Trail Thursday
2025-12-25 05:30 - 07:00, 2026-01-08 05:30 - 07:00, 2026-01-15 05:30 - 07:00, 2026-01-22 05:30 - 07:00, 2026-01-29 05:30 - 07:00, 2026-02-12 05:30 - 07:00 (America/New_York) | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
Looking for a mid-week run? Meet at Ward Pound Ridge Reservation, Michigan Road Lot, on Thursdays at 5:30 a.m. for a run finishing up at 7:00.

Boxing Day Run
2025-12-26 07:30 - 11:00 | Bear Mountain, Hessian Lake Parking, 10911, 55 Hessian Drive, Tomkins Cove, NY, 10986, United States
On Friday, December 26, at 7:30 a.m., meet at the Hessian Lake Parking Lot, Harriman State Mark, near the ice rink at Bear Mountain and come prepared to run a special 9-mile loop on parts of the North Face Endurance Challenge course. Depending on conditions, it might be longer. No worries, the group will keep together sharing holiday cheer up and down the trails. More details to come and you can see the planned route here. If you’re looking to stay closer to home, I’d suggest meeting at Michigan Road Lot at 7:00 a.m. and running the Michigan to Kimberly v3 loop but bring your own maps.

Trailside, Raven, to Tower
2025-12-27 07:00 - 09:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, December 27, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Nature Museum Lot, ready to run the Trailside, Raven to Tower loop. We’ll all head up everyone’s favorite way to start a run—The Fox Hill climb—and then take some of the less-traveled trails from Michigan Road. Options include 4.5, 6, or 7 mile distances and if you’re looking for something longer, continue around Blue to add even more. Early Risers start at 6:00 a.m.
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The last time we ran this course was February 16, 2025

Museum to Blue 2
2025-12-28 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, December 28, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum, when we run the Museum to Blue route. We’ll run this in a counterclockwise direction heading out on the Orange Trail first. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00 a.m.
Rookie Runners start at 7:00 a.m. for a shorter course and easier pace.
Walkers/Hikers start at 8:00 for a short loop.

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Trail Tuesday
2025-12-30 05:30 - 07:00, 2026-01-06 05:30 - 07:00, 2026-01-13 05:30 - 07:00, 2026-01-20 05:30 - 07:00, 2026-01-27 05:30 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
Looking for a mid-week run? Meet at Ward Pound Ridge Reservation, Michigan Road Lot, on Tuesdays at 5:30 a.m. for a run finishing up between 7:00 and 7:30. It’s a great way to get your run in early.

First Run
2026-01-01 07:00 - 08:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Thursday, January 1, at 7:00 a.m., start the new year off right and meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the first run of the year. We’ll take it easy, find some fun trails, and enjoy each other’s company on this first run of 2026.

Blue Moon Loop
2026-01-03 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, January 3, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run a classic—The Blue Moon Loop. This course, courtesy of one of the Loop founders, Dave Cope, has the option to revive an old trail below the Leatherman’s Cave that is on the old Stroller’s Map but absent from more recent ones. We’ll be running the course in a counterclockwise direction, with the arrows. Depending on trail conditions, you have options for different distances. Early Risers start at 6:00.

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The last time we ran this course: January 21, 2025

Raven Lunatic
2026-01-04 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, January 4, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot ready to run the Raven Lunatic—The Raven Rocks course but with snow—because anyone who’s running on these trails has got to be a raven lunatic! We’re not expecting more snow this week but conditions are still challenging. If you have spikes, this might be a good time to use them. Cobweb Crew break trail at 5:00; Early Risers start at 7:00.
Rookie Runners start at 7:00 on a shorter course and easier pace.Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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Previous run: Sunday, February 2, 2025

Son of a Beast
2026-01-10 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, January 10, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run The Son on of a Beast course. Some of you may be familiar with the course titled “The Beast,” but this version is 7.6 miles and says on the trails. You also have the option of the 10 mile Super Beast course if you’re up for the challenge. Early Risers start at 6:00 for the 4 mile green loop on the map.

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The last time we ran this course was January 11, 2025

Michigan to Kimberly v1
2026-01-11 08:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, January 11, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the classic Michigan to Kimberly run. This run heads over to the meadow and follows the northern trails before heading up Blue and returning by way of three different options. One note: the BR trail between intersections 43 and 40 can be icy so you may want to take the DH trail to the north or use the 4 to 41 bypass to avoid some of it. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00 a.m.
Rookie Runners start at 7:00 for a shorter course and easier pace. Walkers/Hikers start at 8:00 for a short loop.

