10 Can’t-Miss Experiences in Nicholasville, Wilmore – Jessamine County

Welcome to Jessamine County – home to award-winning wineries, historic Civil War sites and abundant outdoor adventures along the Kentucky River. From hiking trails through the limestone Palisades to practicing your swing at luxury golf courses, you’ll find plenty of activities in Nicholasville and Wilmore that are perfect for the entire family.


Whether you’re visiting for a day trip or the weekend, here are ten experiences to add to your Kentucky bucket list.  


1. Explore Kentucky Wine Country 


Grapevines at Kentucky winery


Sip your way through Kentucky Wine Country. In Nicholasville, enjoy a taste of history at the aptly named First Vineyard. Established in 1799, it’s the first commercial winery in the United States (President Thomas Jefferson even received wine from here). Sample a glass of Chambourcin, a dry red with notes of blackberries and cherries. Nearby, stop at Ghost Fox Winery, a micro-winery focusing on small-batch wines where you can indulge in adventurous varietals like the spicy cucumber wine. For 100% Kentucky Proud wines made from Kentucky-grown grapes, a visit to 1922 House Vineyards & Winery is a must. Opt for the best-selling bourbon barrel-aged wine or one of the award-winning specialty dry reds. Visiting in June? Mark your calendar for the fun-filled festivities at Kentucky Wine & Vine Fest!


2. Horsing Around 


Horses grazing at Taylor Made Horse Farm.


Step off the beaten path and into the world of Thoroughbred royalty at Taylor Made Horse Farm in Nicholasville. Learn about the legendary horses that established Taylor Made as a world leader in Thoroughbred breeding. Tour the broodmare paddocks, feed carrots to future stars in the making, and pay homage to the racing giants laid to rest here as you explore this iconic horse farm. You can schedule a tour here.


3. Shop Until You Drop 


A woman shopping and holding a cup.


Need a dose of retail therapy? Jessamine County is a haven for trendy and unique boutiques, antique shops and outdoor markets. Discover nostalgic wonders at Clairebourne Antiques in Nicholasville (it’s housed in a former church and full of one-of-a-kind treasures). Coffee lovers should stop by Mercantile Coffee and Feed - a popular downtown stop. Or, check out Dodd’s Corner Farmers Market – a former feed store that’s now a shop, restaurant and café featuring locally made crafts, baked goods and farm-fresh produce. In Wilmore, grab a cup of coffee and browse unique Kentucky-themed shops, cute boutiques, antique spots and specialty stores like Shades of Bluegrass (you can pick up great handmade items like pottery and wood carvings).


4. Eat & Drink Like a Local 


Dining on a sandwich and chips.


Dig into authentic Kentucky flavors in Jessamine County (you’ll never go hungry)! Enjoy some good ‘ole home cooking at Dixie Café in Keene – the smothered chicken and biscuits are a must. For cozy ambiance and artisanal coffees, stop by local favorite Luna’s Coffee, Wine and Butterfly Café in Nicholasville. Unwind in style at Jake’s Cigar Bar, a popular haunt with over 100 bourbons and hand-rolled cigars. Or, if you like things spicy, check out Jordy’s Family Restaurant for their famous tamales, tacos, and chile verde served with pork tenderloin!


5. Hike and Bike the Trails 


A group hiking the trails in Jessamine County.


Bends, bluffs, and natural beauty abound in Jessamine County – the perfect spot for outdoor enthusiasts. Hike the Asbury Trails that weave through the Kentucky River gorge along what used to be a pioneer wagon road. Just minutes from Wilmore, Nicholasville and Lexington, the 155-acre Jessamine Creek Gorge offers a peaceful respite with creek views and lush landscapes. At the Jim Beam Nature Preserve, hiking trails provide postcard-worthy sights of towering cliffs and stunning rock formations in the Kentucky River Palisades (it’s also a popular spot for birders).


6. Practice Your Swing 


Sunset at Golf Club of the Bluegrass in Jessamine County, KY.


If you’re looking for fun recreational activities, aim for a hole-in-one at the diverse golf courses throughout the county! Hit the green at the 18-hole Connemara Golf Course on the grounds of the historic Connemara Farm. Tee off in style at the Thoroughbred Golf Club in the heart of Kentucky horse country (it’s right next door to Taylor Made Farm). Squeeze in a round at Golf Club of the Bluegrass. And in July, watch the pros compete for the million-dollar prize in the PGA’s Kentucky Championship at Champions at Keen Trace Golf Club!


7. Journey to the Past 



Experience Jessamine County’s rich history with a visit to its local historical sites. Tour the Camp Nelson National Monument, the third-largest African-American recruitment center during the Civil War. See the reconstructed army barracks and the museum exhibits highlighting recreations of the post office, camps and battle artillery. Outside, explore the five miles of interpretative trails that wind through the former encampment. Pay homage to the fallen at the historic Camp Nelson Cemetery, the final resting place of more than 2,000 Union soldiers. Continue your journey through time at the Wilmore Railside Museum, a 1950s-era exhibit filled with local artifacts inside a Southern Railway caboose. Here, you’ll learn about the lives of early settlers who made their homes in the region in the late 1700s.  


8. Explore High Bridge Park & Historic Bridge 


High Bridge Park in Jessamine County.


No trip to Jessamine County is complete without a trip to High Bridge Park in Wilmore. Home to the iconic High Bridge, which extends across the Kentucky River and is 275 feet in the air, it’s an excellent spot for an Instagram-worthy photo op. Take in the sights from the lookout. At the top, a reconstructed Victorian pavilion extends beyond the cliff, offering panoramic views of the railroad trestle, limestone Palisades and the mighty Kentucky River. Fun Fact: There’s a model of the bridge in the Smithsonian Institute!


9. See the Sights from the Water 


The Valley View Ferry crossing the river in Kentucky


All aboard the Valley View Ferry! The oldest year-round ferry service in the nation, dating back to 1785, this iconic paddlewheel transports travelers across the majestic Kentucky River. Cruise along the same waters legendary pioneers like Daniel Boone and Ulysses S. Grant once crossed while soaking in panoramic views of the picturesque countryside. Best of all, this two-minute voyage is free!


10. Family-Friendly Entertainment & Events 


Coaster Car Derby in Jessamine County.


In Jessamine County, there’s no shortage of family-friendly entertainment. Bounce and flip on wall-to-wall trampolines at Get Air Trampoline Park. Jam out to local performers at live monthly concerts like the Performance Park series, Stone Bridge Concert series, and Wilmore on the Green. Catch a performance by the KCAL Old Time Radio Show Troupe. Or, visit during the summer for fun events like the Coaster Car Derby and Taste of Jessamine in May. Stop by for the Fourth of July Celebrations in Wilmore; highlights include live music performances, pick-up games, a parade and vendors selling local wares and crafts.

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