Run Calendar

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 […]

Michigan 4×8 Challenge

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

On Sunday, August 28, 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 […]

Catskill Fire Tower Run Part 2

Dry Brook Ridge Trailhead, 72 Balsam Mtn Camp Road, Margaretville, NY 12455 Dry Brook Ridge Trailhead, 72 Balsam Mtn Camp Rd, Margaretville, NY, United States

On Saturday, August 27, at 7:00 a.m., meet at Dry Brook Ridge Trailhead, (72 Balsam Mtn Camp Rd, Margaretville, NY 12455), when we run the second half of our Catskills Fire Tower Challenge. We'll climb Balsam Mountain, drive to the new Red Hill Trailhead Lot on Denning Road (WFPC+374, Denning, NY 12725) and climb from […]

Town Park “Short” Loop

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

On Sunday, August 21, at 8:00 a.m., meet at Lewisboro Town Park, Upper Lot, when we run the Town Park “Short” Loop. This classic course was once a typical run of 4 miles and, while it's kept its name, there are now options that aren't so short including the 9 mile course to Raven Rocks. […]

5 Sisters

Bear Mountain, Hessian Lake Parking 10911, 55 Hessian Drive, Tomkins Cove, NY, United States

On Saturday, August 20, at 7:00 a.m., meet at the Bear Mountain Ice Rink Lot, 3020 Seven Lakes Drive, Tomkins Cove, NY 10986 ready to run some epic trails at Harriman State Park—the 13 mile Five Sisters run. This 13-mile loop with 3,000 feet of vertical gain tackles five of the summits within Harriman so […]

Trailside, Raven, to Tower

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

On Sunday, August 14, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Nature Museum Lot, ready to run the Trailside, Raven to Tower loop. We'll all head up everyone's favorite way to start a run—The Fox Hill climb—and then take some of the less-traveled trails from Michigan Road. Options include 4.5, 6, or […]