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The last time we ran this course was June 15, 2025

Trailside to Green
2026-01-17 07:00 - 09:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, January 17, at 7:00 a.m., meet at the Ward Pound Ridge Reservation, Trailside Nature Museum lot, ready to run the Trailside to Green loop. Options include distances of 5.5, 7.5 and 9 miles. Early Risers start at 6:00

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Last time we ran this course was June 25, 2023

Rock Trail Loop
2026-01-18 08:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, January 18, at 8:00 a.m., meet at Ward Pound Ridge Michigan Road Lot when we run a classic—the Rock Trail. Let’s check out one of the Reservation’s more challenging (and snow-free?) trails and visit Dancing Rock, Indian Rock Shelter, Bear Rock Petroglyph, Castle Rock, Spy Rock, Raven Rocks, and many more rocks in between. Cobweb Crew starts at 5:00; Early Risers at 7:00 for some additional miles.
Rookie Runners start at 7:00 for fewer miles and an easier pace.
Walkers/Hikers start at 8:00 on a short course of around 4 miles (return from Michigan Road via the Magic Stairs).
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The last time we ran this course was August 3, 2025

Sights and Heights
2026-01-24 07:00 - 08:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, January 24, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Sights to Heights course. Options include 5.5, 7, and 8.5 miles. Early risers can start at 6:00 for some extra miles but bundle up—it’s going to be a cold one.

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The last time we ran this course was April 5, 2025.

Trailside To Tower v2
2026-01-25 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, January 25, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, when we run a new variation of the classic Trailside to Tower course. We’ll be running this in a counterclockwise direction as shown. Cobweb Crew starts at 5:00; Early Risers at 7:00 for an additional few miles. With a fair amount of snow forecast, use your best judgement as to whether to come to the run. We’ll have plenty of runs in the future. If you do run, you may want to run earlier rather than later.
Rookie Runners start at 7:00 a.m. for a shorter course and easier pace.
Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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Michigan Road Double
2026-01-31 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, January 31, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan Road Double. This course offers many options for shorter and longer loops depending on conditions. We’ll concentrate on the red loop and see how runnable that is. Skiers and hikers have been out and have compacted the snow some but there are still some areas where “sloggable” is more of an apt description.

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Last time we ran this course was January 12, 2020

Raven Lunatic
2026-02-01 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, February 1, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot ready to run the Raven Lunatic—The Raven Rocks course but with snow—because anyone who’s running on these trails has got to be a raven lunatic! The trails are slow going and it’s unlikely that anyone will finish the entire course but let’s see what we can do. It will be a good workout no matter what. Options for shortening include running back via Michigan Road, taking FH over the Magic Stairs, or turning onto red/yellow at 24 or 22. Snowshoes are welcome and if you’re not up for the trail, run on the road for a somewhat easier workout. Cobweb Crew break trail at 5:00; Early Risers start at 7:00.
Rookie Runners start at 7:00 on a shorter course and easier pace.Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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Previous run: Sunday, January 4

Trail Tuesday
2026-02-03 05:30 - 07:00 | Reservoir Road, 10 Reservoir Road, Katonah, NY, 10536, United States
Looking for a mid-week run? Meet at Reservoir Road, behind the Katonah Art Museum, today, Tuesdays at 5:30 a.m. for a run finishing up between 7:00 and 7:30. It’s a great way to get your run in early.

Trail Thursday
2026-02-05 05:30 - 07:00 | Reservoir Road, 10 Reservoir Road, Katonah, NY, 10536, United States
Looking for a mid-week run? Meet at Reservoir Road, behind the Katonah Art Museum, this Thursdays at 5:30 a.m. for a run finishing up at 7:00.

Looper Bowl Pregame
2026-02-07 07:00 - 09:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, February 7, at 7:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot when we run the pregame edition of the Looper Bowl. We’ll plan to make this a dry loop but if you really have your heart set on that first water crossing and the mud flats, have at. Early Risers start at 6:00 for a few extra miles.

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Looper Bowl
2026-02-08 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, February 8, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot when we run an annual favorite—The Looper Bowl. It’s all the fun of the Leatherman’s Loop but colder and with a chance for snow and ice. You won’t want to miss this! If you don’t want to get your feet wet, there is an option to avoid the water crossings and even the mud flats. Looking to start early? Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter loop and easier pace.Walkers/Hikers start at 8:00 on a short course of around 4 miles.
Hope to see you out there this weekend.
Lee Willett
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Last time we ran this course was February 9, 2025

Trail Tuesday
2026-02-10 05:30 - 07:00 | Reservoir Road, 10 Reservoir Road, Katonah, NY, 10536, United States
Looking for a mid-week run? Today, meet at Reservoir Road, behind the Katonah Museum of Art, on Tuesdays at 5:30 a.m. for a run finishing up between 6:40 and 7:00. It’s a great way to get your run in early.
