May 14, 2026

February 7, Looper Bowl Sunday

This Sunday, February 7, at 8:00 a.m., meet at the Ward Pound Ridge Meadow Parking Lot and rise to the challenge of the Fifth Annual Looper Bowl. Follow the loop […]

January 31, Reis Park / Angle Fly

This Sunday, January 31, at 8:00 a.m., meet at a new location—Reis Park in Somers—when we run the Reis Park/Angle Fly 6 Mile Loop. This set of trails is well marked […]

January 24, Meadow Parking Lot

This Sunday, January 24, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Meadow Lot when we run the RAVEN LUNATIC—all of the fun of the Raven Rocks Run but […]

January 17, Michigan Road Lot

This Sunday, January 17, at 8:00 a.m., meet at the Ward Pound Ridge reservation Michigan Road Lot when we run Rob’s Run—6.5 miles of trails in the southern portion of the […]

January 10, Mountain Lakes Park

This Sunday, January 10, at 8:00 a.m., meet at the trail head to Lookout Point in Mountain Lakes Park (201 Hawley Road, North, Salem, NY) when we run the 10K-ish […]

January 3, Trailside Museum

This Sunday, January 3, at 8:00 a.m., meet at the Ward Pound Ridge Trailside Museum when we run the Museum to Blue Route. This 7-mile course starts down the Orange […]

December 27, Lewisboro Town Park

This Sunday, December 27, at 8:00 a.m., meet at the Lewisboro Town Park upper lot when we run a new variation of our annual Fat Ass run which will take […]

December 20, Meadow Parking Lot

Trail Running, Westchester, New York, rock trail

This Sunday, December 20, at 8:00 a.m., meet at Ward Pound Ridge Meadow lot when we run a new course—the Rock Trail 8 Mile Loop. We’ll head south through the […]

December 13, Zofnass Family Preserve

This Sunday, December 13, 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 […]

December 6, Sylvan Glen / Granite Knolls

This Sunday, December 6, at 8:00 a.m., meet at Sylvan Glen near Yorktown. This is a former quarry that provided the stone for the ramps to the George Washington and […]

November 29, Michigan Road Lot

This Sunday, November 29, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Michigan Road lot when we run a course devised by Eleanor Heppner Hershey and aptly named […]

November 22, Leonard Park

This Sunday, November 22, at 8:00 a.m., meet at the gazebo at Leonard Park in Mt. Kisco (see map) when we tackle some different trails. We’ll start in Leonard park, […]

November 15, Raven Rocks Run

This Sunday, November 15, at 9:00 a.m., be ready for the inaugural Raven Rocks Run—10(ish) kilometers of challenging trails in Ward Pound Ridge Reservation full of great views, rocky climbs, […]

November 8, Mountain Lakes Park

This Sunday, November 8, at 8:00 a.m., meet at the trailhead to Lookout Point in Mountain Lakes Park (201 Hawley Road, North, Salem, NY) when we run the 5.5 mile […]

November 1, Meadow Parking Lot

This Sunday, November 1, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Meadow Lot when we run a course check of the Raven Rocks Run. This will be […]

October 25, Muscoot Farm

Sunday, October 25 This Sunday, October 26, 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 […]

October 18, Lewisboro Town Park

This Sunday, October 18, at 8:00 a.m, meet at the Lewisboro Town Park Upper Lot when we run a new course that includes a new trail in the Reservation—The Town […]

September 13, Mountain Lakes Park

This Sunday, September 13, at 8:00 a.m, meet at Mountain Lakes Park in North Salem (201 Hawley Road) when we do a course check of the 2015 Sarah Bishop Bushwhack. […]

September 6, Meadow Lot

This Sunday, September 6, at 8:00 a.m, meet at the Ward Pound Ridge Reservation Meadow lot when we run the Meadow to Blue Route. This 6.8 mile course starts up […]

August 30, Mountain Lakes Park

This Sunday, August 30, at 8:00 a.m, meet at Mountain Lakes Park in North Salem (201 Hawley Road) when we do a course check of the 2015 Sarah Bishop Bushwhack. […]

August 23, Bennett’s Pond, Ridgefield, CT

This Sunday, August 23, at 8:00 a.m., meet at a new location on the Ridgefield/Danbury border—Bennett’s Pond—when we run an epic 10.5 mile loop designed by Keith Realander. Meet at […]

August 16, Kimberly Bridge

This Sunday, August 16, at 8:00 a.m., meet at the Ward Pound Ridge Kimberly Bridge Lot to run a new course—a double-loop on DH, Brown and Blue. This 8.3 mile […]

August 9, Lewisboro Town Park

This Sunday, August 9, at 8:00 a.m., meet at the Lewisboro Town Park Upper Parking Lot to run a perennial favorite—The Fat-Ass 7mile Loop. This course starts up the hill […]

August 2, Trailside Museum

This Sunday, August 2, at 8:00 a.m., meet at the Ward Pound Ridge Trailside Museum when we run the Trailside, Raven, to Tower loop. You have choices of a 6 […]

