Oldham County Annual Events

The Best Annual Events in the Louisville Region!

Annual Events in Oldham County, Kentucky

Oldham County, KY is the Perfect Getaway for Cool Things To Do Near Louisville

Not only do we offer great events near Louisville, we have unique places to stay, too! No matter the event you choose to attend, whether ours or nearby events, you’ll want to book your stay at one of our convenient hotels, a fabulous bed and breakfast, or bring family and friends to enjoy an entire home to yourself in one of our cool Oldham vacation home rentals. Be sure to visit our Trip Ideas for other things to do including our famous Farm & Garden Tours, our Bourbon Distillery, and Oldham Gardensour 4-acre beer garden of connected greenhouses home to 3rd Turn Brewing, Backside Grill, and Kentucky’s ONLY Meadery, Hive & Barrel Meadery & Cider!


Interested in shopping? Check out our Trains on Main Trip Idea to spend time on Main Street La Grange where HGTV filmed Home Town Kickstart in 2022! Looking for a uniquely Oldham County farm-to-table dinner on a horse farm? Look no farther than Barn8 Restaurant at Hermitage Farm. Need more ideas? Check out our fabulous Oldham Trip Ideas!


Traveling with a GROUP of 8 or more?

Let us help plan your trip to Oldham County by offering you the highlights to make sure your STAY is memorable! Check out our attractions found one place in Kentucky – Only in Oldham!

Ongoing Events in Oldham County


Oldham Farm Tours (April – October)

Oldham County is the “Farm Tour Capital of Kentucky,” with 15 farm tours – the LARGEST number of educational, hands-on farm tours in Kentucky! Horses (carriage driving, race horses, AND all breeds!), alpaca farm fiber art studio, working dairy making artisan cheese, bison (Kentucky Bison Company) farm overlooking the Ohio River, and organic and sustainable farms that supply meat and produce to the region’s best restaurants. Do you love farm-to-table foods? Make a reservation in advance to Barn8 Restaurant & Bourbon Bar at Hermitage Farm AND Sanctuary Farm Thoroughbred Retirement FarmAnother Attraction You’ll LOVE: Our Foodie & Farm Trip Idea!

A woman holding fresh vegetables purchased from the farmer's market

Farmer’s Market & Artisans (Mid-May – October)

Saturdays at Springs Park in La Grange. Besides fresh vegetables, fruits and meats, there are items from local Artisans including handmade cheese, wonderful baked goods, and beautiful works of art. Stroll the lovely Oldham County Courthouse Square, shop, and listen to the sounds of music, laughter, and the occasional train! The market is located in Historic Downtown La Grange so in addition to enjoying the wonderful market, you can have lunch at one of the local restaurants, check out the art galleries on Main Street and browse the variety of shops around town. Spend a leisurely Saturday morning with us and forget the hectic pace of the week! Do you love farm-to-table foods? Make a reservation in advance to Barn8 Restaurant & Bourbon Bar at Hermitage Farm! Another Attraction You’ll LOVE: Our Foodie & Farm Trip Idea!

Quads Custom Car Shows La Grange (April – September)

4th Saturday.  Enjoy a custom antique car show on Main Street in La Grange. Another Attraction You’ll LOVE: Our Trains on Main Trip Idea! Check out the overnight rentals in downtown La Grange!

Pickin’ on the Porch Concert Series (May – September)

Last Saturday (6 – 9pm).  A Westport, KY favorite! Knock on Wood Mercantile & Café hosts this popular summer concert series where visitors can enjoy front porch sitting fun while listening to some great local performers near the Ohio River. Come early and shop for primitive and country home decor!
Another Attraction You’ll LOVE:  follow the Oldham County Lewis & Clark Trail! 

Trackside Tunes Summer Concert Series (May – September)

First Friday (7 – 9pm).  Held in the in the Alley Loop area of La Grange, Trackside Tunes features some great entertainment in an outdoor setting created by HGTV. Most Main Street businesses will be open late on Friday nights during these concerts. Bring your own chair and enjoy a meal from local food trucks.
Another Attraction You’ll LOVE while on the tracks:  Our Trains on Main Trip Idea.

