Shelter Island Biking:
Discover the East End’s hidden gems with Winding Road Tours as your guide.
Nestled between the North and South Forks of Long Island and surrounded by Gardiner’s
Bay and Peconic Bay, Shelter Island provides a backdrop of unparalleled natural beauty
for our riders. Marvel at breathtaking water views as you pedal through historic Shelter
Island Heights, in Dering Harbor (America’s smallest incorporated village), and
around Ram Island (the peninsula leading to Ram Island is so narrow, you could virtually
reach out and touch the water from your bike). Take time to stop and visit the eclectic
mix of shops and landmarks that line our route. Watch for a family of Ospreys, a reminder
of Shelter Island’s preserved natural habitat. There’s certainly a lot
to see, just keep your eyes on the road when necessary, or pull over to extend your
favorite moments of the trip!
One word of advice: be sure to snack, but don’t fill up on the goodies
we provide in our van. As with all Winding Road Tours, you will be treated to a delicious
gourmet lunch featuring locally grown foods!!
Trip Duration:
The trip starts in Greenport’s newly renovated Village Square at 10am. We will
take the North Ferry to Shelter Island to begin our ride. After a full day of cycling
and touring, we will relax on the ferry ride back to Greenport’s Village Square
at approximately 3pm.
PLEASE NOTE: If you are coming from the South Fork/Hamptons, you
can meet us at a predetermined spot on Shelter Island. Or, if the entire group is coming
from the South Fork/Hamptons, we can arrange a pick-up point on the South Fork and start
the trip on Shelter Island.
Trip Length:
The tour has a short option of about 12 miles and a long option of about 26 miles.
However, because Winding Road Tours has a big, beautiful van, with air conditioning,
snacks, drinks, cool tunes, and 12 bike racks on top, our guests should feel free to
flag down the van at any time. A quick re-fueling break, or simply storing your bike
on a rack will allow you to enjoy the rest of the day, sometimes on four wheels instead
of two (trust us, we like the company). We’ll give you the Winding Roads Tours
secret sign for hailing the van at the beginning of the trip.
Terrain:
Flat to rolling hills. “The Heights” has a couple of optional leg-burners.
The rest of the ride is a manageable mix of flat and rolling hills.
Amenities:
- Gourmet Lunch featuring locally grown foods
- Snacks, Water, Sports Drinks
- Fully Van Supported:
- Professional bike support
- Fully-stocked with drinks and snacks
- Experienced Guides: riding the course, as well as driving the van.
- Bike Rentals can be arrange
Points of Interest:
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