The 2025 Raven 100k November Virtual Challenge has kicked off!

Trail Runners,

The Raven 100k November Virtual Challenge has kicked off!

The Virtual Raven 100k Challenge goes from Nov 1st – Nov 30th. Sign up is here and at the link above.

More information on what the challenge entails is below:

Race / challenge shirts are available as long-sleeved cotton and short sleeved tech versions — but we have limited remaining inventory since we placed the final order over a week ago. Order now to ensure your size & style will be on hand.

You can sign up for the 100k Virtual Challenge (Nov 1-30) or the 10k Race (Nov 9th) — or do BOTH!

Note you can sign up for the 100k challenge after November 1st and enter your distances for the prior dates! 

Hope to see you virtually — and on the trails!

….Rob, Ciorsdan, and the Raven volunteers

PS: More detail about the November Raven 100k virtual challenge (and the 10k) is here: https://ravenrocksrun.org/2025/07/raven-rocks-10k-run-and-raven-100k-challenge-return-for-2025-nov-9-2025/ (Click the link to visit the Raven Rocks website.)

PPS: The Raven Rocks Run is the final run of the Trail Mix Series of races in Westchester / Fairfield. More information about the series is here: trailmixseries.org.

Essential Information for the Raven Rocks Run on November 9

To: Everyone who is registered for (or may be thinking of registering for) the 2025 Raven Rocks Run:

Raven 2025 Shirt Art

The TENTH annual Raven Rocks Run is set to go at Ward Pound Ridge Reservation on Sunday, November 9th, 2025.

Register

(The Raven 100k November Challenge is set to start 11/1! More info. You can sign up for the challenge through Nov 15, 2025!)

Race director Rob Cummings, his lovely wife Ciorsdan along with the dedicated raven volunteers have been working hard to set up this year’s event.

Registration link is here if you have any more folks to sign up (or you want to pass this on to a friend!): https://runsignup.com/RavenRocks

Not sure if you registered or want to check if a friend is registered? Click here:
https://runsignup.com/Race/RegistrationLookup/?raceId=25402

Here are some tips that will help you on race morning:

1.) ARRIVE EARLY! The race is set to start at 9am. Bib pickup (and shirt pickup if ordered) begins at 7:15am on race morning. Look for the tent in the Meadow Parking lot. Please plan to arrive at the park by 8:15am — or even earlier if you can swing it.

The regular $10 park entry fee is incorporated in part of the Raven Rocks entry fee so there is no need to stop and pay at the entry booth. Our volunteers will direct you on parking as you arrive. 

If the main meadow lot should fill up, we may need to use our backup lot near the entrance to the park. This would mean about 1/4 mile walk for runners arriving late. Another good reason to be early!

2.) DRIVE SLOWLY in the Park! Pay close attention to the volunteers who are directing the parking. Car pool if you can – this helps the environment – and it makes the race more fun! For a helpful overview of the race location (parking, start, bib pickup), check the logistics page of the website here.

3.) LISTEN ATTENTIVELY TO PRE-RACE ANNOUNCEMENTS! Your Race Director will have important information about the course and safety. You will be instructed about potential hazards on the course and current course conditions. 

4.) LISTEN FOR THE START! Following the instructions, we will start the runners.

5.) STAY ON COURSE IF YOU CAN’T CONTINUE! There will be a number of “sweeps” running the course following the slower runners. If for any reason you can’t continue, wait for them to get to you to assess your needs. The park is over 4,300 acres so don’t leave the course unless you know exactly where you are going.

6.) SAME DAY REGISTRATION – If we hit the cap before next weekend, we will not have this available. Online registration is open! 😉 If you or a friend are looking to run the race, sign up ASAP before we reach the cap! 

7.) RESULTS: Results with time and place will be available soon after the finish at the registration area and online later in the afternoon on the Raven Rocks Run website. Check it out at http://www.ravenrocksrun.org/results.

