Cartoon of Trey and Kelly waving from a black woody wagon at the New Freedom depot at sunset, with Theo and Beau leaning out the back windows

Trails  ·  Eats  ·  Stays

REAL TOWNS
REAL DOGS
REAL RECOMMENDATIONS

Explore Everything  →

Trey, Kelly, Theo & Beau explore dog-friendly small towns
so you can skip the research and start the adventure

Vol. 01 · April 2026

Currently Wagging

Trip Guides

PLAN THE TRIP.
BRING THE DOGS

Curated weekends in dog-friendly small towns. Trails, eats, and stays … walked by us, and by three dogs across ten years

Dogs on the Heritage Rail Trail, New Freedom, PA
Live Now
Walked With Our Dogs 🐾

Pennsylvania

New Freedom

Twenty minutes from our door and the reason this site exists. Eight trailheads on the Heritage Rail Trail, a steam railroad, and a downtown where you park once and walk to all of it

🐾🐾🐾🐾🐾

Heritage Rail TrailEight TrailheadsSteam RailroadDog PatiosHoward TunnelPark Once
Explore the Guide →
Savannah GA
Live Now ✓

Georgia

Savannah, GA

Beaufort SC
Live Now ✓

South Carolina

Beaufort, SC

Harpers Ferry WV
Live Now ✓

West Virginia

Harpers Ferry, WV

Cape Fear Memorial Bridge over the river with downtown Wilmington behind it
Coming Soon

North Carolina

Wilmington, NC

Rainbow Row in Charleston with a horse-drawn carriage passing
Coming Soon

South Carolina

Charleston, SC

Boardwalk and jetty along the beach at Cape Charles, Virginia
Coming Soon

Virginia

Cape Charles, VA

Cannon on the Gettysburg battlefield at sunrise
Coming Soon

Pennsylvania

Gettysburg, PA

St. Mark's Church rising over the rooftops of Jim Thorpe in fall color
Coming Soon

Pennsylvania

Jim Thorpe, PA

White sand and emerald water along the beach at Seaside, Florida
Coming Soon

Florida

Seaside, FL

The coquina walls of the Castillo de San Marcos under a blue sky in St. Augustine
Coming Soon

Florida

St. Augustine, FL

The Stars of the Show

THE
PACK

Sawyer set the standard and Theo learned it from him. Theo is teaching it to Beau now

NCR / Heritage Rail Trail · Howard Tunnel

Sawyer & Theo leading the charge through the historic Howard Tunnel

Seven Valleys, PA

OUR TRAILIN' ADVENTURES

🐾 More Clips & Photos Coming Soon
Trey, Kelly, Sawyer and Theo on the NCR Trail in winter

TREY & KELLY · THE PACK

NCR / Heritage Rail Trail

The trail that started everything. One walk turned into a daily ritual. The ritual turned into Waggin Around Towns

27.3 / 41 MI
67%
READ OUR STORY →

Follow Along

🐾 🐾 🐾 🐾 🐾

@wagginaroundtowns

Trails scouted, patios tested, biscuits distributed … follow the pack and see every adventure before it becomes a guide

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