June 24, 2026

Portfolio Category: Over 9 Miles

Beacon 14 Miler

Print Map Download the PDF KML File GPX File Breakneck 14 Miler This course at Breakneck Ridge is perfect for getting some vert and for getting those quads burning.

Mountain Lakes/Old Sib/Hearst

Print Map Download the PDF KML File GPX File Mountain Lakes Park / Old Sib / Hearst This takes our traditional Mountain Lakes park run and adds the adjacent Old […]

Seven Summits/Five Sisters

Print Map Download the PDF Downloads: 15mi GPX file | 15mi KML file 24mi GPX file | 24mi KML file 28mi GPX file | 28mi KML file

Run The Numbers 50mi

Print Map Download the PDF Run The Numbers 53-ish-mile course This series of loops starts at Michigan Road and goes from intersection to intersection in order. Total distance about 53 […]

Leather Raven

Print Map Download the PDF Leather Raven 12-ish mile loop These courses combine the best of the Leatherman’s Loop course and Raven Rocks course. Runners start in the meadow at […]

Mohonk Preserve 10.5 Mile

Print Map Download the PDF KML File GPX File Jon Birdsall’s Mohonk Preserve 10.5 Miler This 10.5 mile course is a non-technical course through some of the most beautiful trails […]

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 […]

Mink-Clove

Print Map Download the PDF Download the KML Download the GPX Mink Hollow to Platte Clove Loop This is a classic Catskill trek through some of the most technical trails […]

Bear Mountain Fat-Ass 50k

Print Map Download the PDF KML File GPX File Bear Mountain Fat-Ass 50k For those looking for a truly epic run, this course uses many of the same trails that […]

Kessel Run 9.6 Miles

Print Map Download the PDF Kessel Run 9.6 Miles The Kessel Run is a 9.6 mile out-and-back course of some of the fastest trails in the park. Grab your hyperdrive […]

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 […]

Teatown 11 Mile Loop

Teatown Trails Running

Print Map Download the PDF Download the KML Download the GPX TEATOWN 11MILE LOOP This course starts at the Teatown nature center and winds through trails on the southern and […]

Michigan to Caramoor 10 Mile

Print Map Download the PDF Michigan to Caramoor 10 Mile This unique run starts at the Ward Pound Ridge Reservation, Michigan Road lot, and makes an out-and-back to Caramoor center […]

Five Sisters, 13 miles

Print Map Download the PDF 5 Sisters Run This run in Harriman State Park is an aggressive 13 mile, 4700 feet of gain, quad-shredding exercise in futility. You’re absolutely going […]

Maybrook Traverse

Print Map Maybrook Traverse 23 mile point-to-point The Maybrook Traverse follows the old Brewster train line from Brewster to Hopewell Junction. The original “Beacon Line” title reflected the name MNR […]

Saugatuck 13 Loop

Print Map Download the PDF KML File GPX File Saugatuck 13 Mile Loop This loop starts at the trailhead of the Saugatuck trail on Davis Hill Road in Weston and […]

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 Hunt/Parker

Print Map Download the PDF 20 Mile Michigan to Hunt/Parker This run combines trail with dirt road and links the Ward Pound Ridge Reservation to the Hunt and Parker Preserves […]

Devil’s Den to Aspetuck 18mi

Print Map Download the PDF The Devil’s Creamery Run The run, which starts at Devil’s Den and ends at Huntington State Park gets its name because the end is also […]

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 […]

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?

Devil’s Den to Saugatuck

Print Map Download the PDF Download the KML Download the GPX Devil’s Den to Saugatuck This 11 mile point-to-point run connects Devil’s Den in Weston to the Saugatuck Trail in […]

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 […]

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 […]

Slide Mountain Loop

Print Map Download the PDF Download the KML Download the GPX SLIDE MOUNTAIN LOOP This loop hike climbs to the summit of Slide Mountain, the highest peak in the Catskills, […]

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 […]

Appalachian Trail Run from Kent

Print Map Download the PDF APPALACHIAN TRAIL RUN, KENT, CT This run starts at 80 Macedonia Road, Kent New York, and offers runners the option of 11, 14, or 23 […]

Bennett’s Pond Realander Run

Print Map Download the PDF BENNETT’S POND REALANDER RUN This run is courtesy of Kieth Relander and includes options for a 10-mile and a 6-mile loop on some newer trails […]

Six Preserves, 13 Miles

Print Map Download the PDF Six Preserve Half Marathon This course winds its way from the Bedford Audubon Society on Todd Road in Katonah through the Parker Sanctuary, Hunt Sanctuary, […]

Perimeter Loop from the Meadow

Print Map Download the PDF Ward Pound Ridge Perimeter Loop This course links all of the perimeter trails into one epic loop that offers a variety of trails and terrain […]

Teatown to Kitchawan Trail

Print Map Download the PDF Teatown to Kitchawan Trail This trail starts at the Teatown Nature Center (1600 Spring Valley Road, Ossining, NY) and winds its way through several parks […]

Ives Trail

Print Map Download the PDF The Ives Trail, Ridgefield, CT The Ives Trail is a challenging 16-ish mile course from Ridgefield to Redding. Meet at the Bennet’s Pond parking lot […]

Bear Mountain 10K

Print Map Download the PDF Download the GPX Bear Mountain 10k Looking for some different trails? Bear Mountain in Harriman State Park offers plenty including the two 10K courses above. […]

Bennett’s Pond 10 Mile Loop

Print Map Download the PDF Bennett’s Pond / Hemlock Hills / Pine Mountain 10 Mile Loop This course stitches three parks together into one epic course. Meet at Bennett’s Pond […]

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 […]

Mountain Lakes Park 15k v2

Print Map Download the PDF Mountain Lakes 15K v2 This variation of the original Mountain Lakes 15K takes us through the Larch campsite and returns via the OS trail. The […]

Rock Trail/Fire Tower 9.5 Mile

Print Map Download the PDF Rock Trail / Fire Tower Summit 9.5 mile loop This trail is a longer and more challenging version of the Fire Tower Summit Run and […]

Michigan Road Gerrython

Print Map Download the PDF Michigan Gerrython This multi-distance run is inspired by Gerry Sullivan and includes options for 5, 7, 10, and 13 miles. Combine two or more and […]

Mountain Lakes Park 15K

Print Map Download the PDF Mountain Lakes 15K This 15K trail run starts on the shore of Hemlock Lake and makes its way to Lookout Point, Bailey Mountain, and parks/preserves […]

Meadow Two Loops

Print Map Meadow Two Loops This is a great run for anyone looking for a hill workout. Start in the Meadow and head up Howland Drive and down through the […]

Leonard Park to Westmoreland 10mi

Print Map Download the PDF Leonard Park to Westmoreland 10 Mile Run This run connects trails from Leonard Park, Marsh Sanctuary, Merestead, Butler and Westmoreland—five preserves with only two street […]

Leonard Park to Westmoreland 13.1mi

Print Map Download the PDF Leonard Park to Westmoreland Half Marathon Trail Run This run connects trails from Leonard Park, Marsh Sanctuary, Merestead, Butler and Westmoreland—five preserves with only two […]

WPR Half Marathon

Print Map Download the PDF Ward Pound Ridge Half Marathon 13.1 miles of trails all through the park and then some. The first part starts off like the Leatherman’s Loop […]

Kimberly Bridge Multiloop

Print Map Download the PDF Kimberly Bridge Multiloop One of our longer runs, this loop starts at Kimberly Bridge and follows the Blue trail to the Rock trail around the […]