Oldham Annual Events

Oldham County Wedding Expo & Venue Tour

FEBRUARY.  FREE Expo Admission. ADD VIP Venue Shuttle Tour (limited seats available): $40. What better way to see Oldham County’s popular wedding and reception venues throughout Oldham County than by hopping on a shuttle and enjoying the carefree ride! This unique Expo starts with an in-person tour of 4 popular Oldham County wedding venue spaces, includes a VIP Goodie Bag, and ends at the Expo location where you will find vendor booths, DJs, photographers, etc. An event of Oldham County Tourism & Conventions.

Ooh-La-La La Grange! Chocolate Crawl

FEBRUARY.  Held annually on historic Main Street in La Grange, this is a perfect outing for all our chocolate loving folk and tickets sell out quickly. Visit over 20 participating businesses, sample decadent chocolate treats, shop our wonderful, local artisan shops and enjoy the day!

Backyard Bird Count

FEBRUARY.  Get the entire family out and take in some fresh air at Creasy Mahan Nature Preserve in Goshen by participating in their annual bird count. This event is for beginning to advanced bird watchers of all ages. The Louisville Audubon Society helps identify and count birds and reports the sightings to the Cornell Lab of Ornithology.

Clover Leaf 5K

MARCH.  Held for the past 17 years, this run/walk starts and finishes at Briar Hill Park. Sponsored by the Oldham County Parks and Recreation Department, prizes are given in a variety of age groups and all participants receive a T-shirt and finish medal.

Blue Hydrangea Progressive Tea

APRIL.  Held annually on historic Main Street in La Grange, each tea guest receives a ticket and gift bag of assorted goodies and health information and gets to choose a souvenir teacup. Guests then visit the participating locations, for various tea beverages and light snacks. In-store specials, door prizes, and drawings are held during the event. Music and entertainment, and local health services are on hand for simple screenings and health information.

Behind the Scenes Big Bloom.

APRIL.  Stroll through the grounds of Yew Dell Botanical Gardens April – May to witness an amazing display of color and beauty that only takes place this time of the year. A walking discussion reveals a behind-the-scenes look at the 20,000 bulbs and more than 20 varieties planted for this event. Peak bloom occurs in mid-late April.

Hermitage Farm’s Easter Egg Hunt

APRIL.  Join Hermitage Farm for the biggest East Egg Hunt ever! The farm hosts a number of egg hunts for kids of all ages, while families can enjoy a selection of box lunches and pastries. With springtime cocktails available from the mobile bar, an exclusive Hermitage pop-up shop, and a surprise visit from the Easter Bunny, this is the perfect Easter event for the whole family.

Old Kentucky Home Bicycle Tour

JUNE.  An annual event with the Louisville Bicycle Club, OKHT starts and finishes at the beautiful grounds of Yew Dell Botanical Gardens in Crestwood, and features YOUR CHOICE of three routes:   A 62.1mile (100k), 40-mile and 20-mile option – and the World Famous Homemade Cookie Stop is back! A gorgeous ride through the hills and farms of Oldham County’s horse country!

Crestwood Art & Garden Market

JUNE.  First Saturday (9am – 2pm).  A unique annual curated, juried arts and crafts market that also features perennial and annual plants! Shop for unique hand-crafted items from a variety of local artists, let the kids enjoy special activities while you shop, and grab lunch at our food trucks! On the grounds at the Crestwood Civic Club – 7215 Kavanaugh Road, Crestwood.

La Grange ArtsFest

JUNE.  First Saturday (9am – 5pm).  A fun mix of music and art & crafts in the Main Street La Grange District. A curated, juried arts and crafts market + street music + food and drink from our local restaurants. Shop for hand-created items from a variety of vendors and artists/artisans/makers and creators, eat/drink at our great local Main Street area restaurants and enjoy music on the street by local musicians.

