The trail that started everything. Where the workday ends. Where Sawyer and Theo got to be themselves, and where Theo and Beau do now. We're walking it section by section, one trailhead at a time
EVERY TRAIL HAS AN ORIGIN STORY
Ours started with a few walks on a local rail trail nearly four years ago. Somewhere along the way it became a daily ritual.
At 5:00 PM, Sawyer and Theo found us in our home offices and made their case … usually with the stare, sometimes with Theo's howl. They eat fast. Then they follow us up and down the stairs as we change shoes, not letting us out of their sight until we're out the door.
For us, the walk is where the workday ends. No meetings, no screens … just the trail and two dogs who were genuinely thrilled to be alive.
Over time we started exploring different trailheads, stopping for dinner with the boys on the way home. One trail led to one small town. One small town led to a weekend trip. That's how Waggin Around Towns was born.
It started here on the NCR Trail in Maryland. Twenty miles of crushed stone from Ashland to the Pennsylvania line, where the trail crosses into York County and becomes the Heritage Rail Trail.
Heritage Rail Trail · Pennsylvania
Cross the state line and the trail becomes the Heritage Rail Trail … 21 miles through York County, PA. The crown jewel is the Howard Tunnel, built in 1840, the oldest operating railroad tunnel in the United States.
Sawyer & Theo · Howard Tunnel · Seven Valleys, PA
Howard Tunnel · Built 1840
The oldest railroad tunnel in continuous use in the United States. Built by the Baltimore & Susquehanna Railroad, the 375-foot tunnel was hand-cut through solid rock 185 years ago. Today it's a highlight of the Heritage Rail Trail … and Sawyer and Theo walked through it more times than we can count.
Along the Trail · South to North
Maryland · Monkton
The old Monkton station, now a stop on the trail. Sawyer and Theo, holding court on the platform.
From here the trail runs north through Maryland, over the state line and up through York County. These are the places along it we keep coming back to.
Maryland · Monkton
Kelly spotted this sunset just past the station at the end of a long walk, and the boys lined up for it.
Maryland · Freeland
The stretch out of the Freeland trailhead. We call it Turkey Trail, and it’s where a turkey that got loose from a farm once chased us down the path.
Pennsylvania · New Freedom
Just over the state line, the trail runs right past the New Freedom station, and the steam train still boards from this platform. Theo and Beau, holding down the bench.
New Freedom guide →
Pennsylvania · Hanover Junction
On November 18, 1863, the train carrying Abraham Lincoln to the dedication of the cemetery at Gettysburg changed railroads right here. The restored station is a museum now. Sawyer and Theo, guarding the door.
Last updated September 2026
The full trail from Ashland, MD to York, PA … amber sections are walked, dark sections are remaining. Click any access point to toggle.
Every access point, north to south. Segment height is proportional to actual mileage. Click any point to toggle completion
