Loop Lottery FAQ

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We have put together a list of Frequently Asked Questions about the lottery system. If you read through this FAQ and find you have a question that is not covered here, please get in touch via our contact form. If you have questions about the Loop not related to the Lottery, check our main FAQ list here.

Race entry fee is $45 and includes county parking fee of $10 per runner/car that we are charged. Race T-shirts are optional and cost is +$20 including credit card fee.

Critical: When you are selected in the lottery we will notify you via email. You will then have 3 days to finalize your entry by registering for the Loop and paying via credit card at that time. If you do not register within 3 days your spot will be offered to the next runner in the waiting list.

If you participated in the Lottery last year it is a bit different this year as credit card rules have changed. Our registration company is no longer allowed to keep credit cards on file and charge them later like we had done in the past.

For more information about the Loop Lottery, click below:

Loop Lottery Information

To Register for The Loop Lottery, click below:

Loop Lottery Registration

(Loop Lottery Opens Friday, January 8th, 2016)

Q: Can you explain the lottery process?

A: Sure!

1.) Runners sign up for lottery as if they were signing up for the Loop. Runners enter a secure registration processing website and enter their name, date of birth, gender, email address, address, and shirt size (if desired).

2.) If runners are in a group they also enter the group name on the entry form (see below for group information in this FAQ).

3.) Lottery period closes (lottery will be open for 4 days).

4.) You can check to make sure you are signed up for the Loop Lottery here [will be updated for 2016].

5.) Approximately 2 days after the close of the Loop Lottery, we draw the names for the lottery and notify RunSignUp of the lottery winners.

6.) RunSignUp notifies the runners via email that they won a spot in the lottery and provides a link to complete the Loop registration, securing the runner’s spot for 2016.

7.) RunSignUp notifies the runners who were not chosen via email that they were not picked in the lottery. Runners not picked are put into a waiting list and if lottery entrants who were picked do not complete their registration by paying for a spot, the runners can be taken from the waitlist and offered a spot in the Loop.

8.) RunSignUp has (or will have, once the lottery is finished) a searchable list of runners who were picked in the lottery up at their website which will be available AFTER notifications go out (for 2016 that will be sometime pretty soon after January 17th, 2016).

Make sense? We hope so! It is a change from the last 5 years of Loop Lotteries — if you have any questions, let us know.

Q: Do you have a list of people signed up for the Loop Lottery?

A: Check this searchable List of Lottery Entrants (check after lottery has begun):

Check Lottery Registration List

Q: I didn’t get an email about my selection in the Loop Lottery, was I picked?

A: Check this searchable List of Runners in the 2015 Loop. (Note: there won’t be anyone on this list until after the lottery drawing is made after January 16th, 2015.)

Check Loop Registration List

Q: Why don’t you run the lottery for two weeks or a month?

A: The purpose of the Loop Lottery is twofold:

  • First, it eliminates the rush to sign up to a limited event. We had two years of trouble with open registrations and cannot go back to that system.
  • Second, it allows everyone who is interested time to sign up and get a fair shot at running in the Loop.

After running the Loop Lottery for several years, we determined that 4 days is a long enough period for everyone to sign up for the lottery (or have a friend or family member do it for them.) The four day lottery period includes a weekend and two weekdays so there is plenty of time to sign up. Any longer and it is too drawn out and credit card issues start cropping up (cancellations, expirations, etc.) that complicate the lottery drawing process.

During the four day signup period, we post reminders to our social media pages (Facebook, Twitter, Tumblr, Google+) but we do not remind runners again via email.

Q: Can I sign up for the Loop Lottery now in [August | September | October| November | December]? 

A: No. We do this with a short lottery window close to the drawing date based on the registration company’s experience (and our experience) with lotteries.

If you are on the Leatherman Harrier’s email list you will get a note before the Loop Lottery opens in January.

Q: Why did you move to a lottery system?

A: Some history — In 2007, open registration closed in 3 months. (Pretty laid back, but it was a bit of a surprise for us and the runners who got shut out.) In 2008 it closed 34 days after opening (whoa, things are getting interesting). In 2009: capacity filled in 16 hours (wait, what?). In 2010 the registration system blew up (aaaaaaah! want to register but can’t! Evil computers!), was partially restored in an hour (do we have a pulse?), ran agonizingly slowly when it was restored (come on, just take my registration), and still sold out in 3 hours (yikes!). In 2011 we split the registration into open and lottery sections. The 500 open registration spots filled in just over 20 minutes (are you sensing a pattern here?). After the 2011 open registration ended, we took an additional 1,100 lottery registrations and awarded the remaining 700 spots to those that won the drawing.

