Autumn days are here again, and we couldn’t be happier. The Bluegrass is a pretty charming place all year ‘round, but during the fall, it goes from charming to downright magical: October races at Keeneland plus this year’s Breeders’ Cup, apple orchards, brilliant foliage, crisp weather, the promise of fun holidays to come. And of course, pumpkin everything, every day. 
Whether you’ve spent your life here or are new to the region, there is always something new to discover – from the rolling hills of Horse Country, to the stands of America’s most famous thoroughbred racing tracks, to the Kentucky Bourbon Trail and world-class outdoor exploration. We’ve put together our top picks for enjoying all the Bluegrass has to offer this season. We hope you’ll find something new and exciting to explore. So dive in to this guide, and have a good fall, y’all! 
One of the best things about fall is that the weather is perfect for festivals. We put together some ideas for great outdoor adventures and events you’ll definitely want to consider visiting, including music, art, farm fun, and food-themed events, as well as some great family-friendly activities. So throw on a scarf, bring the kids, and come out to enjoy the season! 
Reed Valley Orchard Fall Festival
Located roughly between Cynthiana and Paris, Reed Valley Orchard is easily accessible from several different areas of Kentucky. Owners Dana and Trudie Reed planted their first trees in 1988, hoping to create a place that would exemplify their love of beautiful landscapes, peaceful settings, and a place for people of all ages to relax and have fun. “Apple orchards run in both sides of our family,” said Trudie. “Dana’s father owned an orchard when he was a boy in Western Massachusetts, and my grandfather, Leo LeMaster, helped introduce and promote apple growing in Johnson County, home now to the Kentucky Apple Festival.”
Today, Reed Valley Orchard has over 3,000 apple trees, as well as pumpkins, berries, peaches and pears. There is also an on-site market where guests can purchase fruit, crafts, edible treats, and gift boxes for shipping. Every Saturday in October from 9:30am-5:30pm, they host their annual Country Harvest Trail Days. Visitors can pick fresh apples or berries, take a wagon ride, listen to live music, enjoy delicious barbeque, take a light hike down a nature trail nestled between a rippling creek and swaying cedars, walk the historic Stagecoach Trail that Jesse James and his brother camped along, or enjoy a picnic with family and friends. reedvalleyorchard.com
Kentucky Bluegrass & Bourbon Festival
Taking place September 4-6, at Louisville’s Water Tower Park, the Kentucky Bluegrass & Bourbon Festival is about three things: live bluegrass music, amazing bourbon and savory barbeque. What more can you ask for? 
For years, this popular festival has celebrated the last days of summer, featuring three full days of incredible live bluegrass music from musicians across the country, barbecue, a craft vendor tent, plus the chance to taste a few of the unique craft spirits that make Kentucky the bourbon capitol of the world. Many people agree that the Bluegrass genre has experienced a nationwide explosion of popularity in the past 15 years. Nowhere is that more powerfully demonstrated than right here in our own Kentucky bluegrass-grown backyards. The Kentucky Bluegrass & Bourbon Experience captures the essence of what has made it so popular: a musical experience that comes from the soul. Here is a sample of what you’ll hear:
Hickory & Friends
Hailing from Prospect, KY, it only seems right to have local Hickory & Friends kick off this year’s Bluegrass Festival. Their melodic sound is sure to get you into the mood and warm you up for a long weekend of Kentucky’s homegrown bluegrass sound.
This local band’s sound is often summed up by the title track of their debut album: “Livin’ in the Past”. Louisville, once the epicenter of bluegrass music, bears a rich history of bringing the genre right up to the cutting edge. With their songwriting and multi-genre fusion, Relic is part of a revival of this platform, blending rich vocal harmonies with colorful instrumentation.
Lonesome River Band
Lonesome River Band continues their reputation as one of the most respected names in bluegrass music. Led by five-time International Bluegrass Music Association (IBMA) Banjo Player of the Year and Virginia Country Music Hall of Famer Sammy Shelor, the group holds a powerhouse line-up of award-winning players including vocalist and songwriter Brandon Rickman on guitar, Mike Hartgrove on fiddle, Barry Reed on bass and Randy Jones on mandolin and vocals.
