June 09, 2026

January 6, Meadow Lot

SUNDAY On Sunday, January 6, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow lot ready to run the Meadow to Armstrong course. This 7-mile course starts in the […]

January 1, Lewisboro Town Park

On Tuesday, January 1, at 8:00 a.m., start the new year off right with some fun. Meet at Lewisboro Town Park Upper Lot when we run one of Peeter’s Fun Loops. All […]

December 30, Kimberly Bridge

SUNDAY On Sunday, December 30, at 8:00 a.m., we’ll celebrate our final Sunday run of the year with the Bosque Encantado 8-mile run. Options include the full run and various shorter distances […]

December 23, Dancing Rock Run

SUNDAY On Sunday, December 23, at 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road Lot ready to run a very special course—The Dancing Rock Run. This course revives a […]

December 16, Relays or Loops

SUNDAY On Sunday, December 16, at 8:00 a.m., meet at Blue Mountain in the lot past the main lodge ready to run a double-loop course totaling 7 miles. Kevin Rader […]

December 9, Zofnass Family Preserve

SUNDAY This Sunday, December 9, at 8:00 a.m., meet at the Zofnass Family Preserve in Pound Ridge (259 Upper Shad Road, see Google Map) when we run everyone’s favorite labyrinthian […]

December 2, Trailside Museum

Let’s start December off with a pair of “Blue” runs. SUNDAY On Sunday, December 2, at 8:00 a.m., meet at Ward Pound Ridge Reservation Trailside Museum when we run the […]

November 25, Lewisboro Town Park

SUNDAY This Sunday, November 25, 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. With the […]

November 18, Westmoreland Sanctuary

SUNDAY Sorry folks, Sunday’s Leonard Park run will have to wait. With all of the rain, parts of the course are tmore trouble than they’re worth. We’ll try again in […]

November 11, Raven Rocks Run

SUNDAY On Sunday, November 11, at 9:00 am., meet at Ward Pound Ridge Reservation in Cross River, NY, when we run the Fourth Annual Raven Rocks Run. The race will […]

November 4, Lewisboro Town Park

SUNDAY This Sunday, November 4, at 8:00 a.m., meet at Lewisboro Town Park Upper Lot when we run a new variation of  The Crazy 8 Run. This 8-mile, figure-8 course will take us on the […]

October 28, Meadow Lot

SUNDAY On Sunday, October 28, at 8:00 a.m., meet at Ward Pound Ridge Meadow Lot and come ready to run the Raven Rocks Course. Here’s your chance to get a […]

October 21, Run the Farm

SUNDAY This Sunday, October 21, at 9:30 a.m, meet at Muscoot Farm (http://goo.gl/maps/dTDiT) for  the Run the Farm 5 Mile Trail Race. This 5 mile course starts from the farm […]

October 14, Michigan Road Lot

SUNDAY This Sunday, October 14, at 8:00 a.m, meet at the Ward Pound Ridge Michigan Road Parking lot to run The FH to Overlook Loop. Start at the Michigan Road […]

October 7, Paine to Pain

SUNDAY On Sunday, October 7, at 9:00 a.m., get ready to run everybody’s favorite trail half marathon in southern Westchester—PaineToPain. The course is a giant loop that winds its way […]

September 30, Sarah Bishop Bushwhack

SUNDAY On Sunday, September 30, at 9:00 a.m., get ready to race the 6th Annual Sarah Bishop Bushwhack—a challenging 10K (ish) trail race featuring the highest peak in Westchester, Bailey […]

September 23, Mianus River Park

SUNDAY On Sunday, September 23, at 8:00 a.m., let’s go where we haven’t been in a while—Mianus River Park on the Stamford/Greenwich border. Meet at the Merribrook Lane parking lot […]

September 16, Where the Pavement Ends

SUNDAY On Sunday, September 16, get ready to run Where the Pavement Ends. Started in 2012, Where the Pavement Ends has become one of the most popular trail races in […]

September 9, Trailside Museum

SUNDAY On Sunday, September 9, at 8:00 a.m., meet at Ward Pound Ridge Reservation Trailside Museum ready to run the Trailside to Blue Loop. Options include 6.5, 7.5,  and 8.5 […]

September 2, Mountain Lakes Park

SUNDAY On Sunday, September 2, at 8:00 a.m., meet at Mountain Lakes Park (201 Hawley Road, North Salem, NY) pool parking lot when we run the Sarah Bishop Course. Ok, that […]

August 26, Meadow Lot

SUNDAY This Sunday, August 26, at 8:00 a.m., meet at Ward Pound Ridge Reservation ready to run a very special course. Let’s call this “Run the Numbers.” Starting at the […]

August 19, Bennett’s Pond

SUNDAY This Sunday, August 19, at 8:00 a.m., meet at Bennett’s Pond on the Ridgefield/Danbury border when we run the 10 mile Realander Run. Meet at the parking lot on […]

August 12, Michigan Road

SUNDAY On Sunday, August 12, at 8:00 a.m., meet at Ward Pound Ridge Michigan Road Lot to run the Michigan to Kimberly Loop. This new variation includes distances of 6, 7.5 and […]

