Bundle up for a winter adventure on the Tennessee Whiskey Trail. With reduced crowds and unobstructed outdoor views, it's the perfect time to enjoy a cozy, low-key trip. Full of winter hikes, museum strolls and cozy cocktails at distillery cocktail bars, follow this winter whiskey itinerary in Tennessee for the best places to travel in winter whether for a guys' trip, girls' weekend or romantic getaway.
Chattanooga, Tennessee
Enjoy a quiet mountain escape in Chattanooga, Tennessee’s Scenic City where adventure and luxury blend for an unforgettable weekend.
Southern refinement is on full display at the luxurious Edwin Hotel. Marvel at the art and stylish suites they offer. Make a reservation for dinner or drinks at the hotel’s restaurant, Whitebird to enhance your winter vacation.
Fuel up for your day of exploring at Rembrandt’s Coffee House in the Bluff View Art District. Order one of the delicious sandwiches, Challah French toast or a breakfast pastry like the double chocolate chip scone or Nutella croissant. They also have gluten-safe coconut macaroons, lemon bars and peanut butter cookies.
Take in the winter scenery at Mullens Cove Overlook, a 9.8-mile loop in Prentice Cooper State Forest. You’ll be able to see giant rock formations and natural steps along the trail before coming up to see the view of the Tennessee River Gorge. If you want an easier hike, you can access Snoopers Rock where there are a couple of small water crossings and numerous rock formations along the way.
Freshen up at the Edwin Hotel and then set out to Chattanooga Whiskey Experimental Distillery for a rewarding tour and tasting. The distillery is the only distillery of its kind in the country. Find out why on the 1-hour tour that digs into the history, craft production process and a guided tasting of the whiskey.
Take a stroll before dinner around Sculpture Fields of Montague Park, a collection of art pieces from world-renowned artists. You’ll find 50 large-scale sculptures dotting the 33 acres of winding trails in Chattanooga’s Southside district. You can even hear from the artists themselves with the OtoCast app to have a deeper experience while marveling at the artwork with Lookout Mountain as the backdrop.
Heralded as one of the Top 50 Restaurants in the U.S. by The New York Times, Calliope is quickly becoming a national favorite. The restaurant serves up modern Mediterranean and Middle Eastern dishes. Try the classic chicken shwarma to start followed by Gulf shrimp tossed in Moroccan spices, awarma fried rice with beef confit and toasted nuts as well as the black grouper in tahini, a green tomato chutney and burnt lemon. Pair your dishes with Tennessee spirits from Chattanooga Whiskey and Gate 11 Distillery’s gin.
Dance the night away at Gate 11 Distillery where they host live music throughout the week, including Monday night blues jam sessions. Sip the extraordinary at the cocktail bar where expert mixologists serve up craft and classic cocktails, seamlessly blending Gate 11’s spirits with house-made syrups and infusions.
Nearby Distilleries
Looking to keep the adventure going? Discover additional nearby distilleries just a short drive away—each offering its own story, spirit, and taste of Tennessee craftsmanship.
Pigeon Forge, Tennessee
Have a quintessential mountain getaway in the Great Smoky Mountains. In Pigeon Forge, you’ll find distilleries serving Tennessee whiskey and traditional moonshine, family-friendly attractions even adults will love and Southern cuisine by the platefuls.
Cozy up in a cabin with stunning mountain views. There are so many cabins in the area to choose from whether you want a charming cabin for two or a cabin that rivals luxury ski lodges you’d find out West.
A visit to Pigeon Forge isn’t complete without breakfast at famous The Old Mill Restaurant, popular with locals and visitors alike for their Appalachian-style breakfasts. Get there early for a stack of chocolate chip, blueberry and strawberry pancakes, cinnamon raisin pecan French toast and the signature Old Mill Country Breakfast with two eggs, pancakes, in-house stone-ground corn grits, homemade fluffy biscuits, home fried potatoes and country sausage gravy.
Give your day a kick with a visit to Old Forge Distillery for free, guided moonshine tastings, cocktails in the lounge and more. Browse the bottle shop for the hand forged Tennessee spirits like gin, cream liqueurs, bourbon whiskey and more.
