Town to Orange 6.3 mi
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Portfolio Category: 5 Miles
Michigan, Overlook, Raven Rocks v2
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Leon Levy Preserve
Print Map Download the PDF Leon Levy Preserve The Leon Levy Preserve is located on Route 123 in South Salem (24 Smith Ridge Road, South Salem). The map above shows […]
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 […]
Meadow to Overlook v2
Print Map Download the PDF Meadow to Overlook Loop v2 This course starts at the Meadow Parking Lot and heads to the Overlook. The course splits into differen tdistances, returning […]
Leon Levy Preserve 2.5 Mile Loop
Print Map Download the PDF Leon Levy Preserve, Lewisboro, NY This relatively new preserve contains a variety of terrain in a short, 2.5 mile loop. Park at the lot on […]
Trailside, Raven, to Tower Loop
Print Map Download the PDF Trailside, Raven, to Tower Loop This course starts off with a climb up Fox Hill and down to Michigan Road where we make our way […]
Fire Tower Summit v2
Print Map Download the PDF Fire Tower Summit v2 This is the third variation of the Fire Tower run and undoubtedly the best. Start in the Meadow where the Leatherman’s […]
Eleanor’s Great Escape
Print Map Download the PDF Download the GPX Download the KML Eleanor’s Great Escape This is a modified version of the original Eleanor’s Escape but starting at the Meadow lot. […]
Trailside to Overlook
Print Map Download the PDF Trailside Museum to Overlook This course starts at the Trailside Museum and follows FH to the river then makes its way South via Old Schoolhouse […]
Sights and Heights v1
Print Map Download the PDF Sights and Heights v1 This course takes you from the Michigan Road Lot to the Overlook and Raven Rocks for two of the best sights […]
Mianus River Gorge
Rock Trail Loop v2
Print Map Download the PDF Rock Trail Loop v2 This is an update to the classic, but shorter, Rock Trail loop. In this version, start at Michigan Road and follow […]
Meadow, Museum, Fire Tower, Michigan
Print Map Download the PDF Meadow, Museum, Fire Tower to Michigan Loop From the Meadow parking lot, make your way to the Trailside Museum via the FH trail. Cross the […]
Michigan, Overlook, to Raven Rocks
Print Map Download the PDF Michigan to The Overlook, Leatherman’s Cave, and Raven Rocks You won’t find a more scenic and historic 5-mile run in the Reservation than this one. […]
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 […]
Trailside, Raven, to Tower v2
Print Map Download the PDF Trailside, Raven, to Tower 6 Mile Loop This course starts off with a climb up Fox Hill and down to Michigan Road where we make […]
Town Park Northern Loop v2
Print Map Download the PDF Town Park Northern Loop v2 This loop starts at the Lewisboro Town Park and follows the DH and brown trails to Kimberly Bridge before continuing […]
Town to Magic Stairs Loop
Print Map Download the PDF Town to Magic Stairs loop This loop starts at the Lewisboro Town Park and follows trails to Kimberly Bridge before heading up the blue trail […]
Museum, Michigan, Raven, & Blue
Print Map Download the PDF Museum, Michigan, Raven, & Blue This loop starts over Fox Hill (at 737 feet, one of the highest points in the park) and continues […]
Blue Moon Trail
Print Map Download the PDF Blue Moon Trail This course takes includes some bushwhacking so do yourself a favor and bring a map with you. Start at Michigan Road and […]
Green Rock Trail 6.5 mile
Print Map Download the PDF Green / Rock Trail 6.5 mile loop This course starts out on the beautiful Green trail before turning onto the more technical Rock Trail where […]
Meadow to Overlook
Print Map Download the PDF Meadow to Overlook Loop This course starts at the Meadow Parking Lot and follows the FH trail to the trailside museum where we’ll pass the […]
Eleanor’s Escape
Print Map Download the PDF Download the KML file ›› Eleanor’s Escape 7.5 Mile Loop Named for Eleanor Heppner Hershey who recommended this great run that combines the best of […]
Michigan, Red, and Rock Loop
Print Map Download the PDF Michigan, Red, and Rock 6.8 Mi Loop This course starts at the Michigan Road lot and heads south on the wide yellow and then red […]
Sprain Ridge Park 4.25mi
Print Map A Mild Sprain 4.25mi course at Sprain Ridge Park, Yonkers This course is one of the more technical trails around. While only 4.25 miles, there are plenty of […]
Sarah Bishop 5.2 mile Original loop
Print Map Download the PDF Sarah Bishop 5.2 Mi Original Loop This is the original course of the Sarah Bishop Bushwhack run only the inaugural year of the race in […]
Meadow, Michigan & Museum
Print Map Download the PDF 6.15 mi Meadow, Michigan, and Museum Loop This 6.15 mile loop heads south from the Meadow lot over Fox Hill to the Michigan Road lot […]
Westmoreland Sanctuary 5.2mi
Print Map Download the PDF >Westmoreland Sanctuary 5.2mi This run is located at the Westmoreland Sanctuary and offers runners plenty of hills to climb in a 5.2 loop.
