7-DAY ITINERARY
DAY 1 • Paducah Area
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Purple Toad Winery
Hours: Monday-Saturday 10:30 a.m.-6 p.m.; Sunday 1-6 p.m.
Next Stop: 21 miles, 27 minutes to Fancy Farm Vineyard
Kickstart your morning in Paducah with a fresh cup of coffee and a hearty breakfast at one of the city's beloved local spots like Etcetera Coffehouse, Gold Rush Café, or Piper’s Coffee and Tea.
Known as Quilt City USA® and designated a UNESCO Creative City of Crafts and Folk Art, Paducah is a hub for fiber arts. Your next stop should be The National Quilt Museum, where you'll discover stunning textile art and learn about the city's vibrant quilting community.
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For lunch, indulge in a taste of Kentucky tradition at one of Paducah’s many barbecue joints, where you can savor the flavors that define Southern cuisine.
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Afterward, continue your exploration with a visit to Purple Toad Winery, the largest winery in Kentucky, located just a short drive from downtown Paducah. Enjoy a wine tasting and take in the beautiful vineyard views.
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If you enjoy live entertainment, catch a performance at the Carson Center, or immerse yourself in a play, musical, or comedy at the Market House Theatre, a local favorite for performing arts.
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For dinner, choose from a variety of unique eateries in Paducah’s Historic Downtown. Whether you're in the mood for fresh farm-to-table dishes, gourmet Italian, or something else entirely, there’s a dining option to suit every taste.
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End your day at one of Paducah’s unique lodging options, nestled within the city's walkable cultural district, offering comfort and convenience as you rest up for another day of adventure.
DAY 2 • Mayfield Area
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Fancy Farm Vineyard & Winery
Hours: Friday/Saturday 6-9 p.m.; Sunday Noon-9 p.m.
Next Stop: 26 miles, 36 mins to Poca Terra Winery
Start planning your visit by checking the Mayfield-Graves County Facebook Page and the Fancy Farm Vineyard & Winery Facebook Page for any events or activities happening during your stay.
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Begin your adventure with a stroll through Maplewood Cemetery to view the unique Wooldridge Monuments, an intriguing site with a bit of a paranormal twist. This location is featured on the Kentucky After Dark Paranormal Passport, don't forget to grab a selfie with Colonel Wooldridge and contact the Mayfield-Graves County Tourism Office to collect your commemorative sticker.
Next, step back in time at Cartwright Grove, a recreation of an 1800s Wild West town where you can experience the charm and excitement of the Old West. If you're feeling active, head over to the Kessians Disc Golf Course. Situated along the West Kentucky Disc Golf Trail, you can enjoy a free round of disc golf.
By now, you must be hungry! Satisfy your appetite with a stop at one of the four renowned BBQ spots on the West Kentucky BBQ Belt: A&B BBQ, Carr’s Barn, Hoskins BBQ, or Southern Red’s BBQ.
Cap off your visit with a bit of shopping at one of the more than twenty locally owned boutiques, furniture stores, and flower or gift shops scattered throughout Graves County. Discover unique finds and take a piece of Mayfield back home with you.
DAY 3 • Kentucky Lake Area
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Poca Terra Winery
Hours: Call ahead for a reservation - Friday/Saturday Noon-7 p.m.
Next Stop: 18 miles, 27 mins to Buckhorn Creek Vineyard
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Buckhorn Creek Vineyard
Hours: Call ahead for a reservation - Open 7 days a week 11 a.m.-6 p.m.
Next Stop: 57 miles, ~1 hour to Naimoli Estate
Begin your day by exploring the scenic Kentucky Lake, a top destination for outdoor enthusiasts. Enjoy a peaceful morning fishing or take a boat ride to experience the vast beauty of the lake.
For lunch, savor Southern comfort food or ethnic dishes at local favorites like Popi’s or Los Portales. If you’re looking for a taste of BBQ check out Amazing Blaze BBQ or J-Mack BBQ.
In the afternoon, head to Buckhorn Creek Vineyard for a delightful wine tasting, surrounded by the tranquil landscape. Afterward, visit Poca Terra Winery, where you can continue exploring the region’s unique wines and relax in their scenic vineyard setting.
Discover the spine-tingling local legends and explore the eerie side of the region by visiting the Dogman Folklore site, a must-stop on the Kentucky After Dark Paranormal Passport.