Burn off your breakfast with indoor tubing at Pigeon Forge Snow where the temperatures are always 60-70 degrees inside. Race down the slopes, build snowmen and snow forts for fun even adults will love. If you prefer outdoor winter fun, take a day trip to Gatlinburg’s Ober Mountain, Tennessee’s only ski resort, where you can ski and snowboard all day.
After tubing, head to the new location of Drop Zone Distilling on Teaster Lane, owned by Staff Sergeant Rod Parton, U.S. Paratrooper. This small-batch distillery specializes in hand craft moonshine made from family recipes dating back to the 1930s. Enjoy tastings of the 135 Proof Moonshine, flavored moonshine like candy apple cherry cider, granny’s apple pie and sweet tea as well as salted caramel whiskey and rye whiskey.
Stroll and shop at The Island in Pigeon Forge. Enjoy the lanes of shops that dot both sides of the pathways. Take a ride on the Great Smoky Mountain Wheel for expansive views of the wintery mountains. Belly up to the bar at Ole Smoky Distillery’s “The Barn” for moonshine tastings of a variety of flavors, including seasonal flavors. Shop jars of moonshine, whiskey and Ole Smoky merch.
Head to Junction 35 Spirits, Tennessee’s first distillery and restaurant, for guided tastings and lunch at the restaurant that serves craveable burgers, barbecue, salads and entrees like shrimp & grits, honey bourbon barbecue chicken and beef tips over mashed potatoes and gravy. Enjoy a tasting at the bar with Junction 35 bourbon, rye, whiskey, moonshine and Bam Bam Vodka that tastes just like your favorite childhood cereal.
When the sun sets, stroll the mile-long Winterfest Wonders of Light Walking Trail on Old Mill Avenue. Find 1 million lights and dazzling displays along the Pigeon Forge Riverwalk. It’s part of Smoky Mountain Winterfest, one of the largest free outdoor lights festivals in the U.S. now through Feb. 15, 2026. The free walking trail has more than 45 nature-inspired and musical light displays including a 20-foot ice fountain, wildflowers and caterpillar, making it a great place to snap group shots or have a romantic end to your evening.
Experience the vibrant atmosphere of Azul Cantina for flavorful Tex-Mex that makes for the perfect dinner spot. Enjoy beef birria empanadas, three-meat fajitas and specialty tacos like blackened salmon, crunchy seasoned beef and shaved ribeye with a chile rub.
Nearby Distilleries
Looking to keep the adventure going? Discover additional nearby distilleries just a short drive away—each offering its own story, spirit, and taste of Tennessee craftsmanship.
Franklin, Tennessee
A perfect winter day for couples can be spent strolling downtown Franklin. Heralded as “America’s Favorite Main Street District,” you’ll find historic buildings dating back to the early 1800s now housing chic boutiques, restaurants and Stable Reserve Distillery. Step inside for a taste of the small-batch spirits that blend traditional Tennessee whiskey techniques with modern craftsmanship for a quality that is unmatched. Taste spirits like the Straight Wheated Bourbon Whiskey that tastes of caramelized bananas, candied nuts and dried fruit with a spice finish or the signature gin that is distilled with 14 organic botanicals that gives it a sweet and smooth taste.
After your tasting, stroll the shops that line both sides of Main Street. You’ll find local art at Deann Art Gallery, custom furniture and home decor at City Farmhouse and outdoor gear and outfits at Bink’s Outfitters. Don’t miss Tin Cottage, full of Southern items that are perfect souvenirs or gifts and White’s Mercantile, owned by singer-songwriter Holly Williams, curated with refined home decor, menswear, candles, cookbooks and Southern culinary treats.
Step into the new, intimate Leiper’s Fork Distillery gathering space, House of Spirits. Here, you can lounge and sip a handcrafted cocktail, savor a lingering dinner with friends or a romantic evening with live entertainment. Seasonal menus feature local ingredients, inspired by traditional Southern flavors. Order cocktails and crafted spirits as well as local, regional and imported beers. Shimmy your shoulders and tap your feet to live music each weekend. Catch a comedy night as well as special cigar nights hosted throughout the year.
