Celebrate the season at Christmas on the Square in Downtown Cookeville! Enjoy Christmas train rides, kid-friendly activities, ornament-making, cocoa, live music, Santa photos, and Shop Small Saturday specials — all leading up to the Tree Lighting Ceremony at 5:00 PM, when the square glows with thousands of twinkling lights. A free, festive afternoon of small-town holiday magic for the whole family!
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Discover the beauty of Center Hill Lake with an unforgettable weekend getaway from Escape to Center Hill. This incredible holiday prize includes a two-night stay valued at up to $2,000, giving the winner the freedom to select any of the beautiful properties within that price range. Whether you prefer a secluded wooded retreat, a spacious waterfront lodge, or a stylish modern cabin with panoramic views, Escape to Center Hill offers stunning stays designed for comfort, serenity, and memory-making.
With properties located throughout the scenic hills and lakeshore, every stay offers access to the best of the Upper Cumberland — from boating, fishing, and hiking to relaxing by the fire or exploring charming nearby towns. Escape to Center Hill is known for its warm hospitality, exceptional homes, and a commitment to helping guests experience the lake life at its finest.
Browse available rentals and begin dreaming about your perfect getaway at https://www.centerhillchalets.com/.
Experience Crossville like never before with a one-of-a-kind holiday bundle that brings together two of the community’s greatest treasures — its legendary golf culture and its thriving performing arts scene. This curated combination invites you to spend your days teeing off on scenic courses and your nights enjoying unforgettable productions, all in the heart of the Upper Cumberland.
Explore Crossville – Custom Golf Bag
Begin your adventure with a premium custom golf bag from Explore Crossville, a proud tribute to the city known as Tennessee’s Golf Capital. Designed with both craftsmanship and performance in mind, this bag brings a touch of Crossville pride to every round. Whether you’re swinging on championship-caliber greens or enjoying a casual day out with friends, this bag showcases durability, style, and the spirit of one of the region’s most beloved outdoor pastimes. https://explorecrossville.com/
Cumberland County Playhouse – 4 Tickets
Balance your outdoor fun with an unforgettable cultural experience at the Cumberland County Playhouse, one of the largest professional theaters in rural America. With four tickets to an upcoming show, the winner can enjoy Broadway-style musicals, heartfelt dramas, laugh-out-loud comedies, or family-friendly productions — all performed by exceptional regional and national talent. The Playhouse is known for its superb acoustics, warm atmosphere, and a season filled with inspiring performances that draw audiences from across the Southeast. https://ccplayhouse.com
Together, this bundle showcases the best of what makes Crossville shine — lush rolling fairways, vibrant artistic expression, and small-town hospitality that welcomes visitors near and far. Whether you’re teeing off beneath Tennessee skies or settling into a red velvet seat for a night of storytelling, this experience is a celebration of the Upper Cumberland at its finest.
Step into the wonder of Plenty Bookshop, Cookeville’s beloved nonprofit indie bookstore, where every shelf feels like a story waiting to be discovered. Filled with warmth, beauty, and an atmosphere that instantly invites you to slow down and savor the moment, Plenty is a place where readers, artists, and the community all come together.
This special holiday giveaway features a $100 gift card to explore their thoughtfully selected collection, a hardback edition of O. Henry for the Holidays, a tin of Harney & Sons Paris tea, a handmade Dickens ornament by local artist Wilma Henry Design, and an elegant Victorian book hook — all curated to bring comfort, charm, and literary magic to your season. As a nonprofit bookstore, every purchase directly supports literacy, local creators, and the cultural heartbeat of downtown Cookeville.
To explore more or plan your visit, go to www.plentybookshop.com.
Discover the heart of Sparta with a beautifully balanced holiday bundle that celebrates local craftsmanship, walkable charm, and restorative escape. This experience invites you to slow down, explore, and enjoy the unique blend of outdoor adventure, creative makers, and welcoming hospitality that defines this Upper Cumberland town.
Liberty Square Lofts – 2-Night Stay (One Private Loft)
At the center of this getaway is a two-night stay in one private loft at Liberty Square Lofts, located in the heart of downtown Sparta. Featuring four newly renovated loft spaces, each infused with a modern industrial vibe, Liberty Square Lofts delivers a big-city feel while preserving the warmth and character of small-town Tennessee.
Each loft offers an open, comfortable layout designed to recharge and revitalize you after a full day of hiking, biking, kayaking, canoeing, or taking in the awe-inspiring natural beauty of the area. Original wood floors, exposed ceiling beams, and thoughtfully curated interiors create a space that feels both elevated and inviting.