July 26, Mountain Lakes Park

This Sunday, July 26, at 8:00 a.m., meet at the trailhead to Lookout Point in Mountain Lakes Park (201 Hawley Road, North, Salem, NY) when we run the 5.5 mile […]

July 19, Meadow Parking Lot

This Sunday, July 19, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Meadow parking lot when we run the Meadow to Overlook loop. The six-mile loop will take […]

July 12, Westmoreland Sanctuary

This Sunday, July 12, 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 run […]

July 5, Michigan Road

This Sunday, July 5, at 8:00 a.m., meet at the Ward Pound Ridge Michigan Road lot and run the Rock Trail 6.5 mile loop. This course starts out easy enough […]

June 28, Meadow Parking Lot

This Sunday, June 28, at 8:00 a.m., meet at the Ward Pound Ridge Meadow Parking lot to run the Leatherman’s Loop course in our first ever Summer Loopstice. A couple […]

June 21, Meadow Parking Lot

This Sunday, June 21, at 8:00 a.m., meet at the Ward Pound Ridge Meadow Parking lot to run a truly epic run—Eleanor’s Escape. Start at the Meadow and follow FH […]

June 14, Zofnass Family Preserve

This Sunday, June 14, 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 […]

June 7, Butler Sanctuary

This Sunday, June 7, at 8:00 a.m., meet at the Nature Conservancy Butler Sanctuary on Chestnut Ridge Road in Mt. Kisco (see in Google maps) when we run a new […]

May 31, Michigan Road Lot

This Sunday, May 31, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Michigan Road parking lot when we run the Sights and Heights Loop. On this 7.5 mile […]

May 24, Blue Mountain (From Depew Court)

This Sunday, May 24, at 8:00 a.m., meet at a new location when we run the Blue Mountain Reservation Depew Court Loop. This run is a little farther away but it […]

May 17, Options, Options, Options

This Sunday, May 17, you have some great options to choose from. Option 1: A Mild Sprain 4.25 mile Trail Race, Yonkers, NY This Sunday, May 17 at 9:30 a.m., […]

May 10, Mountain Lakes Park

This Sunday, May 10, at 8:00 a.m, meet at Mountain Lakes Park (201 Hawley Road, North Salem, NY) at the trailhead to lookout point when we run all or parts […]

May 3, Michigan Road Lot

This Sunday, May 3, at 8:00 a.m., meet at the Ward Pound Ridge reservation Michigan Road Lot when we run Rob’s Run—six miles of trails in the southern portion of […]

April 5, Zofnass Family Preserve

This Sunday, April 5, at 8:00 a.m., meet at the Zofnass Family Preserve on Upper Shad Road in Pound Ridge (see Google Map) when we run everyone’s favorite labyrinthian preserve […]

March 29, Meadow Parking Lot

On Sunday, March 29, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow Parking Lot when we run the Meadow Dry Loop. This approximately six-mile course follows much of […]

March 22, Michigan Road

On Sunday, March 22, at 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road lot and run some of the southern trails on the Red/Rock loop. I know we’ve […]

March 15, Lewisboro Town Park

On Sunday, March 15, at 8:00 a.m., meet at Lewisboro Town Park when we celebrate 5 Years of Sunday Runs with our Six-Mile Inaugural Loop. Five years ago Rob started […]

March 8, Reservoir Road, Katonah

With our usual trails in such poor shape, we’re going to switch things up this week with the option of some distance work on a more forgiving surface. Our 5th-year […]

March 1, Michigan Road Lot

Sunday, March 1, 8:00 a.m. This Sunday, meet at Ward Pound Ridge Michigan Road lot when we run some of the large southern trails—Red, Yellow, and Green. This 5.5 mile […]

February 22, Kimberly Bridge

Sunday, February 22, 8:00 a.m. This Sunday, meet at Ward Pound Ridge Reservation Kimberly Bridge lot when we run a new course—Blue and Brown. The 4-mile Blue trail has been […]

February 15, Lewisboro Town Park

Sunday, February 15, 8:00 a.m. Meet at Lewisboro Town Park upper parking lot and run the Town to Michigan Loop. From the Town Park, we’ll follow the DH trail  to […]

February 8, Michigan Road Lot

This Sunday,  February 8, at 8:00 a.m., meet at the Ward Pound Ridge Reservation Michigan Road lot when we run some of the best trails that I can find—the Red […]

February 1, Looper Bowl Sunday

This Sunday, February 1 at 8:00 a.m., meet at the Ward Pound Ridge Meadow Parking Lot and rise to the challenge of the Fourth Annual Looper Bowl. Follow the loop […]

January 25, Mountain Lakes Park

This Sunday, January 25, at 8:00 a.m, meet at the trailhead to Lookout Point at Mountain Lakes Park (201 Hawley Road, North Salem) when we run a new course—The MLP […]