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Shelter Island Aerial View
Shelter Island Aerial View

Shelter Island Shuttle

Sunday, July 14, 2024
Overview & History
Cross Sound FerryThe Shelter Island Shuttle has become a staple over many years. For new members it's become a rite of passage and delivers on unforgettable memories. The ride/event has evolved over time with updated parking arrangements in New London, bike route adjustments and various rest stop changes making it even better and more organized since its inaugural run back in 1998.
This is C / D+ ride set at an average speed of around 13 mph. In a word, the ride is at a "touring" pace. Since all stops are timed out based on this pace, there is no rush to get to any one destination. This means jumping past the ride leader will be frowned upon and those that go ahead will be solely on their own. But even as a single-paced ride, other riders started coming along to share in the social aspect of the ride by riding at their own pace and cutting off pieces of the route in order to meet up with the main group at key stops. In later years it was felt the time had come to officially open up the ride to these slower paces so everyone had a coordinated opportunity to enjoy this day of riding and socializing.
Two alternate versions of the route were developed for the D and E groups, which can be used by any ride leader to lead and they were timed out for meeting up with the main group at critical event locations. Faster riders who show up were resigned to the fact that this ride was going to be a laid-back pace for them and a day of enjoyment without the rigors of breakneck pacelining and often bring along a slower-riding friend or significant other.
Each version of the ride will be formally listed in the SCBC Ride Schedule. The purpose of this web page is to provide you with very detailed information so you can feel comfortable with the knowledge that you will know every aspect of this event before you arrive. So let's get started.
What's New
1.) In years past there was never any registration required to ride. You just showed up in New London like any other SCBC ride. Since the club has mandated Pre-Registration you really need to sign up in advance on the SCBC system. If you are a non-member visiting guest (we've had plenty of them before), E-mail the ride leader in advance and/or just find the ride leader at the dock and we'll get your contact information. This actually helps in the planning for such an event like this.
2.) The main ferry crossing from New London is the Cross Sound Ferry and offers reservations in advance if you like. That information is below. You can still purchase tickets for you and your bike on your arrival at the ferry dock in New London. The following are things you need to know about their policies:
If you booked in advance and need to cancel your reservation for the ferry, YOU MUST do so before the 9:00a ferry leaves on that day. If you do not call and cancel, you will forfeit the fare. When you do cancel successfully you will get a full refund.
You can book a reservation a couple of hours before sail time but it's not recommended. Booking a day or the night before is more ideal.
3.) We have added back in a dinner stop. After we get off the North Ferry at approximately 4:30p, there is La Capricciosa Brick Oven Pizza (serving other things besides pizza) and Sterlington Deli, which closes at 5:00p and just a few doors down from the North Ferry. We can all hang out together a bit longer before heading back for our traditional 7:00p Cross Sound Ferry, which holds a few surprises of its own.
Booking a Ferry Reservation/Ticket Purchase
This is phone number for making an advanced reservations if you so choose for the Cross Sound Ferry: 860-443-5281. Bookings for passengers with a bike must be done by calling. DO NOT use their online system since there are no provisions for booking bikes there. When you make your purchase, you are going to ask for a Same-Day Round Trip with a Bike. The total round trip should be approx. $60.00. You'll want to purchase the ticket for the outgoing 9:00a ferry from New London and the 7:00p ferry for the return from Orient Point.
Once you complete that process you will receive an E-mail with your confirmation. Print that out and also save it on your phone. When you arrive in New London they will scan the boarding number and give you your boarding pass.
As mentioned before, you can still purchase your Same-Day Round Trip Ticket with a Bike in the ticket house that morning but I strongly suggest you get there early if that's the case. I've been told there is always room on the ferry for walk-on passengers and bikes.
Meet & Start Times
It is strongly suggested that you arrive in New London well before the ferry's departure time of 9:00a. Arriving anywhere between 8:00-8:15a at the dock is strongly recommended. Unlike regular club rides, where the ride leader uses a bit of discretion on the start time when a rider shows up a bit late, that will not be the case here because the ferry departs promptly at 9:00a!
North Fork of Long Island
Alternate Meet & Start Times
This ride has a rich history of drawing riders from all over. There are alternative meeting places for riders who would not find it practical to travel up to New London if they are coming from the New York City, Long Island or New Jersey areas. Cyclists have met up with the group right at the Orient Point ferry dock. For those planning on doing that, you should arrive at the Cross Sound Ferry dock in Orient Point at 10:15a and be prepared to join the group when we disembark. Other riders have taken the LIRR to Greenport or driven there. The railroad station terminates right at the North Ferry terminal, where we arrive as a group on bikes. Anyone taking the train or driving to Greenport should arrive and be ready to join the group at that ferry terminal around 11:15-11:30a and wait for the group of riders to arrive. Anyone waiting on Shelter Island by the ferry terminal should expect our arrival around 11:45a.
