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2018 Ride Calendar

Well now...

A couple few years back there were three huge NYC-area charity rides that all took place on the same day. Bad for the event organizers, bad for the cyclists.


I decided to put together an annual list of all the big NY/NJ/CT rides, really as a service to my fellow tour directors. I'm not in charge (and that's good news for EVERYONE!) -- I just organize the calendar. If two big rides are scheduled for the same day, I  pass on the news to the two tour directors. It's up to them to decide what to do next -- change dates; don't change dates... Like I said -- I'm not the boss.


We keep getting requests from the public, asking for a peek at the calendar. so...

That's all a long-winded way of saying that this is NOT a list of every great ride ever. A ride is on this list usually because of one of these reasons:

• It draws so many riders that it would be hard to hold another local event on the same day.

• It draws so many volunteers that it would be hard to hold another local event on the same day.

• It mucks up the roads so much that it would be hard to hold another local event on the same day.

And just to show how unfair this all is, my own rides have lovely photos with them. Sneaky, eh?

Here we go...


April 22

Tour de Staten Island


April 28

The Ride the Ridge Bike Challenge


The High Meadow School, located in Stone Ridge, New York, will hold its 9th Annual Ride The Ridge Bike Challenge to raise funds to benefit the new High Meadow Performing Arts Center. Bicycling Magazine has identified Ride the Ridge to its nationwide readership as one of the best cycling events in the month of June!  The Ride the Ridge Bike Challenge invites riders of all ages to participate in one of four road rides:  50-mile Shawangunk Ridge Ride, 30-mile Countryside Ride, 11-mile Bud Clarke Memorial Ride, 5-mile Family Ride



May 5

The 20th Annual Blessing of the Bikes -- FREE


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OK, it’s not exactly a ride, but it IS one of my favorite NY bike events, and it’s free.

Bring your bicycle INSIDE the Cathedral of St. John the Divine where the reverend will say a few BRIEF words and then sprinkle your bike with holy water.  We take a moment to remember those we’ve lost in the past year, we ring our bicycle bells to celebrate the new riding season ahead, and we are GONE.  Total time: about 25 minutes.  All ages, all religions (or lack thereof) welcome.

May 6

BIKE NEW YORK - The Five Boro Bike Tour


May 12

Ssh!  Top Secret ride coming on this date from Glen.  Stay tuned!


The great undisovered ride. A hidden gem.

Located in Northampton and Amherst, MA, neaer NYC, Boston, Albany, CT, and PA

Come for one, two, or all three days  -- your choice!  (But the optional Saturday Night Dorm Party is so much fun you'll wonder why you wasted all that time pedaling).

Routes for beginners and experts from 25 - 100 miles.

Free post-ride massage • Free hot tubs • Free post-ride meal


Transport available for your bike and you from NYC.

Optional -- Stay on the University of Massachusetts campus.  (Dorm rooms or hotel).  


September 8

NYC Century


T.A.'s premier bike tour is a choose-your-own adventure on New York City streets. With 35, 55, 75 and 100 mile routes, and epic sights on every one, there's the perfect ride for you on the NYC Century Bike Tour.

September 9

Gran Fondo NJ


September 14-16

BRAKING AIDS® Ride (Day 1)


Join us on an extraordinary, full-supported, three-day journey from Boston to New York to support the AIDS services of Housing Works. We're more than a bike ride – we're a civil rights march on two wheels. We'll create a moving community for the fight against AIDS.

September 15



Pedal from the city throgh the Hamptons to MONTAUK -- THE END.

Route distances from 30 - 150 miles (with a new 50-mile route added this year!)  Start lines in Manhattan, Brooklyn, Babylon, Hampton Bays, East Hampton, and Mastic-Shirley.  

