6 Underrated Cities to Visit in Kentucky

An important cultural and geographic component of the southeastern United States, Kentucky’s “Bluegrass State” is a wonderful place of discovery that all ages can truly enjoy on any vacation possible. Kentucky is truly a beautiful destination, from the sounds of Bluegrass music to exceptional regional cuisine, fascinating history and plenty of beautiful natural scenery. While the state’s big cities will still draw a lot of attention, there are several smaller, underrated towns with just as much charm and wonder as their larger counterparts. So when you visit Kentucky, don’t forget these great towns, where the full character of the state is found in great abundance, ready to instill a newfound appreciation for small towns in the US.


Downtown Winchester, Kentucky.  Image credit: Formulanone via
Downtown Winchester, Kentucky. Image credit: Formulanone via

Founded in late 18e century, Winchester serves as the seat of Clark County, today home to a modest population of just over 19,000. It is a historically rich center where visitors can explore some important historical sites from several centuries of America’s past. These include the downtown historic district, the Oakwood Estate House (1820), and the Old Providence Church (1793), among others listed on the National Register of Historic Places. From there, spend an immersive afternoon at the Civil War Fort in Boonesboro or the Bluegrass Heritage Museum, for intimate encounters with important moments in Kentucky history. Finally, no visitor to Winchester can miss the opportunity to taste the most famous regional delicacy, Beer Cheese spread. Native to the county, but now beloved across the state, guests can even enjoy the sights and smells of the Beer Cheese Festival in June. With live music, children’s activities, vendors, and of course plenty of Blue Cheese spread on hand, this is one of the most unique cultural events in Kentucky that the whole family can enjoy.


Aerial view of Augusta, Kentucky.  By Predhead, CC BY-SA 4.0, Wikimedia Commons
Aerial view of Augusta, Kentucky. Image credit: Predhead via Wikimedia Commons.

Located on the southern banks of the Ohio River, Augusta is a charming Kentucky river town whose modern history dates back to the period immediately following the American Revolution. A former trading post, today just over 1,000 residents call this community home where you can enjoy a tranquil and charming snapshot of small-town America in a unique Kentucky setting. Known for its hot and humid summers and mild winters, spending time outdoors in Augusta is always popular, and guests can enjoy activities such as sailing and swimming, and of course a very nostalgic ride on the Augusta Ferry, which has been in operation since 1798. Admire cute riverside houses, stroll along the waterfront or sit in quiet contemplation; Augusta is indeed a very relaxing and underrated town. With a nice assortment of historic sites, small restaurants, shops and other galleries, a perfect weekend getaway awaits in Augusta.


Historic buildings in Maysville, Kentucky.
Historic buildings in Maysville, Kentucky.

Maysville is another quaint river town located along a stretch of the 981 mile long Ohio River. Founded in the late 1700s, this Mason County seat is now home to just under 9,000 residents, and remains a charming and historic destination for anyone in northern Kentucky to explore. Once an important river port, Maysville was known as a prominent exporter of goods such as bourbon and tobacco and was even a stop on the famous network of secret passageways for fugitive slaves, the Underground Railroad. Explore landmarks such as the Simon Kenton Bridge, the Russell Theater and the city’s many beautifully painted murals depicting important moments in the region’s history. Add to that the peaceful river views, picturesque green surroundings, a warm, humid climate and a fine assortment of local businesses and restaurants, and Maysville is sure to leave any visitor with a wonderful set of special memories.


Log cabin in downtown Monticello, Kentucky, built in the early 19th century
Log cabin in downtown Monticello, Kentucky, built in the early 19th century. Image credits Brian Stansberry via Wikimedia Commons.

Also known as the “Houseboat Capital of the World,” the attractive town of Monticello serves as the seat of Wayne County with a population of just under 6,000. Named after President Thomas Jefferson’s plantation residence, this charming community is located along the Lake Cumberland reservoir and guests can enjoy plenty of water recreation. From sailing, swimming, fishing and of course houseboat rental: a relaxing and nature-rich excursion is never far away in Monticello. Additionally, you can marvel at several historic downtown attractions, including the early 1800s John Mill Log Cabin, which are listed on the National Register of Historic Places. Add to that the charming local eateries, shops, galleries and other businesses, and Monticello serves as a fine example of Anytown, USA, with Kentucky’s most quaint and rich character.


Aerial view of Newport, Kentucky.
Aerial view of Newport, Kentucky.

Established in the 1790s, historic Newport enjoys a picturesque location where the Ohio and Licking Rivers meet. Newport is one of two Campbell County seats in northern Kentucky, and a modest population of just under 14,000 calls Newport home. A picturesque town with mild winter and warm summer temperatures. Guests can enjoy fun outdoor activities such as sailing, swimming, cycling and jogging along the waterfront and in one of the city’s inviting green spaces. Meanwhile, an afternoon spent in the historic district takes visitors back to the 19th century, and a number of landmarks are listed on the National Register of Historic Places, including the County Courthouse (1884). Finally, don’t miss a visit to the Newport Aquarium, where a collection of more than 20,000 species can be viewed in a fun and interactive outing, perfect for the whole family.


Historic buildings in downtown Paducah, Kentucky, USA.  Editorial credit: Angela N Perryman /
Historic buildings in downtown Paducah, Kentucky. Image credits: Angela N Perryman via Shutterstock.

Located in the Jackson Purchase Region of Kentucky, Paducah is beautifully situated at the confluence of the Tennessee and Ohio Rivers. Historic Paducah, with a population of just over 27,000, can trace its modern history back to the 1820s and retains a very attractive historic atmosphere. Explore the many buildings listed on the National Register of Historic Places, ranging from the 19e up to 20e centuries. These include the Lloyd Tilghman House (1861) and the Whitehaven Mansion (1865). Meanwhile, as a river town, the opportunities for fishing, swimming and sailing are great ways to enjoy the outdoors and escape big city life. Back in the city, guests can also enjoy Paducah’s colorful and beautifully illustrative murals, which highlight various episodes from the city and region’s past.

Kentucky is a culturally rich and naturally beautiful part of the southeastern US, and for any traveler looking to explore the very best of Americana, the ‘Bluegrass State’ is indeed the place to be. While big cities like Louisville and Frankfort may still draw the most attention, Kentucky is also home to many smaller and underrated cities that are equally fascinating and charming. From the historic streets of Augusta to the “Houseboat Capital” of Monticello, these small Kentucky towns are beautiful places that travelers of all ages can enjoy and appreciate. Then come to Kentucky and experience its unique heritage by visiting these cute, charming and underrated towns!