Run Calendar

Michigan to Clark

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

On Saturday, September 12, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Clark course. This 7.5 out-and-back takes us out of the Rez to the adjoining Clark preserve on the southern part of the park. If we're lucky, we'll get Billy McArthur out on Saturday […]

Kessel Run

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

On Monday, September 7, at 8:00 a.m., meet at Lewisboro Town Park, upper lot, when we navigate the 9.6 mile Kessel Run. This special out-and-back segment starts at Lewisboro Town Park and ends at Gilmore Pond on the southern end of the Rez. Peeter “Millennium Falcon” Muursepp holds the record of less than 12 parsecs […]

Pound Ridge 50K

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

On Sunday, September 6, at 5:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the first ever Pound Ridge 50k. Runners will make four loops—a 12 mile perimeter loop starting at 5:00, an 8 1/2 mile loop starting at 8:00, and two 5 1/2 mile loops of the Red trail. […]

Red All Over

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

On Saturday, September 5, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Red Trail. Since the Pound Ridge 50k is only a day away, I'm sure a number of you will be resting today but I'll offer this anyway. The Red trail loop forms two of the […]

Fire Tower Summit Run

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

On Sunday, August 30, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run a classic—the Fire Tower Summit Run. Before there was the Raven Rocks Race, there was The Fire Tower Run which follows some of the same trails but offers distances from 5 to 7.5 miles and includes the […]

Farringtons Woods

Farringtons Woods Farringtons Park, Brewster, NY, United States

It looks like the weather won't cooperate for the scheduled run in the Catskills so let's run something closer to home. On Saturday, August 29, at 7:00 a.m., meet at Farringtons Woods Trailhead (see Google map) next to I-84 at the New York-Connecticut border. This park offers a variety of twisty trails throughout this 8-mile […]

Michigan FH to Overlook

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

On Sunday, August 23, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan FH to Overlook loop. This time, we'll reverse the direction and get the Overlook first. Options include distances of 5, 6.5, and 8 miles. As usual, the early crews can start at 6:00 and […]

Trout Brook Valley

Trout Brook Valley 5 Bradley Road, Weston, CT, United States

On Saturday, August 22, at 7:00 a.m., meet at the Bradley Road lot of Trout Brook Valley in Weston, CT, when we run a perimeter loop. Distances range from 6 to 8.5 miles on varying terrain from rocky single-track to meadows and orchards. We'll take a side trail to get a view of the Saugatuck […]

Trailside to Green

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

On Sunday, August 16, 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. There are still a lot of trees and branches down across the trails even on some of this course so you'll need to pick […]

Mountain Lakes and Adjacent

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

On Saturday, August 15, at 7:00 a.m., meet at Mountain Lakes Park, Trailhead to Lookout Point, ready to run the Mountain Lakes and Adjacent course. We'll modify the map below to include a bushwhack or two before we head over to the Hearst-Mead and Halmi Preserves. Total distance will be about 7 miles. Print Map […]

Meadow to Armstrong

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

On Sunday, August 9, at 8:00 a.m., meet at Ward Pound Ridge Reservation Meadow lot ready to run the Meadow to Armstrong course. This 7-mile course starts in the reservation, then crosses over to Richard’s Preserve and Armstrong before returning back. The entire course is 7 miles but if you want to cut it short, […]

Blue-Per-Bowl

Depew Ct., Peekskill, NY 1 Depew Court, Peekskill, United States

On Saturday, August 8, at 5:30, 7:30 a.m., and 9:30 a.m., meet at the Depew Court lot at Blue Mountain and run the Fifth Annual Blue-Per Bowl run. Starting at 5:30 a.m., make one 7.5 mile loop and a second starting at 7:30 a.m. Join in for one or both loops or finish a third […]

Dancing Rockish

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

On Sunday, August 2, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot for a very special run—The 7.5 mile Dancing Rockish Run. I know many of you are looking forward for December's annual running of the Dancing Rock run but what could be better than a preview in August? Don't worry, […]

Meyer Preserve

Meyer Preserve 415 Sarles Street, Mt. Kisco, NY, United States

On Saturday, August 1, at 7:00 a.m., meet at the parking lot on Sarles Street and Bretton Ridge Road (415 Sarles St, Mt Kisco, NY 10549) when we run a loop in the Meyer Preserve. This small preserve offers a mix of terrain and we’ll make a side-trip to Byram Lake. Total distance should be […]

Sylvan Glen/Granite Knolls

Sylvan Glen Nature Preserve Grant Ave & Morris Ln, Mohegan Lake, NY, United States

This Saturday, July 25, at 7:00 a.m., meet at the Grant Avenue entrance to Sylvan Glen, ready to run a loop around the park and head over to Granite Knolls. From there we can retrace our steps for a 6 mile run or follow a perimeter course around Granite Knolls for a little extra distance. […]

