Sunday Runs with the Leatherman Harriers

Paine to Pain Half Marathon
2022-10-09 09:00 - 12:00 (America/New_York) | Thomas Paine Cottage, 20 Sicard Avenue, New Rochelle, NY, 10804, 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 dirt (and rocks and roots) in the shade of the woods.
Many of the trails are completely hidden from public view and host a wide variety of wildlife including deer, fox, coyote, turtles, rabbits, hawks, owls, herons, wild turkeys, bald eagles (as of April 2021), and other critters.
Where: Start/End in New Rochelle, just 4 train stops north of midtown Manhattan.
Start at Thomas Paine Cottage, New Rochelle, New York, end at New Rochelle High School. (Both at the intersection of North Ave. and Broadview Ave.)

Eleanor’s Escape
2022-10-09 08:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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 Risers 7:00 a.m.
Rookie Runners start at 7:00 for a shorter course and easier pace.

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Zofnass Family Preserve Run
2022-10-08 07:00 - 08:45 | Zofnass Family Preserve, 258 Upper Shad Rd., Pound Ridge, NY, 10576, 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 right turns except for exiting the park. We’ll make a 6-mile loop counter-clockwise around the preserve excluding the orange, western loop. If you’re looking to turn this into a long run, explore the Zofnass to Mianus River Gorge run of 16 miles or, maybe, we can drive over to Mianus River Gorge for a short 4-mile out-and-back, you know, just for fun.
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Crazy 8
2022-10-02 08:00 - 10:00 | Lewisboro Town Park, Upper Lot, 1091 Old Post Road, Cross River, NY, 10590, 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. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00 a.m. Note: the Lewisboro Horseman’s Association will have its annual Country Pace event in the park starting and ending at the Meadow Lot at 9:00 a.m. Our course is designed to avoid using trails traditionally used for their event so you shouldn’t need to worry about crossing paths. That said, if you follow a different course and encounter a horse and rider, stop and give the right of way to them—they’re much bigger than you.
Rookie Runners start at 7:00 for a shorter course and easier pace.

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Kessel Run
2022-10-01 07:00 - 09:00 | Lewisboro Town Park, Upper Lot, 1091 Old Post Road, Cross River, NY, 10590, 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 distance, turn around whenever you want for a shorter run. A number of runners will be at Cats Tail Marathon, including me, so bring your own maps and have a great run.

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Museum, CB, to Blue 2
2022-09-25 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, 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 4, 5, 6, and 8 miles. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 a.m. for a shorter distance and easier pace.

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Loops of Levy
2022-09-24 07:00 - 09:00 | Leon Levy Preserve, 2-50 Smith Ridge Rd., South Salem, NY, 10590-1701, 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.

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Trail Thursday
2022-09-22 05:30 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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
2022-09-18 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, 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 to reach each intersection and back so you can run whatever distance you want, on whatever trail you want to reach your goal. Cobweb Crew starts at 5:00; Early Risers at 7:00.

Rookie Runners start at 7:00 for a shorter distance and easier pace.

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Sarah Bishop Course
2022-09-17 07:00 - 09:00 | Mountain Lakes Park, 201 Hawley Drive, North Salem, NY, 10560, 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.

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Trail Thursday & Cobweb Crew
2022-09-15 05:00 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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 5:30 because sleep is overrated.

Where the Pavement Ends
2022-09-11 07:30 - 09:00 | Ridgebury School, Ridgefield, CT, 112 Bennetts Farm Rd, Ridgefield, CT, 06877, 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 over the Serfilippi Field, ready to run at 7:30 a.m. or register for the Double starting at 7:00. Cobweb Crew starts at Lewisboro Town Park at 5:00 a.m. but will return in time to make it to the race.
No Rookie Runners run this week but this race is rookie-friendly.

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Gerrython
2022-09-10 07:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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 returning to the lot before 7:00. At 7:00 we’ll run the 10-mile loop. Anyone not up for the full 10 can follow the 5-mile course or head back via Yellow from intersection 36 or a bit over 6 miles.

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End of the Madness
2022-09-05 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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.

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Stark Raven Mad
2022-09-04 08:00 - 22:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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 will be starting his attempt of 17 consecutive loops—100 miles—starting at 8:00 so now you see why the run gets its name. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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Saugatuck Loop
2022-09-03 07:00 - 10:00 | Saugatuck Trailhead, 190 Davis Hill Road, Weston, CT, 06883, 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 parking at the corner of Davis Hill and Valley Forge Road.

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Michigan 4x8 Challenge
2022-08-28 08:00 - 22:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, 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 4×8 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 can be completed within an hour. At 5:00 a.m., we’ll start with the magenta loop, then work our way in a clockwise pattern hitting the purple and then green loops. At 8:00, we’ll start with yellow, then blue, orange and so on, using our cars as aid stations between loops. Total distance would be just over 50k but you can stop whenever you want. This is the last weekend before the close of the Run Like a Wolf challenge so it’s a great opportunity to get those miles logged. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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Catskill Fire Tower Run Part 2
2022-08-27 07:00 - 15:00 | Dry Brook Ridge Trailhead, 72 Balsam Mtn Camp Road, Margaretville, NY 12455, Dry Brook Ridge Trailhead, 72 Balsam Mtn Camp Rd, Margaretville, NY, 12455, 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 there, then head to the Catskill Visitor Center (5096 NY-28, Mt Tremper, NY 12457) for the final Fire Tower of the day. After, we’ll head to the Phoenicia Diner. Total running distance should be under 10 miles with a vertical gain of around 4,000 feet.
If you want to share a ride, meet at the Woods Bridge MTA Commuter Parking Lot in Katonah before 4:45. We’ll be leaving promptly at 4:45 a.m. returning mid-afternoon.

