The Kentucky River meanders along framing the downtown urban core of Frankfort, Kentucky. Image credit Real Window Creative via Shutterstock.

These Towns in Kentucky Have the Best Main Streets

Kentucky, a state of just 4.5 million is often left underrated, despite being a stunning state packed with interesting culture. From smooth bourbon, exciting horse racing, bluegrass, vintage cars and good food, Kentucky is the last state tourists would want to skip over! Kentucky already has a plethora of natural beauty to offer, however imagine driving into a local town, and discovering some of the most charming, unique and picturesque historic downtowns in the country. Walk down pedestrian-friendly streets, bar hop, shop from small businesses, eat some delicious cuisine and check into a local hotel for a good night's sleep. Thankfully, the towns on this list offer all that and more with each attraction and every main street, perfectly representing each town's intriguing history.

Paducah

Row of colorful, historic buildings on the main street in the downtown area of Paducah
Main street in downtown Paducah. Image credit Angela N Perryman via Shutterstock.

Located at the junction of the Tennessee and Ohio Rivers, Paducah is a historic town with approximately 27,137 residents. Originally the home of the Chickasaw and Choctaw, and later colonized and settled by Europeans in 1821, Paducah is a town with a long history from steamboats, railroads, the civil war and unfortunately slavery and a 1937 flood. While walking down the main street of Paducah visitors will notice the historical residences, businesses and architecture that has been extremely well preserved. Paired with the town's many museums, historical sites, such as The National Quilt Museum, and guided tours by Whitehaven Welcome Centre, Paducah is a town perfect for those with an interest in history that transitions to vibrant nightlife when the sun sets. Paducah's downtown is home to multiple local bars, perfect for a night of fun, including Johnson Bar, Barrel & Bond and The Bully Gorilla Bar.

Elizabethtown

Spectators walk in the streets with cars on display during the Cruisin' The Heartland 2021 car show in downtown Elizabethtown, KY.
Cruisin' The Heartland 2021 car show in downtown Elizabethtown. Image credit Brian Koellish via Shutterstock.

With a unique main street. adorned with residences and businesses painted green and blue, and some built with classic red brick, Elizabethtown is a classic and interesting town. This beautifully preserved downtown draws in visitors from all over the picturesque state of Kentucky and beyond. While in this beautiful town of 31,931 residents, visitors will be pleased to discover the various attractions on offer. For car enthusiasts, especially those which are vintage, the Swope's Cars of Yesteryear Museum is an automobile lover's paradise. The Swope's Cars of Yesteryear Museum has an immaculate collection of vintage cars ranging from the early 1900s to the 1960s, and on top of that? It has free admission! This museum is perfect for large families, youth and elders. After a great outing to The Swope's Cars of Yesteryear Museum, a stop at the Historic State Theatre Complex, conveniently located near Public Square, is an aesthetically pleasing section of downtown Elizabethtown, home to picturesque shops, cute cafes, and bustling bars such as Bourbon Barrel Tavern, Cavern Club and much more!

Covington

Aerial view of Covington with water and downtown streets.
Aerial view of Covington with water and downtown streets. Image credit Rotorhead 30A Productions via Shutterstock.

With architecture that will leave visitors in awe, a lively main street, and a mid-size town with an impressive skyline for its size, Covington is absolutely underrated and is just waiting for its next tourist to leave impressed. Taking pride in having some walkable streets in unique and aesthetically impressive neighborhoods, home to eclectic shops, and creative cafes in storybook-like settings, Covington will draw visitors in the moment they learn of this jaw-droppingly stunning town. In Covington, situated in the beautiful state of Kentucky, visitors will undoubtedly love the town's main historic district, commonly known as Mainstrasse Village. Rich in German-American architecture and culture, Mainstrasse is known for its distinctive street art, public statues and features such as The Goose Girl Fountain in the heart of this quirky village. After an exciting day of discovering Covington, stop for some food and drink at one of the town's various restaurants and bars such as Frida 602 or Rosie's Tavern and take in the charming atmosphere of Covington.

Bardstown

Bourbon capital of the world sign and downtown Bardstown, Kentucky.
Bourbon capital of the world sign and downtown Bardstown, Kentucky. Image credit University of College via Shutterstock.

Located in the Bourbon capital of America, formerly named Kentucky's Bluegrass Region, Bardstown is an alluring small town of 13,567 residents. One could say that Bardstown is drunk in love with Bourbon and the art of distilling—well displayed during the annual Kentucky Bourbon Festival in September which celebrates the many distilleries in the area that date as far back as 1776! Thanks to all this history and culture, Bardstown is the location of a picture-perfect downtown which is composed of historic buildings with architectural individuality, one-of-a-kind shops and comforting restaurants such as Mammy's Kitchen & Bar which serve scrumptious meals. Another grand feature of downtown Bardstown, commonly known as court square, is within 16 miles of court square. There are 11 distinct distilleries here, such as the popular Willett Distilling Company, so make sure to enjoy some high-quality local bourbon in the Bourbon Capital of the World!

