Photo by Bob Schuppin

The beautiful photos on this web site were all taken along our backroads route by Ride to Montauk cyclists.

We pedal on quiet back roads past mansions, the ocean, farms, windmills, and the most beautiful sections of the Hamptons. Whether you are a beginner or an expert, this is the ride for you!

One of the reasons the Ride to Montauk is so popular is that it is one of THE flattest rides in the entire area.

Start your day in Manhattan, Brooklyn, Babylon, Hampton Bays, Bridgehampton, or Mastic Shirley and pick the distance that’s right for you -- 25 miles, 50 miles, 73 miles, 108 miles, or 155 miles. (The 155-mile route is only for the certifiably insane. We gotta talk...)


ALL routes end in Montauk, so even if your friends are pedaling a different distance, you can all meet up at a rest stop or at the finish for the post-ride party! (How is that possible? Click here for the secret!)

Another swell ride from yer old pal Glen

25 miles • 50 miles • 73 miles

108 Miles • 155 Miles

The Best Rest Stops No Fundraising Required Superb Support

Start in NYC or Long Island -- All Routes End in Montauk

Free Hot Showers at the Finish Line

Free Post-Ride Massage • Free Post-Ride Meal

All Ages Welcome • E-bikes welcome*

Photo by Holly Ladd

Along the way enjoy our beautiful rest stops in Lynbrook, Babylon, Blue Point, Westhampton Water Mill, and Amagansett.  We’ll be there to welcome you with great food, support, and a place to relax.

Get home from Montauk on your own, or sign up for our optional transportation for your bike and you. The first run is at 2:00 p.m. for a limited number of our super-speedy riders.  There are additional trips home at 3:30 p.m., 5:30 p.m., and the last run is at 7:30 p.m. (We'll make sure you don't miss the last trip home).

Beer and Pie -- Together Again at Last

Bike ride food should be nutritious.

Bike ride food should ALSO be fun.

Photo by Cyndie Burkhardt

This is the sort of cool stuff we serve on The Ride to Montauk:

Homemade pie from legendary Briermere Farms.

Of course peanut butter and jelly. (Or Nutella. Or honey. Or almond butter. Or...)

Hummus or tabouli with Pita (for those who want extra protein in the middle of the ride).

Pickles.  Trust me on this one. Great on a long ride.

Fresh fruit. Not just bananas and oranges, but strawberries or grapes too, depending on what looks best in the market that day.

Now where were we....

Glen here, your tour director and humble servant. Still standing.

In 1964, New York Cycle Club member Joe Manzi and one other cyclist pedaled from NYC to Montauk -- THE END.

Yup, from the city, through the Hamptons, to the ocean.

Maybe others did it earlier, but this is the first we know of. I was five years old at the time, so I think I will not try to take credit for any of this.

I'm told that by the fourth annual ride there were a whopping 10 cyclists.

And now, after a five-year hiatus, when I swore I would never do this again, we are BACK.  

The 60th anniversary.

I owe it to those who came before.

Let's celebrate with just a few of our friends.

The size of the ride, which once hit near 2,000 cyclists, is now restricted by the authorities to 750. No more.

The first time I was the tour director there were no official rest stops. Someone wrote in and asked if we could put together a list of every restaurant or store along the route that would let us use their bathroom. Hmm... wouldn't it be easier to just create some official rest stops?

Now there are five different route lengths. Start lines in Babylon, Brooklyn, Hampton Bays, Manhattan, and Mastic-Shirley. A shower truck. Pies. Beer. Racing jerseys. Mechanics. Paramedics. Custom socks. Backup from our friends at Blue Point Brewery, Montauk Brewing Company, God's Love We Deliver, and the Long Island Rail Road.

There's just no substitute for starting from home and winding up in Montauk -- THE END.

Complete info here in excruciating detail (check out the pull-down menus at the top of this page) or drop a line if you get stuck -- always glad to hear from you.

Come with?

-- Glen

The Route

Photo by Cia Bernales

Sports drink and water, of course.

At the end of the ride there’s a big post-pedal meal with food for vegetarians and meat-eaters at no additional charge.  Gourmet?  No.  But we think you’ll be happy. Plus of course free beer from our friends at Blue Point Brewery and Montauk Brewing Company (provided you are 21 years old and can prove it).

Photo by Sue Ferremi.  Still one of my favorite Montauk photos of all time.  “What?  This little snack?”

Free Hot Showers at the Finish

We offer free luggage service from the morning check-in location of your choice.  Bring a small bag with a towel, shampoo, and a change of clothes for our free hot showers at the finish line -- we’ll truck the bag to Montauk for you so you don’t have to pedal with it.  At the finish you’ll find free massage too.

Help On the Way

We have the best S.A.G. (bike rescue) service around anywhere. Need a hand? Too tired to go on? We have staff and vehicles all along the route.

New to long-distance riding?  We offer an optional escorted ride for the 25-, 50-, 73-, and 108-mile routes at no additional charge -- pedal with our trained leaders who will help you have a great ride.

We Support Our Community

It’s important to us to leave money behind where we ride. That’s why we donate to charities all along the route. You do not need to raise money to pedal this ride -- just pay the basic ride fee and you’re ready to ride.

Photo by Victoria Wilson

Ride With the Experts

Many big bike rides have a new tour director every year -- you pay, and they get to practice on you with your money! Whee!

There are a million things I’m not so good at, but THIS is what I do -- I’ve been running big bike rides for 24 years now, and I think that we do it better than anyone else around. I promise to do my very best for you every day.


The 60th Anniversary

Ride to Montauk

September 14, 2024

Ride hard. Have Fun. Don't Act Like a Jerk.



Free beer at the finish line

(Provided you are 21 years old and can prove it)

from our friends at


* A couple quick notes about e-bikes:

1. They are welcome on this ride!

2. Make sure you are fully charged up before you start the ride.  Please check carefully about how far your e-bike can go on one charge. There is nowhere to charge your e-bike mid-ride that we know of.

3. If you need a lift during the ride just call our HQ -- we'll provide you with the phone number on ride day. Be SURE to tell the dispatcher that you have an e-bike (so we send a truck to pick it up, and not a sports car with a bike rack on the back!)

4. We have great pro BICYCLE mechanics at each rest stop. There is only so much they can do to repair an e-bike.

Clear as mud?  You bet!