Sleigh the Peppermint Trail

Cozy up with a good read and a sweet treat at Addison's Bookstore. Shop their holiday gift mugs filled with peppermint candies, perfect for teachers, friends, and book lovers on your list.

Alice in Appalachia will have boozy and non-boozy peppermint dark chocolate hot cocoa! This is the perfect place to watch the ice skaters on Market Square while enjoying a holiday drink!

Stop by The Arrowmont Gallery for all of your handcrafted gifts this season! Complete a purchase of $15+ before December 6th and you'll be entered into their Holiday Raffle with special gifts from the gallery and Jacks. (All who enter will receive a 10% coupon to Jacks!) The winner of the raffle will be announced at the Shop & Sip event on 12/6, for a fun afternoon of shopping with coffee and treats from Jacks. From jewelry and pottery to collection-worthy works for your walls, don’t miss out on this opportunity to gift an original piece. 

With every purchase at the Art Market Gallery, you'll be treated to a peppermint treat! Plus opportunities for special coupons and gift wrapping. The gallery artists have also special bird ornaments this year to benefit the Community School of the Arts in Knoxville. 

Awaken is a must-stop destination with more holiday drinks than you can try! Try the Peppermint Mocha, Polar Bear Latte, Peppermint Hot Chocolate, Salted Caramel Hot Chocolate, Gingerbread Latte, Sugar Cooke Latte, Eggnog Latte, The Grinch - a twist on the matcha green tea latte. Plus, a sweet drink made with maple syrup that's Buddy the Elf's favorite. They'll also have White Chocolate Peppermint Cookies! Stop in to have your taste buds tingled!

Bethie Lou's Fabulous Gift Store boasts tons of holiday home décor and adorable gifts, crowd-favorite Merman and Mermaid Ornaments, stocking stuffers, and more. Plus, the store will have special Peppermint Pattie Treats. Now that sounds like a good shopping day!

Experience farm-to-table brunch, lunch, or dinner at its finest at the Bistro at the Bijou. Unwind with their Peppermint Trail special – tasty Peppermint Ice Cream with Oreos! They'll also be serving up some festive mocktails!

Get in the spirit at Bliss & Tori Mason Shoes with tons of holiday home décor, unique gifts for everyone on your list, and festive clothing for all occasions and celebrations.

Stay toasty this season with the Mary + Bright, a delicious cocktail made with gin, rosemary syrup, pomegranate juice. Or have a Peppermint Mochatini with The Barker Co. Espresso Martini, and peppermint bark Rum Chata. Jig & Reel also has Hot Cocoa and Hot Apple Cider to warm you up after a brisk walk in the Old City.

Warm up at the Brass Pearl with their Winter Rum Remedy. This jewel-toned cocktail blends bright, cozy flavors and comes topped with a fragrant cinnamon stick for a festive finish. A seasonal sip that feels equal parts merry and soothing.

Again this holiday season, Brother Wolf will transform with nostalgic holiday décor for Miracle, the beloved Christmas-themed pop-up bar launched in 2014 in New York City. Their signature cocktail will be the Snowball Old-Fashioned with Rye Whiskey, Gingerbread Syrup, Angostura Bitters, Wormwood Bitters. They also have a complete festive holiday cocktail menu to check out! Stop by for some holiday cheer.

Café 4 is a delightful spot to have lunch or dinner and enjoy all the holiday activities and lights on Market Square. Get in the spirit with a festive menu of holiday cocktails including the Santa's Sangria (photo) by the glass or a shareable bowl, Peppermint Crunch Espresso Martini, Sugar Cookie Martini, and the Cranberry Rye Old Fashion. We'll be making several trips!

Warm up by the river with a Peppermint Espresso Martini that pairs bold espresso with cool holiday mint. Or, make it a non-alcoholic coffee! It’s the perfect seasonal sip to enjoy alongside your favorite barbecue plates at Calhoun's.

