Monticello is situated between the Cumberland Lake and Daniel Boone National Forest in Kentucky. It boasts rolling hills and lush farmland that are picture-perfect. Not only will you have the opportunity to breathe in the fresh mountain air and do some hiking, but you also have access to plenty of thrilling attractions, such as exploring the area’s natural beauty and eating good food. Book a stay at a Monticello vacation rental today. Here are some of the top things to do in Monticello.

1. Visit Mills Spring Mill

Take in Monticello history at the Mills Spring Mill, a grist mill that dates back to 1817. The huge 48-inch French millstones along with the wooden building were destroyed in a fire but were rebuilt in 1824. However, its place in history doesn’t stop there and instead continues on to the Civil War, serving as the place where one of the first critical battles was fought. Completely restored in the 1970s, the mill is now a gateway back in time.

2. Browse the Exhibits at Wayne County Historical Museum

Explore local history at the Wayne County Historical Museum, an award-winning museum. It features exhibits that display old photographs of the area, relics of 19th-century life in Monticello, and even the old Monticello-Burnside Stagecoach. You can even page through old genealogical records and see if you have ancestors that once settled here.

3. Tour Historic Houses

While exploring Monticello’s history, stop at the Brown-Lanier House, West-Metcalfe House, and Raccoon John Smith Cabin. These restored buildings were some of the original buildings of Monticello and still stand to tell their stories. For example, the Brown-Lanier House hosted three generals of the Union Army during the Civil War. The West-Metcalfe House was the first brick house in the county and also served to house military leaders during the war.

4. Go to a Festival

Monticello might be a small city in size, but it more than makes up for it in yearly festivals and events. There’s something going on every month, such as the Wayne County Farmers Market, which is a great place to pick up fresh, locally-grown produce for your stay, to the Cornbread Festival because nothing says South like food. The autumn Raft-Up is Monticello’s biggest event, but there are plenty of holiday-centric festivals as well.

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5. Learn to Quilt

The Contented Heart Quilt Guild isn’t just a place where women gather to do some quilting. It’s a place where the art of quilting is passed on to new generations through children and adult quilting classes. Experience a bit of the artistry and work that goes into quilting by taking a class, a truly unique experience.

6. Relax at the Monticello Country Club

The Monticello Country Club has something for everybody in the family, including a children’s wading pool for the little ones and an Olympic-size pool for you. You can even do a little golfing while appreciating the lush rolling hills.

7. Visit a Winery

The Lake Cumberland Winery is just a few miles from downtown Monticello and is the perfect place to hang out with your adult children, significant other, or friends. Indulge in some wine tasting and an excellent meal, or walk through the lush countryside. You can even create your own wine bottle label as a souvenir of your trip.

8. Go Boating at Cumberland Lake

Monticello lies just off the Cumberland Lake, making it an ideal attraction to visit while in town. There are plenty of boat rental agencies where you can pick up a watercraft for some fun on the water. The Beaver Creek Marina offers both houseboat rentals and small boat rentals. Conley Bottom Marina has even more options, from pontoon boats to water toys including jet skis.

9. Go Horseback Riding at Moody Farms

Head northeast to Moody Farms where you can go horseback riding. Plus, the on-site petting zoo is a treat for the kids. Another horseback riding option lies southwest of Monticello at Grey Wolf Ranch. You can opt for basic equestrian lessons before taking to the trails. Here, you learn about body language and riding with the horse’s gait. The guided trail rides take you on a tour of the countryside while you put your new skills to use.

10. Visit Jennings Hollow Farm

Jennings Hollow Farm not only focuses on locally sourced sustainable food–a look at the journey of food from the farm to the table–it also has a variety of animals that children can view. You can hike through the pasturelands or take a tour of life on the farm, an interesting experience for any age.

11. Play a Game of Pool

Stop by at City Pool Hall for a rousing game of pool. With its welcoming red brick facade, it’s great for a family night out or just the adults. Plus, rumor has it that the burgers there are the best in town.

12. Try Your Hand at Room Escape Games

Challenge your brain, and the rest of the family, to a rousing game at MindScape Escape Rooms. Using your deductive powers and clues, you have to find a way to escape the rooms. Pair up and challenge your friends or family to beat you out. The Deja Vu theme ups the suspense.

13. Explore the Great Outdoors

Monticello is within a short drive of both the Daniel Boone National Forest and Big South Fork National River and Recreation Area. Spend a day exploring the great outdoors. One of guests’ favorite things to do at the Daniel Boone National Forest is target shoot. There are four ranges available. Another popular activity is hiking. There are dozens of trails suitable for all age and experience levels. If you have children, consider hiking the 1-mile trail up to Knob Overlook.

14. Enjoy a Show

The Historic Wayne Theatre has been a Monticello icon since 1926. After being restored in 2016, it’s become a historic landmark and a place to catch a show. The theater shows movies, speakers, ballet performances, and plays, so there are plenty of options.

15. Enjoy Good Food

The South is all about food, and one of the top eateries is the Black Stallion Steak House featuring steaks, barbecue, and mac and cheese among other Southern favorites. Another great eatery is El Cazador, a Mexican restaurant with burritos, fajitas, and smothered enchiladas.

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