Autumn is an exciting time to visit the Bluegrass State. As Columbus Day nears, temperatures cool in towns and throughout wide stretches of untouched wilderness, while trees begin to don their glorious fall attire of blazing reds, fiery oranges, and golden-jeweled tones. This humble state is home to roughly 175 different species of trees, so you can expect spectacular views from your Kentucky vacation rental. Look forward to unforgettable sights atop a mountain or via a drive through the countryside.
Take a scenic drive through deciduous forests, past horse farms and through hunt country on the self-guided Bluegrass Country driving tour, which is also suited for touring by horseback. If you like horse racing, spend a cool and crisp fall afternoon at Keeneland Race Course placing bets and warming up with a cup of a special Bluegrass stew called burgoo. Paddle-wheel boat rides along the Kentucky River give you spectacular panoramas of changing colors on shore, or you can hike or bike the Legacy Trail, a 12-mile trail with mostly off-street paved paths.
This lovely town dates to 1774, and it’s fun to visit the restored settlement, the Shaker Village of Pleasant Hill. Stop by for a refreshing soda or milkshake at the original 1865 soda fountain in Dedman Drugstore. The Village is a bird sanctuary with over 125 species of local and migrating birds, as well as hikes through the woodlands, rolling fields, and ponds that offer numerous photographic opportunities. If you love to hike, bike or ride horseback, take advantage of 37 miles of trails at the Preserve. Start your holiday shopping early at unique local craft and antique stores in downtown, then relax on the outdoor porch at Old Owl Tavern, where shrimp and grit is a house specialty.
This quaint city on the banks of the Ohio and Tennessee Rivers has a picturesque 20-block downtown district that not only boasts boutiques, indie art galleries, and antique shops, but also beautiful 19th century architecture. To experience a wonderful walking tour, bring your phone when you leave your vacation rental. Paducah has a cell phone tour that explores its rich history; all you need to do is dial, listen, and learn. Greenway Trail is a 4.5-mile track that connects historic downtown to Bob Noble Park, the disc golf course and dog park. Restore your energy with a burger and shake at nostalgic Parker’s Drive-In Restaurant.
Greenville, founded in 1799, has rolling hills, beautiful forests and true hospitality, making it a true leaf-peepers dream. The historic town square has wonderful Beaux-Arts style architecture and plays host to numerous festivals. Rails to Trails is a great place to enjoy the local trees’ glorious fall displays, as the location boasts a six-mile trail with a covered bridge, an antique caboose and plenty of shady spots to enjoy the picnic lunch packed for you at Crossroads Cafe. The trail is paved and handles foot, bike, horses, and rollerbladers. Before retiring back to your vacation rental, plan on a true Southern fare for your dinner meal at Hobby’s Classic Foods.
Augusta is a small, charming spot that’s perfect for a Columbus Day getaway. From Riverside Drive you are witness to picturesque views of the river valley and the gorgeous 18th and 19th-century architecture. Before heading out on AA Highway to Hillside Orchard and Country Store to pick up mementos, pumpkins, and gourds, grab some hot coffee, tea and home-baked pastries at Abloom Barista, or stop for a full country breakfast at Corner Cafe, where all the locals congregate.
Glasgow is the perfect place to find a vacation rental to use a starting point for exploring the beautiful surrounding area. Head out to Mammoth Cave for a guided adventure through some of the 390 miles of passages in the world’s longest known cave. Most of the cave trails and walkways are lighted, but occasionally it’s so dark you must carry a lantern. If you prefer to stay above ground, you can view spectacular foliage at Brigadoon State Nature Preserve while walking the mile-long foot trail through ridge tops, mature forests and next to scenic ravines. For a quick dinner, stop at the all-you-can-eat Evergreen Chinese Restaurant or choose Greek fare at Gondolier.
Murray has been named the Friendliest Small Town in America by Rand McNally-USA Today, and this charming town doesn’t disappoint. Despite its small size, Murray has several art galleries and a community theater housed in a former train depot. Catch the fall colors at Kentucky Lake, where the bass fishing rocks, or take to the trails at Land Between the Lakes, an uninhabited national recreational area with lots of lakes, wildlife and historical attractions including a planetarium, nature station and live elk and bison exhibits. Before heading back to your cozy vacation rental, stop by for a hot or cold buffet-style meal at Sirloin Stockade.
Nestled in the foothills of the Appalachian Mountains, Morehead is a small, charming town with plenty to see and do. Take a leisurely stroll on the campus of Morehead State University, then do some antique shopping on Main Street before making your way to CCC Trail Vineyard and Winery. The Cave Run Lakes area is nearly surrounded by Daniel Boone National Forest, and there’s a host of ways to enjoy the outdoors. Trout, bass, catfish and other species are available to serve as your dinner, and there are numerous trails waiting to take you through a forest abounding in wildlife and autumn hues.
Frankfort, Kentucky’s capital, is in the heart of horse, wine and bourbon country, and you can learn first-hand how bourbon is made when you tour Buffalo Trace Distillery. Stop by for a take-along sandwich at Kentucky Coffeetree Cafe before heading to Cove Springs Park and Nature Preserve for a picnic, a hike or some archery. For spectacular leaf-peeping, take a drive over the Old Frankfort Pike that runs between Frankfort and Lexington and enjoy one of the best ten scenic drives in America. This 16.9-mile drive is ablaze with fall colors from sugar maples, dogwoods, oaks and locust trees.
10. Bowling Green
Bowling Green is home to the National Corvette Museum, so if those iconic masterpieces rev your engine, don’t miss it. The Duncan Hines Scenic Byway is 80 miles long and takes you through stunning countrysides laden with vibrant autumn-colored displays. From the byway, you can ferry over to Mammoth Cave National Park and take the Lost River Cave boat tour, which begins with a stroll through the valley where a guide tells you the tale of the Blue Hole and the missing Civil War soldiers. Enjoy some Cajun-inspired eats in 19th-century digs at 44 Main or cozy up to the bar for some sports and comfort food at Double Dogs.
Start your getaway in Louisville at Wild Eggs, where the variety of eggs Benedict are the star attractions, but are not to be outshone by tasty French Toast and steaming, plump omelets. Baseball fans love visiting the Louisville Slugger Museum and factory, while horse racing fans can’t miss a visit to Churchill Downs and its museum. To catch some breathtaking views of the turning leaves, take River Road, which leads you through 10 miles of country dotted with historic homes and panoramic views of harbors, parks, woodlands and horse farms. Finish your day at Harvest Restaurant and enjoy some rustic, farm-to-table fare.
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