Treat yourself to a Peppermint Espresso Martini at Chesapeake's that blends rich espresso with cool holiday mint for the perfect seasonal pick me up. Smooth, spirited, and ideal for sipping between seafood favorites. And save room for a slice of their delicious cheesecake in rotating seasonal flavors including peppermint, eggnog, and gingerbread!

Treat yourself to their holiday twist on a classic at Chivo... Espresso Martini with Peppermint Cold Foam! It’s smooth, minty, and just the right amount of festive flair to enjoy between tacos.

Take a peaceful break from your downtown stroll and step into Christopher Robin Arts for a peppermint-themed Make and Take (Wednesdays, Thursdays, and Fridays from 1–6 PM and Saturdays from 11 AM–6 PM). Enjoy your festive holiday art project, or browse for unique gifts and take in seasonal paintings and photos throughout their charmingly decorated gallery. A cozy creative stop to refresh your spirit during the holiday rush.

Your four-legged friends can get in on the peppermint fun too! Citifid-O has peppermint, candy cane, and other festive dog and cat toys, as well as special holiday treats. Great little stocking-stuffers and even gifts for under the tree.

Be sure to get your hands on Coffee & Chocolate's adorable Christmas Chocolates! These cute lil things make perfect gifts and sell fast! Featured pastries will include the Snickerdoodle Cookie - soft, buttery, and rolled in cinnamon sugar for that perfect chewy-crisp balance. Or try the Cranberry Orange Muffin - bright citrus and tart cranberries come together in this soft, seasonal muffin. They will also carry a trifecta of drinks: Peppermint Mocha, Cookie Butter Latte, Hot Chocolate, and coffees, including their Peppermint Mocha, Snickerdoodle Latte, and Cookie Butter Latte. What a winning combo!

Warm up with a White Chocolate Peppermint Mocha that tastes like pure holiday comfort at the Maker Exchange. Sip from a locally made mug and buy it afterwards if you’d like. It’s the perfect mix of cozy, creative, and pepperminty.

Ride into the holidays with a fun lineup of festive cocktails and shots at Cowboy Cantina. Sip on drinks like Angry Balls, the bright and zesty Mistle Toe Kiss, Fire Cider with Jack Fire and apple cider, or the Cranberry Mule with vodka, lime, and ginger beer. They’re also serving seasonal shots including the Oatmeal Cookie, Peppermint Patty, and Frost Bite.

Some things are worth melting for… like the Peppermint Martini being served up at The Library lounge at the Crowne Plaza! While you are there, join them for their Friday Night Seafood and Prime Rib Buffet or check out their Marketplace for the perfect gift. Make your holiday season sweeter with a stay right in the heart of Downtown Knoxville at the Crowne Plaza.

Step inside the always festive red-and-white Cruze Farm Ice Cream to have your Peppermint Trail wishes come true with a long list of holiday ice cream flavors – Candy Cane ice cream and toppings, Peppermint Bark Shake with candy cane ice cream, chocolate flakes, whipped cream, crushed candy cane, topped with a cherry; Peppermint Hot Chocolate; Peppermint Mocha; and Candy Cane Brownie Churn with candy cane ice cream and brownies, topped with more brownies and crushed candy cane. Plus lots of other holiday flavors you're going to want to try—at least once!

Sip into the season with two festive favorites from Downtown Grill. The North Pole Tini blends Wheatley Vodka, Peppermint Schnapps, and cream for a smooth and wintry martini, while the MaddieMintz Shot shakes up Crown Chocolate, Bailey’s, and a hint of Rumplemintz with a sweet Hershey’s rim. A perfect pair for peppermint lovers.

Visit the Drawing Room this season and indulge in a White Chocolate Peppermint Martini that feels elegant, rich, and perfectly festive. This creamy holiday cocktail blends sweet winter flavors with a refreshing hint of peppermint, finished with a swirl of white chocolate and a crushed candy rim. A little luxury in every sip.

You'll find a wonderful assortment of holiday inspired gifts at Earth To Old City, including Christmas soaps, holiday-scented candles, decorations, dog treats, and more - plus gifts and stocking stuffers galore!