In addition to great music, The Kentucky Bluegrass & Bourbon Experience wouldn’t be complete without the best local BBQ. Enjoy some of the best pit smoked BBQ in the state of Kentucky. Juicy pulled pork, tender slabs of ribs, and savory chicken, all seasoned with a variety of mouth-watering dry rubs, sauces and seasonings. After dinner, celebrate the true “spirit” of Kentucky with tastings of some of the finest hand-crafted bourbons available in their very own Bourbon Tasting Lounge. For fans of something with a fruity flair, try a featured Sailor Jerry Rum or Four Roses Bourbon cocktail. Or cool off with a cold brew or two at their Budweiser Bar. Plus, no summer festival is complete without traditional fair favorites like ice-cold lemonade, funnel cakes, ice cream, and ribbon fries. kentuckybluegrassfestival.com
Kelley Farms’ Giant Corn Maze
The Kelley Family has been operating their farm in Southern Fayette County for more than a hundred years. They began with a small country store and tobacco operation, and over the years, expanded with produce and livestock. Today, Farmer John, his children, and grandchildren continue the tradition. 
The Kelleys no longer produce tobacco or run the country store, but they do continue to farm fruit, cattle, pumpkins and other vegetables on the soil they love so much. But their claim to fame is Central Kentucky’s original Giant Corn Maze. The 10-acre maze has been a favorite Bluegrass fall destination for years. 
Each year, the maze is designed using a top-secret method. 2014’s design celebrated the 75th anniversary of The Wizard of Oz, and activities included a Wizard of Oz-themed scavenger hunt! With  both a beginner and advanced maze, as well as a special corn maze for children, all visitors can challenge themselves through the unexpected twists and turns. 
When asked how the maze is created, we got this reply: “Our exact process is a secret, but we can tell you we do it the old fashioned way and it takes a lot of practice. We do not use a GPS system! Our corn is planted months in advance, and carefully cut out in a special design. It takes some serious math skills and a lot of patience.” kelleyfamilyfarm.com
Fall Arts Festival at Josephine Sculpture Park
On Sunday, September 13 from 11am-6pm, bring the family to Josephine Sculpture Park in Frankfort and enjoy the Fall Arts Festival. Described by the founders as an “experiential arts festival”, the purpose of the event is to provide the public with free opportunities to make art and watch live demonstrations of exciting new processes and techniques. All workshops are led by experienced artists, and all ages and abilities are encouraged. No experience is required to participate, just a desire to have fun!
A few of the art activities offered include community sculpture projects, pottery wheel demonstrations, book binding, tie-dyeing, storytelling, sticker making, a sculpture scavenger hunt, art facts presented by the Kentucky Historical Society, and more to be announced. 
In addition to hands-on activities, this event is a great opportunity to observe artists at work. Watch German artist-in-residence Heike Endemann use a chainsaw to carve her massive wood sculpture, or see Chris Wilder conduct a traditional raku firing process for ceramics. 
The event will also feature more in-depth workshops for an additional charge. Examples include Hot Metal Pour, in which Sculpture Trails Outdoor Museum helps you create your own cast aluminum relief sculpture ($30), learn glass blowing and create your own Christmas ornament ($35), or take a Blacksmithing class and learn to hammer your own decorative hook on the blacksmith’s anvil ($25). 
Along with art activities, guests can enjoy live music, yoga, hot air balloon rides, professional face painting, and great food vendors like White Lightning, Cheesy Mac, La Fiesta Grande Mexican Cuisine and Crank and Boom Ice Cream. josephinesculpturepark.org
Fall Festival at Evans Orchard & Cider Mill
Evans Orchard & Cider Mill is a fun farm in Georgetown for kids and kids at heart. Join them in kicking off the apple season with their annual Apple Festival on Saturday September 12, from 9:30am-6pm, and Sunday September 13 from 12-6pm. There will be fun for the whole family with pony and hayrides, a fun filled play area, craft booths, and huge selection of great food!  You can pick your own apples, pears, strawberries and blueberries (when in season), and they will be making their famous fried apple pies, caramel apples, and apple cider.
