Bootleggers is proud to be an official Stamp Sheet stop for the 32nd Annual Pontoon Palooza, hosted by the Northwoods Riders Snowmobile Club! This incredible event is the club's massive yearly fundraiser, with all proceeds going directly toward maintaining and grooming Tomahawk's local winter trail networks and supporting community safety.

How to Participate:

• During the Day: Buy a stamp sheet, get out on Lake Nokomis, and map your route. Be sure to pull up at Bootleggers during the day to get your official stamp! Learn where to buy Stamp Sheets here.

• The Main Party: Head over to B's Landing Bar starting at 3:00 PM for the Northwoods Riders' official food tent, boat judging, and raffle drawings.

Kick off your lake day with us! Bootleggers is proud to be an official stamp stop for the annual Pontoon Palooza, hosted by the Northwoods Riders Snowmobile Club. Get the party started early with live music and cocktails before heading to the festivities!

We are pairing our hand-crafted cocktails with a fantastic midday live performance on the deck by Little Winter Sun. Whether you are docking the boat to get your stamp sheet marked or just looking for a great Saturday afternoon patio vibe in Tomahawk, pull up a chair, grab a cold drink, and enjoy the best atmosphere in town.

About the Artist: Little Winter Sun is a captivating acoustic trio known for delivering a rich, warm blend of folk, Americana, and indie-infused rhythms. Featuring soulful vocals, intricate guitar melodies, and a collection of both heartfelt originals and familiar covers, their sound provides the perfect relaxed, feel-good soundtrack for a summer afternoon.

Join us for an evening of great drinks, exceptional company, and live entertainment. We will be serving up our full menu of signature, hand-crafted cocktails while Canaan James takes the Eagles Nest.

About the Artist: Canaan James is a country singer and songwriter known for his powerful, soulful voice and heartfelt lyrics. Blending a raw, country-edge sound with subtle R&B roots, his music ranges from high-energy rhythms to emotionally driving originals.

Celebrate the 4th of July with us at Bootleggers! We are hosting a full day of celebration, starting at 11AM, featuring live music all day, great drinks, and a spectacular fireworks show to cap off the night.

Live Music Schedule:

• Billy Bronsted and Drew Bolder: Performing three sets throughout the day outside on the beach.

• Isiah Driessen: Performing from 6:00 PM to 9:00 PM inside the Eagles Nest.

Grand Finale:

• Fireworks at Sundown: Find a spot on the deck or by the water as we light up the sky at dusk.

Admission is free, and our full bar and menu will be available all day. Bring your friends and family to the best Independence Day party in Tomahawk!

Looking for the perfect way to spend your Saturday evening? Join us for a night of incredible seasonal cocktails and live music featuring Doc Euphonic.

About the Artist: Known for his signature "Acoustical Tonic," Doc Euphonic brings a grooving, feel-good blend of acoustic guitar stylings, soulful instrumentals, and smooth rhythms. From original tracks to a wide variety of easy-listening favorites, his music is the ultimate backdrop for a relaxed, drink-in-hand evening.

Treat Dad to the ultimate lakeside celebration this Father’s Day at Bootleggers! We’re firing up the smokers for a full day of live music with Billy Bronsted & Drew Bolder, cornhole on the beach, cold drinks, and an incredible Southern-inspired feast the whole family will love.

The Father's Day Feast:

• The Pit: Brisket Carving Station (with house-chopped chimichurri), Peachwood Smoked Babyback Ribs, Smoked Korean BBQ Chicken, and Pulled Pork with potato rolls.

• Southern Sides: Crispy Potato Pavé, Cheddar Jalapeño Grits, Brown Buttered Honey Cornbread (with whipped cinnamon honey butter), Southern Braised Collard Greens, Dirty Rice, and Fire-Roasted Sweet Corn.

• To Start & Finish: A loaded ranch hummus crudité board and an assortment of sweet desserts.

Bold Drinks Built for Dad:

• The Pitmaster’s Bloody: Our special Father's Day mix featuring grilled asparagus, pickle, hard-smoked Nueske's bacon, Tajín, and an optional BBQ sauce rim.

• The Bootlegger’s Black Cherry: Rich bourbon kicked up with gourmet black cherry soda.

• Charred Pineapple Smash: Muddled grilled pineapple, Nosotros Reposado Tequila, lime, and agave.

• Pitchers for the Table: Keep the good times flowing with a shareable pitcher of draft beer.

Give Dad the day off! Great food, family fun, and the perfect Northwoods backdrop. Space is limited for this exclusive buffet event!

Unwind with us for an evening of great drinks and incredible live music. We’re thrilled to host indie folk artist Brett Winters, known for his soulful sound and unique, "folkified" acoustic covers of everything from classic hits to modern favorites. Bring your friends, grab a craft cocktail, and enjoy the perfect local soundtrack to your night.

Great drinks. Better company. Unbeatable live music.

Join us Saturday, June 6th, as we welcome Scott Kirby to the Eagles Nest! Sip on our premium, hand-crafted cocktails while enjoying Isiah's live performance. It’s the ultimate Northwoods night out you don't want to miss.

