7 Great Fall Day Trips in Kentucky

7 Great Fall Day Trips in Kentucky
7 Great Fall Day Trips in Kentucky

School is back in full swing and we are all beginning to think about the holidays. But, before we rush too quickly into winter, we have a few more weekends of fall left. I always miss Kentucky the most in the fall. The weather is perfect, just enough nip in the air to have to don a cute sweater or pair of nice boots. And then there’s all things pumpkin of course! But, most of all I miss the changing leaves. Kentucky really shows off as the hillsides become covered in beautiful fall colors. It feels like home to me. As a part of my reminiscing and dealing with being homesick I am sharing my favorite ways to enjoy Fall in Kentucky! Hope that you pick a few of these ideas and have some weekend fun with your family as you enjoy my favorite season in my home state!!

  1. Cumberland Gap National Historical Park 

    Cumberland Gap National Historical Park is located on the border of Kentucky, Tennessee and Virginia. The Gap itself is a narrow pass through the Appalachian Mountains and had historical significance as a key passageway through the mountains.  The national park is now 20,508 acres of trails and historical areas. The Visitor Center is located just southeast of Middlesboro and features a museum with interactive exhibits, a bookstore and a gift shop which sells crafts from the area, souvenirs and gifts. The park exists to preserve the natural beauty of the surrounding area and to interpret and preserve historical sites within the park. There are more than 80 miles of hiking trails, cave tours, and a historic settlement as well as picnic areas and gorgeous scenery. Surrounded by trees in Cumberland Gap National Historic Park is a great way to enjoy the changing leaves this fall!

    91 Bartlett Park Road, Middlesboro, KY 40965, 606-248-2817

    Check out hotels in Middlesboro if you want to turn your day trip into a weekend trip!

  2. Natural Bridge State Resort Parknatural_bridge_ky-27527-3Natural Bridge is an impressive natural sandstone arch 65 feet high and spanning 78 feet. The surrounding park is about 2,300 acres and about half of that area is dedicated as a nature preserve. There are over 20 miles of trails in the park ranging from moderate to strenuous in difficulty. The arch itself can be reached by taking a short, moderate trail 1/2 mile trail from the parking lot. Park campgrounds are open from March 15th – November 15th. Fishing is available in Mill Creek Lake, a small beautiful lake amidst the forest. A Kentucky fishing license is required to fish. There are four picnic shelters with bathrooms, tables and grills as well as access to a playground. If you want a more relaxed way to see the natural bridge, the sky lift is open through the last weekend in October and is located about a half mile from the main entrance to the park. Whichever way you decide to see it, Natural Bridge is a great place to take a day trip this Fall.

    2135 Natural Bridge Road, Slade, KY 40376, 606-663-2214

  3. Cumberland Falls State Resort Park

    Cumberland Falls is a large waterfall which spans the Cumberland River at the border of McCreary and Whitley counties. The 68 feet tall, 125 feet wide falls are also known as “Little Niagara” or the “Niagara of the South.” Many people visit Cumberland Falls because of the unique and elusive moonbow which is sometimes able to be observed at the base of the falls. To find the moonbow dates for the current year, check out their website. Cumberland falls features 17 miles of hiking trails to enjoy while you check out the fall foliage. The drive to Cumberland Falls either from I-75 or from US 27 is beautiful in and of itself. There is a gift shop and snack shop on site, as well as picnic areas if you wish to pack a lunch. Watching gallons upon gallons of water plummet over the Falls as you are surrounded by beautiful changing leaves is the perfect way to spend a day this Fall.

    7351 Hwy. 90, Corbin, KY 40701, 606-528-4121

  4. Louisville Zoo

    I have always loved the zoo but love it even more now that we have an animal loving toddler! Fall is a great time of year to visit the Louisville Zoo. The milder temperatures will have many animals out enjoying their habitat and the kids will be able to last a little longer as well. The Louisville Zoo is 134 acres and exhibits more than 1,700 animals in naturalistic habitats. They also boast having the “world’s largest Halloween party” featuring costumed characters and trick-or-treating. The party is going on weekends in October. Check out their website for more details! Louisville is centrally located and a convenient day trip for most parts of Kentucky. However, if you wish to make it a weekend or longer visit, there is plenty to enjoy in Louisville! Check out our booking.com affiliate page if you are planning to book a hotel for your visit!