Need some healthy stocking stuffers or an energy boost to get you through the season? Eddie's Heath Shoppe can help with that. You'll find Skinny Mixes (sugar free coffee syrups) in the flavors peppermint mocha, white chocolate peppermint, and gingerbread; peppermint bark Barebells Protein Bars; winter wonderland Alani Nu; peppermint chunk puff Built Bar and more. Power on!

Warm up on the Peppermint Trail at Escape Game Knoxville! Stop by for free hot coffee, then head inside for a family-friendly escape adventure or make it a date night! Book online and use promo code Peppermint2025 to enjoy 10% off your game! Located right in the heart of downtown; come escape the cold and make a holiday memory! (Offer valid online only. Reservations required)

Sip on some frozen, seasonal cheer at Fat Tuesday. Try Santa’s White Russian crafted with peppermint bark spiked cream for a sweet and chilly holiday treat. Feeling bold? Order a Frostbite Shot made with Ole Smoky Mountain Java for a spirited winter kick.

Fiori is celebrating the holidays in style with their Peppermint Espresso Martini (pictured) and decadent Chocolate Peppermint Cake, available during this year’s Peppermint Trail! Stop by to enjoy these festive treats and explore their lineup of seasonal holiday cocktails throughout the holiday season.

Not only does the French Market boast delicious sweets, they also have a creative cocktail menu! Try the Poinsettia Mimosa, Irish Coffee with Tullamore Dew Irish Whiskey, Maple Hot Buttered Rum, Fireball Cider, and a Pomegranate Mule with ginger beer! All makings for a joyeux Noël.

Ooh la la! For something sweet to eat, try The French Market Crêperie's Magical Cookie Butter Crepe topped with white chocolate, cookie butter crumble, chocolate chips and sparkle sugar! For something sweet to drink, order up a White Chocolate Peppermint Latte, Maple Chai Tea Latte, Caramel Chocolate Cupcake Latte, or Hot Cocoa!

Ham'n Goodys is decorating their famous lemon cookies with snowmen, holly berries, reindeer, Christmas trees and more – perfect for your holiday gathering. After grabbing a cookie on Gay Street, head to Market Square to drop your letter to Santa in Santa's Cookie-Themed Mailbox. A sweet outing if you ask us! These adorable cookies go fast, so if you want to make sure you get them, please call ahead and order.

Say "hello" to something merry at Hello Teahouse with two festive favorites. Their Peppermint Bubble Milk Tea blends creamy sweetness with a cool mint twist, complete with chewy pearls. They’re also serving a Peppermint Latte for a warm and wintry pick me up. A delightful duo for your holiday stroll downtown.

The spirited mixologists at J.C. Holdway are leaning fully into holiday tradition this year with Avoiding the In-Laws, a boozy nod to seasonal escapism. Buffalo Trace Bourbon, Buffalo Trace Bourbon Cream, Cruz Farm Egg Nog, and freshly grated nutmeg come together in a rich, velvety pour that feels like Tennessee comfort in a glass. This festive riff on classic egg nog brings warmth, cheer, and just enough humor to help you navigate the holiday calendar. It is the kind of nog that pairs beautifully with their wood-fired cooking throughout the season.

Don't miss out on Jacks' host of creative holiday coffees, like their Peppermint Mocha Latte, a cozy blend of chocolate, espresso, and cool mint that’s perfect for sipping while you shop their wonderful selection of perfectly curated local goods.

Stop by K Brew in the Embassy Suites on Gay Street for a warming Peppermint Mocha, because nothing goes better together for the holidays than the flavors of peppermint, chocolate, and coffee!

Step into a world of pure imagination at the Kennedy, with two festive sips made for the season. Their Peppermint Wonka, a dreamy adult take on hot chocolate that mixes cocoa, peppermint, and a touch of sweet magic with a boozy splash that turns every sip into a winter escape. They’re also serving the Gingerbread Espresso Martini (pictured) blends rich espresso with warm gingerbread spice for a cozy, holiday inspired pick me up. It is the perfect pair for adults who want something festive, nostalgic, and a little bit mischievous on the Peppermint Trail.

