Run Calendar

Town Park to Green

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

This Saturday, June 15, at 7:00 a.m, meet at the Lewisboro Town Park upper parking lot (see map) when we run the Town Park to Green course. This course gives you options of 4, 6, and 8 miles of mixed-terrain fun. When you get to the Mill Site, follow the CB trail to Michigan Road […]

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 at 7:00.

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.

Eleanor’s Great Escape

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

On Sunday, June 9, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run a classic—Eleanor's Great Escape. This multidistance run takes you on a great mix of some of the best trails in the park and includes an awesome 8.4 mile option that might run a little long. Cobweb Crew […]

Westmoreland Perimeter Loop

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

On Saturday, June 8, 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 and explore the additional 28-acre parcel that has been recently acquired. Early Risers can meet at Butler Sanctuary just across the street at 6:00 a.m. for a 4-mile 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 at 7:00.

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, June 2, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Dancing Rockish run. We normally run this in December but let's change things up. This version follows much of the old Dancing Rock route while staying on all trails. Cobweb Crew starts at 5:00; Early […]

Mountain Lakes Park

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

On Saturday, June 1, at 7:00 a.m., meet at Mountain Lakes Park, Hemlock Lake Beach Parking Lot, when we run a variation of the Sarah Bishop course that meanders through much of the park. This version takes a turn that we haven't used since the early days of the race but keeps the best parts […]

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 at 7:00.

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.

REDRUN

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

On Memorial Day, Monday, May 27, 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 Grant although the competition for the […]

Trailside Multiloop

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

On Sunday,May 26, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Nature Museum Lot, ready to run a new variation of the Trailside Multiloop. You have several options for distances but starting at 5:00, we'll run the 8 mile course. At 7:00, the 4 mile, and at 8:00, it's your call. Cobweb Crew […]

Bennett’s Pond Overlook Loop

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

On Saturday, May 25, 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. The lot is small but we can get creative with parking if necessary. Early Risers can […]

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.

Spring Run the Farm

Muscoot Farm 51 NY-100, Katonah, NY, United States

This Sunday, May 19, at 9:30 a.m, meet at Muscoot Farm (http://goo.gl/maps/dTDiT) for the Spring Run the Farm 5 Mile Trail Race. This 5 mile course starts from the farm and follows the outlying trails around Muscoot but in the opposite direction as the fall course. You can download a map of the five-mile course […]

Loops of Levy

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

On Saturday, May 18, 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. Early Risers start at 6:00 for an additional 4 miles. […]

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.

Michigan to Kimberly V3

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

On Sunday, May 12, 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. This is a Mother’s Day […]

Dancing Rockish Run

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

On Saturday, May 11, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Dancing Rockish run. This course follows much of the old Dancing Rock route while staying on all trails. Early Risers start at 6:00 for a few extra miles. Print Map Download the PDF From the […]

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 Rock Trail Loop

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

This Sunday, May 5, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow lot, when we run the Meadow to Rock Trail Loop. We’ll head south from the meadow up the CB trail and make one of three loops before returning via FH, the Magic Stairs, and Trailside Museum. In between, you’ll see Dancing […]

Kessel Run

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

On Saturday, May 4, at 7:00 a.m., meet at Lewisboro Town Park, Upper Lot, ready to run the Kessel Run. This out-and-back course is nine non-technical miles on some of the fastest trails in the Rez so you'll be able to stretch your legs and gain some speed. If you're not up for the full […]

Trail Running Film Festival

Bedford Playhouse 633 Old Post Rd, Bedford, United States

On Thursday, May 2, at 7:00 p.m., join the Leatherman Harriers, the trail running community, film buffs, and anyone who wants to see good stories, at the Trail Running Film Festival at Bedford Playhouse. Sunday Runs is sponsoring this one-night-only event that brings to life great tales from the running community. But you don't need […]

$20

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.

36th Annual Leatherman’s Loop

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

On Sunday, April 28, at 9:00 a.m., we’ll be meeting at the Meadow lot for the 35th 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 […]

Night Run

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

On Friday, April 26, at 7:00 p.m., meet at Ward Pound Ridge Reservation, Michigan Road lot at lean-to 5, for a special Night Run. This course is a classic and takes us to the Overlook and Raven Rocks. Bring a headlamp for the run and some food or drink for, you know, recovery afterward. And […]

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 Museum Fire Tower to Michigan

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

On Sunday, April 21, 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 […]

Meadow to Armstrong

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

On Saturday, April 20, at 7:00 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 […]

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 John Jay

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

On Sunday, April 14, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run. If you're signed up for the John Jay 5k, we'll head up Howland and over to John Jay in time for the race to start. If you're not competing, you can continue around the northern perimeter on […]

Museum, CB, to Blue

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

On Saturday, April 13, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum, ready to run the Museum, CB, to Blue Route. All distances start up FH and branch from there. The 6.5 and 8-mile loops take a couple of bushwhacks before meeting up with the 5-mile course. Early Risers start at 6:00 […]

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.

Five Bridges Run

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

On Sunday, April 7, at 8:00 a.m., meet at Lewisboro Town Park (upper lot until full, then lower lot) 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. […]

Butler to Meyer

Butler Sanctuary 265 Chestnut Ridge Rd, Mt Kisco, NY, United States

On Saturday, April 6, at 7:00 a.m., meet at Butler Sanctuary in Mt. Kisco ready to run the Bulter to Meyer course. It's been over three years since we ran this course which includes a section of Byram Lake Road and Oregon Road so you'll have an opportunity to stretch your legs plus get plenty […]

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.

Red/Rock Trail Loop

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

On Sunday, March 31, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, when we run the Red/Rock Trail Loop. We’ll run this in a counterclockwise direction as marked and runners have the opportunity to run distances from 4 to 8.5 miles. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00.Rookie […]

Run the Numbers Part 5

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

On Saturday, March 30, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the fifth part of the Run the Numbers course. Today, those starting at 6:00 a.m. will catch intersections 58 and 59 a four-mile run, then at 7:00, we'll catch 60 through 66 for an additional 7.5 […]

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.

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.

Mudders, Grunters, Trailside, and Town Park

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

On Sunday, March 24, you've got some options. At 10:00 a.m., meet at FDR State Park ready to race Mudders and Grunters, a 5 mile course of trails and mud. But if you'd like to stay closer to home, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the […]

Run the Numbers Part 4

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

On Saturday, March 23, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the fourth part of the Run the Numbers course. For the next several weeks, we'll be running this course a piece at a time. Today, those starting at 6:00 a.m. will catch intersections 47–49 a four-mile […]

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.

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.

Michigan 4×8 Challenge

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

On Sunday, March 17, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan 4x8 Challenge. The entire Challenge starts at 5:00 a.m. but you can start whenever you want, including 8:00 a.m. This course consists of a series of 4-mile (approximate) clockwise loops in the Rez that […]

Run the Numbers Part 3

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

On Saturday, March 16, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the third part of the Run the Numbers course. For the next several weeks, we'll be running this course a piece at a time. Today, those starting at 6:00 a.m. will catch intersections 25 through 32—a […]

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.