8.) THANK A VOLUNTEER! A tremendous amount of volunteer effort goes into making Raven Rocks a special event. T-shirt designers, registration volunteers, pie buyers, course setters, trail wardens, box lifters, water servers, bagel cutters, coffee brewers, parking coordinators, photographers, videographers, course sweeps, and the clean-up crew—not to mention the Pound Ridge, Lewisboro, and Westchester County Police officers and the dedicated members of the Lewisboro Volunteer Ambulance Corps!

If you want to volunteer, please reach out to us at ravenrocksrun@gmail.com. Thank you!

We are grateful that we have such a wonderful group of trail running enthusiasts (YOU!) to share this run with. We are also thankful that we have the thousands of acres of parkland at the Rez to enjoy!

Many runners have become members of the Friends of Trailside Museum and Ward Pound Ridge Reservation group during registration – We thank you for joining! This group, which many of you are now members of, is one of the oldest “Friends” groups in the country and it is powered solely by memberships and volunteers.

Remember, leave only footprints, take only pictures, and please send us your photos via upload!

Expect more news shared on Facebook, Twitter, via email, and our website as the event nears…. See you at the race! 

Good luck and have fun,

….Rob, Ciorsdan, and the rest of the Raven Rocks Run Volunteers!


PS: Some useful links…

Map and Directions to the Reservation
Map of the Raven Rocks Run course
• Follow Raven Rocks on Facebook: https://facebook.com/ravenrocksrun
• Follow Raven Rocks on Instagram: https://instagram.com/ravenrocksrun
Searchable list of registered runners
Run on the trails on Sundays all year round!

Frequently Asked Questions (FAQs)


The Raven Rocks Run is the last race in a series of trail races called The Trail Mix. The Trail Mix will resume in 2026!

2026 Trail Mix races TENTATIVE plan*:

In addition, we support and attend many other local trail (and a few road) races. Send us some of your favorites for 2026!

(Note: this post went out as an email to all registered runners for the 2025 Raven Rocks Run, the 2025 Raven 100k Challenge, as well as past registrants and trail runners on our email list. If you did not receive this via email and you are registered, you may want to check your spam folder and set up ravenrocksrun@gmail.com on your address book/white list. If you have not yet registered and you plan to run – sign up now!) 

Raven November 100k Challenge 2025

The Challenge: Walk, hike, or run 100k during the month of November 2025. Distance can be done anywhere, the only requirement is that it be on your feet.

Challenge Rewards:

  • You stay active as the days shorten and the weather cools down.
  • You can join our Strava Club to track your November progress to (and past!) 100k and share with other challengers.
  • If you are in the local area of the Ward Pound Ridge Reservation, you can check out the Raven Rocks overlook which is on the Raven Rocks 10k Run course (and there have been a pair of Ravens who live there that you might see if your timing is right!).
  • You can earn badges as you unlock the various achievements we have set up.
  • At the end of the month we tally your totals and send or give you a custom finisher “woodallion” with your name and badges and achievements (see image below) along with your shirt (if purchased).
SAMPLE 2024 Raven 100k Challenge “woodallion” (will be updated for 2025!)- The lightly etched outlines will be replaced with physical badge pieces fastened atop as those are earned. So you may have the whole deck filled or just parts. Some of the badges are very difficult to achieve!

Below are the badge images and names from last year and further down are the descriptions of the achievements. We are open to suggestions on adding more badges – especially if you are outside of the local Raven Rocks / Ward Pound Ridge area! Maybe an international badge if you run a Raven related course outside the USA!

Badge descriptions:

– Run 10k on the Raven Rocks Run course (raven badge)
– Run 5x 10k on the Raven Rocks Run course (ultra raven badge)
– Run 10x 10k on the Raven Rocks Run course (full flock badge)
– Take a selfie at the Raven Rocks Overlook and send it in (photographer badge)
– Submit a photo of yourself on a run with your “I Voted” sticker (bald eagle badge) or if you can’t vote in the election, next to someone with an “I Voted” sticker.
– Submit a photo of you running on Thanksgiving (turkey award)
– Photo of a raven anywhere (citizen award) (merged with traveler badge)
– Do a run in the dark to Raven Rocks (night owl badge)
– Do a run at dawn to Raven Rocks (cobweb crew badge)
– 200k distance in November (snowy owl badge)
– 300k distance in November (white raven badge)
– Read a stanza from Edgar Allan Poe’s “The Raven” poem and send us a link. Use SoundCloud, YouTube, Facebook, or whatever audio service you want. (wise owl badge)