Evans Orchard grows over 20 acres of peaches, apples and pears, and more than 20 acres of vegetables. Throughout the summer and fall, you’ll find their Farm Market & Gift Store packed with tasty, locally grown fruits and vegetables, picked at the peak of perfection for the best flavor and nutritional value. While you are in the Gift Store, be sure to sample their delicious, creamy homemade fudge, and try the apple cider donuts or perhaps a fried apple pie, along with a glass their homemade, delicious cider.
If you’re making a day of it, plan to include a visit to the Sweet Apple Café and Bakery for a hamburger, hot dog, grilled chicken sandwich, rib-eye sandwich, pulled pork cooked with their own apples, ice cream, or apple dumplings.
For the kids, there is a fun play area that will entertain everyone from the youngest toddlers to the young at heart, such as the Jumbo Jumper, The Apple Cider Slider, Rat Racers Big Wheel Track, Corn Maze, Swings and Tire Climbs, Corn Bin Play Boxes, Hay Castle and much more.
The play area is open every day that the market is open for a single admission fee. Season passes are also available. evansorchard.com
Bourbon County Secretariat Festival
Mark your calendars for the weekend of September 18-20, and head out to the picture-perfect backdrop of Bourbon County for the 8th Annual Secretariat Festival in historic Paris, Kentucky! The Secretariat Festival offers a schedule of events over the course of three days, inviting visitors of all ages to the heart of horse country to celebrate its most famous resident. Honoring Secretariat, the 1973 Triple Crown winner and showcasing the Commonwealth’s pride in its rich equine history, this event promises to be fun-filled day for all ages. 
The Festival begins with Friday’s Barrel Mane-ia and Bourbon tasting in downtown Paris, and continues on Saturday with a wide range of events at the Bourbon County Fairgrounds including equine demonstrations & competitions, art, craft and memorabilia fair, children’s activities, celebrity autograph signing featuring the Meadow Stable team, silent auction, and a variety of food and entertainment, with free admission for all.
While you’re there, why not take a tour of the farm where Secretariat lived? The official Secretariat Tour takes you through historic Claiborne Farm, one of America’s most prominent horse breeding properties. It’s an intimate look at where the great champion lived out his days as a stallion following his legendary racing career. The tour concludes with a visit to Secretariat’s gravesite. Tours will last approximately forty minutes and depart on the hour beginning at 9:30am until 3:30pm. Those wishing to take the tour can meet the bus at the Bourbon County Fairgrounds Festival tour location 10 minutes prior to departure. Each farm tour participant will receive a complimentary Secretariat gift as a keepsake of their visit. secretariatfestival.com
Poppy Mountain Bluegrass Festival 
If you love bluegrass music, camping, and beautiful scenery, then don’t miss Morehead’s Poppy Mountain Bluegrass Festival! Located at the border of the Daniel Boone National Forest, this festival began as a dream passed on from father to son, and evolved into one of the largest bluegrass festivals in the world. Each year, over 100 bands travel to the gorgeous mountainside retreat to share their love of music. With exciting lineups, the crowd swells to over 20,000 guests each year, making the event large enough to be noticed, but still somehow relaxed and intimate. 
Traveling east from Morehead, Poppy Mountain first comes into view from the Tom T. Hall Highway (US 60). As you pull off the road at the entrance, you’ll immediately feel the bluegrass spirit. The Poppy Mountain Bluegrass Festival begins on September 1 and lasts for twenty fun-filled days. And unlike many other music festivals, you are free to enjoy the land as you choose. You can fish, hike, ride horses, take in the sights, or just relax. And, of course, jam to your hearts’ content to a variety of great bands and artists. 
The festival begins with the Annual Poppy Mountain Round-Up at the top of the hill on August 31. This is a time for die-hard fans to arrive early and claim their campsites, eat, drink, and get reacquainted with old friends. Then at midnight on September 1, the gates to Poppy Mountain open and the festival begins. ATVs and golf carts are welcome, and a diverse array of transportation is available so you can explore an entire world of bluegrass in over 1,400 acres of beautiful Kentucky hill country. poppymountainbluegrass.com
Now in its 13th year, WorldFest brings the world to Louisville! Recognized as one of the Top 10 Fall Festivals and Events by the Kentucky Travel Industry Association, WorldFest, one of the region’s largest free international festivals, is a celebration of world food, music, dance, culture and education. The four-day festival takes place Labor Day weekend is completely free to attend. 