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For nature lovers, the Kentucky Lake area offers opportunities for hiking, biking, wildlife viewing, and boating. If you’re feeling adventurous, try kayaking or paddleboarding on the lake’s calm waters.
As evening approaches, dine with a view at Ralph’s Harborview Bar & Grill, where you can enjoy a lakeside meal while watching the sunset over Kentucky Lake. For overnight accommodations, consider one of our hotels, cottages, campgrounds, or one of the inviting lakeside cabins to complete your stay.
DAY 4 • Hopkinsville Area
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Naimoli Estate
Hours: Call ahead for a reservation - Monday-Saturday
Next Stop: 59 miles, 1 hour 15 mins to Carriage House Vineyards
Get your day moving by joining the Kentucky Capitals Quest with a guided tour of a local batter factory, where you'll learn about the production process and the history of batter manufacturing in Hopkinsville. For lunch, check off a stop on the West Kentucky BBQ Belt with a visit to Big Mike’s, The Wood Shed, or Bar-B-Que Shack.
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Afterward, indulge in a wine tasting at Naimoli Estate Vineyard & Winery, perfect for savoring local flavors. In the afternoon, explore the heart of downtown Hopkinsville, strolling along Main Street and 6th Street. Discover local shops and boutiques, and grab a treat from Joelle’s Cake & Coffee, The Corner Coffeehouse, or Baked Hopkinsville.
Hopkinsville is also a fascinating destination on the Kentucky After Dark Paranormal Passport trail, where you can visit the site of the infamous Kelly Little Green Men encounter, one of Kentucky’s most intriguing UFO stories.
End your day with dinner at The Local Irish Pub & Kitchen, where you can enjoy local cuisine in a warm, inviting setting.
DAY 5 • Logan County Area
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Carriage House Vineyards ​​
Hours: Tuesday-Saturday 11 a.m.-6 p.m.
Next Stop: 17 miles, 23 mins to Traveler’s Cellar Winery
Journey into the past at the South Union Shaker Village, where you can explore the fascinating history of the Shakers, their innovative spirit, and beautiful craftsmanship. Then, dive deeper into local culture at the SEEK Museum, which highlights the rich African American heritage of the region.
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For lunch, knock out a stop on the West Kentucky BBQ Belt by visiting Roy’s BBQ for a taste of smoky, savory goodness. If you're in the mood for something different, try a signature hoagie from The Hoagie House or enjoy a touch of Italy with dishes from Ariella’s or Sylfoni’s Pizza.
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Afterward, explore the charming boutique shops scattered throughout Logan County, perfect for finding unique gifts and local treasures. For those who love the outdoors, spend the afternoon golfing at Rolling Hills Golf Course, a beautiful and challenging course set against the rolling landscapes of Kentucky. If you prefer water activities, head over to Lake Malone for fishing, boating, or simply enjoying the serene natural beauty of the area.
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Wrap up your day by relaxing at one of Logan County's cozy accommodations, where you can unwind and plan your next adventure in this welcoming corner of Kentucky.
DAYS 6-7 • Bowling Green Area
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Traveler’s Cellar Winery
Hours: Thursday-Saturday 11 a.m.-7 p.m.; Sunday 1-5 p.m.
Next Stop: 21 miles, 28 mins to Reid’s Livery Winery
Reid’s Livery Winery
Hours: Call ahead for a reservation
Next Stop: 25 miles, 29 mins to Bluegrass Vineyard
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Bluegrass Vineyard
Hours: Monday-Thursday 10 a.m.-6 p.m.; Friday/Saturday 10 a.m.-7 p.m.; Sunday Noon-6 p.m.
Head to Bowling Green to explore the National Corvette Museum and perhaps grab lunch at the museum’s Stingray Grill. Don't miss a visit to Chaney's Dairy Barn for some of the best homemade ice cream in the region, a true taste of Kentucky's dairy excellence.
For the adventurous, scope out the hidden wonders of Lost River Cave, where an underground boat tour takes you deep into a captivating cave system filled with history and natural beauty.
Enjoy amazing cuisine and shopping in Bowling Green's lively downtown district, with local shops, eateries like Gerard’s and The Bistro, and the Aviation Heritage Park & Museum, which encapsulates the spirit of American air travel. Check into the Hyatt Place or the Embassy Suites.