Thursdays 4 at 6:00
2025-06-19 18:00 - 19:00, 2025-06-26 18:00 - 19:00, 2025-07-03 18:00 - 19:00, 2025-07-10 18:00 - 19:00, 2025-07-17 18:00 - 19:00 (America/New_York) | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
Looking for something new? How about Thursdays this summer at 6:00 p.m.? Meet at Ward Pound Ridge Reservation, Michigan Road Lot, to run an easy four-mile loop. We’ll keep it simple and fun. For anyone who isn’t an early riser, this is the perfect introduction to our trail running community.

Michigan to Kimberly
2025-06-21 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, June 21, 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. Early Risers start at 6:00 a.m. for a few extra miles.

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The last time we ran this course was July 28, 2024

Museum to Blue 2
2025-06-22 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, June 22, 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
2025-06-24 05:30 - 07:00, 2025-07-01 05:30 - 07:00, 2025-07-08 05:30 - 07:00, 2025-07-15 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
2025-06-25 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
2025-06-26 05:30 - 07:00, 2025-07-03 05:30 - 07:00, 2025-07-10 05:30 - 07:00, 2025-07-17 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.

Night Run
2025-06-27 19:00 - 23:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Friday, June 27, at 7:00 p.m., meet at Ward Pound Ridge Reservation, lean-to 10, just past the Bergfield picnic area on Reservation Road, for a special Night Run. Bring a headlamp for the run—sunset is at 8:21 so you may be back before dark—and some food or drink for, you know, recovery afterward. And get ready for a fun evening around the campfire. Bring a few dollars to help cover the cost and thank Matt Hart for spearheading this.

Important note: There is a Firefly Festival at the Meadow starting at 6:30 with an admission fee of $15. Unless you’re planning to attend that as well, if you’re questioned at the booth for a ticket to the festival, let them know that you’re headed to lean-to 10 and not the festival.

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Michigan to Dancing Rock
2025-06-28 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, June 28, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Dancing Rock course. This loop starts with a climb to the Overlook then follows some of the lesser-used trails in the park. Options include 4.5, 6.6, 8 and 9 mile loops. Early Risers start at 6:00 for a few extra miles.

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Last time we ran this course was February 1, 2025

Raven Flashback
2025-06-29 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, June 29, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Raven Flashback. Those of you in the group may remember that the Raven Rocks Run once went up the CB trail for a memorable climb near the start. We’re bringing that climb back today with the Raven Flashback. You’ll also have options of longer and shorter distances as well. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter loop and and easier pace.Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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Last time we ran this course was March 9, 2025

Workout Wednesday—Kimberly Bridge
2025-07-02 05:30 - 07:00, 2025-07-09 05:30 - 07:00, 2025-07-16 05:30 - 07:00 | Ward Pound Ridge Reservation, Kimberly Bridge, 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, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the Rez and the perfect training ground for any upcoming race. The .6 mile uphill contains just over 400 feet of vertical gain while the downhill is a great quad-shredding exercise. If you need to train with poles, this is a good course to do so. We’ll aim for 4 or 5 repeats and see what we have left after that.

Independence Day Run
2025-07-04 05:30 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Friday July 4, at 5:30 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run a special Independence Day run. We celebrate July 4, 1776, as Independence Day so let’s run those numbers—1776 Starting at Michigan Road, let’s hit intersections 17, 7, and 6, for a run of about 7 miles.

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Westmoreland Perimeter Loop
2025-07-05 07:00 - 09:00 | Westmoreland Sanctuary, 260 Chestnut Ridge Rd, Mt. Kisco, NY, 10549, United States
On Saturday, July 5, at 7:00 a.m., meet at Westmoreland Sanctuary on Chestnut Ridge Road in Mount Kisco when we run the 6 mile perimeter loop including the newest acquisition—the Raptor Ridge trail. Early Risers can meet at Butler Sanctuary just across the street at 6:00 a.m. for a 4-mile loop first. See the map ››. Then, after the run, head over to Mimi’s Coffee House in Mt. Kisco for a cup of coffee, tea, or whatever.

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Last time we ran here was July 27, 2024

Subway Series
2025-07-06 08:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, July 6, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run something a little different. You’re all used to running in the Rez with the usual map but this time, I’ll bring some of the “Subway” maps to guide you. Instead of a defined course, you have three destinations—Raven Rocks, Kimberly Bridge, and the Meadow Lot. The most direct path should yield a 6-mile run while you have options of cutting it short or taking a longer course. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter loop and and easier pace.Walkers/Hikers start at 8:00 on a short course of around 4 miles to Raven Rocks and back.

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Last time we ran this course was April 15, 2012

Kimberly Blue & Brown Loop
2025-07-12 07:00 - 09:00 | Ward Pound Ridge Reservation, Kimberly Bridge, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, July 12, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, when we run the Kimberly Bridge Blue & Brown loop. This 8.3 mile double looped course starts with a loop to Raven Rocks then over the Fire Tower before returning to the cars and making another northern loop on DH and Brown. Options include from 4 to 9.5 miles. Early Risers start at 6:00 for additional miles.

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The last time we ran this course was way back on January 25, 2020

Trailside to Overlook
2025-07-13 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, July 13, at 8:00 a.m., meet at the Trailside Museum at Ward Pound Ridge Reservation when we run the classic Trailside to Overlook loop. This course offers multiple distances but all start toward the Overlook and return via FH. Cobweb Crew starts at 5:00 for an extra eight miles; Early Risers start at 7:00 for an extra four miles.
Rookie Runners arrive at 7:00 a.m. for a shorter loop at 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 June 30, 2024

Town to Trailside
2025-07-19 07:00 - 08:30 | Lewisboro Town Park, Upper Lot, 1091 Old Post Road, Cross River, NY, 10590, United States
On Saturday, July 19, at 7:00 a.m., meet at Lewisboro Town Park, upper lot, ready to run the Town to Trailside course which includes distances of 5.5, 6, 7, and 9 miles, running counterclockwise, down “fun climb”. Early Risers start at 6:00. for a few extra miles.

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Last time we ran this course was August 11, 2024

Fabulous Fahnestock Preview
2025-07-19 08:00 - 10:00 | Fahnestock Park, 362 Glynnwood Rd, Cold Spring, NY, 10516, United States
On Saturday, July 19, at 8:00 a.m., meet at the 14,000-acre Clarence Fahnestock Memorial State Park, at the Dennytown Road/Appalachian Trail Parking Lot (Dennytown Rd, Putnam Valley, NY 10579) for a preview of the Fabulous Fahnestock Trail Race. This 10 mile course will follow the 50k and 25k routes including passing through the Sunken Mine area of Aid Station 2 which will be manned by Sunday Runs this year. You don’t need to be registered for the event to enjoy the mix of trails. Travel time is about an hour from us so plan accordingly. Please be prepared to be self-sufficient for 3 hours.
If you’re looking to stay closer to home, meet at Lewisboro Town Park for the Town to Trailside loop starting at 7:00. Early Risers can meet at Michigan Road and start at 6:00.

For more details, check out the Strava event page and sign up there to give us a better idea of numbers. Parking is a bit limited so please consider car pooling.

Michigan to Kimberly V1
2025-07-20 08:00 - 09:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, July 20, 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.
Walkers/Hikers start at 8:00 for a 4-mile loop.

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The last time we ran this course was April 13, 2025
