June 24, 2026

Portfolio Category: Lewisboro Town Park

Ward Pound Ridge 1940s Map

Print Map Ward Pound Ridge Reservation 1940s Map This map of the Rez dates from the 1930s or 1940s. The original was black and white and oriented so that north […]

Ward Pound Ridge Stroller’s Map

Print Map Download the PDF Ward Pound Ridge Reservation Stroller’s Map This map was sold from the “Trading Post” in the reservation from the 1950s to the 1970s. Visitors could […]

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 […]

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 […]

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 […]

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?

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 […]

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 […]

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 […]

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 […]

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 […]

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 […]

Inaugural Loop

Print Map Download the PDF 6/7 Mile Inaugural Loop from Town Park This is the run that started it all in spring of 2010. A few local runners got together […]

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 […]

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 […]

Town to Michigan

Print Map Download the PDF Town to Michigan 6.8 mi / 1,583 ft Elevation Gain If you started in the Lewisboro Town Park and wanted to run, say, six miles, […]

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 […]

Town Park Dry Loop

Print Map Download the PDF Town Park “Dry Loop” Run Meet at the Lewisboro Town Park upper lot when we follow much of the Leatherman’s Loop trail sans water crossings.

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 […]

Run the Numbers

Print Map Download the PDF Run the Numbers This version of the full Ward Pound Ridge Reservation map as enlarged intersection numbers. Choose a series of numbers you want to […]

Ward Pound Ridge Reservation

Print Map Download the PDF Pound Ridge Trail Map Looking to set off on your own course? Use this map to help you find your way. I’ll update this periodically […]