New badges last year include the “Peeter Badge” named for Peeter Muursepp who during 2020’s Raven 100k Challenge did 32 loops of the 10k Raven Rocks course. Get 32 loops or more to earn the badge. In 2021 Peeter upped the ante with 62 Raven Rocks 10k loops during the month of November. That’s more than 2 per day! If you surpass it with 62 (or more) and the badge name changes to your name. But we think Peeter is safe since that is a huge number. Only 3 people have ever earned this badge.

Jacob Benesch proposed a badge for anyone doing 5x Raven Rocks 10k course in one day (50k total in a day!). We already had a badge named the Ultra Raven Badge (for 5x course runs over the a month), so we now have a new badge called “The Raven Rockstar Badge” which is shown on the photo sample above. Only 3 people earned this badge in 2021-2024.

Note – If you are in contention or you think you might be in contention for one of the “TOP 3” achievements (first, second, or third to 100k, top 3 finisher overall at end of November), you must enter your distances within 36 hours of completing them. That way the others in the challenge who are pushing themselves to the limit can track how they are doing relative to the competition. If you enter all of your data in batches and you come into contention for one of these achievements late in the challenge, you will not be eligible for the achievement.

More information about badges and achievements can be found here: https://ravenrocksrun.org/raven-challenge-badges-and-achievements/

Let us know if you have any questions about the Raven 100k Challenge for November 2025 – email ravenrocksrun@gmail.com. Thanks!

See you on the trails!

Rob

Raven Rocks Run and Raven 100k Challenge in 2025

The Raven Rocks Run is a challenging 10k trail run at Ward Pound Ridge Reservation in Cross River, NY.

Race is Sunday, November 9th, 2025 starting at 9am. 

The race will start in the Meadow – parking is in the meadow lot and overflow parking is on the upper meadow.

The course passes by the spot where the Leatherman’s Loop begins. Instead of heading towards the river as the Loop does, the Raven Rocks Run 10k course climbs and climbs up to the two highest points in the park (Raven Rocks Overlook and the Fire Tower Summit) before heading back for a (mostly) downhill and (relatively) flat finish.

The course passes by the site of the former Cross River Mountain fire tower which is the highest point in the park. We have been heavily involved with a group working towards getting back the tower to its former spot in the park and there is good news on the return of the fire tower!

See Course Map page for course details.

More information about the race and tower project is on the About page and the FAQ page of our ravenrocksrun.org website.

Sign up ASAP – summer and early fall signups get the early raven discount! 

We have gotten close to our limit the last few times we put on the race — so it could get full, or it may not. It depends on the runner demand!

2025 Raven Rocks Run and Raven Challenge Open for Early Bird Registration

If you like to plan your races in advance, sign up now! There is a special combo discount if you sign up for both events (10k race and 100k challenge) at the same time. There’s even a bonus EARLY RAVEN PRICING to celebrate opening of Raven registration.

There’s currently a TRIPLE TRAIL bundle that lets you sign up for the TWO Run the Farm 5 mile races plus Raven Rocks 10k Run at the same time – and get a bundle discount!

Raven Rocks 10k Run will be held Sunday, November 9, 2025.

The Raven 100k Challenge is set for Nov 1-30, 2025.

Both events are open for registration now! https://runsignup.com/ravenrocks

Sign Up

Thanks for supporting the race — and the Friends of Trailside Museum and Ward Pound Ridge Reservation!


PS: Run the Farm now has a SPRING race event (May 17, 2026) and a FALL race event (Oct 19, 2025). For more information visit the registration links at https://runsignup.com/muscootspring (May race) and https://runsignup.com/muscoot (October race).