Knox Whiskey Works is upping their cocktail game this season with two signature cocktails – Santa's Nightcap with their very own Three Rivers Maple Rum, Coffee Liqueur, non-dairy oat creamer, and candy cane; and crowd favorite Festivity Fizz – as well as a Holiday Cocktail Flight featuring four mini cocktails: Winter Party Punch, Whiskey Wonderland, Apple of my Rye & the Bourbon Brew. While you're there, stock up on locally-made spirits for those on your gift list that have been good this year.

Discover unique gifts at the Knoxville Museum of Art! This holiday season, find the perfect gift at the Knoxville Museum of Art Shop! Explore an array of one-of-a-kind items, from exhibition-inspired merchandise and novelty gifts to handcrafted jewelry, artisan textiles, ceramics, and glassware—all crafted by talented regional artists. Plus, you’ll find a delightful selection of toys and books for children. As a special treat, every purchase includes a peppermint surprise. Shop local and support the arts this season!

Visit Knoxville’s Visitor Center Gift Shop is full of locally made gifts and holiday event information. Check out the assortment of small batch toffees including decadent White Chocolate Peppermint Toffee from Towns Toffee, Soft Peppermint Candies from Tennessee’s Best, and a special Peppermint Trail Candle designed by 865 Candle Co.

Sip something très festive with their Egg Nog Espresso Martini. Made with house-made egg nog, French coffee liqueur, and local Honeybee espresso, this cozy cocktail is rich, velvety, and full of holiday charm. A chic seasonal treat from Knoxville’s favorite French escape. They’re also serving Le Criquet, a boozy chocolate mint martini that’s smooth, decadent, and perfectly pepperminty.

Celebrate the season with one of the festive drink specials at Lonesome Dove. Try the warm and spiced Turtledove Martini, featuring Blackstrap rum, Benedictine, and spiced eggnog (made in-house)! Perfect for cozying up and toasting to the joys of the holidays! Join friends for a round of drinks in the picturesque holiday scene, featuring a twelve-foot Christmas tree framed by the antique stained glass windows.

Roll into the holidays with a festive flight of cocktails. Warm up with the Ginger Bells Toddy made with Canadian Club Whiskey, honger-ginger syrup, and hot water. Try the Dude-ish featuring Numbskull chocolate mint whiskey, Buffalo Trace bourbon cream, house-made cold brew, and vanilla. Mrs. Claus’ Cherry Pie mixes Wheatley vodka, cherry pie syrup, ginger beer, and lime for a bright, nostalgic sip. And Merry & Spritzy blends Astobiza gin, cranberry juice, rosemary syrup, bubbles, and sparkling water for something light and refreshing.

Marble City Kitchen at the Hilton Downtown has two cheerful ways to toast the season! Their Mistletoe Margarita (pictured), a festive twist on a classic. This bright holiday margarita blends Corazón Añejo, triple sec, cranberry, and lime for a sweet and tart sip. Or try the Chocolate Peppermint Espresso: rich, bold, and perfectly pepperminty. This decadent espresso cocktail mixes chocolate liqueur, vodka, peppermint syrup, and fresh espresso, then arrives in a copper martini glass with a crushed peppermint rim. A holiday treat for coffee lovers.

Find Provisioners Peppermint Dream Bar at Mast General Store. It's a dreamy blend of crushed peppermint and lavish dark chocolate brownie. And of course, take home a stocking-full of their old-fashioned candy!

Visit the Museum of East Tennessee History to explore permanent and changing exhibits. Plus free peppermint treats.

This year's collection of holiday tees at Nothing Too Fancy includes designs featuring a Gingerbread Sunsphere, Knoxville Snowflake, a Raccoon Santa and more! As always, these locally designed & printed vintage style t-shirts are available along with cozy sweatshirts & blankets, locally made jewelry & artwork and one of a kind items. Nothing Too Fancy is great option to shop local and satisfy everyone on your gift list this season!