Greenport, Long Island, New York
Pace & Terrain
The main ride pace is listed as a C (13 avg. mph - also a D+ pace) and the terrain is about 85% flat with a few rolling sections and a few short hills scattered on the island. While the total distance is 50 miles (80 kilometers), the actual riding is done in segments – interrupted by ferry crossings, lunch and beach stops. We will not be riding the entire 50 miles in one shot. We make every effort to keep the pace at a touring level so you have an opportunity to enjoy the scenery. Since everything is timed out, there is no need to jump ahead of the ride leader.
The alternate ride paces will be D & E and the terrain is mostly flat with perhaps a few rollers. These routes were created for those wishing to do a slower, shorter ride. There is a 36-mile route (57 kilometers) and a 29-mile route (47 kilometers) with crossroads connecting sections of the main route so slower riders can meet up with the main group at major stops. Again, the actual riding for all groups is done in segments.
There is no guarantee that a ride leader for these slower groups will list a ride. It is totally voluntary on their part. However, in the event there are no ride leaders for the shorter rides but you still want to come along, no worries. Sign up for the C ride so we know you're coming. You can download the RWGPS files or the cue sheets and still be with us for all the key stops, which is the whole point of this ride.
Full Route – 50 Miles
Shortened Route – 36 Miles
Shortest Route – 29 Miles
Lunch Menu
North Ferry and IGA Market
Ride Event Details
The Cross Sound Ferry departs New London with our group and our bikes at 9:00a. For those who booked in advance, you should have receive a confirmation E-mail with your reservation, which will contain a bar code/booking number. Have that ready at the dock. It will be scanned and you will receive a boarding pass. The crossing takes about an hour and twenty minutes from New London to Orient Point (the tip of the north fork of Long Island, NY). During that time on board lunch orders will be taken from riders who would like to order deli selections from our lunch stop on Shelter Island. By ordering items from the deli counter in advance, it speeds up the process for people getting their food and eating together. These orders will be sent electronically to the IGA Market on Shelter Island right from the ferry and will be waiting for us on our arrival. Alternately, cyclists may wander around the market for other food and drink selections.
Shelter Island, New York
When we disembark from the ferry on Long Island, we will be regrouping over to the side of the terminal area for what I hope will be an entertaining list of introductions and instructions. We might be picking up a few more riders meeting us in Orient Point. We start riding around 10:30a from Orient Point to Greenport to catch the North Ferry to Shelter Island. Here we may be meeting up with other riders. When we arrive on Shelter Island, we will first cycle a short distance to our lunch stop and eat before continuing on our way. Those who ordered in advance, your lunch will be waiting at the front of the store. Names will be written on each sandwich. As your name is called, you grab your order and pay at the register. There is a spot outside where we all eat together.
Sunset Beach, Shelter Island
Just before 1:00p, we mount our bikes and we're on our way again, cycling first across the island to the east and onto Ram Island before looping around to the north to the community of Dering Harbor. We'll crisscross our route through Shelter Island Heights and then head to the southwest tip of the island, turn and head due west and then north, along beautiful Crescent Beach to our traditional beach stop at Sunset Beach arriving around 3:00p. Other groups will take shorter, slightly different routes but the timing should coincide with the beach stop. You can bring swimwear and a towel if you like. Showers are available. There is a bar, as well as food and plenty of interesting people watching.
A little after 4:00p, we cycle back to the North Ferry and cruise back over to Greenport. We get some food right near the North Ferry for our dinner stop. We should aim to finish up in Greenport around 5:45p-6:00p for the remaining 9-mile ride back to Orient Point for the 7:00p ferry and the start of our sunset cruise back to New London, where even more surprises await.
Money to Bring
To avoid parking fees, arrive early and park on side streets away from the ferry area (see Special Hints below). Otherwise, parking in New London can be found in the area around the ferry terminal in New London. DO NOT drive into the ferry terminal. There is no parking there. A Cross Sound Ferry same day round trip ticket with your bike is approx. $60.00. The North Ferry same day round trip ticket with your bike is $6.00. Bring small bills so we can pay for the North Ferry crossing with exact change. Collecting money from a large group of cyclists during the short ferry crossing can become a problem. Allow for money to buy lunch and drinks.
Driving/Biking Directions
Take I-95 North to Exit 83. You will see signs before getting off the exit for Transportation Center and State Pier. Counting the traffic light at the top of the exit, go straight and then follow the road around to the right to the third traffic light. At the third light, turn left onto Governor Winthrop Blvd. only if you plan on parking in a garage (not recommended) or turn right onto Broad Street and look for side street parking off of Broad Street. To get to the ferry terminal you will eventually cycle down Governor Winthrop Blvd. to the end. Cross Sound FerryThere will be railroad tracks to cross at the bottom of the hill at the traffic light. Turn right at the entrance to the ferry terminal.
