Woodsboro was laid out long before its larger neighbor Walkersville. The town was founded in 1786 by Joseph Wood (1743-1800) on an Indian trail used by Pennsylvania migrants on their way to recently opened lands in Virginia. Many liked the Maryland land and were able to rent property in Monocacy Manor. Some English settlers moved from New York state and New Jersey. Woodsboro has had several names: Woodstown, Woodsberry, Woodsborough, and now Woodsboro.

President George Washington passed through as he traveled the road that became Md. 194 from Virginia to Lancaster and Philadelphia. Yes, "Washington slept here" at least twice, once in Slagle's Inn at the Sign of White Charger where Md. 194 now meets Md. 550. A monument was erected in 1932 by the Frederick Chapter Daughters of the American Revolution as a part of the Washington Bicentennial celebration. More recently, war monuments from the American Revolution through today have been added. Washington also stayed at Cookerly's Tavern on Md. 194 near New Midway.

After Md. 194 became an official road, it was made a toll road. James Madison Smith (born 1841) became director of the Woodsboro and Detour Turnpike Company. Three turnpike locations existed between Woodsboro and Frederick.

Many new residents arrived from Pennsylvania, including the family of John Delaplaine (1740-1804). His father was Joshua Delaplaine, who moved his family from Philadelphia to Berks County, Pa., and later to Oley, Pa. in 1768. John moved to Woodsboro before the Revolutionary War and served in the Committee of Observation in 1775. He purchased land from Joseph Wood in 1779 and 1789. He voted in the election of 1796.

John died in 1804 and was buried in the Rocky Hill Church Cemetery. Rocky Hill Church was founded in 1768 by several Lutheran families. A group of Reformed Church members worshipped there also from 1768 but split in 1887. Today the church, located on Coppermine Road east of Woodsboro, is called Grace Rocky Hill Lutheran Church.

St. John's Reformed Church was formed in 1768 and built a new building in 1802. Woodsboro Lutheran Church was organized in 1805. The Rev. David Franklin Shaeffer came to the church and was claimed as the father of Lutheranism in Frederick County. The Church of God had its first services in the Methodist Protestant church in 1908. It disbanded in 1944.

The area around Woodsboro has been primarily agricultural. The town grew during the past centuries with many businesses serving not only residents but a wide area. A grist mill erected by Joseph Wood Jr. was said to be the first mill in Frederick County. In the 1800s the town had two hotels -- the Smith Hotel and Anderson's Hotel, which was a saloon, not an overnight facility. The Glade Valley Milling Company was founded in 1909 and ceased operation in 1957. The building was sold in 2014 for a new business.

Copper was discovered in 1760 and the Fountain Mine was opened on Coppermine Road. It was not profitable and soon closed. Copper was expensive to produce and transporting it to the east and Europe was difficult and costly.

The Rosebud Perfume Company is a long-standing business still active in Woodsboro. Dr. George F. Smith, born in 1865, taught school for five years and later became a pharmacist. He started the perfume company in 1895 and began manufacturing Rosebud Salve. The company flourished and is still in business today. The salve is sold in many places all over the world.

Dr. Smith had other interests as well. He served on the board of Woodsboro Bank, was mayor of the town and owned a drug store (one of the first stores to sell Coca-Cola). Upon Dr. Smith's death in 1952, his son Allen Smith (1899-1971) inherited the business. When Allen died, the business was left in trust to his heirs, who remain in charge today.

The town grew and more businesses were established in the late 1800s and early 1900s. The Frederick-Pennsylvania Railroad made it easier for businesses to ship their products, as well as providing transportation for travelers. At one time, railroad business and growth in the town caused the post office to expand its services.

In 1899 Woodsboro Savings Bank was organized. A three-story building was built in 1901 and has since been modernized. The upper stories of this landmark building were used for other activities. The bank now has eight branches serving patrons in Frederick County.

Limestone is found in the area and two large quarries were established near Woodsboro -- the LeGore Lime Company founded by John LeGore in 1861 and S.W. Barrick and Sons, Inc. founded in 1874. The LeGore company consolidated with several other companies in 1970 and produces stone for road building.

Another business opened in the early 1900s -- goldfish ponds operated by the Powell brothers. The fish were sent all over the world. The business closed about the time of World War I.

John Dorsey opened his "Dorsey Pork Products" in 1890. The company is now a wholesale meat business, supplying many stores and other businesses.

More than 50 years ago, Nelson Trout opened a food market. In 1963 a new building was built on Main Street (with a parking lot). Today "Trout's Seafood and Deli Mart" sells a full line of groceries.

Bowers Lumber Company formed in Frederick in 1868, and moved to Woodsboro in 1964.

In the early years of Woodsboro and the surrounding area, children were taught in homes or churches. Very few children were able to attend school.

One-room schools were built in the early 1800s in and near Woodsboro, offering education through the seventh grade. No records exist of when the first school was built, but the second one was built in 1870. By 1891 parents were keeping their children at home because they feared the brick walls in the school were unsafe. The building was demolished in 1892 and a new one was erected. An annex was built in 1952. A bell in a tower called the children to school.

A new open-space school was erected in 1973 on and around the older building.

In the 1930s at least some students attended Frederick High School. Later they began attending Walkersville High School.

Woodsboro Elementary School now has kindergarten through third grades, and fourth grade and above are at New Midway School. New Midway children have the same arrangement.

Life was not all work for early residents. Winter brought snow with hills available for sledding and nearby ponds for skating. There were the usual parties and church socials. In 1917 a roller skating rink opened; it closed in 1934.

An opera house existed on the second floor of the bank building the site of all kinds of music, drama, movies and community activities. These activities ceased in 1953 when the second floor was considered to be a fire hazard.

Woodsboro Regional Park now supplies space for many outdoor activities. A recreation commission was formed in 1970.

High on the list of popular activities is a train ride on the Walkersville Southern Railroad, which runs from Walkersville to Woodsboro on the original tracks of the Frederick and Pennsylvania Railroad. The recreation commission and the Woodsboro Historical Society began restoration in 1999 of the town's station built in 1883. Rides are offered on weekends during the summer and on special dates.