Our driving tour of Kent County begins as you leave Chestertown on Maryland Route 20, heading southwest towards Rock Hall. After leaving the outskirts of Chestertown, stay on Route 20 for 3.5 miles, then turn left onto Route 446, also called Broad Neck Road. At the first four-cornered intersection, turn right onto Ricaud's Branch Road and continue for 2 miles. The inset map below will help orient you.
You are now driving on one of the first turnpikes constructed in this country. It was along this route that Col. Tench Tilghman, Secretary and Aide de Camp to George Washington, made his famous ride from Virginia to Philadelphia to carry the news of the Colonial victory over Cornwallis at Yorktown.On the right at the 2-mile mark is St. Paul's Episcopal Church, the oldest surviving Anglican Church on the Eastern Shore. The present building was erected in 1711 to replace an earlier church on the same site completed in 1696. St. Paul's is surrounded by a magnificent 19-acre churchyard and is one of two churches in Maryland with a separate Vestry house. The Vestry, now restored, was completed in 1766 and has been used as a court, a schoolhouse and a barracks for British troops during the War of 1812. The site is well worth a visit.Return to Ricaud's Branch Road and turn right. On your left is Chesapeake Farms, a 3,300 acre wildlife preserve and agricultural management area owned and operated by the DuPont Corporation. You can take a self-guided tour of a part of the wildlife habitat by turning right off Route 20 onto the dirt road just beyond its intersection with Ricaud's Branch Road. At that intersection, turn left and follow Route 20 toward Rock Hall. The detailed tour of Rock Hall is accessible here.Leave Rock Hall traveling north on Route 445 towards Tolchester. At the intersection of Routes 445 and 21, turn left and travel along the northern boundary of the Kent County Agricultural Center towards Tolchester Marina. The Marina is built on the site of what was once Tolchester Beach, and atop the hill on the right there was once a well-known and popular amusement park. Founded in 1877, Tolchester was a thriving port and a favored holiday destination through the turn of the century. The construction of the Bay Bridge and of modern roads put an end to the regular ferry runs from the Western Shore to Tolchester, and today the area is the site of an extensive residential complex.Leave Tolchester and return east on Route 21. Near the intersection of Routes 20 and 21, you will see Caulk's Field, the site of a battle between the local militia and raiding British troops during the War of 1812. The historical marker on the field's western border describes the militia's victory and the subsequent British retreat.At the intersection of Route 21 with Route 20, turn left and proceed north on Route 20 to its intersection with Route 298. Turn left here and proceed north on Route 298 through the small town of Fairlee. In about 5 miles, you will pass through Butlertown and see Kent County High School on your right. Immediately on the left is the I.U. Episcopal Church, built in 1765. The church takes its name from the initials, "I.U.", found on a large boundary stone nearby. In colonial times, residents made the letter, "J", like the letter, "I", so in all likelihood the stone demarcated a boundary belonging to a J. Usilton or Urie, early residents of the county, and had nothing to do with the church.