Run Calendar

Fat Ass Run

Lewisboro Town Park, Upper Lot 1091 Old Post Road, Cross River, NY, United States

This Sunday, November 28, at 8:00 a.m, meet at the Lewisboro Town Park upper parking lot (see map) when we run a perennial favorite—the Fat Ass Run. The course runs over the Bergfield bridge and returns via the Meadow and give you from 6 to 11 miles of calorie-burning fun. Cobweb Crew starts at 5:00 […]

Museum to Blue 2

Trailside Museum Reservation Road, Pound Ridge, NY, United States

On Saturday, November 27, at 7:00 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. If you have sharp eyes, you'll see that I've made a mistake and labeled the blue and orange […]

Black Friday: Five Bridges Run

Lewisboro Town Park, Upper Lot 1091 Old Post Road, Cross River, NY, United States

On Friday, November 26, at 7:00 a.m., meet at Lewisboro Town Park ready to run the Five Bridges run. The 7.5 mile version of the run passes by five of the major bridges in the park but you have options for longer and shorter distances. So ditch the Black Friday crowds and come out for […]

Annual Turkey Trot

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United States

On Thursday, November 25, at 6:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Bushwhack Bonanza run. Many of you know the Dancing Rock run, well, this course uses many of the same trails and bushwhacks so you know it's going to be fun. As such, this makes for […]

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Leather Raven

Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United States

On Sunday, November 21, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the ultimate in courses—the Leather Raven. While the full course is 12 miles, you have some options. You can start from the old oak tree and head in either direction. Head east and run the Loop course […]

Leonard Park to Butler

Leonard Park 104 Main St., Mt. Kisco, NY, United States

This Saturday, November 20, at 7:00 a.m., meet at the gazebo at Leonard Park in Mt. Kisco (see map) when we tackle the different trails from Leonard Park. We’ll start in Leonard park, go through Marsh Sanctuary, Merestead, and Butler. This is a test run for the Leonard Park Half scheduled for December 5 so […]

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Raven Rocks Run

Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United States

On Sunday, November 14, at 9:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run The Raven Rocks Run—a challenging 10k trail race. This year, the race is in-person plus you can join the Raven 100K Challenge and collect as many badges as you can over the course of the month. Register […]

Michigan to Clark

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United States

On Saturday, November 13, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Clark course. This 7.5 out-and-back takes us out of the Rez to the adjoining Clark preserve on the southern part of the park. If you're looking for a longer run, follow the Rock […]

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Nevermore

Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United States

On Sunday, November 7, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow lot, for the first of our Ravember runs—the Nevermore Loop. You'll recognize this as the Raven Rocks course except this time, run the course in reverse, heading toward the Trailside museum first and ending through the meadow field. If you had […]

Raven Rocks Course Check

Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United States

Ready to start the month of Ravember? On Saturday, November 6, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Raven Rocks Course Check. This might be the first time you'll run this course this month but it won't the last. Print Map Download the PDF Download the KML […]

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Annunaki Trail

Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United States

On Sunday, October 31, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Kimberly Bridge lot, when we run something special—The Annunaki Trail. Most of you have seen the two large Annunaki paintings in the Rez but there is one more, visible from the Blue Trail, but if you want to get a good look […]

The Devil’s Ledge

Devil's Den Preserve 33 Pent Road, Weston, CT, United States

On Saturday, October 30, at 7:00 a.m., meet at Devil's Den Preserve (33 Pent Road, Weston), ready to run the Devil's Ledge 8-mile course. Devil's Den is the perfect preserve for a Halloween weekend run. The park has been closed since the start of the pandemic and only recently opened. I don't know what we'll […]

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Dancing Rockish Run

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United States

On Sunday, October 24, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Dancing Rockish run. Excitement is building about this year's Dancing Rock run—and whether someone will actually finish the course this year—so this is your chance to see some of the trails on the course. This […]

Westmoreland Perimeter Loop

Westmoreland Sanctuary 260 Chestnut Ridge Rd, Mt. Kisco, NY, United States

Saturday, October 23, at 7:00 a.m., meet at Westmoreland Sanctuary on Chestnut Ridge Road in Mount Kisco when we run the 5.25 mile perimeter loop. This time, we run the course in a clockwise direction (against the arrows) and return to the main lot. Those who want an extra challenge can do the Butler loop […]

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Trail Tuesday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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.

Meadow to Armstrong

Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United States

On Sunday, October 17, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow to Armstrong Loop. This course offers distances of 5, 7, and 8.5 miles and takes us off the reservation into two small preserves to the west of the park. The out-and-back nature of this gives […]

Bennett’s Pond Run

Bennett’s Pond 550-698 Bennetts Farm Rd, Ridgefield, CT, United States

On Saturday, October 16, at 7:00 a.m., meet at the Bennett’s Pond main lot when we run a course that takes us on a counterclockwise loop to the overlook and back. Print Map Download the PDFKML File GPX File

Trail Thursday

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, 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 between 7:00 and 7:30. It's a great way to get your run in early.

Town Park “Short” Loop

Lewisboro Town Park, Upper Lot 1091 Old Post Road, Cross River, NY, United States

Good luck to anyone running Paine to Pain. For those who aren't, on Sunday, October 10, at 8:00 a.m., meet at Lewisboro Town Park, Upper Lot, when we run the Town Park “Short” Loop. This classic course was once a typical run of 4 miles and, while it's kept its name, there are now options […]

Stayin’ Alive 5K
to benefit first responders

On Saturday, October 9, at 8:00 a.m., meet at the Windmill Club in Armonk for the Stayin’ Alive 5K road race to benefit first responders in northern Westchester. Funds raised through the annual 5K Fun Run, grants, and donations from individuals provide equipment to our emergency responders that is not covered in their annual budget. […]

Virtual Stayin’ Alive 5K
to benefit first responders

Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United States

On Saturday, October 9, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, where we'll run the Green Loop for our own Virtual Stayin’ Alive 5K trail race. Stayin’ Alive benefits first responders in northern Westchester and funds raised through the annual 5K Fun Run, virtual 5k, grants, and donations from individuals […]