Town Park “Short” Loop
2022-08-21 08:00 - 10:00 | Lewisboro Town Park, Upper Lot, 1091 Old Post Road, Cross River, NY, 10590, 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. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00.
Rookie Runners start at 7:00 a.m. for a shorter distance and easier pace.

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5 Sisters
2022-08-20 07:00 - 12:00 | Bear Mountain, Hessian Lake Parking, 10911, 55 Hessian Drive, Tomkins Cove, NY, 10986, 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 it’s an aggressive course to be sure. Make sure you bring plenty of water since there’s no aid station along the way. If you’re looking to share a ride, meet at the Woods Bridge Metro North commuter lot in Katonah at 6:00 a.m.

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Trailside, Raven, to Tower
2022-08-14 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, 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 7 mile distances and if you’re looking for something longer, continue around Blue to add even more. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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KMA to Hunt-Parker
2022-08-13 07:00 - 09:00 | Reservoir Road, 10 Reservoir Road, Katonah, NY, 10536, United States
On Saturday, August 13, at 7:00 a.m., meet at Reservoir Road in Katonah, behind the Katonah Museum of Art, ready to run the KMA to Hunt-Parker 7-mile course. This run starts on dirt roads, crosses the Cross River Dam, and heads over to Hunt-Parker Preserve—home of the Bedford Audubon Society—with various trails including single-track and open field running. This time, we’ll actually follow the map (which hasn’t always been the case). If you’re looking for something longer, print out the Six Preserves Run map and I can point you to the easement to get to Mount Holly Sanctuary from North Salem Road.

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Meadow to Armstrong
2022-08-07 08:00 - 10:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, August 7, 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 you plenty of choices to customize distance including returning through the BRLA trail off Honey Hollow Road.Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter course and an easier pace.

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Blue-Per Bowl
2022-08-06 05:00 - 12:00 | Depew Ct., Peekskill, NY, 1 Depew Court, Peekskill, 10566, United States
On Saturday, August 6, at 5:00, 7:00 a.m., and 9:00 a.m., meet at the Depew Court lot at Blue Mountain and run the Fifth Annual Blue-Per Bowl run. Starting at 5:00 a.m., make one 7.5 mile loop and a second starting at 7:00 a.m. Join in for one or both loops or finish a third loop and enter the Blue-Per hall of fame. Finish a fourth loop and you’ll become the undisputed Blue-Per Master and be regaled in stories and song. Who’s game?! Kevin Rader will be on hand to make sure you find your way. I’m in for at least the 7:00 loop.

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Green Rock Trail
2022-07-31 08:00 - 09:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, July 31, 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, Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.

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Loops of Levy
2022-07-30 07:00 - 09:00 | Leon Levy Preserve, 2-50 Smith Ridge Rd., South Salem, NY, 10590-1701, United States
On Saturday, July 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 you’re looking for something longer, you’ll have fun on your own.

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Kimberly Blue Route
2022-07-24 08:00 - 09:30 | Ward Pound Ridge Reservation, Kimberly Bridge, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, July 24, 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. Cobweb Crew starts at 5:00; Early Risers at 7:00. Make sure you bring plenty of water, it’s going to be a warm one.
Rookie Runners start at 7:00 for a shorter loop and easier pace.

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Catskill Fire Tower Run
2022-07-23 07:00 - 19:00 | Becker Hollow Parking Lot, 4120 NY-214, Elka Park, NY, Becker Hollow Parking Lot, 4120 NY-214, Elka Park, NY, 12427, United States
On Saturday, July 23, at 7:00 a.m., meet at Becker Hollow Parking Lot, 4120 NY-214, Elka Park, NY (Google map ››) when we run the Catskills Fire Tower Challenge. We’re going to start at the Hunter Mountain trailhead and hit Tremper, and Overlook. Anyone who wants to hit all five can continue to Red Hill and Balsam, but considering the temperature, I’m going to suggest we leave those until September. I’ve left Upper Esopus off the list which is at the Catskills Visitor Center, not actually on a mountain. The course I’ve laid out gets us to the three towers that are closest together so, after we finish with Overlook, we can visit the Phoenicia Diner. Make sure you bring plenty of water on this run.
If you want to share a ride, meet at the Woods Bridge MTA Commuter Parking Lot in Katonah before 5:00. We’ll be leaving promptly at 5:00.

Trailside to Green
2022-07-17 08:00 - 10:00 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, July 17, 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.

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Kimberly Blue Route
2022-07-16 07:00 - 09:30 | Ward Pound Ridge Reservation, Kimberly Bridge, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, July 16, 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 we’ll opt for the 6.5 mile loop. If you need a longer run, there’s always that option as well.

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