LEXtoday City Guide Live Banner

13 historic street names in Lexington

Lexington, KY has nearly 200 years of history. In this guide, we’re diving into the city’s oldest streets and how they got their names.

The outside of the Lyric Theatre at night.

The Lyric Theatre sits on the corner of East Third Street + Elm Tree Lane. | Photo courtesy of VisitLEX

Table of Contents

The city of Lexington was incorporated in 1831, but named in 1775 — 17 years before Kentucky officially became a state. Now that 190+ years have passed, the city and its streets are chock-full of vibrant history.

It’s safe to say that over the years, the city has been touched by countless historical figures and happenings — many of which have shaped the names of Lexington’s buildings, parks, and streets. In this guide, we’re delving into the history of Lexington’s streets — specifically how they were named.

East End

The East End — which was once owned by affluent families in Lexington who then sold these areas to Black families needing refuge in the post-Civil War era. Now, the neighborhood commemorates its struggle and history through artistic creativity and bustling businesses.

DeWeese Street — After segregation made housing difficult for Black families, DeWeese Street became the epicenter of Lexington’s Black culture and led to the founding of iconic businesses such as The Lyric Theatre.

Elm Tree Lane — Part of the Kinkeadtown neighborhood, which was divided by abolitionist George B. Kinkead and sold to Black Lexingtonians after the Civil War.

Goodloe Street — Named after local physician and landowner David S. Goodloe, who — like George Kinkead — subdivided parts of his land and reserved the majority of it for Black residents.

Wilgus Avenue — Garret Davis Wilgus, a contractor in the 1880s, owned a portion of this area. You can view The Wilgus House on the corner of East Third and Chestnut Streets.

Wickliffe Street — This street is likely named for the well-known Wickliffe Family, particularly Robert + Charles Wickliffe. Robert served in the Kentucky state government from 1818 to 1833, while Charles served as Kentucky governor for just one year.

The facade of Henry Clay's mansion

Ashland, the Henry Clay Estate, is located off Richmond Road on Sycamore Lane. | Photo courtesy of VisitLEX

Ashland Park

Sitting on the edge of downtown, Ashland Park is one of the more eye-catching neighborhoods in town. But its stunning architecture tells only part of the story.

Fincastle Road — In 1776, Fincastle County, VA helped with the formation of Kentucky County, VA. Fincastle then became the name of a city in Jefferson County, thus inspiring the Ashland-area street name.

McDowell Road — Madeline McDowell Breckinridge, one of the first leaders of the women’s suffragette movement, was the great-granddaughter of Henry Clay.

Desha Road — This road is named after Desha Breckinridge, the husband of Madeline. He served as the editor + publisher for Lexington Herald, which we all now know as The Lexington Herald-Leader.

A bust that reads "John E. Madden, The Wizard of the Turf, Founder of Hamburg Place"

The Hamburg Place Horse Cemetery on Sir Barton Way pays homage to John Madden. | Photo by LEXtoday

Hamburg

What was once acres and acres of farmland is now a sprawling suburban area of town. However, the area’s ties to the thoroughbred history are honored through its street names.

Madden Drive — This street is named after the well-known Madden family, particularly John E. Madden, who was known for his massive farm that bred multiple champion racehorses.

Sir Barton Way — Sir Barton was the first-ever horse to complete the Triple Crown (before it even had a name) after winning the Kentucky Derby, Preakness Stakes, and Belmont Stakes in 1919.

Star Shoot Parkway — Star Shoot lived on the Madden’s Hamburg Place farm and was the sire of Sir Barton.

Alysheba Way — Trained and bred by the Madden family, Alysheba was known as a winner of the 1988 Breeder’s Cup and completed two-thirds of the Triple Crown.

War Admiral Way — War Admiral, sire of Man O’ War, was another Triple Crown winner, having won the three races in 1937.

Check out our other Guides
This list of volunteer opportunities in Lexington, KY includes everything from fostering a pet to getting hands-on at local build sites.
Check out these 13 yoga studios around the Horse Capital of the World, which offer everything from hot power classes to beginner sessions.
From tiny homes to 21c, Lexington is full of special places to stay that offer guests a break from traditional motels and hotels.
Whether you’re a history buff, art aficionado, or sports fan, these 13 museums in Lexington have it all.
Dining in Lexington is always a fresh experience with new restaurants popping up all the time — and more on the way.
These 10 hiking trails cater to all skill levels in and around town.
If you don’t have coffee already in hand, consider this your sign to grab some.
Explore the Horse Capital of the World through its history, food, drink, and art on these tours.
Check out some of the coolest, most unique Airbnb and Vrbo rentals around Lexington and plan for your next adventure or staycation.
When the sun’s out, the world is your workspace.
LEXtoday phone
Good news for Lexington.
Get the best local news & events sent to your inbox each morning, for free.