From your loft, step out and explore Sparta’s locally owned antique shops, herbal markets, cafés, and boutiques — all within easy walking distance. Spend your evenings enjoying local cuisine, spirits, and music, or opt for a quiet night in, cooking dinner and sipping your favorite wine from the comfort of your loft. Liberty Square Lofts is the perfect home base for experiencing Sparta — walkable, welcoming, and full of character.
Website: https://www.libertysquarelofts.com/
Northfield Vineyards – Artisan Cider, Wine & Pizza Gift Card
Complement your stay with handcrafted flavors from Northfield Vineyards, a family-owned vineyard nestled in the rolling farmland of Sparta. This bundle includes their crisp Hard Apple Cider, festive Cranberry Wine, and a Brick Oven Pizza gift card — perfect for cozy evenings, relaxed afternoons, or sharing a fireside meal with friends. Known for warm hospitality and thoughtfully crafted pours, Northfield Vineyards captures the essence of Upper Cumberland winemaking with every glass.
Facebook: https://www.facebook.com/northfieldvineyardswinery
Synergy (Sparta) – Locally Crafted Tea Blends
Round out the experience with soothing, locally crafted tea from Synergy, where herbs, wellness, and creativity come together in beautifully balanced blends. Perfect for slow mornings, quiet evenings, or moments of reflection, these small-batch teas add a calming, sensory element to your Sparta escape — inviting you to pause, sip, and savor the season.
Discover the artistic heartbeat of Smithville with a holiday bundle that shines a spotlight on creativity, craftsmanship, and the warm, small-town charm that makes this community so special. This collection brings together artisan gifts, delicious local dining, handmade treasures, and a nostalgic theater experience — offering a heartfelt taste of the Upper Cumberland’s rich cultural soul.
Appalachian Center for Craft
Begin your journey with an extraordinary handmade piece from the Appalachian Center for Craft, a nationally renowned studio hub dedicated to preserving and elevating fine craft traditions. The winner will receive a custom artisan work selected especially for this holiday giveaway – a meaningful keepsake that reflects the Center’s commitment to craftsmanship, creativity, and functional art.
Visitors can explore even more fine craft in the Center’s beautifully curated Gallery Store and sign up for hands-on workshops and community programs through their course offerings.
Main Website: https://www.tntech.edu/fine-arts/craftcenter/index.php
Gallery Store: https://www.tntech.edu/fine-arts/craftcenter/gallery-store.php
Workshops & Programs: https://www.tntech.edu/fine-arts/craftcenter/summer.php
Cheryl’s Beau Bees
Add a taste of Smithville’s hospitality with a delicious meal from Cheryl’s Beau Bees, a beloved local favorite known for homemade comfort food served with heart. With lunch for two and a $50 gift certificate, the winner can savor fresh dishes, signature entrées, and sweet treats in a warm, welcoming space that feels like gathering with family. In addition to its memorable menu, Cheryl’s features a beautifully curated gift shop offering handcrafted gifts, home décor, boutique items, and locally sourced treasures.
Smithville Downtown Shops
Explore the whimsical charm of Smithville’s downtown shops with a selection of festive artisan goods, including handcrafted wooden ornaments, whimsical coasters, locally sourced honey, and small-batch Tennessee hot crackers – small-town creativity wrapped in holiday cheer. Make sure to stop by Cafe Healthyish.
The Purple Door
Griffins Produce
Historic Granville’s Mayberry Valentine Dinner Theater
Enjoy a nostalgic evening inspired by the world of Mayberry with two tickets to the Valentine’s Dinner Theater at Historic Granville – a heartwarming blend of storytelling, humor, and small-town charm.
Historic Granville Bed & Breakfast
After the show, settle into a cozy overnight stay at the Historic Granville Bed & Breakfast, where Southern hospitality meets riverfront nostalgia. Wake up to Tennessee’s most charming heritage town – museums, shops, and historic sites right outside your door.
Together, these treasures create a holiday bundle that celebrates the artistry, flavor, heritage, and heartfelt warmth of Smithville and Granville — a delightful journey through handmade craft, delicious food, nostalgic theater, and small-town hospitality in Tennessee’s Upper Cumberland.
Discover Cookeville through its most charming downtown experiences — where creative boutiques, small businesses, and warm hospitality come together to create an unforgettable Upper Cumberland getaway. This thoughtfully designed bundle places you right in the heart of the city, inviting you to slow down, shop local, and enjoy the simple pleasures that make Cookeville so special.