About the Artist: Scott Kirby is a celebrated singer-songwriter, guitarist, and storyteller known for his distinct brand of "coastal acoustic folk" and Americana. With a career spanning decades, Kirby has shared the stage with legends like Jimmy Buffett and Carole King, carving out a reputation for evocative lyrical storytelling, humor, and brilliant fingerstyle guitar work.

Two great partners working to bring a historical boulevard to our downtown! Join Tomahawk Main Street & the Tomahawk Area Historical Society for an evening of haunted history on Tuesday, June 9, 2026.

This fundraiser will be held right here at Bootleggers. Come enjoy the ambiance, dive deep into the fascinating history of bootlegging, and do a little ghost hunting too!

Event Timeline:

4:00 PM: Registration begins

5:00 PM: Event kicks off

Ticket Details Price: $40.00 per ticket Includes: Your first drink, delicious snacks, and a commemorative picture by Vicky’s Photo Shop to remember your evening!

Please note: This reservation secures your entry. The $40.00 ticket fee will be collected at the door upon arrival.

Great drinks. Better company. Unbeatable live music.

Join us Saturday, June 6th, as we welcome Isiah Driessen to the Eagles Nest! Sip on our premium, hand-crafted cocktails while enjoying Isiah's live performance. It’s the ultimate Northwoods night out you don't want to miss.

About the Artist: Isiah Driessen is a Wisconsin-based singer-songwriter and the visionary frontman behind Isiah & The New People. Known for pioneering a captivating "Western Psychedelic Folk" sound, Isiah weaves together haunting, cinematic melodies with raw, evocative storytelling. Drawing deep inspiration from roots-rock traditions and a personal spiritual journey, his music balances gritty, frontier-style songwriting with dreamy, atmospheric soundscapes. Combine that with a reputation for dry humor and a deeply engaging stage presence, and Isiah delivers an immersive live music experience that redefines modern folk.

Looking for the perfect way to spend your evening? Join us at Bootleggers for an incredible night of live music featuring the talented Scott Kirby!

Bring your friends, grab a cold drink, and settle in for great tunes, fantastic company, and the best atmosphere in town. Music starts at 7PM, but come early to snag a good seat and catch our Saturday Prime Rib special before. See you there!

We are CLOSED today, May 16th 2026, for a private event. We apologize for any inconvenience and look forward to serving you soon!

Interested in having your next celebration or gathering at Bootleggers?

Show the mothers, grandmothers, and maternal figures in your life just how much they mean to you!

Bootleggers is proud to host a Premium Mother’s Day Brunch Buffet featuring live music from local favorite, Jeff Calhoun. As a special gift, every Mom whose party reserves a table by May 3rd will receive a beautiful, complimentary spring bouquet!

Giving Back to Our Seniors: We believe no one should go uncelebrated. This year, we’re bringing bouquets to the ladies at Tomahawk Milestone Senior Living, and we need your help! While you’re here for brunch, have your kids stop by our craft table to hand-make a Mother’s Day card for a local senior. When we did this at Christmas, the residents were incredibly touched—let’s come together again to make a difference in our community!

48/adult, 24/child under 12, FREE for children under 2.

Join us at Bootleggers for a day of southern sophistication, specialty bourbon, and high-stakes excitement!

12:00 PM – 3:30 PM: Start your afternoon with our exclusive Derby Happy Hour. Enjoy specially priced drinks and apps before our standard opening hours. It’s the perfect time to showcase your finest Derby hat and settle in with the crowd. Our bar team has curated a triple-crown cocktail menu for the occasion:

The Classic Mint Julep: The timeless tradition of the Derby.
The Derby Mule: A bold kick of barrel-strength bourbon, fresh lime, and spicy ginger beer.
The Lemon Berry Highballer: House-made lemonade, fresh raspberry, and smooth bourbon.

5:57 PM: Gather around for the running of the 152nd Kentucky Derby.

7:00 PM – 10:00 PM: The celebration continues with live music by Karley Davidson.

Attire: Derby chic. We highly encourage your best, boldest, and most creative Derby hats.

Spaces are limited for this special engagement. Secure your reservation to ensure you have a front-row seat to the fastest afternoon in sports!

Experience the authentic sounds of Scott Kirby. Known for his unique blend of alternative blues, folk, and rock, Scott delivers a performance that is soulful and engaging. With his guitar and harmonica in hand, he creates the ultimate soundtrack for our Late Night Cocktail Hour. Pull up a stool, order a signature cocktail, and settle in for a night of world-class local music from a true Northwoods original.

Reservations are not required, but highly encouraged as space fills up quickly.

Escape into an evening of atmospheric indie-folk with Northern Wisconsin’s own Brett Winters. Known for his introspective songwriting and "folkified" take on classics, Brett creates a soundscape inspired by the very lakes and pines that surround us. From reimagined hits to soulful originals, his music offers a deep, whimsical energy that is perfect for a Late Night Cocktail Hour. Pull up a chair, grab a craft drink, and let Brett’s "old soul" folk provide the perfect soundtrack to your night.