In 2012 we changed to a full lottery for ALL entry spots. It worked well — with no rush or computer glitches. We received around 1,700 entries for around 1,250 spots. Pretty good odds of selection – but a massive reduction in angst from both runners and organizers. From 2013-2015 we followed the same Loop Lottery process and all went well with about a 75% selection rate for entries.

For 2016 the credit card companies have tightened up their security and will no longer allow registration companies to take in credit card information, store it, and then charge money at a later date. This necessitates a small change in our Loop Lottery — we will not collect credit card numbers up front then automatically charge winners. Instead we will send out winning notices to runners who were picked. Runners picked then have 3 days to finalize/pay for their entry.

Q: I never got the notification email from the lottery — was I selected? Was my credit card charged? Why didn’t I get an email?

A: You should get a Lottery Confirmation Email right after you sign up for the lottery.

If you DON’T get a Lottery Confirmation Email when you enter your name into the Lottery, contact us right away. Your confirmation email might be trapped in a spam filter, it may have a typo in your email address, or you may have left your lottery registration incomplete.

When the lottery selections have been made, we will send out all notifications via email within a day.

For those who won a spot in the lottery and get a notice from RunSignUp, you MUST then finalize your entry by paying for the Loop spot.

We are not sure why a few emails may not reach runners (possibly spam filters, corporate blocks, deleted accidentally, job change, email typo, etc?) but if you search and find your name at the list of picked runners (coming in January) you need to pay for your entry within 3 days.

Q: Is there a charge to enter the lottery?

A: There is NO CHARGE for entering the lottery.

Q: What will happen if I am selected for the lottery? How will I know?

A: You will be notified via email of your selection — and you need to finalize your Loop entry by paying for the registration. We also have a searchable list of lottery winners available online at the registration provider.

Q: What are the odds of getting in?

A: It will depend on the number of runners who register for the lottery. For example, in 2011 we had a total of around 1,700 registrations for around 1,250 spots. That is around a 75% acceptance rate — pretty favorable. However, If the number of entries goes up, the odds will go down. Conversely, if we get the same number of entrants as spots then everyone gets in! 😉


Q: I want to sign up for the lottery but don’t want to run if my friends/group/family are not also selected. Can you accommodate us? 

A: YES – but read below carefully about our group entry process — it is “all or none” in the group get in when signed up as a group.

  • Put the name of your group in the “group” field in the lottery registration form. We will assume that all groups with the same name are “all or none” so pick a unique name and make sure your fellow runners know the name before signing up.
  • Groups can be as small as two people — it is up to you.
  • You can combine as many people into a group as you want by entering the group name in the group field when registering for the lottery. We have had groups of 30+ runners sign up.
  • If you forget to put a group name in and want to add it BEFORE the lottery drawing, contact us immediately via email with your name and the name of the group you want to be part of.
  • IMPORTANT NOTE: If some runners in your group don’t put the group name in and the group gets in but the individual runner does not, we can’t let the unfortunate runner in as part of the group after the lottery drawing.
  • ANOTHER IMPORTANT NOTE: If you register your group/family/friends on one credit card transaction, this will be an “all or none” group by default since once the credit card is authorized for a dollar amount, we can’t change that amount (that is a credit card company rule put there for a good reason: it prevents people from charging you more than you signed off on).
    • In other words, if you register yourself and your spouse and a friend on one credit card transaction, we will either pick all three of you or none of the three (“all or none”) in the lottery.
  • We will not attempt to match up anyone in different transactions unless they have a matching group name entered.
  • YET ANOTHER IMPORTANT NOTE: Entering as a group does not increase or decrease your chances of being picked in the lottery when compared to individual entry.
  • Click below to see what the “group entry” question looks like

Q: How will you deal with the possibility of multiple entries by runners trying to increase their odds of being picked (i.e. “Stuffing the Ballot Box”)?

A: To date this has not been a problem — but we have various ways to deal with it if it becomes one. It is fairly easy to check for duplicates before we do the lottery selection since we can see everyone’s name in the lottery.