Arts on the Green at The Maples Park

JUNE.  Second Saturday (10am-4pm) & Sunday (11am-5pm). Featuring juried artists from across the country in the beautiful setting of The Maples Park. Professional and local entertainment, children’s art activities, food trucks, and adult beverages. Free parking and free admission at the Railroad Avenue entrance in Crestwood. Saturday & Sunday 11am-5pm. Another Attraction You’ll LOVE? Make is weekend getaway by adding our Botanical Gardens down the street!

Kentucky Classic at Hermitage Farm
(Takes place ONLY on even-numbered years).

JUNE.  First weekend (10am – 4pm). From live music to food trucks and beverage tents, to three days of combined driving competitions in Goshen, KY, there will be something for everyone to enjoy. Three days of FUN featuring competitors from around the world include Dressage, Marathon, and Cones. Bring your lawn chair and watch the action.

Old-Ham Half Marathon

JUNE.  A brand new marathon begun in 2022 and sponsored by Oldham County Parks & Rec. This 13.1 mile road race traverses the Commerce Parkway/Pedestrian Bridge/Oldham Reserve areas in La Grange and will showcase Oldham County’s park-like residential and commercial campus which flanks the I-71 corridor. Overall winners, male and female, receive a ham!

Children in the Dell

JUNE and JULY.  Saturdays. (10:30am – Noon). Special outdoor family activities geared to sparking a passion for plants and gardening held just for children at beautiful Yew Dell Botanical Gardens. Learn about Pollinators and the garden plants they love. This event is included with admission and will be canceled in case of inclement weather.

Oldham County Day

JULY.  Third Saturday (9am-6pm). Watch the parade in Downtown La Grange near the Courthouse Square on Saturday morning. Anticipate seeing the Grand Marshall, local school marching bands, tractors, horses, fire trucks, church, local business and other group floats that match the parade’s theme for the year. Kids are also invited to decorate their bikes and ride in the parade! Check out the booths on the courthouse square. Meet local politicians, learn more about locally owned businesses, churches, maybe get a freebie or enter a raffle! Food and drinks are also on the courthouse square. Bounce houses, balloon artists, living statues.

Barney’s Auto Fest

JULY.  (9am – 5pm). Open car show featuring cars, trucks and motorcycles held on the grounds of The Cherry House in La Grange. Includes door prizes and give-a-ways. Named in honor of Barney Barnett, longtime member of Quads Rod & Custom Car Club.

Quads, Rods and Custom Cars at Maples Park, Crestwood

JULY 29th | SEPT 16th (Fridays, 6pm-9pm). Join us for quads, rods and custom cars at the Maples Park with Live Entertainment and Food Trucks!  July Entertainment:  Allen Lane Band, September Entertainment: Misty Mountain String Band. July Food Trucks:  Cookie Cabin Creamery, Annie Up Pizza Cones, Fistful of Tacos, Mile Wide Brewing, Hive & Barrel Meadery & Cider. September Food Trucks:  Celtic Pig, Philly Best Frozen Desserts, Fistful of Tacos.

Up, Up, and Away at the Maples Park

AUGUST.  FREE. This is a bucket list item for height seekers! Bring a chair or blanket and come out to the Park for first come, first serve hot air balloon tethered rides!  Oldham County Public Library will offer kids activities to celebrate the end of summer reading program!  Live Entertainment by Billy Goat Strut Revue. Food Trucks:  Rollin Rubys, The Cookie Cabin Creamery, Ramira’s Cantina, Celtic Pig, Longshot Lobsta, Fitz Freeze, Mile Wide Brewing, and Hive & Barrel Meadery & Cider. PARKING only in lot at 6431 Railroad Avenue, Crestwood

Oldham County Fair

AUGUST.  Join us for our annual Oldham County Fair! We offer live music, beer tent, unlimited rides with paid admission, pageants, and tractor pulls. All the makings of an awesome county fair can be found in Oldham County! Gates open at 4pm, midway opens at 5pm.

Trackside Market

SEPTEMBER.  A fun, new mix of music, vintage and art/crafts in the Main Street La Grange District. Shop for vintage and hand-created items from a variety of vintage vendors, artisans and creators, eat and drink from a food truck or at one of our great local Main Street restaurants and enjoy the street musicians while you shop.

