Main Street of Midway, Kentucky. Image credit Alexey Stiop via

7 Picturesque Small Towns in Kentucky for a Weekend Retreat

Kentucky, a state in the southeastern United States, is famed for its eccentric culture and outdoor opportunities. Whether it is the mysterious Mammoth Cave National Park or the cascading Mississippi River, this state is a wellspring of beautiful sights. Taking advantage of Kentucky’s scenery are various small towns, each with its own slice of beauty. From cultural charm to picturesque scenery, these towns are perfect for a weekend retreat in The Bluegrass State. Moreover, without the hustle and bustle of urban cities, one can enjoy a peaceful time in Kentucky’s small towns.


Main street of Midway, Kentucky.
Main street of Midway, Kentucky. Image credit:Alexey Stiop via Shutterstock

Midway, as the name suggests, is a stunning town that offers tourists a mid-point between history and nature. Resting in Woodford County, history enthusiasts flock here to unravel the 150-year history embedded in the streets. Most head straight to Main Street, where rustic buildings transport one to a bygone era. Sites like the City Hall, Visitor Center, and D. Lehman & Sons stand out. They offer plenty of fun opportunities, from learning about the town’s past to buying antiquities to take home as souvenirs.

Outside the historic streets of town, Midway charms with ample outdoor sights, such as the Equus Run Vineyards. Here, visitors can enjoy acres of lush vineyards accompanied by a range of activities, depending on one’s preference. Wine tasting, corporate get-togethers, and the famed Murder Mystery event are just a few ways to have a blast here. Alternatively, the UnBridled Horse Tours is perfect for horse riders, with lovely animals to meet and ride. After the fun, tourists can book a room in the nearby city of Lexington, where options like the Holiday Inn Express and Staybridge Suites are ideal.


Main Street, Greenville, Kentucky
Main Street, Greenville, Kentucky. Image credit J. Stephen Conn via Flickr

The county seat of Muhlenberg County, Greenville is a small town with plenty of urban features. Upon arrival, tourists are greeted by the smiling faces of the 4,500 amicable residents in town. Stop by spots like the J & H Tasty Bakery or Papa Manzo’s II to enjoy some delicious food and lively conversations. Continue the relaxing vibe at the Brizendine Brothers Nature Park, a lovely retreat just outside town. It is a great place to relax, with a swimming pool, walking trails, and tons of greenery. If this isn’t enough, the Greenville Rails to Trails hiking route is sure to quench the thirst of outdoor enthusiasts in town.

Those interested in a cultural retreat on their weekend trip rejoice at Greenville’s attractions. Take a step back in time at the 9/11 Memorial, which commemorates the tragic event that took place in 2001. Or, spend the evening at the Muhlenberg Community Theatre, where the rustic ambiance and joyous plays create a wonderful vibe. After the show, choose from nearby accommodations such as CCI Express Inn, which features affordable rooms.


Main Street, Augusta, Kentucky.
Main Street, Augusta, Kentucky. Image credit: J. Stephen Conn via

Nature lovers can retreat into Kentucky’s wilderness in the scenic abode of Augusta, a town in Bracken County. Nestled along the southern bank of the Ohio River, there is no shortage of outdoor pursuits. Those interested in the river opt for the Augusta Ferry, which connects Ohio and Kentucky via a relaxing journey on the Ohio River. It runs seven days a week from 8 am to 8 pm with room for vehicles, so travelers have no trouble on the journey. Alternatively, people who want to stay on land can venture out along the Bracken Creek Horse and Hiking trails. Whether on horseback or one’s feet, the trails cut through thick wilderness, providing a glimpse into natural allure. End the day off with a drink at the Baker-Bird Winery for a fun start to your weekend in Augusta.

Back in town, Augusta has plenty of history to share, palpable through the array of iconic landmarks. The Rosemary Clooney House and Old Pioneer Jail stand out for their rustic charm. The former is an 1835 home that showcases over 700 clothing items worn by famous actors, musicians, and comedians. The latter is a jail from 1811, believed to be the oldest jail in the state. End the day at either Stay Augusta Ky or the Augusta Guest House for a fun weekend retreat in this Kentucky town.


Historic district of Maysville, Kentucky.
Historic district of Maysville, Kentucky. Image credit: Greg Hume (Greg5030) via Wikimedia Commons.