Final Update for 2024 Raven 100k Challenge

FINAL UPDATE / RECAP:

  • 52 of our participants have entered enough distance to qualify for a challenge woodallion!
  • If you ended the month of November lower than the cutoff (under the 100k mark) unfortunately you did not qualify for a 100k challenge finisher woodallion this year 🙁 … There’s always next year!
  • The cutoff for submissions was 12/4. The table below shows what was sent to the custom laser engraving company on 12/5 (including distances and badges earned!).
  • We need to get our custom woodallion engraver (Raven Tree Works) the data to print the name and distance customized woodallions — plus the custom badges — so we can get the woodallions to the 100k challenge finishers in a timely manner.

Anyone registered who reached 100k or higher walking, hiking, or running in November gets a custom Raven Challenge Woodallion suitable for display — and even suitable to hang on holiday decorations!

FINAL TALLY was made 12/4/24 with the badge claims and distances you and other challenge participants have reported.

These are the final tallies:

Raven November 100k Challenge 2024 Distance and Badge Claims

Some highlights from the 2024 Raven 100k Challenge include:

Paul Woolley – 1st overall male – 449.2k ••• Jillian Swope – 1st overall female – 327.2k

Kevin Ascher – 2nd overall male – 323.7k ••• Mea Sgaglio – 2nd overall female – 325.7k

Gregory Boland – 3rd overall male – 268.1k ••• Jennifer Kehl – 3rd overall female – 318.0k

Mark Shaner – 4th overall male – 249.2k ••• Katherine Blanque – 4th overall female – 254.6k

William Fraoli – 5th overall male – 243.0k ••• Liz Osterhus – 5th overall female – 253.7k

•••••••

Kevin Ascher – 1st male to 100k ••• Mea Sgaglio – 1st female to 100k

Mark Shaner – 2nd male to 100k ••• Liz Osterhus – 2nd female to 100k

Todd Jonasz – 3rd male to 100k ••• Jennifer Kehl – 3rd female to 100k

•••••

  • Number of 2024 participants: 52 total – 27 women, 25 men
  • Total badge types: 17 unique badges
  • Most total badge types possible for one person to earn this year: 15* 
  • Number of participants who earned the maximum number of 15 badges: 0
  • Number of badges earned total: 292
  • Most common badge earned: Bald Eagle badge (44 of 52)
  • Second most common: Turkey badge and Veteran’s Day badge (43 of 52 for both)
  • Least common badge earned: Peeter Badge, Raven Rockstar Badge, Full Flock (all three 1 of 52)
  • Second least common badges: Ultra Raven, Raven Meteor (both 3 of 52)
  • Number of GPS challenge items hidden at the Rez: 28
  • Number of GPS challenge badges earned: 26
  • Number of GPS challenge items still hidden at the park: 2, we will be searching for them during an upcoming SundayRun!
  • 2024 Participant who completed the most Raven Rocks Run 10k courses: Paul Wooley (36 times! Including 5x Raven 10k loops on November 30th to earn the Raven Rockstar Badge).
  • Number of participants who reached at least 32 Raven Rocks 10k Loop courses completed in November 2024 to earn the most difficult badge of all: The Peeter Badge: 1 of 52 
  • Note: if a participant exceeds 62 Raven Rocks courses in an upcoming year, the Peeter badge gets renamed for them… I don’t know if anyone will ever exceed the record on this. 
  • The Raven Meteor badge is for participants who witness a meteor while running during November. Three of our participants achieved this: Ivan, Chris, and Jillian. Congrats! You get a special meteor flair for your woodallion this year. Note for next year’s participants: The annual Leonid Meteor Shower is in Mid-Nov each year and it is a perfect time for a night run/walk/hike and meteor gazing!
  • Other new badge ideas that challenge participants have suggested include the Volunteer Badge, the Fowl Weather Badge (run/walk/hike in foul weather to a Raven feature), 1st day flair and last day flair (for run/walk/hike day 1 and day 30 of the month), Coven Badge (run/walk/hike with 13 or more friends). We are open to other badge suggestions as well – ravenrocksrun.org/contact-us

Next year we plan to have the 10th annual Raven Rocks Run 10k Trail Race at 9 a.m. on Sunday, November 9, 2025. We also plan to bring back the Raven 100k Challenge as well for a 6th year. Anyone who signs up for both events at the same time will get a break on the dual registration. In addition to bundle discount, there also will be a super early raven discount when registration opens in January 2025. We appreciate the early support of the race and challenge! And it is one more chance to Join the Friends of Trailside Museum and Ward Pound Ridge Reservation for 2025!