Quads, Rods and Custom Cars at Maples Park, Crestwood

SEPTEMBER 16th  (Fridays, 6pm-9pm). Join us for quads, rods and custom cars at the Maples Park with Live Entertainment and Food Trucks!  July Entertainment:  Allen Lane Band, September Entertainment: Misty Mountain String Band. July Food Trucks:  Cookie Cabin Creamery, Annie Up Pizza Cones, Fistful of Tacos, Mile Wide Brewing, Hive & Barrel Meadery & Cider. September Food Trucks:  Celtic Pig, Philly Best Frozen Desserts, Fistful of Tacos.

Foxhollow Sunset Concerts

SEPTEMBER.  (2nd Friday & Saturday, 5pm-9pm). Foxhollow Farm’s Sunset Concerts are a great opportunity for folks to come together to enjoy live music, farm-fresh food, and libations. Bring a blanket, lawn chairs, or comfy outdoor cushions to sit on as you enjoy some great music. Seating limited to 350 adult tickets.

Historic Candlelight Cemetery Walk – Floydsburg Cemetery

SEPTEMBER and OCTOBER.  (Thursdays, September 29/October 6, 7 – 9pm.) Join the Oldham County History Center for a Candlelight Cemetery Walk through Floydsburg Cemetery and a tour of the Duncan Memorial Chapel. Floydsburg Cemetery is one of the oldest cemeteries in the region, created in 1799 by the William Boulware family.

Halloween MAINia

OCTOBER.  This event is when the Main Street merchants welcome families for Trick-or-Treating at participating shops. There is also a costume contest for all ages and pets!

South Oldham Rotary Scavenger Hunt at the Maples Park

OCTOBER.  Last Saturday. Join us for a family-friendly scavenger hunt through Crestwood where no potions are needed to concoct a cauldron-full of fun! Get your first clue at a local business and end at the Maples Park with a goodie bag and prize for The Spookiest” and “Best Themed” car. $20 per carload.

Skeleton 5K/Run/Walk & Spooktacular Festival

OCTOBER.  (5K begins at 2pm/Festival follows the race from 3:30 – 5pm). In its 17th year, this fun run/walk will start and finish at Wendell Moore Park in Buckner, KY. Race is followed by the Spooktacular Festival from 3:30 – 5:00 pm – Trick or Treat in the lower parking lot (behind the pool). Free for families with kiddos ages 0 – 12.

Halloweenie Pet Walk at the Maples Park

OCTOBER.  A leisurely walk through the Maples Park for animal lovers and their fur babies! Collect treats (no tricks!) along the path form event sponsors. Enjoy food trucks Big R’s BBQ and Annie Up Pizza Cones.​ An event by Adopt Me Bluegrass Pet Rescue.

Haunted Hike at Creasey Mahan Nature Preserve

OCTOBER.  (First Sunday, 3pm-7pm). The kid-friendly Haunted Hike is the most popular event of the year and should not be missed! This is a great day to debut your family’s Halloween costumes, collect A LOT of candy, and have a blast of a time in a beautiful setting of Creasey Mahan Nature Preserve.

Spirits of La Grange Ghost Tours

OCTOBER.  One of the most popular tours in the region, some say it’s the best they’ve ever taken! Combining a historical aspect to introductions to our “spirits,” you can learn all about haunted LaGrange on the two-hour candlelit walking tour of downtown La Grange. Proceeds from the due to the potential spirit activity, all 100% genuine, tours are not recommended for children under 12. ​

Rollin on the River

OCTOBER.  (11 am – 5 pm). Food Truck Festival at Westport’s Schamback Park. Enjoy a beautiful fall day on the Ohio River featuring some of the greatest eats around and fantastic music.

YMCA Monster Mash Dash 5K

OCTOBER.  (Last Saturday, Noon – 1pm). Join the YMCA, 3rd Turn, and Backside Grill for a fun festive 5K Spooktacular that started in 2021! All runners receive a box lunch, drink token, festive t-shirt and festive medal. Costume contest included. Great family event, open to those ages 6 and up. Awards given.