“Cities that embrace and encourage their international citizens and cultures will thrive, have a stronger quality of life, and will attract new growth and jobs,” Louisville Mayor Greg Fischer said. “WorldFest is a great event for exploring and celebrating Louisville’s many faces and cultures and we always look to make it more vibrant, diverse and educational. So, it’s exciting to add many new features and attractions each year.”
WorldFest takes place September 4-7 in downtown Louisville at the Belvedere, located at 5th Street and Main Street. louisvilleky.gov/government/city-events/worldfest
adult festi-fun!
Lexington Fest of Ales
If you love beer, you won’t want to miss the 2015 Fest of Ales! Taking place in downtown Lexington at the Cheapside Pavilion on Friday September 4 from 5:30-8:30pm, this yearly event gives beer fans a chance to sample brews from over 60 local and national breweries. The $30 ticket price gets you a collectible tasting glass and 20 beer samples. Food trucks from various vendors will be available, as well as free transportation to the official after party at Pazzo’s. Tickets are available at the Liquor Barn locations, Pazzo’s, The Beer Trappe, and at Central Bank Thursday Night Live. lexbeerscene.com/lexingtonfestofales
The Kentucky Bourbon Festival
If you haven’t had your fill of bourbon festivals, head over to Bardstown, named the “Most Beautiful Small Town in America” by Rand McNally and USA Today. As the second oldest city in the state, Bardstown has over 11,000 residents, the first diocese of the west, as well as many historic buildings and museums. Since 1776, the people of Bardstown have been making Bourbon. Their dedication to the fine art of distilling eventually gave Bardstown the title of Bourbon Capital of the World.  It’s home to five distilleries, including Jim Beam and Maker’s Mark, so it is only fitting that the annual Kentucky Bourbon Festival is celebrated there. Come celebrate the passion, craftsmanship, and history in a beautiful, historic setting.
Taking place September 16-20, this event gives you 6 full days of smooth bourbon, delicious food, and great entertainment, with a healthy dose of Kentucky hospitality thrown in for good measure. From black tie galas to historical tours, there is something for all ages and interests. 
If you haven’t been to this quaint town hidden away in the Kentucky countryside, there is so much to explore -- shops, fine restaurants, trains, museums and of course the distilleries that have made Bardstown famous. kybourbonfestival.com
The Kentucky Bourbon Trail
If you haven’t taken part in this quintessential Kentucky experience, what are you waiting for? The Kentucky Bourbon Trail is known around the world for being the ideal way to experience Kentucky’s history and enjoy its most loved beverage. Perhaps the easiest way to plan your trip is through kybourbontrail.com. There, you can request your passport to any one (or all nine!) of the distilleries on the trail. You can also download their app to have all the information you need in your pocket. At your first distillery stop, you’ll be given your passport, which serves as a fun way to keep track of the distilleries you’ve visited and a souvenir of your trip. Each time you visit a member distillery, you’ll collect stamps in your Passport. Those that finish the entire Bourbon Trail will earn a complimentary t-shirt. Bragging rights, anyone? 
According to the Kentucky Distiller’s Association, the Bourbon Trail is best experienced over the course of at least three days. Exploring the nine legendary distilleries and all that our Commonwealth has to offer isn’t something that can be done quickly. After all, the point of bourbon making (and drinking) is to savor the experience. Contrary to what the name suggests, The Kentucky Bourbon Trail has no beginning or end, so it’s best to plan your trip around the activities you enjoy, whether it’s big-city nightlife, picturesque country towns, Bourbon-themed hotels or historic bed & breakfast accommodations. kybourbontrail.com
Heaven & Evan Tour 
The Heaven & Evan is an intimate touring and tasting experience no bourbon lover will soon forget. The tour transports you from downtown Louisville to nearby Bardstown and back in just five and a half hours, making it the perfect option for folks looking to maximize their time.
