Run Calendar

Meadow to Rock Trail Loop

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

This Sunday, June 12, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow lot, when we run the Meadow to Rock Trail Loop, v2. We’ll head south from the meadow heading up the CB trail and make one of three loops before returning via FH, the Magic Stairs, and Trailside Museum. In between, you’ll […]

Giant Pizza Run

Sleeping Giant State Park 200 Mt. Carmel Ave, Hamden, CT, United States

This Saturday, June 11, at 8:00 a.m., meet at Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT 06518, for up to 10 miles of hills, trails, rocks, and one very cool castle. If you want to ride share, meet at Lewisboro Town Park lower lot at 7:00 a.m. Bring a change of clothes and some cash […]

A Mild Sprain

Sprain Ridge Park 149 Jackson Ave, Yonkers, NY, United States

On Sunday, June 5, at 9:45 a.m., don’t miss out on the annual “A Mild Sprain” Trail Run (5 mile run/3 mile walk/hike) on Sunday, June 5, 2022, at Sprain Ridge Park, Hastings-on-Hudson, NY. “A Mild Sprain” is one of Westchester’s largest grassroots fundraisers. Over the past 9 years, the event has raised more than […]

Pound Ridge Color Run

Looking for something a little different? While not trail, the Pound Ridge Color Run is a fun 5k hosted by the Pound Ridge Partnership in collaboration with the Human Rights Advisory Committee. The run is the town’s first-ever 5K road race and is dedicated exclusively to celebrating Pride Month—with a splash of Holi-inspired color! After […]

Town Park Perimeter Loop

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

On Saturday, June 4, at 7:00 a.m., meet at Lewisboro Town Park, upper lot, ready to run a clockwise loop around Ward Pound Ridge Reservation. The full loop is 12 miles but you have options for 6 and 8 miles as well. Bring your own maps, though, I'm not sure I can make this one. […]

REDRUN

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

On Memorial Day, Monday, May 30, at 7:00 a.m., meet at Michigan Road Lot to test yourself and find out who’s going to get the crown on one counterclockwise loop of Red. It's simple. 5.32 miles. The current course records are 36:09 for Chris Irwin and 41:50 for Julie Piddington although the competition for the […]

Michigan Multiloop

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

On Sunday, May 29, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run all or part of the Michigan Multiloop Course (A.K.A. The Death Spiral). The 8:00 start will follow the 8 or 5 mile loop and you can continue with whatever loops you'd like. Those looking for a […]

Zofnass Family Preserve Run

Zofnass Family Preserve 258 Upper Shad Rd., Pound Ridge, NY, United States

This Saturday, May 28, at 7:00 a.m, meet at the Zofnass Family Preserve on Upper Shad Road in Pound Ridge (see Google Map) when we take a break from our epic Saturday runs and run everyone’s favorite labyrinthian preserve with a network of trails noted for its crags and rock outcrops. Meet at the main […]

Meadow to Green Loop

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

On Sunday, May 22, at 8:00 a.m., meet at the Ward Pound Ridge Meadow Lot when we run the Meadow to Green Loop. This course heads to the Trailside Museum before circling around to Michigan Road. From there, take the Green trail to some of the smaller, lesser-used white trails in the Southern portion of […]

Westmoreland Perimeter Loop

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

Saturday,May 21, 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. You can choose which direction you want to run when you arrive but bring a map—I won't be there for this one. Those who want an extra challenge can do the […]

Flower Blood Moon Run—CANCELLED

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

FORECAST shows 85% cloud cover for tonight so I'm going to cancel the run. If it clears up, you can always head over to the Meadow Lot for the eclipse anyway—it's a great place to see it. On Sunday, May 15, at 11:00 p.m., meet at Lewisboro Town Park for a special night run—the Flower […]

Five Bridges Run

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

On Sunday, May 15, at 8:00 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 Rez but you have options for longer and shorter distances should you choose. Cobweb Crew starts at 5:00; Early Risers […]

Mountain Lakes and Adjacent

Mountain Lakes Park 201 Hawley Drive, North Salem, NY, United States

On Saturday, May 14, at 7:00 a.m., meet at Mountain Lakes Park, Trailhead to Lookout Point, ready to run the Mountain Lakes and Adjacent course. This course will take us to the Hearst-Mead and Halmi Preserve—two unique preserves that are part of the North Salem Open Lands Foundation. Anyone interested in extending the run can […]

Trailside to Overlook

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

On Sunday, May 8, 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 […]

Bennett’s Pond Overlook Loop

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

On Saturday, May 7, at 7:00 a.m., meet at Bennett's Pond parking lot ready to run the 7-mile Overlook Loop. This course takes us to the overlook and back and has a nice mix of hills and winding single-track. Anyone who knows Bennett's Pond knows that the first part of this run can get overgrown […]

Eleanor’s Escape on Godino Day

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

On Sunday, May 1, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run a classic on a very special day. Sunday, May 1, 2022, has been designated Judy and Tony Godino Day by the Westchester County Board of Legislators so we'll be running a classic course from Michigan Road—Eleanor's […]

Loops of Levy

Leon Levy Preserve 2-50 Smith Ridge Rd., South Salem, NY, United States

On Saturday, April 30, at 7:00 a.m., meet at the Leon Levy Preserve lot, 2-50 Smith Ridge Rd, South Salem, NY, ready to run a convoluted course of around 7 miles and using every trail in the park including the Levy East half mile extension. I'm good for one trip through this maze so if […]

Arbor Day Celebration

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

Join the Sunday Runners on a Special Tuesday Night at an Arbor Day Party $20 before the event or cash at the door of Westmoreland Sanctuary gets you drinks, decorations, and great conversation. We’ll have space inside and outside the nature center so you'll have plenty of space to hang out. Optional to bring a […]

$20

34th Annual Leatherman’s Loop

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

On Sunday, April 24, at 9:00 a.m., we’ll be meeting at the Meadow lot for the 34th 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. For those who like to get organized ahead of time, we will have early bib & shirt pickup […]

Meadow Museum Fire Tower to Michigan

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

On Saturday, April 23, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, when we run the Meadow Museum, Fire Tower to Michigan loop. Sure, we ran this last Sunday. This time, though, we may take some wrong turns. Might want a change of clothes. Just sayin'. Print Map Download the PDF

Meadow Museum Fire Tower to Michigan

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

On Sunday, April 17, 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 […]