June 25, 2026

Portfolio Category: 8 Miles

Meadow to John Jay

Print Map Download the PDF Meadow to John Jay Looking for a mix of track and trails? This course shows the path to connect the John Jay track with Ward […]

Trout Brook Valley

Print Map Download the PDF Trout Brook Valley A pristine landscape with nearly 14 miles of trails, ranging from easy to difficult. The trails take the hiker past dramatic displays […]

Pound Ridge 50k

Print Map Download the PDF Pound Ridge 50k The Pound Ridge 50k is a classic all-trail 50k course starting at Ward Pound Ridge Reservation, Michigan Road lot. Runers will make […]

Trailside to Town Park

Print Map Download the PDF Trailside to Town Park This course offers runners different distances starting at the Trailside Nature Museum and heading toward Lewisboro Town Park. Options include a […]

Michigan Zig-Zags

Print Map Download the PDF Michigan Zig Zags This course is designed to test your mapping abilities. While it’s not complicated, it does require runners to keep on their toes […]

Dancing Rockish 7.5k

Print Map Download the PDF Dancing Rockish 7.5mi This course follows many of the trails of the Dancing Rock Run without following most of the bushwhacks. As such, it’s a […]

Annunaki Bushwhack

Print Map Download the PDF ANNUNAKI BUSHWHACK The Annunaki Bushwhack is a multi-distance run that includes a steep bushwhack to reach the Annunaki near Blue then through the forest to […]

Devil’s Ledge 8 Mile

Print Map Download the PDF Download the KML file Download the GPX file Devil’s Ledge 8 Mile Loop This version of the classic Devil’s Den run includes a wider perimeter […]

Meadow Multiloop

Print Map Download the PDF Meadow Multiloop Designed as a great training run for that ultra you signed up for, I suggest running this starting with the outermost loop and […]

Michigan to Clark

Print Map Download the PDF Michigan to Clark 7.5 mile run This run will get you off the reservation—literally. Start at Michigan road and head south on the Rock Trail. […]

Boutonville Oak Multidistance

Print Map Download the PDF Boutonville Oak Multidistance This course offers runners a chance to see the Boutonville Oak, a storied landmark on the eastern side of the reservation. Distances […]

Rock Trail v1

Print Map Download the PDF WPR Rock Trail 7.5mi One of the newer and more challenging trails in the reservation starts from the Michigan Road lot and passes the Indian […]

Bosque Encantado

Print Map Download the PDF Bosque Encantado 8-Mile Run The Bosque Encantado is an area around a knoll just off the Blue trail between intersections 13 and 14. The knoll […]

Dancing Rock Ultra

Print Map Download the PDF Dancing Rock Run and Ultra (50k) This version of the classic Dancing Rock Run takes a good thing and adds a lot more. How much […]

Fat Ass Run v2

Print Map Download the PDF Fat Ass V3 This version of our perennial favorite Fat Ass run starts at Lewisboro Town Park but avoids the bridge at intersection 2. While […]

Crazy 8, Version 2

Print Map Download the PDF Town Park Crazy 8, version 2 This version of the Town Park Crazy 8 run reverses the direction and includes a slight bushwhack to avoid […]

Nimham Mountain

Print Map Download the PDF Nimham Mountain Ninham Mountain (parking at 5 Mt. Nimham Court, Carmel, NY) offers hiking and biking trails  and great views from the Nimham Fire Tower […]

Meadow 8×4 Loops

Print Map Download the PDF Meadow 8 x 4 Mile Loops Looking for a long run? The Meadow 8 x 4 is a collection of 8 (approximately) 4-mile loops which […]

Perimeter Loop from Town Park

Print Map Download the PDF Ward Pound Ridge Perimeter Loop from Lewisboro Town Park I think the name says it all, right?

Mountain Lakes/Old Sib 7 Mile

Print Map Download the PDF Mountain Lakes Park Old Sib Run This takes our traditional Mountain Lakes park run and adds and adjacent new preserve—the Old Sib preserve. While small, […]

Boutonville Oak Multidistance Loop

Print Map Download the PDF Boutonville Oak Multidistance Loop This course starts at Kimberly Bridge then heads East where it crosses the road then takes a brief out-and-back to the […]

Peeter’s Ultra Fun Multidistance Loops

Print Map Download the PDF Peeter’s Ultra Fun Multi-distance Loops This series of loops by Peeter Muursepp were created with one goal in mind—take advantage of a Strava Segment called […]

Meadow to Armstrong Preserve

Print Map Download the PDF Meadow to Armstrong Loop This course starts at the Ward Pound Ridge Meadow Lot and winds its way toward Honey Hollow Road where it crosses […]

