June 17, 2026
On Saturday, June 24, 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. We haven't been to Bennett's Pond in a while since the parking lot isn't very large. […]
On Sunday, June 24, at 8:00 a.m., meet at the Trailside Nature Museum lot ready to run the Trailside to Green loop. Options include distances of 5.5, 7.5 and 9 miles. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00 Rookie Runners arrive at 7:00 a.m. for a shorter loop at an easier pace. […]
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the […]
Race director (and multi-time winner of the Loop) Gerry Sullivan says anyone can race on a weekend. The toughest do it on a weekday. Anyone can relax and rewind after a day of work but how about a nice trail run on a gorgeous (hopefully) summer evening? Sounds good? Then join us at Bowdoin Park […]
This Saturday, July 1, at 7:00 a.m., meet at Tazza Café, 408 Main St, Ridgefield, CT, and prepare to run the 11 mile Brew to Brews run through Devil’s Den and Saugatuck. Options include the full 11 miles and an abbreviated 6 mile version. 7:00 to 7:30 a.m. Get Some Fresh Brewed Meet at Tazza Café, […]
On Sunday, July 2, at 8:00 a.m., meet at Michigan Road Lot ready to run the Michigan to Kimberly (v2) run. Options include 6.5, 7.5, and 9 mile distances. Cobweb Crew starts at 5:00; Early Risers at 7:00. Rookie Runners start at 7:00 for a shorter distance and easier pace. Print Map Download the PDF
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of stride workout. We'll warm up with a loop of DH to Reservation Road then head over to Blue […]
On Friday, July 7, 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 […]
On Saturday, July 8, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Michigan to Armstrong Loop. We'll follow the Meadow to Armstrong map that takes us off the reservation into two small preserves to the west of the park. But we'll start at Michigan Road and customize the […]
This Sunday, July 9, at 8:00 a.m., meet at Lewisboro Town Park Upper Lot, when we run The Crazy 8 Run. This 8-mile, figure-8 course will take runners on the Blue trail and over the fire tower. Multiple distances are available and if you’re not up for the full distance, turn back at Kimberly Bridge […]
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the […]
On Saturday, July 15, 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 […]
On Sunday, July 16, 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 […]
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the […]
On Saturday, July 22, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Dancing Rock course. This loop starts with a climb to the Overlook then follows some of the lesser-used trails in the park. Options include 4.5, 6.6, 8 and 9 mile loops. Early Risers […]
On Sunday, July 23, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road lot, ready to run the Green Rock Trail course which includes the Overlook, Spy Rock, the Stairs, and Raven Rocks. Options include 4.5, 6.5, 7.5, and 8.5 miles, running counterclockwise, down the stairs, toward Raven Rocks. Cobweb Crew starts at 5:00, […]
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the […]
On Saturday, July 29, at 7:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot ready to run the Kimberly to Blue Route. Start down the Blue trail and choose from 5 miles, 6.5 miles, or 8 miles. Or, for those looking for something more aggressive, spend a few hours doing blue hill repeats […]
On Sunday, July 30, 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 […]