June 24, 2026

Portfolio Category: 5 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 […]

Michigan to Kimberly v3

Print Map Download the PDF Michigan Road to Kimberly Bridge V3 This run starts at Michigan Road and offers three courses that pass through Kimberly Bridge and up Blue.

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 […]

Five Bridges Run

Print Map Download the PDF Five Bridges Run The Five Bridges Run gets its name from the course that passes over five bridges in Ward Pound Ridge Reservation—Old Schoolhouse Road […]

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 […]

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 […]

Town Park to Kimberly Multidistance

Print Map Download the PDF Lewisboro Town Park to Kimberly Multidistance Loops This course starts at Lewisboro Town Park and makes its way to Kimberly Bridge. From there, runners have […]

Trailside to Green

Print Map Download the PDF Trailside to Green 6mi/8mi Loop This course starts at the Trailside Museum and makes a loop up Blue, down Green, up FH, and down CB. […]

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 […]

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 […]

Conquer the Forest 5k

Print Map Download the PDF Conquer the Forest 5k The Conquer the Forest 5k is on the Green Chimneys Clearpool Campus, 33 Clearpool Road, Carmel, NY, a private facility. Please […]

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 […]

Michigan Road Double

Print Map Download the PDF Michigan Road Double This course is perfect if you’re looking to get some mileage on the fast, larger trails in the south. Head out on […]

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 […]

Old Field Preserve

Print Map Download the PDF   Old Field Preserve, Lewisboro, NY This small preserve lies opposite route 35 from Lewisboro Town Park and is also accessible from a parking lot […]

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 […]

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 […]

Meadow to Green

Print Map Download the PDF Meadow to Green 6.8 Mile Loop This course starts at the Meadow lot and heads to the Trailside Museum before circling around to Michigan Road. […]

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 […]

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 […]

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 […]

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 Hemlock Loop

Print Map Download the PDF   Mountain Lakes Park Hemlock Loop 5.25 miles This loop starts at Hemlock Lake and makes a loop that includes Lookout Point and Bailey Mountain. […]

Mountain Lakes Park Larch Loop

Print Map   Mountain Lakes Park Larch Loop This 5.5-mile loop starts at Larch Campsite, a mile into the camp from the Park Office. The full course is 5.5 miles […]

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. […]

Butler / Westmoreland Loops v2

Print Map Download the PDF Butler and Westmoreland Preserves V2 Meet at Butler Preserve for this hilly and challenging run. We’ll start out on the Red trail then take a […]

Blue Mountain Depew Court Loop

Print Map Download the PDF Blue Mountain Depew Court Loop This course gives you a few options. Follow the solid orange trail for a 4.5-ish loop mostly on double-track around […]

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 […]

Red 5.5 Mi Loop

Print Map Download the PDF Download the KML Michigan Road Red 5.5 Mile Loop While not the most challenging run in the park, these southern trails are wide and generally […]

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 […]

Blue Mountain 5.5 Mile MYX Loop

Print Map Download the PDF Blue Mountain Reservation 5.5 Mile MYX Loop Located in Peekskill (Cortlandt), New York, Blue Mountain Reservation is a 1,538-acre park in the northwest section of […]

Red and Green Loop

Print Map Download the PDF Red and Green Loop We’ll start out on the Red Green trail and make a loop toward the Leatherman’s Loop trail (watch for the small […]