Photo by Bob Schuppin

Take a look at the beautiful photos on this web site, all taken along our backroads route. The ride has wonderful scenery, fantastic rest stops, free bike repair, and full S.A.G. (bike rescue) support.

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

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!

Start your day in Manhattan, Babylon, or Mastic Shirley and pick the distance that’s right for you -- 25 miles, 50 miles, 73 miles, 108 miles, or 150 miles.


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!)

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 12:00 p.m. for our super-speedy riders!  The last run is at 8:00 p.m., and we’ll make sure you don’t miss the last trip home.

The Best Bike Ride Food Ever

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, along with fresh whipped cream that is made on the spot.

Our Peanut Butter & Jelly Buffet at each rest stop.

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.

Graham warned bands that if they started playing huge stadiums it would require a bigger sound system, a larger stage, more lighting, and extra trucks to haul all that gear from show to show.

All that stuff costs a lot of money, so then you have to either raise prices or attract more people. And when you add more people, you need an even bigger sound system and...

My goal for Montauk was always to make it bigger, bigger, bigger, but then Ouroboros started to eat its own tail...

Thanks to everyone who made The Ride to Montauk a blast, especialy the good folks at Blue Point Brewery, Larbar, and Nuun -- they always stood by us.

See you on the road at our other cool rides.






Photo by Cia Bernales

Pound cake in a half-dozen different flavors from La Bonne Boulangerie.

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.

Do we seem food obsessed? We are! Our menus change every year, but if it’s not incredible, we don’t serve it.

Compare all of this to what you were served on the last big bike ride you did. OK? OK.

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- 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 21 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.

We Love to Eat!

For years I purchased Larabar energy bars at full price because they are my favorite -- all natural, and the only energy bar I actually put in my own mouth (because it’s the only energy bar I’ve tried that actually tastes good!) Great for a mid-ride boost.  

The Larabar folks are sponsoring us again this year and I couldn’t be happier -- enjoy them at our rest stops. (By the way, when I say that Larabar is a “sponsor” that means that they are giving us free Larabars, and that’s great! It does NOT mean that they have given me piles of cash or a new carbon custom bike. Yet.)

We will also be serving energy drink donated by our friends at Nuun. I’d never tried the stuff, so I went out and bought some (you know... with my own money...) and gave it a shot during my trip through the Riff Mountains in Morocco. (Giant climbs in 90 degree heat...)  I can only tell you that this stuff worked -- not sure I would have made it otherwise. We get offered lots of sports drink -- this is the stuff I put in my own mouth. (By the way... is there any more pretentious conversation starter than, “There I was... pedaling through the Riff Mountains in Morocco...”)


So what’s all of this luxury going to cost you?

The price of the ride ranges from $200 - $395, depending on which options you choose. (But you would have to choose a LOT of options to reach that $395 level).  Kids 12 and under on Montauk day ride for free on the 25-mile route.

There is no fundraising required for this ride.

We are definitely not the cheapest ride around, but I’ve been doing this for 22 years now, and we just might be the best.

We’re looking forward to a fantastic day of riding.  On the following pages is everything you need to know -- how to register, what to pack, when to show up, where to start the ride, and much, much more.

Dear Friends,

The 2019 ride was the LAST Ride to Montauk, at least for the foreseeable future.

Yeah, I can imagine "getting the band back together" for a 60th anniversary or some such thing, but not right now.  (Save the date!  September 14, 2024!)

I highly recommend that you check out our North Fork Century, which is just lovely. (Actually lovlier than Montauk in my opinion, but why quibble?)

Why did we stop doing Montauk?  (Any sane person would stop reading right here, but if you insist...)

1. Most of the towns in the Hamptons are a joy to work with, and others are... uh... less-than-joyful.  It felt like every year some administrators would think up a new creative way to annoy us.

It worked.

The obvious finally hit me: why not ride where people are glad to see us, instead of banging my head against a wall, trying to pedal where we're not wanted.  Ugh.

2. The late great rock concert impresario Bill Graham talked about the legend of Ouroboros -- the serpent that eats its own tail.