    1100 Trevilian Way, Louisville, KY 40213, 502-459-2181

  5. Shakertown
    Shaker Village of Pleasant Hill, known as “Shakertown” by locals, is the site of a former Shaker religious community that was active for about 100 years (1805-1910). The Shakers were a innovative and hard-working group of people but their community dissolved partly because they were strictly celibate. Today the site is preserved as a historical site, nature preserve and educational center. The property has 3,000 acres to explore including 40 miles of hiking trails to enjoy the foliage, a working farm that visitors can participate in and several historic buildings and preserved artifacts. Their restaurants boasts delicious local favorites and quality southern cooking and they have a full-service catering company for onsite events. Shakertown is particularly beautiful in the fall. From the pumpkins, cornstalks and hay bales throughout the village to the hayrides pulled by tractors, it is a special time to visit. This year they also have a couple of fall events. Check their website linked above for more info.  To make your visit particularly special, stay at the Shaker Village Inn. Located in 13 restored Shaker buildings, the rooms are comfortable but also offer the unique charm that one would expect from Shakertown.

    3501 Lexington Road, Harrodsburg, KY 40330, 859-734-5411

  6. Big South Fork Scenic Railway

    Big South Fork Scenic Railway
    Photo Credit: By treewoman8 (Flickr) [CC BY 2.0 (http://creativecommons.org/licenses/by/2.0)], via Wikimedia Commons

    Big South Fork Scenic Railway is a historical railway in Stearns, KY. Visitors can climb aboard as the train follows 16 miles of track through the Big South Fork National River and Recreation Area which is absolutely gorgeous in Fall. The tour stops in the historic coal mining town of Blue Heron, Kentucky. While you are in Blue Heron, make sure to take a walk down to the Big South Fork River and check out the impressive boulders that dot the banks of the river. There are hiking trails nearby as well as a gift shop and snack bar. Admission to the McCreary County Museum is included in the price of train tickets and houses exhibits related to life in Kentucky’s early 20th century coal mining towns. The railway runs a 3-hour long tour Tuesday-Sunday in October and then Thursday-Saturday in November. The scenery this time of year is unbelievable and well-worth the trip.

    66 Henderson Street, Suite A, Stearns, KY 42647, 800-462-5664

  7. Keeneland

    By David Ohmer – Flickr, CC BY 2.0, https://commons.wikimedia.org/w/index.php?curid=34052336

    Keeneland is a farm turned Thoroughbred racing facility in Lexington. The track hosts their fall meet the next two weekends of October and the weather will be perfect to dress up in your racing day best and head out to the tracks! The grounds are absolutely gorgeous during the fall with rolling Kentucky hills and beautiful foliage, it is the perfect day or weekend trip. Keeneland has been a Kentucky tradition since 1936 and thankfully  there are still a couple or weekends of racing left in the fall meet. In addition to racing, Keeneland is the world’s largest Thoroughbred auction house and it hosts three sales annually. The Breeding Stock Sale happens each fall in November. Horses from Keeneland Sales have won virtually all of the major horse races. Keeneland offers guided walking tours that allow guests to walk through the Paddock, Grandstand and the Keeneland Library which has an impressive collection of Thoroughbred related volumes. New this fall Keeneland is also offering behind the scenes tour of their race days and sales day. Check out their website for more details.

    4201 Versailles Road, Lexington, KY 40510, 859-254-3412


  1. Set in the heart of Carter County, which boasts the highest concentration of caves in Kentucky, the Carter Caves State Resort Park is a great place to spend an active weekend.

    • Thanks for the reminder about Carter Caves State Resort Park, another great one! We will make a note to remember it when we update this article!

  2. Set in the heart of Carter County, which boasts the highest concentration of caves in Kentucky, the Carter Caves State Resort Park is a great place to spend an active weekend.