Hideout Hotels – Overnight Stay
At the center of this experience is an overnight stay at Hideout Hotels — a stylish, modern retreat designed for comfort, rest, and easy access to downtown Cookeville. With thoughtfully curated spaces and warm hospitality, Hideout Hotels offers the perfect place to unwind after a day of browsing boutiques, sipping coffee, and enjoying the WestSide’s creative energy.
https://hideouthotels.co/cookville-tn/
Cookeville WestSide Downtown Shops – Curated Boutique Gift Collection
Step outside your stay and into the vibrant charm of Cookeville’s WestSide downtown district. This bundle includes a curated collection of gifts from local boutiques and downtown shops — showcasing handmade goods, unique home décor, artistic accents, and small-batch finds that reflect the personality and creativity of Cookeville’s small business community. It’s like taking a piece of downtown home with you.
Broadway Boutique: https://broadwayboutiquemall.square.site/
Synergy: https://www.synergyherbalworks.com/
Meg’s Bread – Gift Card
Add a delicious highlight with a gift card to Meg’s Bread, one of Cookeville’s most loved local bakeries. Known for its fresh-baked artisan breads, pastries, and welcoming atmosphere, Meg’s Bread is a must-stop while exploring downtown — whether for breakfast, lunch, or a cozy afternoon treat.
https://www.megsbreadtn.com/
Glass Tangerine – Curated Gift
Add a touch of creativity and style with a curated gift from Glass Tangerine, a beloved Cookeville shop known for blending botanical beauty with artistic expression. This thoughtfully selected piece reflects the shop’s eclectic, creative spirit — bringing warmth, character, and visual charm into any space.
https://www.glasstangerine.com/
Mountaintop Candle Shop – Two Artisan Candles
Create the perfect cozy atmosphere with two small-batch artisan candles from Mountaintop Candle Shop. Handcrafted with rich seasonal scents and mountain-made warmth, these candles are ideal for winding down after a day of shopping or setting the mood for slow, relaxing evenings.
https://www.mountaintopshoptn.com/
Bonus Experience – Historic Granville Bluegrass Show (2 Tickets)
As a special bonus, enjoy two tickets to the Sutton Ole Time Bluegrass Show in nearby Historic Granville. Just a short drive from Cookeville, this authentic Appalachian music experience adds a touch of regional tradition to your getaway — a perfect optional night out while staying in the area.
https://www.granvilletn.com/upcoming-events
Experience the serenity of Waterloo Venue with a two-night stay in your choice of a custom-built tiny home or a beautifully styled glamping “Tent in the Trees.” Each space is designed for comfort and connection with nature — offering king or queen bedding, indoor or outdoor lounging areas, and either a full kitchen or thoughtfully provided camping cookware. Tucked into the peaceful forests of Livingston, this unique retreat invites you to slow down, breathe deeply, and embrace the natural world around you.
One of the most breathtaking features of the property is its two stunning on-site waterfalls, creating a peaceful backdrop for exploring wooded trails, relaxing by the water’s edge, or simply unwinding to the soothing sound of cascading falls. With creek views, forest pathways, and plenty of space to disconnect from the rush of daily life, Waterloo Venue offers a refreshing escape perfect for couples, solo travelers, or anyone seeking a restorative getaway.
Explore more or plan your stay at https://waterloovenueandevents.com/.
Escape to a one-of-a-kind outdoor retreat with a two-night stay from Your Glamping Adventures, where comfort meets nature in the most unforgettable way. Located just minutes from Center Hill Lake and surrounded by the peaceful beauty of the Upper Cumberland, this unique glamping experience offers cozy interiors, thoughtful amenities, and the perfect balance between rustic charm and boutique comfort. Whether you’re unwinding under the stars, sipping morning coffee on a private deck, or exploring the nearby trails, waterfalls, and small-town treasures, every moment feels like a breath of fresh air.
This holiday giveaway highlights Your Glamping Adventures’ commitment to creating meaningful, memory-filled getaways — perfect for romantic weekends, girls’ trips, solo escapes, or a new adventure with friends. With creative accommodations, warm hospitality, and easy access to the region’s most iconic outdoor attractions, it’s an experience that invites you to slow down, reconnect, and embrace the beauty of Tennessee’s Upper Cumberland.
Plan your glamping getaway or explore more at https://yourglampingadventure.com/
Discover the beauty and hospitality of McMinnville with a thoughtfully curated weekend escape that blends relaxation, wellness, delicious local flavor, and one of the region’s most anticipated live music events. This bundle invites you to slow down, explore, and enjoy the warm, welcoming charm that makes Warren County such a beloved Tennessee destination.