We will start with sorting the list by last name and looking for obvious dupes. Then we will proceed to other checks the registration company has available that match likely dupes in other less obvious ways (they have done this before and know the potential ways this can happen).

We realize honest mistakes can be made — and these are the only cases we have seen. For example, one spouse registers a couple and then the other spouse registers the same couple a day or so later not realizing they were already entered. Another example is a person registering a team and adding the same person twice by mistake rather than another member of their team/group. We will address each case individually before the lottery selection is made.

In cases of obvious and continuous abuse (which we do not expect and have never seen) we will notify the runner and eliminate the runner from the lottery, effectively banning them from the event. We don’t expect to ever have to do this because people won’t carry it that far.

All we are really trying to do is to keep a runner from being charged twice for entry into the Loop. If a runner happens to enter twice by mistake — and we don’t catch it for some reason — and then they get picked twice (pretty unlikely, but it did happen to one runner over the last 4 years lottery selections) we will fix it. We don’t think the other stuff will happen — but we are prepared for it if it does.

Q: I was rejected by the lottery last year, does that increase my odds for this year?

A: No*. Everyone has the same odds each year. Trying to keep track of everyone’s status over the years is complicated and conflicts with our desire to keep things as simple as possible. Please contact us if you have had any registration problems with this year’s lottery BEFORE the drawing.

*We may make exceptions to this for a given year if we feel it will not greatly complicate the lottery process for the next year. If you did NOT get picked in the 2015 Loop Lottery, we will offer you a guaranteed spot in the 2016 Loop if you register for the 2016 Lottery. This offer does not carry over indefinitely nor will it apply if you forget to sign up for the 2016 lottery. Depending on how many entrants we get for 2016 may or may not be extended for the 2017 Loop.

Q: I have run the loop for [X] years… This is not fair! How can you do this to me?

A: No easy answer to that. We feel your pain. We have always accommodated our longtime runners. IF you are one of these — please contact us for assistance.

If you don’t make it in via the lottery we encourage you to volunteer at the Loop to be part of the day and support friends and family. Plus there are pre-Loop course checks in the sundays leading up to the Loop that draw increasing interest each year (in 2015 over 75 runners did the full course check on the sundays before the Loop).

There are lots of other trail races out there (Run the Farm! Raven Rocks!). We encourage you to get out with a local running group as well. NY Trail Running Meetup group is a large and growing group that runners post events and group run meetups!

Q: My credit card company rejected the charge for the lottery, will this impact my entry into the Loop? 

A: Please get in touch with us with any credit card issues or unrecognized charges you think may be from us. We have had scattered problems in the past with runners not recognizing the registration charge and reversing it. If this happens, we will contact you to resolve the issue and get the charge reinstated.

If we cannot resolve it and the payment is removed from our account, we will remove your entry from the Loop and you and members of your group will be banned from entering future Loops. We firmly believe refusing or denying a legitimate charge is not the way to handle things and it can cost us many times the cost of your entry (not even including the charge reversal and the time we have to spend attempting to resolve the issue). Contact us FIRST.

Q: Why do you only allow 3 days for runners to sign up after they are selected?

A: Bottom line: We assume if you are signing up for the lottery that you want to run the Loop. That is a pretty fair assumption we think… Being selected should make you happy 😉 We will have many runners who are not selected and we want to be able to offer them a spot if runners picked ahead of them do not sign up for their spot in the time given.

If you have ideas for a better way to do Loop registration we’re all ears.

Q: Are there any ways other than the Loop Lottery to get into the Loop?

A: In the past we have provided a very small number of entries to selected non-profit organizations in surrounding communities to use in “Silent Auction” type fundraising events.

We have provided these to several local elementary school PTAs, the Lewisboro Volunteer Ambulance Corps, a local pre-school, and several other charity organizations in the last few years. The spots have always sold for more than the entry price to the Loop but auction winners are guaranteed entry.

Any money raised by these auctions goes directly to the non-profit hosting the auction and winners are instructed to contact us to get their registration entered. If you are holding a fundraiser and would like to talk with us about a donation of loop registrations for use in local fundraising, please contact us. We say local since beyond a certain radius the Loop is not as well known generally and may not get the interest a more local event would.

Have a question that is not addressed here? Contact us!


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