Fantastic rest stops, free hot showers at the finish line, free post-ride massage, free post-ride all-you-can-eat meal.  All the details, beautiful photos, and on-line registration at www.ridetomontauk.com

September 15

Escape New York



Come join the New York Cycle Club on Saturday, September 15th for it's 22nd Annual Escape New York bike ride.  Each year, cyclists from all over the Tri-State area and beyond look forward to this ride - known for its beautiful routes, cheerful volunteer hosts and amazing food.  Choose one of four scenic and well marked routes - 25, 50, 65, or 100 miles - all beginning and ending in Manhattan.   Enjoy the hospitality of the New York Cycle Club as we go all out to deliver a food- and fun-filled day of riding to all our friends in the cycling community.  

September 15

Long Island Cycle for Life


Join us for the 5th annual Long Island Cycle For Life charity bike ride. Cycle For Life Long Island is a one-day ride where hundreds of men and women will come together to participate in an event to find a cure for cystic fibrosis.  Participants will have a choice between a 30 mile, 60 mile or 100 mile century ride.  Cycle at your own pace!

September 23

Tour of the Hamptons


September 30

Twin Lights Ride


With ocean views on some routes and treats like pies and chocolate fountains, cyclists will enjoy riding the back roads of Monmouth County, New Jersey, more than ever. The annual Twin Lights Ride begins and ends beneath the famed Twin Lights overlooking Sandy Hook. Twin Lights Ride is produced in partnership with the Highlands Business Partnership. The tour includes route choices from 30 to 100 miles, so there’s something for everyone!

September 30

Tour de Cure Greater New York




October 6

Seagull Century


Again, not a local ride, but it draws a lot of New Yorkers. Tour directors beware!

October 14

Bike the River Valley


Beautiful foliage ride, starting at Bard College.

Routes from 25-100 miles.  

Great rest stops, full support, free post-ride massage, free post-ride meal.

Transport available for your bike and you from NYC.

October 21

Bike MS - NYC


Details on Catskills Fond Weekend coming soon!  Stay tuned!

July 22-28



Glen says, “Believe the hype. The granddaddy of all multi-day rides.  Everyone should do this one at least once.”  

Tour directors -- be aware that a fair number of New Yorkers attend this event.


August 10-12



May 20

Bloomin Metric


May 20

Gran Fondo NY





June 3

Bike-MS Traffic Free/Farmingdale, NY


June 3

Bike Boat Bike

Suffolk Bicycle Riders Association


25- 50-, 68-, 106- and 137-mile routes over flat to gently rolling terrain with some hills on Shelter Island and in Montauk.  Free event T-shirt for al pre-registered riders.  Maps, cue sheets and clearly marked roads.  Rest stops provide food and refreshments.  Roving S.A.G. support if you need assistance.  Raffle, digital photos, free snacks, ice cream, and other goodies after the ride.


June 8

Bike to the Beach NYC


iBike to the Beach is a fully supported century ride from downtown Manhattan to West Hampton Beach to benefit Autism Speaks.

Registration includes rider jersey, food/water, SAG/mechanic/medic for the trip out.

Leaving early Friday the marked route ends on the beach with a finish line party for riders and volunteers. All rider abilities welcome, bike rentals and bag transport are available. 

June 10

NYC Pride Ride



We Cycle to Celebrate - The 4th Annual NYC Pride Ride is presented by OutCycliing as part of national LGBT Pride Month in June, and in celebration of the historic accomplishments of the LGBT community in the New York Metro region. We have 4 distance options from 15 – 100 miles and a fabulous finish line celebration along Manhattan’s Hudson Shore. To register for the ride visit us at www.nycprideride.org To learn more about OutCycling visit us at www.outcycling.org and follow us on Facebook and Twitter.

June 24

Discover Hudston Valley


Whether you ride 15 miles or 100, Discover Hudson Valley has something for the beginner all the way up to a century rider. The jewels of this ride are the Walkway over the Hudson and the Hudson Valley Rail Trail. The entertainment and food concessions offered at the Waryas Park finish festival will be the perfect ending to an already wonderful experience.


July 6-7

Hudson Valley Triathlon


July 20-21

The Catskills Fondo Weekend