Boo Dell!! At Yew Dell

OCTOBER.  (Last Sunday, Noon – 4pm). Yew Dell Botanical Gardens’ annual community Halloween festival is a frightfully fun day and always a family favorite. Kids of all ages can enjoy trick-or-treating along the Trail-o-Treats where dozens of local businesses will entertain with their creatively creepy booths and costumes. Hayrides, a straw maze, scavenger hunts, and music.

Light Up The Maples Park

NOVEMBER.  Come to the park for the 2nd annual Crestwood sponsored holiday Light Up ceremony! The Deibel Barn and Tree will be filled with lights again this holiday season. Special guest announcement coming soon!

Shop Winter in Kentucky Gallery 104 Artists Boutique

NOVEMBER – JANUARY.  A variety of different art mediums are always represented in this holiday display at Gallery 104 in La Grange. Shoppers can find a full range of gift-appropriate art at all price points and it provides Oldham County artists the opportunity to display additional inventory during the holidays. Suitable holiday gift giving ideas include pottery, sculpture, fabric, glass, fiber, painting, wood, jewelry, photography and multimedia.

Yuletide at Yew Dell

NOVEMBER – DECEMBER.  Weekends. This magical event never disappoints! Get in the holiday spirit with the dazzling light and décor displays, enjoy the model train village, say hello to Santa and hear a story, enjoy snacks, beverages (of both the kid and adult varieties) and other surprises that all combine to make a wonderful holiday family outing at Yew Dell Botanical Gardens.

Christmas in the Country

DECEMBER.  First weekend. Festive events take place on Main Street La Grange with Light Up La Grange, at Yew Dell Botanical Gardens, Creasey Mahan Nature Preserve, and Oldham Gardens.

Holiday Tea at Hermitage

DECEMBER.  Celebrate the season with crafted herbal teas, miniature sandwiches, and delicious desserts at Hermitage Farm’s Main House. To set the mood, carolers stroll the grounds while singing in the spirit of Christmas cheer.

Festival of Nativities

DECEMBER.  Celebrates the beauty and diversity of the Christmas Creche. See first-hand over 300 Nativities on display from around the world. Visitors can enjoy family photos, cookies, children’s craft, traditional Nacimiento, live nativity, nativity story tours and community concerts all free of charge. Experience a wonderful evening of art and Christmas spirit that will be sure to become part of your annual holiday traditions.

Breakfast with the Grinch

DECEMBER.  (First Saturday). Kick off Light Up La Grange by having Breakfast with the Grinch! This annual event features special children’s activities, treats, crafts, and fun photo opportunities throughout the Oldham County History Center campus. Admission for families is a new unwrapped toy or $3 per person.

History Center Campus Events

Gatewood Plantation Archaeological Digs

APRIL/MAY and SEPTEMBER/OCTOBER.  These seasonal FREE public archaeological digs are given by the Oldham County History Center at the Bibb Escapes/Gatewood Plantation location, a National Park Service site on the National Underground Railroad Network to Freedom. Since 2007 the History Center has conducted archaeology research on this historic site which honors Henry Bibb and his family, who were enslaved by William GatewoodAnother Attraction You’ll LOVE:  Our Creasey Mahan Nature Preserve or Yew Dell Botanical Gardens.

Archaeology Field Institute at the Bibb Escapes/Gatewood Plantation

JULY.  Since 2007 the Oldham County History Center has conducted archaeology research on this site which is now recognized by the National Park Service as a site on the National Underground Railroad Network to Freedom. The site honors Henry Bibb and his family, enslaved by William Gatewood and described by Bibb in his own narratives – The Life and Adventures of Henry Bibb: An American Slave. Participants work with licensed archaeologists to uncover clues to the past. Open to ages 10+.

Barnyard Fun at the Dahlgren Barn

MAY – SEPTEMBER.  (Saturdays, 10am – Noon). These hands-on events take place at the Dahlgren Pioneer Barn on the Oldham County History Center campus! From Abe Lincoln Day to Nature Day, kiddos will love learning something new about history.