Thanks again for being a part of this event! (This page including any late updates can be found at ravenrocksrun.org)

*the Full Flock badge (10x on the course) supersedes the Ultra Raven badge (5x on the course) which supersedes the Raven Badge (1x on the course).

Check ravenrocksrun.org/photos for links to pictures (from this year and past years) of the Raven 100k Challenge and the Raven Rocks Run.

2024 Last Caw!

Get your badge submissions in — and your distances in BY 12/4!

A bunch of participants are SO CLOSE – don’t forget to count all of your Ks and report them!

Let us know if you are having trouble getting anything to us and we will help!

Thanks!

2024 Raven 100k Challenge Status [ FINAL 12/5 ]

There are 62 raven 100k challenge participants reporting their distance results to date.

  • FINAL: 52 of these participants have entered enough distance to qualify for a challenge woodallion to date.
  • over 1,360 distance entries have been made by our 62 challenge participants to date. Over 9,600 kilometers have been walked/hiked/run AND REPORTED by our challengers!
  • If you end the month of November LOWER than the 100k cutoff (aka under the 100k mark) unfortunately you will NOT qualify for a 100k challenge finisher woodallion 🙁 So…. get moving and get those K’s reported ASAP! We know you’ve done them!
  • The CUTOFF FOR SUBMISSIONS is Wednesday 12/4. The table below shows what will be sent to the custom laser engraving company on 12/5 (including distances and badges earned!).
  • We need to get our custom woodallion engraver (Raven Tree Works) the data to print the name and distance customized woodallions — plus the custom badges — so we can get the woodallions to the 100k challenge finishers in a timely manner.

Anyone registered who reaches 100k or higher walking, hiking, or running in November gets a custom Raven Challenge Woodallion suitable for display — and even suitable to hang on holiday decorations!

FINAL TALLY will be made 12/4/24 at midnight with the badge claims and distances you and other challenge participants have reported.

If you need the link to claim your badges, click here. If you have new badges to claim, you can submit the form as many times as needed and we will “super score” your badge claims (i.e. once you claim a badge you don’t need to claim it again on a subsequent form submission — but it doesn’t hurt to claim it again if you can’t remember!).

Raven November 100k Challenge 2024 Distance and Badge Claims

2024 Raven Rocks Recap

Hello Raven Runners!

Last Sunday was a bit chilly – there was frost on the ground at 6am as your volunteers arrived for the race day setup. It quickly warmed up as the sun got higher in the sky.

The drought conditions and red flag fire warning prevented us from having a fire pit this year unfortunately. But the s’mores fixings were available raw for anyone who wanted to grab a chocolate bar, graham cracker, or marshmallow post race!

2024 PHOTOS

First and foremost – the PHOTOS from this year are available here: https://leathermansloop.smugmug.com/Raven-Rocks-Run/2024

Thank you to photographers Carol, Mark, Bill, Dean, Orion, Rob, plus runners and spectators who sent in or tagged us in photos!

If you have any to upload – click or tap here: https://leathermansloop.smugmug.com/upload/cfVpF2/2024 to share with everyone in the 2024 Raven Rocks Run runner upload gallery.

Raven Rocks 2024 Results

Congratulations to the 286 runners who finished the race on Sunday! The race day was backed by a team of around 40 race volunteers including registration and t-shirt table help, kitchen/food setup, course checkers, timing volunteers, photographers, parking crew, the utility team, and more.

We also could not have put on the race without the help of Ward Pound Ridge Reservation staff — led by Taro Ietaka and helped by Mike Vogt and Mario Rodriguez (who also ran in the race!) plus others at the Rez. We also want to thank the County of Westchester Department of Parks, Recreation, and Conservation for hosting us at the park. The Lewisboro Volunteer Ambulance Corps came to the race to be on standby to help in case of injury.