Leonard to Butler 8 mile loop
Print Map Download the PDF Leonard Park to Butler Sanctuary 8+ mi This run starts in Leonard Park and winds its way through Marsh Sanctuary, Merestead, and Butler Preserve. The […]
Trailside to Tower
Print Map Download the PDF Trailside to Tower 5.8 mile Loop This trail starts at the Trailside Museum and includes the Fire Tower hill and Brown trails, two hills that […]
Meadow to Blue Route
Print Map Download the PDF Meadow to Blue Route 6.8 mi This is one of the longer runs in the group that has a little of everything—wide open trails, narrow […]
Town to Tower
Print Map Download the PDF Town to Tower 7.3 mi Loop This trail starts at the Lewisboro Town Park and includes a hill at the start, another before the Trailside […]
Meadow Northern Loop
Print Map Download the PDF Meadow Northern Loop This course starts at the Meadow parking lot, crosses the footbridges at intersections 1 and 2, up to the trailside museum and […]
Michigan to Dancing Rock
Print Map Download the PDF Michigan to Dancing Rock 6 Mile What kind of run do you get when you try to keep to mostly secondary trails in the reservation? […]
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 […]
Boutonville Blue Trail
Print Map Download the PDF Boutonville Blue Trail 5 Mile Loop This loop starts and ends on the Eastern portion of the reservation at Boutonville and Rt. 124. There is […]
Town to Trailside
Print Map Download the PDF Town Park to Trailside Museum A good training run for anyone interested in running the Leatherman’s Loop. Start at the Lewisboro Town Park and follow […]
Town Park Short Loop
Print Map Download the PDF Town Park Short Loop The green loop is one of our shorter runs when conditions are poor or time is tight. Even though it’s only […]
Ups and Downs
Print Map Download the PDF Ups and Downs 5 Mile Hill Workout Nothing will get you in shape faster than hills and this run has plenty of them. Only 5 […]
Fat Ass Run v1
Print Map Download the PDF Fat Ass Run 7mi Originally conceived as a way to get the group off our backsides during the holiday season, this run is a perennial […]
Rob’s Run
Print Map Download the PDF Rob’s Run v1 6.5 mi This course starts at Michigan Road and follows some of the lesser-used trails in the Southern part of the park. […]
Fire Tower Summit v1
Print Map Download the PDF WPR Fire Tower Loop 6.2mi Another challenging but fun run starts at the Meadow Parking Lot and follows the FH trail to Michigan Road. From […]
Kimberly Blue Route
Print Map Download the PDF WPR Kimbery Blue Route 5 to 8 mile Start at Kimberly Bridge and follow the blue route around fire tower hill then return via the […]
Museum to Raven Rocks
Print Map Download the PDF WPR Museum to Raven Rocks This route starts at the Trailside Museum and follows the FH trail up and over the Magic Stairs to Michigan […]
Muscoot Run the Farm 5mi
Print Map Download the PDF Muscoot Farm Run 5mi This course will prepare you for the annual Run the Farm trail race at Muscoot farm. Start in the main parking […]