Do you hear what I hear? Old City Sports Bar will turn into a holiday wonderland through December, complete with nostalgic tacky holiday decor and their festive menu! ! Don't miss a special Peppermint Trail drink menu featuring items like their Flaming Snowball Shot, Santa's Cifer Mule,or the Grinch's Melon Sour, and more. Join them for happy hour pricing Monday through Thursday, all evening long; plus Sunday funday happy hour deals all day on Sundays.

Enjoy the romantic, holiday atmosphere at Oliver Royale with a choice of specialty cocktails, including this year's Peppermint Trail treat – Statemint Piece, featuring Borghetti espresso liqueur, Branca-Menta, and house-made milk syrup. It’s smooth and creamy and a perfect balance of coffee and mint. Cheers! 

Follow the Ghost of Christmas Past to downtown Knoxville's speakeasy, Peter Kern Library, and their seasonal cocktail: the Haha Jones. Named for the 1956 A Christmas Memory by Truman Capote, this cocktail features Weller Special Reserve, Post Modern Cacao, Mr. Black, Five & Hoek espresso, and candy cane syrup. It's guaranteed to convert you into a believer of speakeasy magic.

Enjoy the ambiance, old school Christmas music, and the waves of nostalgia at the Phoenix Apothecary this holiday season! Get (and stay) in that Christmas spirit with a scoop (or two) of their seasonal Peppermint Ice Cream or their signature Peppermint Shake! They will also be serving up Peppermint Mocha and Peppermint Hot Chocolate throughout the holidays. They will also have a few other seasonal ice cream flavors including Christmas Cookie! 

PostModern will be hosting a themed pop up bar in the Tasting Room: Winter "Cocktail" Wonderland. Join them through January 4th for seasonal sips and merriment! This year their talented bartending elves have created some new holiday cocktails to help spread holiday cheer. Frosty in Wonderland is like a winter holiday on a tropical island, the Snowdrift Martini is a fun, elevated vodka peppermint treat, and the Wonderland Fruitcake, featuring gin sweet fruit. Stop in for cocktails, spirit tasting, and pick up the perfect stocking stuffer!

Sip into something frosty with their Peppermint Candy Cane Nitro beer on tap at Pour Taproom. It’s smooth, creamy, and filled with holiday cheer in every pour. A festive sip for the grown ups following the trail of peppermint delights.

Proper Popcorn has popped up several holiday mixes we're looking forward to! The red, white, and green Festive Mix is as colorful as it is delicious, the Red Cinnamon popcorn comes with a kick, and the Reindeer Munch is a fan-favorite with candy pieces, pretzels, cereal, and white chocolate!

Head to Radius Rooftop Lounge for a sweet and boozy treat by fireside: the Chocolate Peppermint Martini is just the dessert cocktail you need while overlooking stunning views of Downtown Knoxville, Tennessee!

Rocket Fizz Soda Pop and Candy Shop is definitely the sweetest place on Market Square. You’ll find the South's most delicious selection of nostalgic candies, quirky sodas and the latest brands of toys and sweets from around the world. A must stop on the Peppermint Trail for favorite peppermint sweet treats, stocking stuffers, and more.

This festive season, treat yourself to the perfect blend of sweet and strong with Ruby Sunshine's Winter Sangria. A wintery mix of brandy, macerated cranberry juice, OJ, and sparkling wine with crystallized cranberries, this holiday drink is the ultimate indulgence. Be sure to also try the non-alcoholic Dirty Chai Latte, served hot or iced. In need of a sweet treat? Don't skip out on the White Chocolate Cranberry Beignets or the White Chocolate Cranberry Stuffed French Toast.

Teas the Season to be be merry—and Spice & Tea Exchange has quite the selection of festive flavors for sipping on at the Tea Bar. Along with enchanting Chocolate Candy Cane Black Tea, Hazelnut Cookie Tea, Bourbon Chestnut Tea, Red Hot Toddy Cinnamon Herbal Tea, or White Chocolate Peppermint Green Tea! Sugars? Yep, they have those too—Peppermint Patty, Cinnamon Sugar, and Dark Cocoa are just a few of our favorites. And candles and mulling spices to transport you to a winter wonderland. (Their items make for perfect stocking stuffers!)

