Trey & Kelly · The Pack

NCR /
Heritage Rail
Trail

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

Trey, Kelly, Sawyer and Theo on the NCR Trail in winter

NCR Trail · Winter 2025

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 and Theo at Howard Tunnel

Sawyer & Theo · Howard Tunnel · Seven Valleys, PA

Trail approach to Howard Tunnel

The approach … tunnel appears through the trees

Howard Tunnel architecture

Hand-cut stone arch … built 1840, still standing

Inside Howard Tunnel looking out

Light at the end … 375 feet through solid rock

Howard Tunnel 1840 nameplate

Howard Tunnel · 1840 · chiseled in stone

Sawyer and Theo at Howard Tunnel

Two good boys. One historic tunnel

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.

27.3
Miles Done
13.7
Miles Left
67%
Complete
12/19
Sections Done

Last updated September 2026

The Map
Interactive Map

The full trail from Ashland, MD to York, PA … amber sections are walked, dark sections are remaining. Click any access point to toggle.

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Gunpowder Falls
I-83
The Progress
Progress Timeline

Every access point, north to south. Segment height is proportional to actual mileage. Click any point to toggle completion

↑ North  ·  York, PA
↓ South  ·  Ashland, MD