Ready for wine, outdoor adventures and a little Kentucky history? Jessamine County packs plenty into a getaway, from the towering limestone cliffs of the Kentucky River Palisades to award-winning wineries, Civil War sites and scenic golf courses.
Whether you’re exploring Nicholasville, Wilmore or both, these ten experiences are worth adding to your Kentucky bucket list.
1. Explore Kentucky Wine Country
Taste your way through Kentucky Wine Country on the Jessamine Wine + Spirits Trail. Start at First Vineyard, established in 1799 and recognized as the first commercial winery in the United States. Try a glass of Chambourcin, a dry red with blackberry and cherry notes, then head to Ghost Fox Winery for small-batch pours and unexpected flavors like spicy cucumber wine. At 1922 House Vineyards & Winery, sip Kentucky Proud wines made with locally grown grapes, including bourbon barrel-aged favorites and award-winning dry reds. Visiting in June? Add the Kentucky Wine & Vine Fest to your plans.
2. Horsing Around
Get an up-close look at Kentucky’s Thoroughbred tradition at Taylor Made Horse Farm in Nicholasville. Tour the broodmare paddocks, meet future racing stars, and learn about the legendary horses that helped make Taylor Made a leader in Thoroughbred breeding. You can book a tour here.
Keep the horse-themed fun going at the Kentucky Equine Adoption Center, one of the state’s largest all-breed equine rescues. Meet the horses, learn about their journeys, and see how the center helps prepare them for new homes.
3. Shop Until You Drop
Need a little retail therapy? Jessamine County is packed with boutiques, antique shops, local markets and one-of-a-kind finds. Browse spots like Alternative Jewelry, Bliss on Brannon, Boxwood + Birch, Real Deals and Boutique on Maple at 721, then make time to hunt for vintage treasures at the area’s many antique stores.
In Wilmore, stop by Shades of Bluegrass for Kentucky-themed gifts and handmade finds, including pottery and wood carvings. Visiting in summer? Both Nicholasville and Wilmore host farmers markets where you can shop for local produce, handmade goods and seasonal finds.
4. Eat & Drink Like a Local
Come hungry because Jessamine County has plenty of local flavors to discover. Dig into down-home favorites at Dixie Café in Keene, where the smothered chicken and biscuits are a must or spice things up with tamales, tacos and chile verde at Jordy’s Family Restaurant. Add even more variety with a stop at Soul on Main or Taste of Ukraine for authentic Ukrainian dishes. For a different kind of night out, settle in at Jake’s Cigar Bar, home to more than 100 bourbons and hand-rolled cigars.
5. Outdoor Adventures
If fresh air is calling, Jessamine County has plenty of ways to get outside. Hike the Asbury Trails through the Kentucky River gorge along a former pioneer wagon road or explore the 155-acre Jessamine Creek Gorge for peaceful creek views and leafy scenery just minutes from Wilmore, Nicholasville and Lexington. At the Jim Beam Nature Preserve, trails lead to dramatic cliffs and rock formations in the Kentucky River Palisades, with plenty of birdwatching along the way.
6. Jessamine Coffee Crawl
Caffeine lovers can sip their way through Jessamine County on a coffee crawl packed with cozy cafes and creative drinks. Stops include Unify Coffee, Mercantile Coffee & Feed, Luna’s Coffee, Wine, & Butterfly Cafe, European Delights, Solomon’s Porch Cafe, Ethnos Cafe, Barrel & Bean Coffee House, and Drinklings Coffee Shop in Wilmore. Along the way, look for specialty lattes, locally roasted coffee, fresh pastries, European sweets and Ukrainian-inspired bites. With everything from playful seasonal drinks to laid-back neighborhood coffeehouses, there’s plenty to keep your cup and your itinerary full.
7. Journey to the Past
Discover Jessamine County’s past through some of its most fascinating historic sites. At Camp Nelson National Monument, learn about its role as the third-largest African American recruitment center during the Civil War while exploring reconstructed army barracks and museum exhibits featuring recreations of the post office, camps and battle artillery. Outside, five miles of interpretive trails wind through the former encampment grounds. Nearby, pay your respects at Camp Nelson National Cemetery, the final resting place of more than 2,000 Union soldiers. Then head to the Wilmore Railside Museum, where a 1950s-era exhibit inside a Southern Railway caboose showcases local artifacts and stories about the region’s earliest settlers.
8. Explore High Bridge Park & Historic Bridge
No trip to Jessamine County is complete without a stop at High Bridge Park in Wilmore. Home to the iconic High Bridge, which soars 275 feet above the Kentucky River, it’s a favorite spot for photos and sweeping views. From the lookout, a reconstructed Victorian pavilion extends beyond the cliff, offering panoramic sights of the railroad trestle, limestone Palisades and the river below. Want to get even closer to the scenery? Launch a kayak or canoe from the nearby High Bridge boat ramp and paddle along the Kentucky River beneath the dramatic Palisades. Fun fact: A model of High Bridge is on display at the Smithsonian Institution.
9. See the Sights from the Water
Hop aboard the Valley View Ferry for one of Jessamine County’s most unique historic experiences. Operating since 1785, it’s the oldest year-round ferry service in the nation and still carries travelers across the Kentucky River today. Along the short ride, take in peaceful countryside views while crossing waters once traveled by figures like Daniel Boone and Ulysses S. Grant. The best part? The two-minute trip is completely free.
10. Family-Friendly Entertainment & Events
In Jessamine County, there’s no shortage of family-friendly fun. Bounce and flip on wall-to-wall trampolines at Get Air Trampoline Park, or let little ones play and explore at The Bluebird Social in Wilmore. Catch local performers during the Performance Park series, Stone Bridge Concert series and Wilmore on the Green or enjoy a show by the KCAL Old Time Radio Show Troupe. The calendar also fills up with community favorites like the Coaster Car Derby, Taste of Jessamine, More Tales Storytelling Festival, Ginkgo Galore Festival, Wilmore Arts & Crafts Fair and Downtown Days. Summer brings Wilmore’s Fourth of July celebration, complete with live music, pick-up games, a parade and vendors selling local wares and crafts.