Follow the Ohio River east from Augusta, and you’ll find yourself in the bustling town of Maysville in half an hour. This lively town in Mason County is a world of fun, seeping with culture through unique alleys. Most people adore the array of museums in town, such as the National Underground Railroad Museum, the Kentucky Gateway Museum Center, and the old Washington Visitors Center. These sites are full of exhibits, showcasing everything from local artifacts to guided tours of the underground railroad. Beyond the museums, the cultural journey continues for tourists through vibrant options like the Russel Theatre and EAT Gallery. The former provides historic plays and performances, while the latter is a lovely display of local arts and crafts.

After indulging in the local charm, stop by the Old Pogue Distillery for a fun end to the day. Built around the historic home of the Pogue family, one will find an array of spirits, including bourbons, ryes, and more to relish. Add on a tasting room, fun conversations, and riverside views for a fantastic time. Opt for rooms in the Hampton Inn Maysville or Super 8 by Wyndham Maysville for a comfortable stay in town.


Downtown Bardstown, Kentucky in winter
Downtown Bardstown, Kentucky in winter. Image credit University of Collegevia Shutterstock

Bardstown is a mini-metropolis often touted as one of the best small towns in the state. The town caters to all kinds of travelers, no matter what they are interested in. For example, lots of people come here for the local distilleries, with tons of amazing drinking options. The Willett Distilling Company, Lux Row Distillers, and Heaven Hill Bourbon Experience are among the top spots, boasting great spirits, ambiance, and tours. Hand in hand with these sights, history is prevalent along the streets, and the historic downtown area is lined with rustic buildings. Head into sites like the 1892 Old Courthouse, 1779 Old Talbott Tavern, or Bardstown Civil War Museum to learn about the town’s exciting past. With stories of battles, guided tours, and a souvenir shop, there is little more one can ask for.

While there is no end to the historical sights in Bardstown, nature lovers can find reprieve at the Bernheim Arboretum and Research Forest. Spanning 16,000 acres 20 minutes from town, it is a wellspring of natural beauty. One can travel 35 miles of trails as they adore the 8,000 tree variants, fishing opportunities, and the on-site cafe. After the excursion, you’re sure to be tired, making it the perfect time to look for accommodation in town. The Fairfield Inn & Suites by Marriot Bardstown and Old Bardstown Inn are two ideal options located near attractions in town.

Grand Rivers

Downtown Grand Rivers, Kentucky
Downtown Grand Rivers, Kentucky

As the name suggests, Grand Rivers is a waterside town nestled along the Cumberland River and Kentucky Lake. To this end, outdoor scenery is plentiful, and the Land Between the Lakes National Recreation Area is a hotspot nearby. Spanning 170,000 acres, this area boasts endless sights and attractions like the Elk & Bison Prairie, Golden Pond Planetarium, and Woodland’s Nature Station. Choose between activities like watching elk roam free, learning about local history, or meeting local wildlife. Meanwhile, for a more intense experience, sailing and swimming are available along the coast.

Continue the waterside charm even in town at the Lighthouse Landing Lighthouse. This iconic structure is out in the waters, providing a panoramic view of the waves, perfect for memorable photos. The best part is that the Lighthouse Landing Resort & Marina is next door, offering a homely vibe that tourists adore.


Berea Crafts Festival in Berea, Kentucky.
Berea Crafts Festival in Berea, Kentucky. Image credit: Stephen Nwaloziri via Shutterstock.

Berea is a treasure trove for artists, with a colorful artistic scene that attracts people from all over. Home to the Berea College, a liberal arts college, there is creativity in each corner, and plenty of outlets put it on display. For example, stop by the Kentucky Artisan Center, Berea Arts Council, or the Artisan Village District. From shops selling local art pieces to wonderful learning opportunities, it is a world of vibrance. The town’s culture is also palpable through its past and landmarks like Union Church and the Boone Trace Marker. Or, choose to spend the day enjoying nature’s beauty at the Berea Pinnacles, which is full of hiking trails, wildlife, and forests. No matter how you choose to spend the day, end it at the Historic Boone Tavern Hotel and Restaurant for an authentic night in this lovely town.

Exploring these towns is the perfect way to witness Kentucky’s picturesque beauty. Each destination has something unique to share, whether it is history, entertainment, or nature. There is something for everyone, from the historic streets of Midway to the watersports in Grand Rivers. Moreover, with great accommodation options, a weekend in these towns is sure to be a blast!

  1. Home
  2. Places
  3. Cities
  4. 7 Picturesque Small Towns in Kentucky for a Weekend Retreat

More in Places