LVAC Standby Crew at the Raven Rocks Run for the 9th year!

The race supports the Friends of Trailside Museum and Ward Pound Ridge Reservation. Participants have the opportunity to join the Friends group during registration — and nearly 80 of you took advantage. You can STILL JOIN the friends group via this link: https://runsignup.com/Race/Donate/NY/CrossRiver/RavenRocksRun

Friends of Trailside Membership is at any dollar level. Give what you can. The most popular level is the $100 “Wood Turtle” level which gets the member a year long parking pass for the Rez. We raised over $6,000 for the friends group through the membership program on the registration website this year. Thank you Raven Runners, Hikers, and Walkers!

Musical Guests

We also featured the return of the Pell Hill band of Casey Stanford (Guitar) and Layne Krulik (Drums) rocking mile 5.5 at Pell Hill in the meadow next to the “Town Line Tree” for the second year. They were joined this year by vocalist Ellie Tsiropanas.

Runners heard Led Zeppelin, Metallica, and many other rockin’ tunes as they headed (mostly) downhill towards the finish around 3/4 mile away. The band members currently attend John Jay Middle School. Our thanks to them for braving the cold morning — and thanks to their roadies for getting them there! We hope they will come back for another return engagement!

The Pell Hill Band: Casey Stanford (Guitar), Layne Krulik (Drums), Ellie Tsiropanas (Vocals). (Photo by Dean Leggiero)
The Pell Hill Band in action – video by Dean Leggiero

Cobweb Crew

The Cobweb Crew pre-ran the 10k course – and some of these folks also were sweeps (photo by Lee Willett).

The Cobweb Crew is a group of runners that go out well before the race and run the course to check that the markings are still there and everything is set for the race. We are confident in our trail course setting ability, but the whims of four legged (and two legged) creatures can lead to unplanned new paths. We rely on the cobweb crew for this vital service — which helps to keep all raven runners and hikers on course.

The Cobweb Crew is comprised of some of the SundayRuns.org crew — trail runners who come out for group runs every Sunday morning at 8am (and other days and times!) to run local (and occasionally more distant) trails.

Race Highlights

The race had one repeat winner this year and one new winner.

Katie Claiborne (57:17) won for the first time and Eamonn Sullivan (43:24) won for the third time. Both runners set new Raven Rocks course records due to the new slightly longer course due to starting in the grass field rather than the meadow triangle. Though Eamonn’s time was a record even for the standard shorter course.

The youngest finishers were a pair of 9-year olds running the race for the SECOND time: Christian Piddington and Wyatt Nable.

Pell Hill – Mile 5.5. Alexander Grano helped by friends Kimberly and Kevin Condon. This was Alexander’s first trail race (photo by Dean Leggiero).

All in all a very fun and energetic Sunday. Thank you to all who came, ran, helped, and watched. A great day all around!

Note: If you have registered for the Raven 100k November Challenge please report your distances here: https://runsignup.com/Race/Results/25402#resultSetId-431881;perpage:100 and submit your Raven Woodallion Badge Claims here: https://ravenrocksrun.org/raven-100k-challenge-badge-submission-form/.

If you haven’t registered for the 100k November Challenge you can still sign up – today (11/16) is the last day though!

Thanks for helping make it a very Ravember month! 

….Rob

Photo Gallery for 2024 (and prior years!)

We have a group of volunteer photographers (thank you Carol, Orion, Mark, Dean, Bill, and Rob) who came out to the race to help document the event. Their 2024 photos are available on our permanent gallery website here: https://leathermansloop.smugmug.com/Raven-Rocks-Run/2024

Links to prior years photos (2015-2023) is at this link: https://ravenrocksrun.org/photos/

Lastly – if you have photos YOU’D like to share (and be able to find years later!) post them to the 2024 runner’s upload album gallery using this link: https://leathermansloop.smugmug.com/upload/cfVpF2/2024

Runners also share photos and video via Instagram – tag us @ravenrocksrun https://www.instagram.com/ravenrocksrun/

Some selected photos from 2024: