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Welcome to Lexington, our Old Kentucky Home, we hope you enjoy your stay with us.  We have compiled a list of some of our favorite places to visit and more importantly unique truly Kentucky places to eat.

A brief history of Lexington

When European settlers arrived, the Bluegrass region was in use as a hunting ground by numerous Native American tribes. Daniel Boone was one of the first non-natives to explore the area. He helped establish Kentucky’s first forts in Harrodsburg and Boonesborough.

Lexington was founded in 1775, seventeen years before Kentucky became a state. William McConnell and a group of frontier explorers were camped at a natural spring when word came from nearby Fort Boonesborough that the first battle of the American Revolution had been fought in Lexington, Massachusetts. In honor of the battle, the group named their site “Lexington”. By 1820, Lexington, Kentucky, was one of the largest and wealthiest towns west of the Allegheny Mountains. So cultured was its lifestyle, our city soon gained the nickname “Athens of the West.” And with that…

Let’s Eat!

I could go on for days!  Like many metropolitan areas, you can find the same old chain restaurants here but we encourage you to try some of our local favorites.  I’ll start with breakfast.


I could go on for days! I’ll start with breakfast. I love donuts and if you do too, you must visit Spaldings. They are open Wednesday through Sunday, you can expect a line, and bring cash. They are family run since 1929 and my favorite donut ever! Also, Magees is a local favorite serving breakfast and lunch. Best buttercream icing in the world.

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Kentucky Hot Brown

Winchell’s has many southern favorites. I usually get the trout and eggs. Must try the jalapeno grits. Biscuits and gravy can’t beat either.  If so inclined, you can grab a stiff Bloody Mary or Screwdriver while you wait.

If you’ve never had a Kentucky Hot Brown, here’s your chance. Ramseys Diner is also a local breakfast favorite. They specialize in locally sourced meats and produce.

DV8 Kitchen  Offers sandwiches and many bakery items, the Cinnamon Roll is their signature. The proprietor is a personal friend of mine and he created DV8 Kitchen as a second chance employment opportunity for people who are trying to redirect their lives. People in the early stage of substance abuse recovery often find it difficult to find employers willing to take a chance on them.


For lunch with a beautiful drive through horse farms, try Wallace Station on Old Frankfort Pike. Have lunch and just keep on driving to see more beautiful farms and the sweet little town of Midway. Another Kentucky favorite, Burgoo, is a vegetable and wild game type stew. Try a bowl at Stella’s Deli.

Other neat lunch spots worth the drive are Windy Corner, The Parkette a 50’s style drive-in diner. Lexington has had a few good BBQ places pop up over the past few years and these are our favorites, Lyles BBQ, Red StateDouble H and Blue Door.


Dinner options would be Carson’s. It’s newer but delicious! Malone’s / Harrys is a local favorite steakhouse with a bit of everything. Ramsey’s mentioned earlier is a nearby favorite, go ready for some artery clogging southern cooking. Merrick Inn is nice for some fine dining. Other local favorites are classic Italian Giuseppe’s, a new local casual concept, Saul Good, and of course Winchells.

The Summit is close to the house and full of shopping and dining options.

Be sure to pick up some Kentucky Favorites at the store. Ale-8-1 a citrusy ginger ale type drink. Best drank from an ice cold bottle. Many “secret” recipes exist but Kentucky Beer Cheese is typically a snappy cheddar cheese spread flavored and blended with beer.  Kentucky Ale is a beer aged in previously used bourbon barrels. It has the hints of vanilla and bourbon and packs a punch.

Farmers Markets

photo by Curious Craig

Downtown Farmer Market –  Saturday mornings in downtown are filled with farmers, food trucks, and other locally produced products,

The Summit – Wednesday’s –  The Summit is the newest market, and its location gives visitors the opportunity to include shopping at the Lexington Farmers’ Market as part of an exciting evening out! There are a number of restaurants and stores nearby, and plenty of parking throughout the shopping center.