Eleanor’s Great Escape

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

On Sunday, July 19, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run Eleanor's Great Escape. This course starts from the Meadow and makes a counterclockwise loop around the Rez. The longest distance manages to avoid most of the hills in the park save for two, but you have options […]

Bennett’s Pond Overlook Loop

Bennett’s Pond 550-698 Bennetts Farm Rd, Ridgefield, CT, United States

On Saturday, July 18, at 7:00 a.m., meet at Bennett's Pond parking lot ready to run the 7-mile Overlook Loop. The most overgrown part of the trail has been recently trimmed so we should be OK to follow the map as is. If you're looking for a longer run, you can continue on the yellow […]

Michigan Road “Stairmaster”

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

On Sunday, July 12, at 8:00 a.m., meet at Ward Pound Ridge Michigan Road Lot ready to run the Michigan to Spy Rock 7 Mile Loop, or as I like to call it, The Stairmaster. This course starts up the FH trail and heads over the Magic Stairs before turning south past Castle Rock and […]

Slide Mountain (Burroughs Range) Loop

Slide Mountain Trailhead Parking Lot 2027 Oliverea Road Lot, Phoenicia, NY, United States

On Saturday, July 11, meet for a special run in the Catskills—the Slide Mountain/Burroughs Range Loop. This 14.5 mile loop offers 5,000 feet of elevation gain and crosses Slide Mountain (the highest peak in the Catskill range), Cornell, and Whittenberg. Meet at the Woods Bridge commuter lot in Katonah at 5:30 a.m. if you'd like […]

Meadow Museum Fire Tower to Michigan

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

On Sunday, July 5, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, when we run the Meadow Museum, Fire Tower to Michigan loop. We'll run this in a clockwise direction as marked and runners have the opportunity to run distances from 5 to 8.5 miles. Since a number of you will be […]

McArthur Multipark Marathon

Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United States

On July 4, join us for a special event—the McArthur Multipark Marathon. This course starts at Kimberly Bridge and makes a perimeter loop of the Rez, exiting at Lewisboro Town Park. From there, runers sprint across Route 35 to Old Field Preserve then take a combination of roads to Mountain Lakes Park. You'll make a […]

Museum to Blue Route

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

On Sunday, June 28, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Museum to Blue Route. This course offers distances of 6.5, 7.5, or 8.5 miles but even the shortest begins with a climb to the Magic Stairs so be prepared. Early risers can start at 5:00 […]

Virtual 5K and More

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

On Saturday, June 27, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run a special Blythedale Children’s Hospital Virtual 5K event. This event is the spring fundraiser of the Blythedale Advisory Council, providing an opportunity for people to "come together" to help children managing significant health conditions and their families. […]

Meadow Northern Loop

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

On Sunday, June 21, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow Northern Loop course. We haven't seen much of the northern trails in the Rez so this course will remedy that. Options include 5.5, 6.5, and 8-mile distances. Runners can start at 5:00, 6:00, or 7:00 […]

Trailside Multiloop

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

On Saturday, June 20, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Trailside Multiloop. This course offers a variety of distances from 2 to 13 miles and can be run in either clockwise or counterclockwise direction. Print Map Download the PDF

Two Crescents Run

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

Two crescents—the Moon and Venus—meet in the sky in the wee hours of June 19. Should weather conditions be favorable, be sure to set your alarm clock for around 4 a.m. local time on Friday, June 19th, then proceed to a location where you have a clear and unobstructed view of the east-northeast horizon. A […]

Sights and Heights

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

On Sunday, June 14, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Sights to Heights v2 course. Options include 5.5, 7.5, and8.5 miles and can be run in either direction. The mountain laurel are starting to bloom so the trail up to the Fire Tower will be […]

Trailside to Tower

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

On Sunday, June 7, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum lot, when we run the Trailside to Tower loop. Options include 5, 6, 7, and 9 miles and the course can be run in either direction. The early crew can arrive at 7:00 for a 4-mile loop. Rookie Runners can […]

Green Rock Trail

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

On Saturday, June 6, at 7:00 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, 6.5, 7.5, and 8.5 mile course and you can run this in either direction. There's a fair […]

Meadow to Blue

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

On Sunday, May 31, start between 7:00 and 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow to Blue Route. Options include 5, 6.5, and 8 mile distances and you can run this course in either direction to avoid crowding. I'll be there at 7:00 and put a few […]

Red & Green Loop

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

On Monday, May 25, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Red and Green Loop. Options include 4.5, 6, and 7.5 mile distances. Vary your start times and directions, wear a buff or mask around others, and practice social distancing. Print Map Download the PDF

Meadow Half Marathon (or less)

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

On Sunday, May 24, between 7:00 and 8:00, meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow Half Marathon. You have options for distances from 4.5 to 13.1 miles (by combining the two longest loops) and the course can be run in either direction. Vary your start times and directions, wear […]