For just $175 per person, you have the opportunity to visit two classic stops on The Kentucky Bourbon Trail—Heaven Hill’s Bourbon Heritage Center in Bardstown, Kentucky, and the Evan Williams Bourbon Experience in downtown Louisville. Along the way, you can learn from master distillers and taste some of the world’s finest bourbons, including some that are exclusive to each of the properties.
The experience begins at The Galt House, where Mint Julep Tours will pick you up and transport you to Heaven Hill’s Bourbon Heritage Center. Once there, you can whet your appetite with heavy appetizers and specialty cocktails before partaking in an intimate bourbon tasting held inside a working rickhouse of America’s largest independent, family-owned producer of bourbon. Master Distiller Denny Potter will lead the tasting, which will include Larceny and William Heaven Hill Bottled-In-Bond, a product available exclusively at the Bourbon Heritage Center. While inside the rickhouse, guests will also be given the rare opportunity to pull and taste Elijah Craig 12-Year-Old Bourbon straight from a barrel utilizing a Whiskey Thief!
After your experience at the Bourbon Heritage Center, Mint Julep Tours will transport you back to Louisville to the Evan Williams Bourbon Experience. There, inside the Prohibition-Era Speakeasy Lounge, guests will be treated to even more heavy appetizers, desserts and specialty cocktails. Artisanal Distiller Charlie Downs will lead a bourbon tasting that includes Evan Williams Single Barrel and two premium offerings: Evan Williams 12-Year-Old, and Evan Williams 23-Year-Old, which normally retails for $289 per bottle. The night wraps with a guided tour of the Evan Williams Bourbon Experience, during which everyone will get the opportunity to sign a barrel of bourbon. As a keepsake, guests will receive a complimentary specialty-labeled bottle of Evan Williams Single Barrel signed by Master Distiller Denny Potter and Artisanal Distiller Charlie Downs.
Heaven & Evan will take place on Friday September 25. The event begins at 4pm and ends at approximately 9:30pm. kybourbontrail.com/enjoy-the-heaven-evan-tour
Wine Tours
What could be better than a beautiful fall day, spectacular landscapes, interesting architecture and locally produced wine? Take a guided tour through the rolling hills and horse farms of the Bluegrass Region to some of Kentucky’s unique and beautiful vineyards and wineries. While there are numerous wineries worth exploring, we’ve rounded up a few of our favorites.
Prodigy Vineyards and Winery 
Located in the heart of the Bluegrass on the Peach Family Farm, Prodigy Vineyards and Winery in Woodford County offers a variety of award winning wines in an idyllic setting. Join them for their year round “Sip & Savor” Fridays. Enjoy free, live music from 6:30–8:30pm featuring local artists! If you’re hungry, they offer a diverse menu with delicious selections from their grill and deli to compliment your wine tasting experience. Seating is available at the Onyx bar and tables. While you’re there, browse their gift boutique for unique fashion and wine accessories. 
Wine tasting is just $5 or $8 to sample your choice of six award-winning wines. The tasting comes with a complimentary glass to take home. True wine devotees can join their Wine Club and receive special discounts and member privileges. If you just want to stop by and relax, check out their weekly specials at prodigyvineyards.com.  For example, Tuesday is Ladies Night, or “W.I.N.O.S (Women In Need Of Sanity). From 4-6pm, ladies can get their favorite glass of wine at half the price or a Wine Frappé (Slushie) when on tap. Cheers to that! prodigyvineyards.com
Black Barn Winery 
Those who have visited Black Barn Winery say that it truly embodies the Kentucky spirit. The small, family owned winery is housed inside a renovated tobacco barn, located just 4 miles from the Kentucky Horse Park. The friendly staff and the breathtaking property sets the mood for the whole experience. And their wines are uniquely flavored and made with great care.  
Black Barn Winery was conceived by Collin Boyd and is home to fine national award winning dry red wine blends crafted in Kentucky. Collin concentrates on crafting one full-bodied wine per year, made with grapes brought fresh to the winery from California. 