Frankfort

Frankfort, Kentucky, USA town skyline on the Kentucky River at dusk.
Frankfort, Kentucky skyline on the Kentucky River at dusk. Image credit Sean Pavone via Shutterstock.

Packed with museums and historic sites, the state capital town of Frankfort has encountered numerous obstacles in its history. This includesovercoming an attempt at making Kentucky part of the Spanish Empire, the occupation of the confederate army, catastrophic fires, floods which came from the Kentucky River and beyond! This abundance of history has been preserved and taught to visitors and locals through various museums and historic sites, many of which are downtown! The main street in this important Kentucky capital town is made up of beautiful cobblestones and is lined with unique businesses and restaurants. Experience Frankfort’s timeless design and its restaurants which serve up Frankfort's history through local food. Visit the Capital City Museum to explore the captivating history of the historic town, initially settled in 1786!

La Grange

Train rolling along Main Street in La Grange, Kentucky, USA
Train rolling along Main Street in La Grange, Kentucky. Image credit Morgan via Wikimedia Commons.

Famous for the town's trains, La Grange is an extremely unique small town in Kentucky, not far north of Louisville. One of the city's greatest and most distinctive features is the CSX rail line, which runs through the core of the city's stunning business district. Close to the rail lies the one-of-a-kind downtown area of La Grange which is home to the intriguing La Grange Railroad Museum! Within this eclectic museum, visitors may experience seeing a real steam engine, a 1929 dining car, a caboose, and various museum exhibits that explore La Grange's abundant history. The first thing tourists will immediately notice when trekking through La Grange's historic downtown is the rows of perfectly preserved historic buildings which are built along the charming streets of La Grange and home to local businesses, such as One Nineteen West Main. These red brick structures on this historic street were built with pride and innovation and showcases the strength of the community while preserving the stories of past and present generations.

Shelbyville

Midland Trail, or Main Street, Shelbyville, Kentucky with buildings and cars.
Main Street, Shelbyville. Image credit Chris Light via Wikimedia Commons.

Illuminated by classically crafted street lights, the charming streets of Shelbyville are lined with beautifully built classic businesses. These were constructed during the rebuilding of Shelbyville streets following a large fire in 1909 ravaged the area. The 19th century was undoubtedly a revival for Shelbyville and is reflected today as these historical structures stand and are admired to this day. One important reason to visit this lovely town is the Shelbyville Horse Show. Kentucky has long been known for its equestrian race culture, which is reflected through Shelbyville's title as the Saddlebred Capital of the World! Some exciting downtown experiences include Jeptha Creed, Wakefield-Scearce Gallery, Capone's Downtown Speakeasy, Cadillac Jacks, Cholula Mexican Restaurant and beyond!

Cave City

Aerial view of small town Cave City, Kentucky
Aerial via of small town Cave City, Kentucky. Image credit Rachel via AdobeStock. 

Crystal Onyx Caves, antique Shops, wildlife museums, bars and more, Cave City is a tourist paradise with an array of attractions paired with a charming main street. Cave City is sure to please everyone who stops by this eclectic Kentucky town! Home to only about 2,356 residents, Cave City is definitely small, but behind the town's quaint exterior lives a plethora of exciting attractions: some natural, some historical and some modern and man-made. Acquired in the month of October in the year 1853 by the Knob City Land Company, composed of members Messrs. Graham, Hopson and Quigly, Adams. These men were originally based in Louisville and envisioned the place as a popular resort town due to the land's close proximity to Mammoth Cave. Mammoth Cave is a stunning limestone labyrinth with over 400 miles of it already having been explored. The park estimates that there are over 600 miles of cave within the park. Cave City was then incorporated in 1866. After an exciting day of adventuring within Mammoth Cave, Cave City's charming main street is the perfect way to end the day. Grab a delicious bite to eat at Cave City Pizza while exploring the quaint streets, and admire old-fashioned architecture. End the night in one of Cave City's excellent hotels and motels!

Conclusion

After discovering so many interesting, charming and beautiful towns, anyone would say it would be a regrettable decision to skip over the stunning bluegrass state of Kentucky. To miss the Crystal Onyx Caves and quaint downtown of Cave City, or the colorful and eclectic main street of Covington would be unfortunate, as Kentucky has more to offer than one can ever imagine. The architecture of these towns perfectly reflects the history of each unique community. Some are perfectly preserved, nearly unchanged; meanwhile, others may have revamped their historic downtowns, blending modern and classic into one, creating the perfect atmosphere for new visitors.

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