Franklin is rich in Civil War history, being ground zero for the Battle of Franklin. Learn about the McGavock family that witnessed the battle and its devastation first-hand at Carnton. Take a tour to dive deep into the home’s history, slavery and what happened during the hours of the Battle of Franklin. Upstairs, you’ll see the bedrooms that were used as operating rooms and treatment rooms for wounded soldiers. Finish your tour with a walk along the Eastern Flank Battlefield onsite as well as the McGavock Confederate Cemetery, the largest private Confederate cemetery in the U.S.
End your day with a cozy meal in Red Pony Restaurant. Warm up with shareable plates like the grilled lamb chops, burrata with apple, fennel arugula and caramelized honey or the fried Brussels sprouts garnished with pork belly and tamarind sweet & sour. Dig in to Southern classics like shrimp & grits, hickory grilled bone-in ribeye steaks and bacon wrapped elk meatloaf. With sides like garlic roasted mashed potatoes, cheese grits and grilled broccolini, you’ll leave satisfied and ready to plan your next dinner here.
Nearby Distilleries
Looking to keep the adventure going? Discover additional nearby distilleries just a short drive away—each offering its own story, spirit, and taste of Tennessee craftsmanship.
Lynchburg, Tennessee
If you’re traveling to Nashville, tack on a day trip to Lynchburg, located about 74 miles south of downtown Nashville. Start your cozy winter getaway with a visit to the world-famous Jack Daniel Distillery. Take the classic Jack Daniel Distillery tour where you’ll learn about Jack, how Tennessee whiskey is crafted and get a taste of six different Jack Daniel Tennessee Whiskey samples.
After the tour, head downtown for a Southern lunch at Miss Mary Bobo’s. Served family-style, savor the comfort foods stacked high like fried chicken, meatloaf, fried catfish and barbecue ribs with sides such as macaroni & cheese, mashed potatoes, cornbread and the famous Lynchburg candied apples featuring Jack Daniel’s Tennessee Whiskey. Save room for dessert – the coconut buttermilk pie is a must-try.
Walk off your lunch by strolling downtown to Company Distilling for tours and tastings as well as cocktails and mocktails in the indoor lounge. It’s a place to enjoy deep conversation and slow, small town living. Tap your feet to live music on weekends.
Cap off your visit with shopping at the Tennessee Whiskey Trailhead. Here, you can find exclusive Tennessee Whiskey Trail merchandise from sweatshirts to cooking sauces, keepsakes and gifts for your special someone, friend or family member, and insightful details as you plan your Whiskey Trail adventures.
Tullahoma, Tennessee
Travel 17 miles north from Lynchburg to Tullahoma. Here, you’ll find aviation history, local eateries and Cascade Hollow Distilling Co. The distillery celebrates the life of George A. Dickel, a Nashville merchant born 40 years after the signing of the Declaration of Independence and a whisky aficionado. Cascade Hollow Distillery opened in 1878 and Dickel bought a large share. Here, it’s believed that whisky made in the winter produces a mellower sip, so all spirits are chilled to 40 degrees before charcoal filtering, resulting in a smooth and complex taste that rivals the world’s finest scotch whiskies. Take a tour and have a taste yourself Thursdays-Tuesdays.
Head to the historic downtown Tullahoma for lunch at the local restaurant, One22West, an upscale eatery that serves locally produced food, craft beer and cocktails. Start with the classic fried pickles or the fried mushrooms. Enjoy locally sourced beef with a filet mignon or prime rib, pasta, chicken florentine, pizzas and burgers. Enjoy sides like fire roasted corn, loaded baked potatoes, fried okra and creamy mac n’ cheese.
Get some fresh air with friends or your soulmate on a hike to Rutledge Falls, located about 6 miles near downtown Tullahoma. While the waterfall is located on private property, the owners allow the public to visit from dusk to dawn. The path is 0.2 miles and leads you to the 40-foot waterfall. Enjoy unobstructed views of the falls. Or, head out to Old Stone Fort State Archaeological Park, about 14 miles north of Tullahoma. Follow the Enclosure Trail, a 1.4-mile easy to moderate trail that leads you to Step Falls, Blue Hole Falls and Big Falls as well as remnants of an old paper mill foundation.
