Kilmarnock is a small town where you’ll find big things going on. From dining to shopping to just enjoying a walk down Main Street you’ll be transported to a relaxing place and time. First, you’ll dock at what locals call the “Kilmarnock Wharf” at the Chesapeake Boat Basin, where steamboats landed in the 19th and early 20th centuries when they were the mode of transportation for humans and commerce alike. Walk, hop a bike or catch a lift on Chesapeake Boat Basin’s courtesy van the 1.5 miles into charming Kilmarnock.

First settled in the mid-1600s, Kilmarnock was originally known as “The Crossroads.” The town probably had its beginnings at the intersection of Indian paths, which later became the locations of Main St. and East Church St. It was here in the early 1700s that William Steptoe began to operate a storehouse and ordinary so that the crossroads came to be called “Steptoe’s Ordinary.” There’s a restaurant at this location today. In 1764, Robert Gilmour, an agent for a mercantile firm based in Glasgow, Scotland, is thought to have been involved in giving the name of “Kilmarnock” to the crossroads location using the name of Kilmarnock, Scotland, where he also owned land (hence the Scottish theme on the town water tower). The earliest known record referenced to “Kilmarnock, Virginia,” can be found in a deed recorded in 1778. It was incorporated as the “Town of Kilmarnock” by an act of the Virginia General Assembly in 1930.

Want to explore a little further afield? Visit Historic Christ Church (804-438-6855) or the Irvington Steamboat Era Museum (804-438-6888) aboard the Triangle Trolley, which operates on Fridays and Saturdays from Memorial Day to early October. The trolley runs a 1-hour round trip through Kilmarnock and on to the towns of Irvington and White Stone. 

Two wineries on the Chesapeake Bay Wine Trail are a few short miles away. Good Luck Cellars (804-435-1416) and The Dog and Oyster Vineyard (800-438-9463) are within a short driving distance by Chesapeake Boat Basin’s courtesy van.