If you’re interested in a tour, call ahead 859-552-2525. Black Barn is by appointment only (Monday-Saturday), so you’ll know in advance what wines are available when you come to visit.  If you’re looking for a fun fall activity and enjoy a great wine tasting experience, put Black Barn Winery on your list! blackbarnwinery.com
Equus Run Vineyards 
Located on 35 acres in the heart of Central Kentucky’s Bluegrass Region, Equus Run Vineyards was voted by CNN Travel as a “Must See Hidden Treasure of the United States”.  Amidst quaint thoroughbred horse farms, centuries-old stone fences and the pictureesque charm of Midway, Equus Run is the ideal place to enjoy a picnic, take in a game of croquet or bocce, enjoy a game of golf on the putting green, take a leisurely walk through the promenade gardens, or go fishing or kayaking on the scenic South Elkhorn Creek.
Nestled among birch trees and flower beds is their stone-faced Tasting Room and Gift Shop, which was once a farm tool shed. There, you can enjoy wine tastings and a picnic garden area with a tiered deck overlooking the Riesling vineyards and golf putting green. It’s the perfect setting for an idle afternoon of sipping and socializing. Remember to take a photo with their horse sculpture, Vegetariat, or any of their other Horsemania sculptures. equusrunvineyards.com
Talon Winery
This lovely winery’s original tasting room is located in a historic farmhouse from the 1790s. Guests can take part in a variety of wonderful wine tastings and tours. You can experience the entire bottling process from vine to wine at their Corking Complex. Or take the reins and participate in self-guided tours featuring a sneak peek at their vineyards, processing center, and Kentucky Oak barrels.
If you’re looking to host an event, the landscaped grounds and covered porches surrounding the winery offer unlimited possibilities. A private tasting room is available for small group functions, business meetings, luncheons, club outings, bridal showers, and much more. Guests are invited to enjoy indoor and outdoor picnicking year-round. Talon’s open-air pavilion and new enclosed party barn are equipped with full service catering capabilities, too.
At Talon Winery’s Shelbyville location, you’ll find a beautiful tongue and groove barrel ceiling that evokes the Kentucky oak barrels used to age their delicious wines. A scenic covered porch overlooks a five-acre limestone quarry lake. Plus, their Kentucky Proud gift shop is an exciting place to find that perfect gift for yourself or a friend. They offer a wide range of unique wine related gifts and accessories, as well as Talon souvenirs.
Don’t miss their Fall Farm Fest, taking place at the Lexington location on Saturday September 12 from 12-7pm. Featuring Billy’s BBQ, local vendors, games, live music, and of course, delicious wine! talonwine.com
McIntyre’s Winery & Berries
At McIntyre’s Winery, owners Tommy and Debbie McIntyre know that locally grown, fresh-picked berries make the most delicious wines. Visitors can choose from homemade dry, sweet, or fruit wines, or take a tour and indulge in a tasting. If you can’t make it to the winery, you can order wine direct from their online store. 
In 1987, Tommy and Debbie bought a small farm on a piece of land in Bardstown that originally belonged to Tommy’s grandparents. Tommy had always enjoyed making fruit wines from wild-growing berries and grapes. As time went by, wild berries became harder to find. The couple did some research and decided to start growing their own blackberries and blueberries on their farm. 
McIntyre’s fruit wines are completely grown in Kentucky. They had the soil analyzed, and then amended to produce the sweetest and juiciest berries possible, and they use only all natural supplements on their berries. The fruit is ripened to perfection by the sun while still hanging on the vine and is picked by hand for perfection. 
Today, the staff of McIntyre’s Winery & Berries are proud of their reputation for creating some of the best wine around, such as Black Wine, a dry Blackberry wine aged in a whiskey/black rum barrel, and blueberry, blackberry or elderberry table wines. Other flavors like peach, pear and strawberry are also available. No matter your preference, McIntyre’s has a wine for you. “We offer a wide range of sweetness levels on our wines. We can provide you with a completely dry wine to a sweet wine that has the level of sweetness you want,” said Tommy. mcintyreswinery.com

Posted on 2015-09-11 by Michelle Aiello