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Bluegrass Hills and Horses of Lexington

College Town

Lexington, the “Horse Capital of the World,” is a quiet college city. It is said to be the second-largest city in Kentucky, but you will only see a handful of skyscrapers here. The cityscape quickly spreads out into the rolling bluegrass countryside making it a large city by land area alone. There is a small airport, which gives easy access to this city for weekend getaways. We took a walk around and got a few great shots of the fun urban art around the downtown area.


When a childhood friend calls you up and says she wants to do a marathon you say, “noooo, but I will do two half marathons!” Our little adventure brought us to the rolling hills of Lexington, Kentucky countryside.

The RunTheBluegrass Half Marathon has been said to be one of the most beautiful races, and if not, it was pretty close. The race began and ended at the Keeneland Race Course, famously known for training contenders for the Kentucky Derby. The route winds through the rolling bluegrass hills of the thoroughbred horse farms. Some horses ran along the fences with the runners, and one farm had chickens and turkeys.

The hills were very steep, and at times I felt like I was standing still while running up. It was a real challenge for anyone, but one superhuman in a wheelchair completed it all on his own. Everyone had tears in their eyes and applauded when he crossed the finish line. I am not a super fast runner, but I give myself a pass on this very slow time. The elevation is much more than what I am used to, which is zero.

Hiking Natural Bridges State Park Resort (in Winchester)

About 45 minutes outside of Lexington, you will find great hiking spots, one being the Natural Bridges State Park Resort. There are ten different trails you can choose from ranging up to 7.5 miles. We hiked almost 2.5 miles by starting on the Original Natural Bridge Trail. We got to the Natural Bridge within a mile, but was met with a crowd of people. The rock formation is a known tourist attraction with a Skylift (chairlift) and there were too many people brought up there. It took away from the natural beauty, and I couldn’t capture a picture without someone standing in front. I would suggest picking a weekday to visit the bridge when the trails are less travelled. The remainder of our hike was more secluded and enjoyable through Laurel Ridge, Devil’s Gulch and Battleship Rock.

Wineries & Foodies

Although Kentucky is widely known for its Bourbon trail, Kentucky was the first state to have a commercial winery and was the leading wine producer up until Prohibition. We have explored two wineries in the area, but there are several to choose from.

Harkness Edwards Vineyards (in Winchester)

Once you drive through the gates of Harkness Edwards Vineyards, you only see a barn with a sign saying “This way ⬆️.” After a short walk, or what feels like a scavenger hunt through the barn, you arrive at a charming peach cottage. At the front door you are greeted by a cheerful staff, and you are introduced to a few different flight combinations. While they prepare your wine flight of choice, you are given the liberty of exploring the home. You can also choose any room to sit in or go out back. Since it was a beautiful day, we chose to sip our wine in the backyard by the walnut trees while gazing out at the countryside. Harkness Edwards Vineyards definitely wins at ambiance, one of the most quiet and relaxing wine tastings you can experience.

Jean Farris Winery & Bistro

The Jean Farris Winery & Bistro cheese selection and gastronomic dishes were a real treat along with our wine. We chose four cheeses: honey goat, three cream brie, fiery cheddar, and smoked cheddar. All very tasty and unique. For our meals, we ordered pickle-brined pan-fried chicken, seared duck with homemade ravioli, and beef truffle stroganoff. All were outstanding, and you could tell the chef took time and pride on each dish.

Castle Farm at The Kentucky Castle

The Kentucky Castle of 110 acres of farmland is located outside of Lexington in Versailles just past the Keeneland Race Course. The original incomplete castle from 1969 remained dormant for 30 years and then was destroyed by fire in 2004. The castle was reconstructed again in 2007 into a bed and breakfast. Now, with it’s new owners, the castle serves as a boutique hotel and event center with a farm-to-table restaurant. The Castle Farm restaurant takes advantages of its surroundings, outsourcing only from local farmers and growing any additional ingredients needed. They host private or public events, including fairy tale / princess tea time and murder mystery dinners.

Le Deauville

This cozy classy French bistro is located in the historic section of Lexington. With reservations, we were seated and served with appetizers and wine fairly quickly, but our food came over an hour later. Le Deauville can get crowded, so plan to sit and feast in a slow traditional fashion. The frequent locals were seated in their ‘usual’ spots and were treated first class, which gives off an old-school, pretentious vibe.

Carson’s Food & Drink

This classical Kentucky atmosphere combines creative recipes with prohibition cocktails. We started our brunch with a mimosa toast to the end of an epic weekend with friends. The baked brie appetizer topped with bourbon pear chutney, candied pecans, and berries was mouth watering. The main courses we chose were filet medallions with shrimp and eggs benedict and petite filet with scallops and lobster on top. Carson’s Food & Drink, Lexington’s top brunch spot, did not disappoint!

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