Run Calendar

Paine to Pain Half Marathon

Thomas Paine Cottage 20 Sicard Avenue, New Rochelle, NY, United States

On Sunday, October 9, at 9:00 a.m., meet at Thomas Paine Cottage in New Rochelle to run Paine to Pain half maraton—a giant single loop that winds its way through the woods and trails of five different lower Westchester parks. You never run the same trail twice and will spend 90% of your time on […]

Eleanor’s Escape

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

On Sunday, October 9, at 8:00 a.m., if you're not running Paine to Pain, meet at Ward Pound Ridge Reservation, Michigan Road 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. Cobweb Crew starts at 5:00 a.m.; Early […]

Zofnass Family Preserve Run

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

This Saturday, October 8, at 7:00 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 with a network of trails noted for its crags and rock outcrops. Meet at the main entrance and we’ll follow a perimeter loop making all […]

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.

Crazy 8

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

This Sunday, October 2, 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. If you’re not up for the full distance, turn back at Kimberly Bridge for a respectable 4.5-mile run. […]

Kessel Run

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

On Saturday, October 1, 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 […]

Museum, CB, to Blue 2

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

On Sunday, September 25, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum, when we run the Museum, CB, to Blue Route. All distances start up FH and branch from there. The 8 mile loop takes a bushwhack to get to CB before meeting up with the other distances on Green. Options include […]

Loops of Levy

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

On Saturday, September 24, 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. Print Map Download the PDF

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.

Three is a Magic Number

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

On Sunday, September 18, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, and discover why three is a magic number. No specific course today, that's going to be up to you, but the goal is to reach consecutive intersections counting by three. I've included a map that gives very approximate cumulative distances […]

Sarah Bishop Course

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

On Saturday, September 17, at 7:00 a.m., meet at Mountain Lakes Park, Pool Parking Lot, ready to run the Sarah Bishop course. While there is no Sarah Bishop race this year, we can still enjoy some awesome trails there. Print Map Download the PDF Download the KML Download the GPX

Trail Thursday & Cobweb Crew

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. Want to start earlier? Cobweb Crew will begin at 5:00 and circle back to the lot at […]

Where the Pavement Ends

Ridgebury School, Ridgefield, CT 112 Bennetts Farm Rd, Ridgefield, CT, United States

On Sunday, September 11, 7:30 a.m., run Where the Pavement Ends, a fun and challenging 4-plus miles of sometimes narrow, sometimes hilly, always beautiful trails. It is a great mix of fire road, single track, flats, hills, and one fast downhill section right towards the end. Park at the Ridgebury School, Ridgefield, CT and walk […]

Gerrython

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

On Saturday, September 10, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run an all-time favorite: the Gerrython. This course, designed by Gerry Sullivan, gives you options for 13, 10, 7, and 5 mile distances. Our plan: Cobweb Crew meets at 5:00 a.m. and will complete the 7-mile course […]

End of the Madness

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

On Monday, September 5, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, when we run the Stark Raven Mad course backwards. Also known as the "Where's Jacob" run, we'll see if he's still out on the course. Print Map Download the PDF

Stark Raven Mad

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

On Sunday, September 4, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run a new course that's Stark Raven Mad. This the 6.2 mile course follows the Raven Rocks course but starts at Michigan Road. You also have options for longer and shorter distances. Sunday Runs regular Jacob Benesch […]

Saugatuck Loop

Saugatuck Trailhead 190 Davis Hill Road, Weston, CT, United States

On Saturday, September 3, at 7:00 a.m., start your Labor Day weekend off with a long run. Meet at the trailhead of the Saugatuck trail on 190 Davis Hill Road in Weston ready to run the 13 mile Saugatuck Loop which takes us on the Saugatuck Trail and through Trout Brook Valley. There is also […]