Market on Southland Drive – On Sunday the Market moves to Southland Drive. The Sunday market is laid-back and festive, with many visitors stopping by as they do other shopping with local businesses on Southland Drive.  There are also a number of local restaurants nearby that serve farmers’ market produce, so you can plan to stay in the area for lunch after you stock up on fresh fruits and vegetables!

Market at the Castle – Wednesday afternoons check out a true castle in Kentucky. In addition to the farmers market, the Castle offers dining and tour options

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Things to Do


Need to work off some of those calories?   Lexington offers the Legacy Trail a 12-mile paved multi-use trail that begins in downtown and works its way to the Kentucky Horse Park.  Bike Rentals are available from several locations.

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Buckley Sanctuary

Prefer to hike off-road, check out Ravens Run nature sanctuary with miles of trails, along the Kentucky River and creeks, unfortunately, dogs are not allowed on the trails.

Buckley Wildlife Sanctuary – The Sanctuary consists of 374 acres along the Kentucky River. Habitats include approximately fifty acres of fields, and two ponds surrounded multiple trails along the Kentucky River.

Veterans Park offers disc golf,  mountain biking, and hiking trails.  The trails are shared and often intersect with the disc golf course. The park is surrounded by Elkhorn creek which offers bluegill and smallmouth bass.  As a city park, weekends can be a bit busy.

While there aren’t many water features in Lexington, Elkhorn creek does offer a chance to canoe or kayak. Canoe Kentucky is a great outfitter.

To get Fido out for some play time Lexington offers several dog parks, the 7-acre park on Wellington Way is closest to the house.


Old Friends in Georgetown. It is a retirement farm for retired racehorses. Silver Charm a former derby winner is there and many others. Tours are offered throughout the day.  Feeding these elite athletes carrots and posing for pix is too cool. Look for the horse named Special Ring. He’ll have a surprise for you.

Kentucky Horse Park – Very near Old Friends is the  Kentucky Horse Park, the  Park is a working horse farm and an educational theme park opened in 1978 and offers a museum and many other attractions.

Keeneland Morning Workouts and Track Kitchen – Racing is in session in April and October.  But morning workouts are open to the public year round. Consider an early morning (6-7 am) and watch these horses storm the track. The Track kitchen underneath the black water tower offers a fantastic no-frills breakfast.

WinStar Farm offers shuttle tours. That allows guests to first see the stallions of an all-star roster and walk through our state-of-the-art stallion barn to get a glimpse of the day to day life of each of their stallions. Guests then receive a tour of our breeding shed. Afterward, guests will climb aboard an electric shuttle and see all the beauty the rest of the farm has to offer. The Shuttle Tour experience will vary seasonally, offering a unique look at a working horse farm at every time of year!

Visit Horse Country offers various tours and itineraries.

Kentucky Bourbon Trail

There are about 13 Bourbon Distilleries along the Kentucky Bourbon Trail.  If you are a true aficionado and want to visit them all, be sure to pick up a passport and get it stamped at all distilleries and earn a free commemorative sipping glass.  If you’re just curious about bourbon, all distillers offer tours and tastings. Curious Craig - Bourbon-Glass.jpgCheck out their website for times.  I recommend the following.

Due to its proximity, just a few miles away, check out Town Branch.  They have some impressive stills.

Just a little further away is my favorite of them all (yes I’ve seen em all) Woodford Reserve Distillery. The grounds are beautiful, the tours educational. They have a small cafeteria and an excellent gift shop for unique bourbon related unique gifts, including bourbon balls.

Just a little over an hour away is the classic Makers Mark.  The grounds are also impressive and you can try your hand at dipping your own bottle in the iconic red wax.

Jasons House of Bourbon Want to see some rare and vintage Bourbons, as well as modern varieties, check out the House of Bourbon in downtown Lexington.