Celebrate the season with a lineup of festive favorites at Starbucks. Enjoy Peppermint Mochas in classic or white chocolate for a cool minty treat, or cozy up with a Peppermint Hot Chocolate. Try a Gingerbread Latte for warm holiday spice or a Caramel Brulée Latte for sweet, creamy indulgence. Pair your drink with seasonal treats like the Sugar Plum Cheese Danish, Polar Bear Cake Pops, Cinnamon Pull-Apart, or the classic Cranberry Bliss Bar. A merry stop for sips and sweets on your holiday stroll.

Celebrate the season with a Peppermint Chocolate Cake Doughnut or a Chocolate Glazed Old Fashioned paired with a Peppermint White Mocha (hot or iced)! Plus, grab a dozen of your favorite buttermilk old fashioned, glazed, or flavorful cream-filled doughnuts alongside a Cinnamon Hazelnut Shaken Espresso.

Stock & Barrel is spicing up the party with three seasonal cocktails! The Tinsel Toddy (back) mixes Elijah Craig Small Batch with cran-apple, lemon, and allspice simple syrup for a warm seasonal glow. Their Peppermint Hot Chocolate (right) is cozy and minty with a candy cane twist and the Peppermint Milkshake (left) is a creamy chocolate drizzled treat topped with whipped cream and crushed peppermint.

Step into holiday magic at the Sunsphere Welcome Center Gift Shop! Explore locally made treasures, hand-painted Sunsphere and World’s Fair Park ornaments, and sparkling Knoxville snow globes — plus all the info on festive events around town! Take your holiday fun to new heights! The 4th-floor Observation Deck is decked out with a peppermint-themed scavenger hunt — spot the clues, solve the puzzle, and claim your wintery Sunsphere prize!

Sip something bold at Suttrees with two festive holiday cocktails. Their Peppermint White Russian is creamy, cool, and delightfully mint kissed. They’re also serving a Mint Chocolate Chip Espresso Martini that blends rich coffee with chocolate and mint for a spirited seasonal treat.

Try the Candy Cane Margarita at the Tavern for a bright and merry twist on a classic. This colorful holiday drink mixes tequila, cranberry, and a touch of peppermint, then gets topped with a splash of bubbly seltzer. Finished with a sugared rim and a crushed candy cane garnish, it’s equal parts cheerful and refreshing.

Take a tropical vacation to Tern Club and enjoy a break with their holiday cocktail menu featuring Menta Clause with vodka, Branca Menta, creme de cacao, coconut milk and cold brew coffee; Tingle Bells with Barbados rum and pineapple; and It's a Wonderful Spice with bourbon and maple brown ale syrup and spice! Enjoy delicious libations on their outdoor patio or inside their stylish bar. Merry, merry!

Tree & Vine's seasonal balsamic flavors are oh-so delicious – the Cranberry, White Cranberry, and Pear Balsamics elevate holiday dishes to a new level. Plus you'll find Christmas-Themed Kitchen Items, like this Nordic Ware snow-inspired cake pan to warm your heart. It's all in the beautiful details.

Pick up a festive stocking at TVA Credit Union stuffed with candy and fun goodies as you make your way along the Peppermint Trail. It’s a sweet little surprise to keep your holiday spirit going while you explore downtown!

You've been walking the Peppermint Trail. Now it's time to dip your toes into it with a seasonal soak at Wake Foot Sanctuary. Come try their refreshing Peppermint Stick Soak, made to refresh and revitalize. Infused with energizing peppermint oils and enriched with cacao husks, this luxurious soak offers a delightful aromatherapy experience. Cocoa butter and revitalizing clays work together to leave your skin exceptionally soft and deeply moisturized. Enjoy a 20-minute foot and lower leg massage.

After your soak, enjoy self care at home for you and loved ones with Wake's signature brand of rosemary and mint body wash, peppermint shea butter, and refreshing tea tree and mint soaps!