Warm up from your outdoor adventure at Beechcraft Heritage Museum. Inside, a wealth of aviation history and stories like Louise Thaden, the acclaimed 1929 Women’s Air Derby Trophy winner. Her exhibit includes her pilot’s certificate signed by famous Orville Wright. Step into the Walter Beech Hanger to marvel at the first Travel Air 1925 Model “A”, Staggerwing and many other Beech aircraft.
Nearby Distilleries
Looking to keep the adventure going? Discover additional nearby distilleries just a short drive away—each offering its own story, spirit, and taste of Tennessee craftsmanship.
Memphis, Tennessee
Chase the winter blues away with a friends’ trip or romantic Memphis weekend. Cozy up in the new Hotel Potonoc. You’ll love the restored 1906 architecture, the European-style design and spacious suites.
Start your day the right way at Sunrise Memphis, a locals’ favorite diner where you can enjoy a full Southern breakfast with a plate piled high with country ham, fluffy biscuits and buttermilk pancakes. Dig into the Kitchen Sink plate with two eggs your way, sausage, bacon, hash browns, grits and biscuit. Enjoy the Tennessee Jed biscuit sandwich stuffed with country ham, egg and cheddar cheese.
Feel the heartbeat of the city by diving into Memphis’ music history. Tour Sun Studio where music legends Elvis Presley, Jerry Lee Lewis, Carl Perkins and Johnny Cash became the Million Dollar Quartet after a spontaneous jam session that led to the studio becoming the “Birthplace of Rock n’ Roll.” Hear recordings and stories of artists from B.B. King to Roy Orbison as you stand where Elvis recorded, see the recording equipment used and more. Learn even more at music sites around the city like Memphis Rock n’ Soul Museum, Blues Hall of Fame Museum and, of course, Elvis Presley’s Graceland.
Grab lunch where Elvis used to frequent at Arcade Restaurant, Memphis’ oldest cafe. See Elvis’ booth and then order pizza, salads, and sandwiches like the famous Fried Peanut Butter N’Banana or “A Memphis Thang,” a sandwich piled with smoked turkey, brie cheese, red onions, roasted red pepper and a creole mustard with just enough kick.
A sweet treat is always a great idea and Tous les Jours, a French Asian bakery in Memphis’ MidCity DIstrict is where to go. Order a coffee and pastry like the fluffy Guava Danish, caramel apple handpie, the classic French fruit pastry with fluffy cloud cream and custard cream, strawberry, blueberry and raspberry or a traditional Pain Au Chocolat.
After lunch, enjoy a sensory tour and tasting at Old Dominick Distillery, Memphis’ sole distillery. Journey through Old Dominick’s 150-year history on the one-hour tour that also includes a guided tasting. See the technique and passion behind the spirits they make. Then, hop on a barstool at The Bar to enjoy a craft cocktail, made exclusively with Old Dominick spirits.
Continue your artistry tour of the city with a visit to the Metal Museum. Catch a metalworking demonstration Saturdays and Sundays beginning at 1:30 p.m. Enjoy a guided tour for a unique Metal Museum experience that includes the history of the museum and viewing artwork in the Sculpture Garden.
Before you kick up your feet on Beale Street, celebrate your love and friendship at Fawn in the Cooper Young District, where you’ll find a menu of tapas style dishes made with local ingredients. Start with the miso deviled eggs with red miso, kewpie and furikake. Enjoy main courses like the confit duck served with cannellini beans and braised collard greens or the New York Strip of Wagyu beef with a side of broccolini.
Amanda Stravinsky Burton, Founder/Owner of The 375 Company, LLC
The 375 Company, LLC is a female-owned and -operated boutique digital marketing agency specializing in content creation, influencer partnerships, social media consultation and search engine optimization. Step into your digital spotlight with The 375. Learn more at the375company.com.
