The town of La Grange, Kentucky is home to the Alley Loop , a charming and unique attraction that offers visitors a glimpse into the town's history and architecture. The Alley Loop is a series of interconnected alleys that wind through the town, providing a delightful and unexpected adventure for those who take the time to explore them. One of the best ways to experience the Alley Loop is on foot. Visitors can stroll down the alleys and take in the historic buildings and homes that line the streets. Many of these buildings date back to the 1800s and are made of beautiful, locally sourced limestone. The architecture is a blend of styles, from Federal to Victorian, and offers a fascinating glimpse into the town's past. One of the highlights of the Alley Loop is the Oldham County Courthouse , which is located at the heart of the town. It is currently being restored and is expected to be completed in July, 2025. This impressive building was constructed in 1874 and features a clock tower that is visible from nearly every vantage point in the town. The courthouse is still in use today and visitors can often catch a glimpse of the local officials going about their business. Another notable stop on the Alley Loop is the John W. Smith House , which was built in 1835 and also known as the Roberta Nicholson house. This beautiful home features a mix of Federal and Greek Revival architecture and is a must-see for anyone interested in historic homes. The home is privately owned, but visitors can still admire it from the outside and imagine what life was like for the original inhabitants. In addition to the historic architecture, the Alley Loop is also home to a number of local businesses , including shops, restaurants, and galleries. Visitors can take a break from their stroll and enjoy a cup of coffee or a meal at one of the many cafes and restaurants that line the alleys. For train enthusiasts, take note that In the midst of your shopping, you may be fortunate enough to watch the train pass by on one of the few remaining street-running train tracks in the country. A visit to our La Grange Railroad Museum on Main Street is a must if you’re interested in train cars and historic train artifacts! Outdoors you’ll find a Steam Engine, 1929 Dining Car, L & N Caboose, and a train-yard jitney. The steam engine was constructed in England and was initially used to move coal for the Meaford Power Generating Station prior to its replacement by more modern diesel-driven engines. There are many ideal times to visit the Alley Loop throughout the year. Some of these events are held on an annual basis . Other events are planned for as the inspiration arises. On the first Saturday in February the La Grange Chocolate Crawl is held on historic Main Street in La Grange. Visit over 20 participating businesses, sample decadent chocolate treats, shop our wonderful, local artisan shops and enjoy the day! What a perfect outing for all our chocolate loving folk but just be aware that tickets sell out quickly. In April, also on Historic Main Street in the Alley Loop in La Grange, the Blue Hydrangea Progressive Tea which is also a benefit to support ovarian cancer research is held. 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. On Saturdays from the middle of May to the end of October you can visit La Grange Kentucky’s weekly Farmer's Market where you will find fresh produce, fruits and meats, handmade cheese, sweet and savory baked goods and beautiful artisan crafts. 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! On the first weekend in June the Arts on the Green Festival takes place. During the festival, in the alleys you will be able to enjoy art from local artisans, music from talented musicians and delicious food from vendors who work together to create a lively and festive atmosphere that is not to be missed! From the beginning of June - September from 7:00-9:00 pm on the first Saturday of every month the Trackside Tunes Summer Concert Series is held 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 Saturday nights during these concerts. Bring your own chair and enjoy a meal from local food trucks. On Saturday, July 19th, 2025, which is the third Saturday of the month from (9am-6pm) it’s Oldham County Day . In the morning you can watch the parade near historic Main Street. 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, meet local politicians, learn more about locally owned businesses, churches, maybe get a freebie or enter a raffle! Food and drinks are also available. Bounce houses, balloon artists, living statues & more! This year's theme is "Duty Calls, Heroes Answer!". Project Guild is organizing the event. In the fall, Oldham County gets in the spirit of the holidays. In October there will be a series of ghost tours as the town hosts Spirits of La Grange . Are you a history buff, or a ghost hunter? If so the Spirits of La Grange Ghost tours will lead you in discovering the strange things that happen there. Watch for ghost sightings along this candlelit outdoor walk that takes you inside some of our oldest buildings and down the famous Alley Loop. This tour is not for children under 12 years old. In November, shortly after Thanksgiving you will have an opportunity to do some Christmas shopping. And on December 6th there will be a tree lighting ceremony. The Alley Loop is a delightful attraction that offers visitors a unique glimpse into the history and culture of La Grange. Whether you're a history buff, architecture enthusiast, or just looking for a charming place to stroll, the Alley Loop is well worth a visit. In addition to the Alley Loop there are many nearby Kentucky juried art shows, KY bourbon distillery tours, KY horse farm tours, trains on Main in La Grange, and the Underground Railroad! You will find some of the best Kentucky festivals, unique attractions, and events near Louisville in Oldham, KY! Add an Oldham Getaway Package to your Event Weekend in Oldham, KY! Pillow and Paddock Bed & Breakfast For an Oldham Getaway Package to your Event Weekend join us and enjoy a stay at the Pillow and Paddock less than five minutes from and to the Alley Loop. A travel package welcomes you for a luxurious and relaxing yet exquisite place to stay before, between and after your experiences. Staying at the Pillow and Paddock Bed & Breakfast , you will find tasteful elegance in lodging. Just outside Louisville, located in the heart of Oldham County, and in the town of La Grange, Kentucky , this inn offers you a welcoming atmosphere with a touch of luxury. Enjoy this exquisite Bed & Breakfast enveloped by stunning rolling hills, verdant pastures, elegant estates and prestigious thoroughbred horse farms in bluegrass country. As long as you book with plenty of time before your arrival you will have your pick of gorgeous suites with king or queen beds , hypoallergenic bedding, a flat screen TV, and 24/7 access to the Guest Pantry for complimentary hot and cold drinks, ice and snacks. Each suite has a private bathroom featuring a walk-in shower. Selecting a king suite offers the additional indulgence of a soothing bath. Book the Paddock Apartment that sleeps up to 4 people, a large spa bathroom and is both child and pet friendly. Or book the Whole-Inn which can accommodate up to 18 people. Wake up each morning to a scrumptious made from scratch breakfast that will nourish and sustain you. Relax outside on the porch. Take a walk around the grounds to visit the horses and pigs. Calm your mind and body in the jacuzzi. Watch a movie in the theater. Or sample your favorite alcoholic beverage in our Speakeasy Lounge .

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