Reservations are not required, but highly encouraged as space does fill up.

An Agave Masterclass with Nosotros Tequila.

Tequila is more than just a cocktail base—it's a craft spirit with the complexity of a fine Scotch. On April 18th, join us at Bootleggers for an exclusive exploration of Nosotros Tequila, winner of 'Best Tequila' at the San Francisco World Spirits Competition.

Move beyond the Margarita. We will guide you through crafting three spirit-forward cocktails. Each cocktail is served alongside a curated small-plate pairing designed to highlight the additive-free botanicals of the spirit. Limited to 22 seats to maintain an intimate, educational environment.

Stay after the class to enjoy live music starting at 7:00 PM with Brett Winters.

$75/person. Includes hands-on instruction, all ingredients for three signature cocktails, and light bites. Please inform us in advance of any dietary restrictions.

Get ready for a night of powerhouse vocals and all your favorite hits. Join us for a live performance by Landon McMahon, a dynamic artist known for his massive range and high-energy delivery. Covering everything from country anthems to rock classics and modern pop, Landon’s versatile style creates the perfect high-octane atmosphere for our Late Night Cocktail Hour. Grab a signature drink, find a spot by the bar, and enjoy a night of non-stop live music.

Reservations are not required, but highly encouraged as space fills up quickly.

Celebrate Easter Sunday with the whole family at Bootleggers! We’re hosting a festive morning filled with Northwoods charm, featuring our Grand Easter Brunch Buffet. From classic holiday favorites to kid-friendly bites, there’s something for everyone to enjoy before or after the big event.

The morning is packed with excitement, featuring a Live Petting Zoo and our annual Easter Egg Hunt across the grounds. Watch the kids discover hidden treasures and get up close with friendly animals in our beautiful lakeside setting. It’s the perfect way to create lasting holiday memories.

Inside Bootleggers you’ll enjoy the mellow sounds of local favorite, Jeff Calhoun playing live in the Eagle’s Nest!

Reservations are not required, but highly encouraged as space fills up quickly.

Elevate your Saturday night.

The party doesn’t stop when the sun goes down! Experience an evening of raw talent and Northwoods soul. Join us for a live performance by Scott Kirby, a premier singer-songwriter known for his signature "Indie Folk" sound and gritty, "in-the-pocket" vocals. With a style that blends the storytelling of the 70s folk-rock movement with incredible finger-style guitar work, Scott creates an atmosphere that is both intimate and powerful. It’s the perfect soundtrack for our Late Night Cocktail Hour—grab a seat, order a signature pour, and enjoy a night of world-class Americana.

Reservations are not required, but highly encouraged to ensure your spot.

The party doesn’t stop when the tasting ends! Join us at Bootleggers for the Taste of Tomahawk After-Party. We’re keeping the energy high with a live performance by the incredible Amanda Anderson, whose soulful vocals and captivating stage presence are the perfect way to cap off the day.

Whether you’re winding down from the festival or just getting your night started, our Late Night Cocktail Hour will be in full swing with signature pours and a lively Northwoods atmosphere.

Reservations are not required, but highly encouraged to ensure your spot.

Luck is in the air at Bootleggers Lodge! Join us for a St. Patrick’s Day celebration featuring Live Music and our famous Corned Beef Dinner.

Enjoy FREE green beer all day and keep your eyes peeled—there’s a Leprechaun hidden in the lodge with a prize for whoever finds him first.

Elevate your Saturday night.

The party doesn’t stop when the sun goes down! Join us for Live Music and our Late-Night Cocktail Hour from 7–10 PM. Sip on $8 cocktails while soaking in the historic Northwoods charm of Bootleggers.

Cheers to living life to the fullest!

Warm up at Bootleggers Lodge this Winter.

Every Saturday in January, Bootleggers Lodge is turning up the heat on Lake Nokomis. Whether you’re arriving by car or pulling up on your snowmobile, join us for the ultimate Northwoods weekend tradition. We’ve combined the best of winter—bonfires, premium spirits, and live music—with a dessert you have to see to believe.

The Saturday Lineup:

• 4 PM – 7 PM | The Lakefront Bonfire: We’re lighting a massive fire right next to the frozen lake. Bundle up, grab a drink, and enjoy the glow of the sunset over the snow.

• All Night | Bourbon Flights & "The Slice": Warm your soul with our curated premium bourbon flights. While you’re at it, take on our newest menu item: A chocolate cake slice the size of your head! It’s massive, decadent, and built for sharing (or a very serious challenge).

• 7 PM – 10 PM | Live Music: Head inside the Lodge to thaw out and catch live sets from local favorites.

When: Every Saturday in January Where: Bootleggers Lodge (On the shores of Lake Nokomis) Cost: Free to attend; Food & Drink specials available all night.

Riders: We are located right off Northwoods Passage Trail 10 (near Corridor 17) and just a half-mile from the Bearskin State Trail. Look for the bonfire on the shore of Indian Pine Point—plenty of room to park your sleds!

No reservations required for the bonfire—just show up and find a spot by the flames! Reservations are highly recommended for Saturday dinner—click below to save your spot.