August 5, Lewisboro Town Park

SUNDAY On Sunday, August 5, at 8:00 a.m., meet at Lewisboro Town Park Upper Lot when we run the Town Park to Overlook loop. Options include distances from under 5 […]

July 28, Meadow Lot

SUNDAY On Sunday, July 29, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot when we run a variation of Eleanor’s Escape. This classic run offers 6-mile and […]

July 22, Trailside Museum

SUNDAY On Sunday, July 22, at 8:00 a.m., meet at Ward Pound Ridge Trailside Nature Museum when we run the classic Trailside Museum Multiloop. This course offers runners a variety […]

July 15, Westmoreland Sanctuary

SUNDAY This Sunday, July 15, at 8:00 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 […]

July 8, Michigan Road

SUNDAY On Sunday, July 8, at 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road lot ready to run the Michigan Road Gerrython. Named for Gerry Sullivan, this course […]

July 1, Meadow Lot

SUNDAY This Sunday, July 1, at 8:00 a.m., meet at Ward Pound Ridge Reservation when we run using an entirely new map—the Reservation Subway Series. For the past years, we’ve […]

June 24, Meadow Lot

SUNDAY This Sunday, June 24, at 8:00 a.m., meet at the Ward Pound Ridge Meadow Parking lot to run the Leatherman’s Loop course in our second annual Summer Loopstice. To […]

June 17, Kimberly Bridge

SUNDAY This Sunday, June 17, at 8:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot when we run a course that will take us off the reservation—literally—to Richard’s […]

June 10, Michigan Road Lot

SUNDAY On Sunday, June 10, at 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road lot when we run the Green/Rock trail loop. This 6.5 mile loop will take […]

Wednesday, June 6: Meadow Lot

Wednesday, June 6, is Global Running Day. To celebrate, let’s run the Raven Rocks course. Meet at Ward Pound Ridge Reservation Meadow Lot at 5:00 a.m. ready to run. We’ll […]

June 3, A Mild Sprain

SUNDAY This Sunday, June 3, at 9:45 a.m., meet at Sprain Ridge Park, Yonkers, for the seventh annual A Mild Sprain—the second in the Trail Mix Series of races. Race […]

May 27, Lewisboro Town Park

SUNDAY This Sunday, May 27, at 8:00 a.m, meet at the Lewisboro Town Park Upper Lot when we run a course that includes some of the newest trails in the Reservation—The Town […]

May 20, Mountain Lakes Park

SUNDAY On Sunday, May 20, at 8:00 a.m., meet at Mountain Lake Park, Trailhead to Lookout Point, when we run a course that includes the Old Sib Preserve—the new “lollypop” […]

May 13, Michigan Road Lot

On Sunday, May 13, at 8:00 a.m., meet at Ward Pound Ridge Michigan Road Lot ready to run Eleanor’s Escape. This 7.5 mile loop combines some level double-track trails with […]

May 6, Zofnass Family Preserve

This Sunday, May 6, at 8:00 a.m., meet at the Zofnass Family Preserve in Pound Ridge (259 Upper Shad Road, see Google Map) when we run everyone’s favorite labyrinthian preserve […]

April 29, Kimberly Bridge

SUNDAY On Sunday, April 29, at 8:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot when we run the Boutonville Oak Multidistance Loop. This run gives you opportunities […]

April 22, Leatherman’s Loop

On Sunday, April 22, I hope to see many of you at the 32nd Annual Leatherman’s Loop. For detailed instructions, visit LeathermansLoop.org. You can pick your bib and shirt up […]

April 15, Meadow Lot

On Sunday, April 15, at 8:00 a.m., we’ll be running from the Ward Pound Ridge Reservation Meadow lot with two great options. SUNDAY OPTION 1: JOHN JAY 5K At 8:00 […]

April 8, Michigan Road Lot

SUNDAY On Sunday, April 8, at 8:00 a.m., get ready to run a very special course—The Dancing Rock Run. This course revives a race that was held by Tony Godino […]

April 1, Trailside Museum

SUNDAY On Sunday, April 1, at 8:00 a.m., meet at Ward Pound Ridge Reservation Trailside Nature Museum and run the Trailside Multiloop, the 8.5 mile course. This course will take […]

March 25, Lewisboro Town Park

SUNDAY On Sunday, March 25, at 8:00 a.m., meet at Lewisboro Town Park ready to run our inaugural loop on the northern trails and commemorate the start of the group […]

March 18, Michigan Road

SUNDAY On Sunday, March 18, at 8:00 a.m., meet at Ward Pound Ridge Michigan Road lot and run the Michigan Double—7 miles of a double-loop course on some of the […]

March 11, Raven Lunatic

SUNDAY On Sunday, March 11, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Lot and run the Raven Lunatic—The Raven Rocks course but with snow—because anyone who’s running […]

March 4, Michigan Road

SUNDAY On Sunday, March 4, at 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road lot and run the Gerrython. This run is normally reserved for fall but the […]

February 25, Trailside Museum

SUNDAY This Sunday, February 25, at 8:00 a.m., meet at Ward Pound Ridge Trailside Museum lot when we run the Trailside, Raven, to Tower loop. This course has a great […]