Run the Numbers Part 4
2025-03-22 07:00 - 09:00 (America/New_York) | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, March 22, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the fourth part of the Run the Numbers course. Today, those starting at 6:00 a.m. will catch intersections 47–49 a four-mile run, then at 7:00, we’ll catch 50 to 56 (at least). Anyone who wants a longer run can continue.

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Mudders & Grunters or Trailside & Town Park
2025-03-23 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, March 23, you’ve got some options. At 10:00 a.m., meet at FDR State Park ready to race Mudders and Grunters, a 5 mile course of trails and mud. But if you’d like to stay closer to home and get a warmup run in, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Trailside to Town Park loop. This course loops around the northern part of the Rez, up the Howland Drive segment, before taking four different options for returning to the lot. An optional excursion into Lewisboro Town Park for the longer distances will add a half mile or so. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for an easier pace and shorter distance.

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Last time we ran this course was March 24, 2024

Trail Tuesday
2025-03-25 05:30 - 07:00, 2025-04-01 05:30 - 07:00, 2025-04-08 05:30 - 07:00, 2025-04-15 05:30 - 07:00, 2025-04-22 05:30 - 07:00, 2025-04-29 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.

Workout Wednesday—Trailside Museum
2025-03-26 05:30 - 07:00, 2025-04-02 05:30 - 07:00, 2025-04-09 05:30 - 07:00, 2025-04-16 05:30 - 07:00, 2025-04-23 05:30 - 07:00, 2025-04-30 05:30 - 07:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Trailside Museum Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 10% average incline, the FH to Lean-to 7 segment (Happy Ending on Strava—don’t ask!) is less steep than Blue but also less technical.

Trail Thursday
2025-03-27 05:30 - 07:00, 2025-04-03 05:30 - 07:00, 2025-04-10 05:30 - 07:00, 2025-04-17 05:30 - 07:00, 2025-04-24 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 Thursdays at 5:30 a.m. for a run finishing up at 7:00.

Run the Numbers Part 5
2025-03-29 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, March 29, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the fifth part of the Run the Numbers course. Today, those starting at 6:00 a.m. will catch intersections 61 and 62 a four-mile run, then at 7:00, we’ll catch 63 through 70 to complete the course.

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Red/Rock Trail Loop
2025-03-30 08:00 - 09:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, March 30, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, when we run the Red/Rock Trail Loop. We’ll run this in a counterclockwise direction as marked and runners have the opportunity to run distances from 4 to 8.5 miles on the always fun Rock Trail. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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The last time we ran this course was Sunday, January 26

Sights and Heights
2025-04-05 07:00 - 08:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, April 5, 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 and we will have the option of taking a course variation we haven’t taken in a blue moon. Early risers can start at 6:00 for some extra miles.

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The last time we ran this course was way back on February 15.

Meadow to John Jay
2025-04-06 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, April 6, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run. If you’re signed up for the John Jay 5k, we’ll head up Howland and over to John Jay in time for the race to start. If you’re not competing, you can continue around the northern perimeter on either the 5.5 or 8.5-mile courses. 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.

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The last time we ran this course was April 14, 2024

Museum, CB, to Blue
2025-04-12 07:00 - 09:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, April 12, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum, ready to run the Museum, CB, to Blue Route. All distances start up FH and branch from there. The 6.5 and 8-mile loops take a couple of bushwhacks before meeting up with the 5-mile course. Early Risers start at 6:00 for a few extra miles.

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From the archives: Last time we ran this course was April 13, 2024.

Michigan to Kimberly V3
2025-04-13 08:00 - 09:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, April 13, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Kimberly v3 loop. This version of the classic course offers distances from 5 to 7.5 miles but you can visit the Overlook as well to add even more. Cobweb Crew starts at 5:00; Early Risers at 6:00 a.m.
Rookie Runners start at 7:00 a.m. for a shorter distance and easier pace if necessary.

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The last time we ran this course was September 22, 2024

Butler to Meyer
2025-04-19 07:00 - 09:00 | Butler Sanctuary, 265 Chestnut Ridge Rd, Mt Kisco, NY, 10549, United States
On Saturday, April 19, at 7:00 a.m., meet at Butler Sanctuary in Mt. Kisco ready to run the Butler to Meyer course which includes a section of Byram Lake Road and Oregon Road so you’ll have an opportunity to stretch your legs plus get plenty of climb on the trails. Course should be around 8 miles but if you’re looking for a longer run, you can extend the course in Meyer or head over for a perimeter loop of Westmoreland and turn this into a half marathon. Early Risers can start at 6:00 for a perimeter loop of Butler and a view from the hawk watch before the main run. Afterwards, head over to Mimi’s in Mt. Kisco for a coffee, quiche, or your favorite recovery pastry.

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Last time we ran this course was November 16, 2024

Meadow Museum Fire Tower to Michigan
2025-04-20 08:00 - 09:30 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, April 20, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, when we run the Meadow Museum, Fire Tower, to Michigan loop. We’ll run this in a clockwise direction as marked and runners have the opportunity to run distances from 5 to 8.5 miles. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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From the archives: Last time we ran this course was April 21, 2024

Meadow Museum Fire Tower to Michigan
2025-04-26 07:00 - 08:30 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, April 26, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, when we run the Meadow Museum, Fire Tower, to Michigan loop. We’ll run this in a clockwise direction as marked and runners have the opportunity to run distances from 5 to 8.5 miles. Early Risers start at 6:00. I’ll bring a couple of maps in case anyone goes off course accidentally

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From the archives: Last time we ran this course was April 21, 2024

37th Annual Leatherman’s Loop
2025-04-27 09:00 - 12:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, April 27, at 9:00 a.m., we’ll be meeting at the Meadow lot for the 37th annual Leatherman’s Loop. Cobweb Crew meets at 5:00 a.m. No Rookie Runners session or official 7:00 a.m. start this week.
Learn more and check out the opportunities to volunteer at LeathermansLoop.org
Don’t forget to ARRIVE EARLY! Please plan to arrive at the park before 8:15 a.m. — or even earlier if you can swing it.
For more information, visit leathermansloop.org

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Trail Running Film Festival
2025-04-30 19:00 - 20:30 | Bedford Playhouse, 633 Old Post Rd, Bedford, 10506, United States
On Wednesday, April 30, at 7:00 p.m., join the Leatherman Harriers, the trail running community, film buffs, and anyone who wants to see good stories, at the Trail Running Film Festival at Bedford Playhouse. This one-night-only event brings to life great tales from the running community but you don’t need to be a trail runner to enjoy an evening of fun and camaraderie. Tickets are on sale at the Bedford Playhouse. General admission seating only; reserve your tickets in advance.
The Bedford Playhouse offers noshes and a full bar so plan to come and relax for this two-hour festival of shorts. Visit the Bedford Playhouse site for more info ››
Tickets on sale ›› | Trail Running Film Festival ››

TRFF 2025 Global Tour Trailer ››.