Crazy 8, version 1

Print Map Download the PDF Town Park Crazy 8 This run starts at Lewisboro Town Park upper lot and follows the trails on the Eastern edge of the Reservation. But […]

Michigan Multiloop Course

Print Map Download the PDF MICHIGAN MULTILOOP This course offers runners an opportunity to run different distances or combine one or more (or all) to create a run of 31 […]

3 x 8 Mile Twisted Loops

Print Map Download the PDF Three x Eight Mile Twisted Loops Three options for 8 miles loops that weave through the trails in Ward Pound Ridge Reservation. Each loop offers […]

Trailside Multiloop Course

Print Map Download the PDF TRAILSIDE MULTILOOP This course offers runners an opportunity to run different distances or combine one or more (or all) to create a run of over […]

Michigan to Spy Rock “Stairmaster”

Print Map Download the PDF Michigan to Spy Rock “Stairmaster” This loops starts with a significant climb up the FH trail and over the Magic Stairs. Then you’ll head to […]

Sights and Heights v2

Print Map Download the PDF Sights & Heights Loop, version 2 This version of the Sights & Heights loop takes runners to the Overlook Dancing Rock, Raven Rocks, and the […]

Kimberly/Raven Loop

Print Map Download the PDF Kimberly Bridge to Raven Rocks Run This course starts out on the beautiful Blue trail which lulls you into a sense of accomplishment before hitting […]

Dancing Rock Run

Print Map Download the PDF Dowload the KML Download the GPX Dancing Rock Run, 7.8 Miles This course revives a race created by Tony Godino and Dave Cope around the […]

Town Park to Green

Print Map Download the PDF TOWN PARK TO GREEN This course starts at the Lewisboro Town Park then heads down DH toward the Meadow and across the field toward the […]

Mountain Lakes Adjacent

Print Map Download the PDF Mountain Lakes Park Adjacent Preserves This run begins at the Trailhead to Lookout point and follows the Orange trail (the road) to the Herst-Mead and […]

Trailside, CB, to Blue

Print Map Download the PDF Trailside, CB, to Blue This course starts at the Trailside Museum and heads up toward the Magic Stairs. You might notice a slight uphill along […]

Michigan FH to Overlook Loop

Print Map Download the PDF FH to Overlook 7.75 Mile Loop This course starts at the Michigan Road lot and heads up the FH trail over the Magic Stairs and […]

Blue Mountain Twin Peaks

Print Map Download the PDF Blue Mountain Twin Peaks 7.7 Mile Run Located in Peekskill (Cortlandt), New York, Blue Mountain Reservation is a 1,538-acre park in the northwest section of […]

Town Park to Overlook

Print Map Download the PDF Town Park to Overlook 7.8 Mile Loop This loop starts at the Town Park and winds its way to the Overlook. There’s a crossover between […]

Meadow to Rock Trail Loop

Print Map Download the PDF Meadow to ROCK TRAIL LOOP This variation of the rock trail loop starts in the Meadow and follows the meadow paths south before entering the […]

Town Park to CB Multidistance Run

Print Map Download the PDF Town Park to Covered Bridge Multidistance Run This run starts at the Lewisboro Town Park and heads into the Reservation, through the Meadow lot, up […]

Sylvan Glen 10K

Print Map Download the PDF Sylvan Glen/Granite Knolls Park 10K Tucked away on a hillside in northern Westchester County, NY, Sylvan Glen Nature Preserve is the site of a former […]

Kimberly Blue & Brown v2

Print Map Download the PDF Kimberly Bridge Brown/Blue Loop v2 This double-loop course offers runners the opportunity to return rehydrate between two sizable hills. Start by following the DH trail […]

Mountain Lakes Park Perimeter

Print Map Download the PDF   Mountain Lakes Park Perimeter Loop This perimeter loop starts at the trailhead to Lookout Point and follows the white trail up to the overlook. […]

Town Park Northern Loop

Print Map Download the PDF Town Park Northern Loop This course starts at the Lewisboro Town Park and makes a counterclockwise loop through the Ward Pound Ridge Reservation (mostly) northern […]

Michigan Red/Rock v2

Print Map Download the PDF Michigan Red/Rock v2 This course gives you plenty of options. The main route follows the LL to Red trail from Michigan Road before arriving at […]

Kimberly Blue & Brown v1

Print Map Download the PDF Kimberly Blue and Brown Loops v1 Start at Kimberly Bridge and make a 4-Mile clockwise loop on the blue trail. Once back to the parking […]