Run Calendar
End of the Madness
Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United StatesOn 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 StatesOn 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 StatesOn 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 StatesOn 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 StatesOn 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 StatesOn 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 StatesOn 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 StatesOn 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 […]
KMA to Hunt-Parker
Reservoir Road 10 Reservoir Road, Katonah, NY, United StatesOn 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 […]
Meadow to Armstrong
Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United StatesOn 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 […]
Blue-Per Bowl
Depew Ct., Peekskill, NY 1 Depew Court, Peekskill, United StatesOn 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 […]
Green Rock Trail
Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United StatesOn 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, […]
Loops of Levy
Leon Levy Preserve 2-50 Smith Ridge Rd., South Salem, NY, United StatesOn 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 […]
Kimberly Blue Route
Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United StatesOn 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, […]
Catskill Fire Tower Run
Becker Hollow Parking Lot, 4120 NY-214, Elka Park, NY Becker Hollow Parking Lot, 4120 NY-214, Elka Park, NY, United StatesOn 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 […]
Trailside to Green
Trailside Museum Reservation Road, Pound Ridge, NY, United StatesOn 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. […]
Kimberly Blue Route
Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United StatesOn 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. Print Map Download the PDF
Mountain Lakes Park
Mountain Lakes Park 201 Hawley Drive, North Salem, NY, United StatesOn Sunday, July 10, at 8:00 a.m., meet at Mountain Lakes Park, Pool Parking Lot (see the map for Sarah Bishop parking), when we run the 2019 Sarah Bishop course that meanders through much of the park. Options include extending the run through Old Sib, Hearst, and Mead-Halmi preserves in case you're looking for a […]
Meyer Preserve
Meyer Preserve 415 Sarles Street, Mt. Kisco, NY, United StatesOn Saturday, July 9, at 7:00 a.m., meet at the parking lot on Sarles Street and Bretton Ridge Road (near 415 Sarles St, Mt Kisco, NY 10549) when we run a loop in the Meyer Preserve. This small preserve offers a mix of terrain, hopefully a load of wineberries, and an access trail to Byram […]
Westmoreland Perimeter Loop
Westmoreland Sanctuary 260 Chestnut Ridge Rd, Mt. Kisco, NY, United StatesOn Monday, July 4, 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. We can choose which direction we want to run when you arrive but plan on taking the extra out-and-back to the Fox Lane ropes course. Those who want an […]
Kessel Run
Lewisboro Town Park, Upper Lot 1091 Old Post Road, Cross River, NY, United StatesOn Sunday, July 3, at 8:00 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 […]
Brew to Brews
Devil's Den Preserve 33 Pent Road, Weston, CT, United StatesThis Saturday, July 2, 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, […]
Michigan to Kimberly
Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United StatesOn Sunday, June 26, 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. The Planetary Society Runners will meet at 4:20 a.m. on Sunday for a predawn glimpse of the […]
Butler Sanctuary
Butler Sanctuary 265 Chestnut Ridge Rd, Mt Kisco, NY, United StatesOn Saturday, June 25, at7:00 a.m., meet at the Nature Conservancy Butler Sanctuary on Chestnut Ridge Road in Mt. Kisco (see in Google maps) when we run a combination of trails covering most of the park. Since Butler is a relatively small preserve, we’ll be following a double loop course to get to 5 to […]
Kimberly Blue Route
Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United StatesOn Sunday, June 19, at 8:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot ready to run the Kimberly to Blue Route. Start down the Blue train and take your choice of 5, 6.5, and 8 mile loops. Cobweb Crew starts at 5:00 a.m.; Early Risers at 7:00. Rookie Runners start at 7:00 […]
Mountain Lakes Park
Mountain Lakes Park 201 Hawley Drive, North Salem, NY, United StatesOn Saturday, June 18, at 7:00 a.m., meet at Mountain Lakes Park trailhead to Lookout Point and run the 2019 Sarah Bishop course that meanders through much of the park. Park at trailhead to Lookout Point, finish at Hemlock South campsite, and head over to the pool area and check out who's still running the […]
Night Run
Ward Pound Ridge Reservation, Michigan Road Lot Michigan Road, Pound Ridge, NY, United StatesOn Friday, June 17, at 7:00 p.m., meet at Ward Pound Ridge Reservation, Lean-To 5 (at Michigan Road), for a special Night Run. While we don't need any special occasion for a night run, come out and celebrate my 60th birthday—even if you don't run. Please, no gifts, just bring yourselves. Sunset is at 8:30 […]
Meadow to Rock Trail Loop
Ward Pound Ridge Reservation, Meadow Lot Reservation Road, Pound Ridge, NY, United StatesThis Sunday, June 12, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow lot, when we run the Meadow to Rock Trail Loop, v2. We’ll head south from the meadow heading up the CB trail and make one of three loops before returning via FH, the Magic Stairs, and Trailside Museum. In between, you’ll […]
Giant Pizza Run
Sleeping Giant State Park 200 Mt. Carmel Ave, Hamden, CT, United StatesThis Saturday, June 11, at 8:00 a.m., meet at Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT 06518, for up to 10 miles of hills, trails, rocks, and one very cool castle. If you want to ride share, meet at Lewisboro Town Park lower lot at 7:00 a.m. Bring a change of clothes and some cash […]
A Mild Sprain
Sprain Ridge Park 149 Jackson Ave, Yonkers, NY, United StatesOn Sunday, June 5, at 9:45 a.m., don’t miss out on the annual “A Mild Sprain” Trail Run (5 mile run/3 mile walk/hike) on Sunday, June 5, 2022, at Sprain Ridge Park, Hastings-on-Hudson, NY. “A Mild Sprain” is one of Westchester’s largest grassroots fundraisers. Over the past 9 years, the event has raised more than […]
Pound Ridge Color Run
Looking for something a little different? While not trail, the Pound Ridge Color Run is a fun 5k hosted by the Pound Ridge Partnership in collaboration with the Human Rights Advisory Committee. The run is the town’s first-ever 5K road race and is dedicated exclusively to celebrating Pride Month—with a splash of Holi-inspired color! After […]