Southern Blue – Two-Night Stay
Settle into comfort and style with a two-night stay at Southern Blue, a beautifully designed short-term rental that feels like a blend of Southern charm and boutique elegance. With its inviting interiors, thoughtful décor, and serene atmosphere, Southern Blue provides the perfect home base for exploring McMinnville’s trails, shops, restaurants, and scenic attractions — from Cumberland Caverns to Rock Island State Park. Website: https://southernbluetn.com/
Urban Glow Med Spa – 1-Hour Facial
Pamper yourself with a rejuvenating, glow-enhancing facial from Urban Glow Med Spa. This one-hour treatment is designed to refresh and restore your skin while offering the kind of peaceful, spa-level relaxation that makes a getaway truly unforgettable. It’s the perfect way to unwind between exploring downtown or enjoying your stay at Southern Blue. Booking Link: https://urbanglowmed.glossgenius.com/
Juicy’s Wellness Café – Gift Card
Refuel with wholesome, flavorful goodness from Juicy’s Wellness Café, McMinnville’s go-to destination for fresh-pressed juices, nourishing bowls, smoothies, and healthy comfort foods. A perfect complement to your spa treatment, this gift card gives the winner a taste of clean, local, energy-filled dining — thoughtfully crafted for wellness and enjoyment. Website: https://www.juicyscafetn.com/
The Park Theater – 2 Tickets to Balsam Range
Finish your weekend with an unforgettable night of world-class bluegrass at The Park Theater, a beautifully restored historic venue in downtown McMinnville. Your giveaway includes two tickets to see Balsam Range, one of the nation’s most celebrated bluegrass bands, known for their soaring harmonies, incredible musicianship, and dynamic stage presence. Events & Info: https://visitmcminnvilletn.com
Together, this McMinnville getaway blends rest, renewal, and entertainment into one beautifully balanced experience — giving you the chance to relax deeply, explore freely, and enjoy the magic of Warren County at its finest.
Step into the timeless charm of The Lodge, an architectural treasure near Center Hill Lake that spans 5,500 square feet and accommodates up to 21 guests. Once the largest home in the region and featured in Homes & Gardens as well as a national Ford commercial with country legend Alan Jackson, this beautifully restored property is truly an icon of Tennessee hospitality. Every room reflects thoughtful craftsmanship, inviting you to explore, relax, and reconnect in a home designed for gathering.
This holiday giveaway includes a two-night stay at this extraordinary retreat, ideal for groups of any size — from family reunions and wedding parties to corporate gatherings or creative weekends away. Guests can elevate their stay with curated add-on experiences such as lake, waterfall, or boat tours; yoga sessions; private chef dinners; wine tastings; live music performances; and more. For architecture lovers, The Lodge is a paradise waiting to be discovered, offering history, beauty, and inspiration around every corner.
Explore The Lodge or plan your visit: https://www.airbnb.com/rooms/1473960269241095259
Get ready for adventure with an incredible gift from Canoe the Caney, one of Tennessee’s most iconic outdoor recreation outfitters. This giveaway features a brand-new FeelFree kayak valued at $650, designed for stability, comfort, and smooth paddling across lakes, rivers, and quiet hidden coves. Prefer a different model? The winner may choose $400 in store credit toward a kayak that perfectly fits their outdoor lifestyle — whether that’s fishing, exploring, or leisurely floating through the Upper Cumberland’s tranquil waters.
For more than 20 years, Canoe the Caney has been a leading destination for unforgettable outdoor experiences. They’re known for their guided waterfall paddling excursions to the base of Burgess Falls, daily self-guided trips on the beautiful Caney Fork River, and the region’s famously spooky Haunted Canoe Tours during the Halloween season. With a large rental fleet, special events, and a deep dedication to showcasing the natural beauty of the Caney Fork, Canoe the Caney has helped thousands connect with the water, discover breathtaking local landscapes, and make memories that last long after the paddle ends.
Plan your next adventure or explore their kayak selections at www.canoethecaney.com.
Experience the flavor and tradition of the Upper Cumberland with a holiday wine basket from Highland Manor Winery, thoughtfully offered by the Fentress County Chamber of Commerce. As Tennessee’s oldest licensed winery, Highland Manor blends time-honored craftsmanship with the unique character of local grapes, creating wines that perfectly capture the spirit of the region. This special giveaway brings those flavors to your home with a beautifully arranged selection — ideal for holiday gatherings, cozy winter evenings, or sharing with friends who appreciate artisan wine.
The Fentress County Chamber works year-round to highlight the community’s heritage, outdoor beauty, and vibrant local businesses, and this festive wine basket reflects that same sense of pride and hospitality.
Learn more about the region at www.bigsouthfork.org, and explore Highland Manor’s wines at https://highlandmanorwinery.com/.