You can try to arrange to car pool for the ride to New London by using the club's Facebook page. If the weather is questionable, keep an eye out for Ride News messages. If you have never signed up for RIde News I would strongly suggest you do. This is how Ride Leaders communicate to riders when there is a change in status of a ride. Go to and Sign Up today. Rain cancels, clouds do not. Remember, we don't make landfall until late morning, so if the forecast that day happens to call for only early morning showers, chances are the ride will go on.
Getting More Answers
There are always questions needing answers so feel free to contact me at 203-261-5545 (home), 203-362-9927 (mobile) or at for any additional questions. The only request is that on the morning of the ride, please use my mobile number. This ride is intended to keep cyclists together at its social pace and we regroup often, all while keeping to the schedule. Every aspect of the ride has been timed out. Approximate arrival and departure times for each segment appear throughout the cue sheet which you can download. The ride is also available on RWGPS. For pre-planners or for those who need a bit more motivation in getting organized for this ride, I have provide the following hints. I encourage you to read these Special Hints:
Special Hints – The Preamble
Shelter Island Sign
Don't make the mistake some others have made in the past upon waking up the morning of the ride and, for some unknown, crazy reason (I've heard them all), decide to skip the ride with no real explanation at the time.
What happens, 9 times out of 10, is you'll find out later from others what a great time they had. That's when the phone calls and e-mails start coming asking me when I'm planning to do the ride again. It's only done once a year!
Three Rules of Thumb
Rule #1
Set your alarm clock earlier than you think you need to.
Rule #2:
Jump out of bed with excitement and enthusiasm!
Rule #3:
Call any of your friends that may be going with you that morning and wake them up (with excitement and enthusiasm, of course).
The Important Hints
Hint #1:
Give yourself plenty of time to get to New London. You'll see when driving on I-95 at Exit 54, Branford becomes only 2 lanes. On Saturday morning it's not usually busy, but you never know. New London is just under an hour's drive from Bridgeport. Fill your gas tank the day or night before. You'll need time to park, collect your bike and stuff and then double check again that you have everything before getting down to the dock.
Hint #2:
If there should be an accident on I-95 slowing your progress up to New London, US Route 1 is always a good bail-out route. It pretty much parallels I-95 and makes a good go-around to circumvent any problems.
Hint #3:
Check over your bike a few days before the ride. Your tires aren't going to lose air overnight so pump 'em the night before. Got a spare tube and a patch kit? Good!  If not, go get them!
Hint #4:
Don't let clouds scare you away from the ride. I love beautiful blue-sky ride days just like the next person, but clouds help break up the beating sun when we are in open areas. Bring sunscreen, which most people wait to apply after boarding the ferry.
Hint #5:
Make sure you bring your water bottles. Here's a great tip. Fill your bottles with what you drink to about 3/4 - 7/8 of the way to the top and put them in your freezer. Don't put the tops on because the liquid will expand a bit. Make a note that the bottles are in the freezer. The following morning, fill the bottle the rest of the way and wrap the bottles in tin foil. If you plan to carry a backpack or have a bag on your bike, put them in there and keep them covered, especially during the ferry trip over to Orient Point. You won't be drinking for a while and this will keep the liquid cold for a long time. There will be places to refill.
Hint #6:
Don't forget your helmet. In fact, you should take all the things you're bringing and put them in your car the night before - if you're driving. If you're going with a friend, put your stuff by the door where you will be leaving. Make yourself a note about the water bottles in the freezer. Bring spare tubes that fit your bike, along with a mini pump or CO2 cartridges and inflator. A patch kit can come in handy as well.
Hint #7:
If you have one, you might want to bring a camera. This may be something you'll want to capture. Shelter Island is very scenic and you'll want to snap pictures of it, as well as grabbing some shots of old and new friends. Since the club has created a Facebook page, there'll be places to post your shots. They may also end up on the website's gallery.
Hint #8:
If you purchase a ticket that morning, make sure you purchased a same day round trip ticket with a bike - 9:00a New London ferry/7:00p return ferry from Orient Point. GET TO NEW LONDON EARLY for same day purchase. Then wait with the others just outside the main building until boarding time. Once boarded, go to the upper-most deck where everyone will gather so you can write down your lunch order. After that you may stroll around the decks. Food will be available on board.
Other Parking
There are parking lots and garages all around the area. If you decide you would rather park in a garage, drive down Governor Winthrop Blvd. and you will see the garages toward the bottom of the hill. However, to save yourselves parking fees, my suggestion is to follow directions above to Broad Street and use on-street parking like Cottage Street. Leaving earlier gives you plenty of time to find parking on the streets away from the ferry, getting your stuff together and then riding your bike down to the ferry.
Jeff Munk Signature

See you there – with excitement and enthusiasm, of course!