Loop Lottery FAQ

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The 2024 Loop Lottery starts Friday 5 January 2024 at 12:00am and will extend through Monday 8 January 2024 at 11:59pm.

Loop Lottery drawing will be on or around Friday 12 January 2024.

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 a question about the Loop that is not related to the Lottery, check our main Loop FAQ list here.

Race entry fee incorporates a county parking fee (regular fee is $10 per car) that we are charged. Race T-shirts are optional and cost is +$23. A credit card processing fee and state and local tax (as determined by your address) is added to the total.

You will get TWO emails from us if you enter the Loop Lottery.

If you do not get these emails, especially the first one (which starts everything off), please let us know ASAP.

  1. FIRST EMAIL: You will get an email confirmation immediately after you sign up for the Loop Lottery online. 
  2. SECOND EMAIL: When you are selected (or not selected) in the lottery we will notify you via email. This email will be sent January 12th, 2024.

IMPORTANT: If you ARE selected in the lottery, your credit card will be charged immediately upon selection. There is no need for you to do anything else. You will get a short confirmation/congratulations email.

If you are NOT selected, you will be placed in the wait list and notified if any spots become available.

For more information about the Loop Lottery, click below:

Loop Lottery Information

To Register for The Loop Lottery, click below:

Loop Lottery Registration

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, shirt size (if desired), and credit card number.

2.) If runners want to sign up 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. (depending on the year if the Monday after lottery weekend is MLK day holiday we will an additional day for the lottery entry).

4.) You can check to make sure you are signed up for the Loop Lottery here.

5.) Approximately 3-4 days after the close of the Loop Lottery, we draw the names for the lottery and notify RunSignUp.com of the lottery winners.

6.) RunSignUp notifies the runners via email that they won a spot in the lottery — and runner’s credit card is charged immediately. Make sure you have info@runsignup.com in your address book so this confirmation email does not get tagged as spam.

7.) RunSignUp notifies the runners who were not chosen via email that they were not picked in the lottery.

8.) Runners not picked are put into a waiting list of lottery entrants. If a spot opens up we will notify the wait listed runner about the opening. If they are still available to run we can then authorize payment on their credit card from their original lottery entry. We will exhaust this list of lottery-entered but “not chosen” runners before taking anyone off of the post-lottery wait list (i.e. runners who did NOT enter the lottery but requested after the Loop Lottery to be added to the wait list). If you entered the loop lottery and did not win and wish to be removed from the wait list, let us know via leathermansloop@gmail.com.

9.) We will have a searchable list of runners who were picked in the lottery available AFTER loop lottery winner notifications go out.

Make sense? We hope so! We simplified the process so fewer emails are sent and potentially missed. 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 page for a 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 selected for the Loop. (Note: there won’t be anyone on this list until after the lottery drawing is made after the drawing date listed above.)

Check Loop Registration List

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

A: The purpose of the Loop Lottery is twofold:

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

After running the Loop Lottery for many 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 lottery period includes a weekend and at least two weekdays so there is plenty of time to sign up. Any longer and it is too drawn out.

Also, since you need to input your credit card to enter the Loop Lottery, that also makes a shorter turnaround desirable since credit cards have expiration dates which can cause problems when a valid credit card was entered for one month but the charge was made in the next month and the card expired during the prior month.

During the signup period, we post reminders to our social media pages (Facebook, Twitter, Tumblr, Instagram) and we remind runners 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 – see above for details.

If you are on the Leatherman Harriers email list you will get a note a few weeks before the Loop Lottery opens in January.

If you follow us on social media we post updates there.

If you are on the Trail Mix email list we will send out an announcements about all of the upcoming Trail Mix Series races including the Leatherman’s Loop.

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 a few weeks before.)

• In 2008 it closed 34 days after opening (whoa, things are getting interesting).

• In 2009: capacity filled in 16 hours (wait, what? Welcome to the new internet…)

• In 2010 the registration system crashed due to race demand (aaaaaaah! want to register but can’t! Evil computers!). It 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!). That was the year we knew we had to do something different.

• 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. Nobody really liked this system — neither runners nor organizers. It had both the stress of an open first come first serve system — plus the uncertainty of entering a lottery for those who missed out on the first come first serve. Really the worst of both worlds. Needless to say, we changed that quickly.

• 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-present we have followed the same basic Loop Lottery process and all went well with about a 75-85% selection rate for entries depending on the year.

