus an alternative/bail to return to New Haven either directly from New London, or by dropping south toward the LI Sound/shore towns from our cue sheet route.]

cycling trips