Chocolate Tours

Two prominent chocolatiers are located nearby and both offer tours and great selections of chocolates. Old Kentucky Chocolate and  Ruth Hunt.

Toyota Factory Tour

Unless you follow such things you probably didn’t know 10,000 Camry’s and Avalons roll of the assembly lines in Georgetown, Kentucky each year. This is America’s first and the world’s largest Toyota manufacturing facility. The hour-long tour runs multiple times during the week. Tours are free and can be booked here:

Red Mile

The Red Mile featuring live harness racing through the summer months and gaming (slot machines) and simulcasting year round. They also offer a variety of other events throughout the year. My favorite is the Weiner dog races in August.

Thursday Night Live

During April – October in downtown every Thursday, Join a block party for live music, local food and beverage vendors, and the hottest party in town. The event takes place each week at the Fifth Third Bank Pavilion at Cheapside Park.

Historic Venues

The Shaker Village at Pleasant Hil The Shakers embraced a kinship with the land and with each other, forging a legacy that continues to inspire us today. Their gifts are simple—architectural marvels, breathtaking landscapes, and lessons in community, ingenuity, and sustainability. The Shakers were 19th century America’s largest and best-known communal society. Nearly 3,500 Shakers lived in communities from Maine to Kentucky. In 1805, a group of Shakers came to central Kentucky and established a village they named Pleasant Hill. Learn about there lives and enjoy a traditional dinner at the Trustees table.

Henry Clay’s Ashland Estate – Ashland is the name of the plantation of the 19th-century Kentucky statesman Henry Clay. The highlight of a visit to Ashland is the one hour guided tour of the 18-room mansion.  You willCurious Craig - Kentucky-Theater.jpg enter the front door and begin a  journey through the Clay family mansion and time travel from the 18th century to the present.

Mary Todd Lincoln House –  Located in downtown Lexington,  was the family home of the future wife of the sixteenth President of the United States. In 1977, the girlhood home opened to the public and became the first house museum in the country to honor a First Lady.

Kentucky Theatre is a historic cinema in downtown Lexington,  that first opened in 1922. It is currently that shows films and also hosts concerts. The theatre’s schedule emphasizes foreign, independent, and art films, although more typical Hollywood movies are occasionally shown as well. It is one of a few[remaining movie palaces in the United States.

Sports Bars

There are several sports bars nearby. All offer good food and drink. If UK is playing expect them to be packed hours before game time.

Banners offer an elevated traditional bar food. Sports on the dozens of TVs. Live music Thursday-Saturday.

Roosters – a Large casual dining and sports venue that offers a Hooters-style wing but the staff is fully clothed.

SEC Pub – Live Music Friday and Saturday Pool Tables etc.

Night Life

For a taste of Lexington nightlife and some crafted cocktails, downtown is the place to go.  Several local favorites are. Parlay SocialBigg Blue Martini,  21C MuseumSkybar Lounge

Ready for a road trip

Newport Aquarium – About 90 minutes away, the Newport Aquarium is an aquarium located in Newport, Kentucky, near Cincinnati at Newport on the Levee. The aquarium has 70 exhibits and 14 galleries, including five seamless acrylic tunnels totaling over 200 feet in length.

Berea is a must-see destination for folk arts, crafts, and music. A thriving artisan community offers glass, pottery, jewelry, painters, sculptors and features dulcimer makers. Also, check out the nearby Kentucky Artisan Center.

Mammoth Cave  & Kentucky Down Under – 2 hours away is Mammoth Cave National Park is a long cave system of chambers and subterranean passageways. Sites include the Frozen Niagara section, known for waterfall-like flowstone formations, and Gothic Avenue, its ceiling covered in 19th-century visitors’ signatures. While touring the cave check out Kentucky Down under for a chance to see Australian wildlife and feed the kangaroos.  

We hope you enjoy your stay, let us know if we can answer any other questions or make additional recommendations.

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Ainslie & Craig

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