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 Entry Confirmation Email when you enter your name into the Lottery, contact us right away. You can also check here to look up your registration.

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.

We are not sure why a small number emails may not reach runners (possibly spam filters, corporate blocks, deleted accidentally, job change, email typo, etc?) but even if you miss the initial acceptance email, you are still in the race if you win a spot via entering the lottery.

Q: Is there a charge to enter the lottery?

A: There is NO CHARGE for entering the lottery. BUT runners must enter a valid credit card to secure their spot in the loop lottery.

Your card will be charged immediately upon your selection in the loop lottery.

Runners who wish to withdraw before the selection date can email us before midnight the day before the drawing.

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. We also have a searchable list of lottery winners available online at the registration provider here https://runsignup.com/Race/RegistrationLookup/?raceId=5968

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 2012 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! 😉 

Note: We have no idea what the demand will be each year so we can’t make any promises. You have to enter to be selected!

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? [I.E. CAN WE ENTER AS GROUP?]

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

  • Put the name of your group in the “group” field in the lottery registration form.
  • 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 accidentally forget to put your 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 and we can add the group name to your entry.
    • 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.
  • If you register your group/family/friends for the lottery together on the same entry transaction, we will group your entry by default.
    • For example, if you register yourself and your spouse plus a friend on lottery entry, we will either pick all three of you or none of the three (“all or none”) in the lottery.
  • Entering as a group does not increase or decrease your chances of being picked in the lottery when compared to individual entry.

Q: What happens if we enter the lottery as a group member, but one or more individuals that entered with the group decide they do not want to be in the Loop after all. Does this eliminate the whole group or just those individuals?

A: If the group gets in then everyone from that group gets in. If someone from the group does not want to be with the group, they must withdraw their lottery entry before selections are made.

Once lottery selections are made and email confirmations have gone out, there are no refunds

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 on purpose — 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 always start with sorting the list by last name and looking for obvious dupes. Then we 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 typically see. For example, one spouse registers the couple and then the other spouse registers the same couple a day or so later not realizing they were already entered. This happens a couple of times each year. 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 we will fix it. This is pretty unlikely, but it did happen to one runner over the last 5 years lottery selections. 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 this from year to year 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 for the coming year.

*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. But we have not done this for at least 5 years.  

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

A: We have always accommodated our longtime “muddiest” runners. IF you are one of these — please contact us for assistance and assurances sooner rather than later. BEFORE THE LOTTERY SELECTION! We can usually tell when longtime runners register in the lottery, but sometimes we miss it if you register under a nickname or a spelling variant of your name – or if you changed your name.

If you miss the lottery we encourage you to volunteer at the Loop to be part of the day and support friends and family. Plus there are sometimes pre-Loop course checks in the winter leading up to the Loop that draw increasing interest each year (in 2015 over 75 runners did the Looper Bowl on super bowl Sunday – sign up for emails at SundayRuns.org to hear about these group runs).

There are lots of other trail races out there (Run the Farm! Raven Rocks! The Trail Mix Series!). We encourage you to get out with our local Sunday Runs running group as well.

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

A: In case something happens with credit cards, please get in touch with us ASAP with any credit card issues or unrecognized charges you think may be from us.

We have had minimal 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.

Warning: If you reverse the Loop registration card via your card issuer, we will remove your entry from the Loop AND you and others on your transaction WILL be banned from entering all future Loops. This is a very unlikely sequence of events, but it has happened a few times in the past 10 years and these runners are not welcome in the race.

We firmly believe refusing or denying a legitimate charge that you authorized is NOT the way to handle things. 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). It wastes our volunteer’s time and energy and we take a dim view of fraud attempts. Contact us FIRST, we are reasonable and understanding.

Q: Why do you automatically charge runners after they are selected in the Loop Lottery?

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. We will have many runners who are not selected.

If you have ideas for a better way to do Loop registration we’re all ears. But we’ve thought about this far longer that most people — and we’ve been through the alternatives.

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

A: Yes! There are a couple of ways, but they require some advance planning.

If you complete the Trail Mix Series your Loop Lottery entry will be automatically selected the following year. (Note: you have to enter the Loop Lottery in order to be automatically selected.)

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 auction entries 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 since we reserve those spots in advance.

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 area fundraising, please contact us. We say local since beyond a certain radius the Loop is not as well known 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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