Monocacy River, Maryland.
The Monocacy Trail was an old Indian path that ran parallel to the Monocacy River, leading from present-day Philadelphia, Pennsylvania, to Taneytown, Maryland.
Big Pipe Creek and Little Pipe Creek flow into the Monocacy River about ten miles south of the present-day Pennsylvania-Maryland border and form part of the Monocacy watershed. The exact route of the trail is not known today, but from Taneytown it led to the village of Monocacy, the first settlement in Frederick County, Maryland. Today, it is known as Creagerstown. Monocacy was located at a crossroads and consisted of just a few log cabins and a blacksmith shop.
The Monocacy path is believed to run parallel to present-day Route 15 and parts of Old Frederick Road. Then, it traveled to Frederick, connected with Braddock’s Road, and ran through South Mountain. Immigrants who were traveling from Pennsylvania to Virginia used the Monocacy Trail. Many of these emigrants who traveled the Monocacy Trail settled in the area known today as Frederick County. The Monocacy River watershed was the site of many land surveys, claims, and roads in the early days of American settlement. The border between Maryland and Pennsylvania was in dispute for many years before the Mason-Dixon survey found that many of Maryland’s claims extended into Pennsylvania.
Monocacy Trail.
Parts of the trail also became known as the “Great Wagon Road” by colonial travelers making their way to Philadelphia, Pennsylvania.
©Kathy Alexander/Legends of America, updated March 2026.
Also See:
Tales & Trails of the American Frontier
See Sources.