Kimberly Blue Route

Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United States

If you're looking to stay in the Rez, on Saturday, May 23, at 7:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot ready to run the Kimberly to Blue Route. Options include 5, 6.5, and 8 miles. Vary your start times and directions, wear a buff or mask around others, and practice social […]

Huntington 15K

Huntington, State Park, Redding, CT 79-45 Sunset Hill Road, Redding, CT, United States

On Saturday, May 23, at 7:00 a.m., meet at Huntington State Park, 58 Sunset Hill Road, Redding, CT., for a 15k perimeter loop. We'll follow the course in a clockwise direction making sure to keep proper social distancing. Print Map Download the PDF

Eleanor’s Great Escape

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

On Sunday, May 17, start anytime between 7:00 and 8:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run Eleanor's Great Escape. You might notice that I've updated this longer version of the classic Eleanor's Escape to include multiple distances so now you have some choices as to how far you'd like […]

Michigan Zig-Zags

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

On Saturday, May 16, start anytime between 7:00 and 8:00 a.m., meet at Ward Pound Ridge Reservation Michigan Road Lot ready to run the Michigan Zig-Zags. Options include 8, 6.5, and 5 mile distances or get lost and see how many miles you can do. Remember to socially distance, wear a mask or buff in […]

Trailside Multiloop

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

On Sunday, March 22, between 7:00 and 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Trailside Multiloop. This course offers a variety of distances from 2 to 13 miles and can be run in either clockwise or counterclockwise direction. To minimize the risk of spreading coronavirus by keeping […]

Meadow Half Marathon (or less)

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

On Saturday, March 21, between 7:00 and 7:30, meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow Half Marathon. You have options for distances from 4.5 to 13.1 miles (by combining the two longest loops) and the course can be run in either direction. To minimize the risk of spreading coronavirus […]

Michigan Road Gerrython

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

On Sunday, March 15, at 8:00 a.m., if you're not self-quarantining, then meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Gerrython. Since the New York half marathon has been canceled, I'll give you the option of your own half marathon with a modified perimeter loop. But you also have options […]

Meadow Multiloop

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

On Saturday, March 14, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow lot, ready to run the Meadow Multiloop. This course gives you options for distances from 2 to 11 miles and can be run in either direction so as to minimize virus exposure. Print Map Download the PDF

Five Bridges Run

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

On Sunday, March 8, at 8:00 a.m., meet at Lewisboro Town Park, Upper Parking Lot, ready to run a new course—the Five Bridges Run. This course offers three options for different lengths—9, 6.5, and 5.5 miles—all of which pass over all four bridges in the Rez. Three of the bridges have been closed since late […]

Boutonville Oak Run

Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United States

On Saturday, March 7, at 6:00 a.m., meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, and run an hour of hill repeats up Blue. You should be able to get in 3 or 4 before you return to the lot at 7:00 a.m. to run the Boutonville Oak Loop. This multidistance run offers lengths […]

Rock Trail 8 Mile Loop

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

This Sunday, March 1, at 8:00 a.m., meet at Ward Pound Ridge Meadow lot when we run the Rock Trail 8 Mile Loop. We’ll head south through the meadow trails and return via FH. In between, you’ll see the Bear Rock Petroglyph, Spy Rock, the Stairs, Castle Rock, Raven Rocks, Indian Rock Shelter, and plenty […]

Snowy Owl Run

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

On Saturday, February 29, at 7:00 a.m., meet at Ward Pound Ridge Reservation ready to run the Snowy Owl Run. This course is almost the same as the Raven Rocks run but starts with a climb up FH then down the CB trail—and everyone loves a good climb at the start, right? Before the run, […]

Kimberly To Armstrong

Ward Pound Ridge Reservation, Kimberly Bridge Reservation Road, Pound Ridge, NY, United States

Sunday, February 23, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, ready to run the Kimberly to Armstrong 9 mile run. Options include the full 9 miles but since this is an out-and-back course, you can turn around at any point for a shorter run. This course passes through three different […]

5 Sisters Run

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

On Saturday, February 22, at 7:30 a.m., meet at Bear Mountain, Ice Rink Lot, when we run the 5 Sisters course. This 13 mile, quad-shredding exercise in futility, contains 4700 feet of gain so you know it's going to be a tough run. Come prepared, you have been warned. I won't be there for this […]

Town Park to Kimberly

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

On Saturday, February 22, at 7:00 a.m., meet at Lewisboro Town Park, Upper Lot, ready to run the Town Park to Kimberly Multidistance Loop. This offers runners distances from 6 to 11 miles starting and finishing on the same trails. I recommend the 7 or 9 mile loops. The group can decide on site. Print […]

Museum to Blue Route

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

On Monday, February 17, at 7:00, meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Museum to Blue Route, 7.5 mile option. Since the Bergfield Bridge isn't up yet, take the trail through the trailside meadow to complete the loop. Print Map Download the PDF