365ink Festivals Calendar

Our 2023–2024 Winter Festivals & Special Events Calendar, sponsored by Travel Dubquue, features more than 50 events in the Tri-State area to keep you entertained this winter

365ink Magazine 2023-2024 Winter Festivals and Special Events Calendar

Download the 365ink Winter Festivals & Special Events Calendar

Vesperman Farms
Now–Oct 29 @ 8149 Stage Rd, Lancaster, WI

One of the biggest and most challenging corn mazes in the Midwest is just the beginning of a big day! You gotta see the pumpkin trebuchet throw ‘em a quarter mile! Visit the pumpkin patch, play games, meet farm animals, watch the air cannon, the 100’ zip line, the snack barn with everything from BBQ pork to caramel apples, apple cider doughnuts, and ice cream. Open seven days a week. vespermanfarms.com.

A Year with Frog & Toad
Sept 29–Oct 8 @ Grand Opera House

A hit on Broadway, A Year with Frog and Toad is based on Arnold Lobel’s well-loved books, and featuring a hummable score by Robert and Willie Reale, this whimsical show follows two great friends through four fun-filled seasons.

Dubuque Latinx Fiesta
Sept 30 @ Smokestack 

Celebrating and honoring Hispanic Heritage Month by bringing together the Dubuque community through food, live music, dancing, resources, and vendors. Held outdoors, 2–8 PM.

Galena Oktoberfest
Sept 30 @ Depot Park (Galena, IL)

Hosted by the Galena Lions Club. The 16th annual event features a ceremonial tapping of the keg, non-stop live music, wiener dog races, polka lessons and dancing, bean bag tournament, beer stein endurance contest, a free bounce house and pumpkin decorating for the kids and lots of food and beer. Free admission! Noon–10 PM. galenalions.org.

Dark Chambers Haunted Attraction
October 6–7, 13–14, 19–21, 26–29 & 31 @ 1341 Frontage Rd, Hazel Green, WI

The Tri-States’ most exciting haunted attraction experience. With all the scares you love, dark turns and terrifying sights that will get your heart pounding. Grab your friends and anyone else you think will help you make it out and come test your mortality inside the Chambers. Light Fright, Full Fright, and Fast Pass options available. darkchambershaunt.com.

Shullsburg Cheesefest
Oct 6–7 @ Water St, Shullsburg, WI

The free, family-friendly festival is held on the city’s historic Water Street with entertainment and events for two days in 2023. Copeland Porchfest with live music and food trucks on Friday. Then Saturday starts with the fireman’s breakfast and onto food and craft vendors, live music, beer, wine and cheese pairings, cheese making, food and cheese, curd eating contest, mac and cheese tasting, cheese and more cheese! Test your cheese IQ, enjoy hayrides, children’s activities, a scarecrow contest, and a raffle. 7 AM–4 PM.

41st Annual Galena Country Fair
Oct 7–8 @ Grant Park (Galena IL)

More than 100 hand-selected vendors offering original, handmade arts, crafts and fine arts. Delight your taste buds with fair favorites including caramel apples, homemade French fries, funnel cakes, fudge, baked potatoes, and ice cream plus farmers’ market goodies and country bake shop treats. Plus live bands, Irish dancing, and more. Children’s games, a silent auction, raffle, and more. 10 AM–5 PM. galenacountryfair.com.

Dock Dogs World Championships 2023
Oct 11–15 @ Five Flags Arena

The amazing flying pups return to Dubuque for another weekend full of fun competition that’s free to watch. Bring the kids and check out these amazing pooches doing their thing.

Millwork Night Market
Oct 12 @ 7th–9th and Jackson St

Millwork Night Market has brought high-quality local food producers, artists, musicians, and brewers to the Millwork District for six years! They’re celebrating the independent evening farmers’ market with live music. Smoke free and pet free. BYO reusable grocery bags and lawn chairs. MillworkNightMarket.com.

Drinking Habits 2
Oct 13–29 @ Bell Tower Theater

The Sisters of Perpetual Sewing return when they discover that the local orphanage is in peril of closing and resolve to act. Everyone pitches in to mount a play to raise money and hilarious hijinks ensue. Anything that can go wrong does.

Jeeps on the Mountain
Oct 13–14 @ Sundown Mountain Resort

Enjoy live music, food trucks, cash bar, Jeep Show, primitive camping, off-road the mountain trails on designated trails, and more. sundownmtn.com.

Twenty Dirty Hands
Oct 13–15 @ Various Locations in the Tri-States

A free self-guided pottery tour highlighting the works of 24 local potters and regional guest artists at 7 studios, now in its 22nd season. 10 AM–6 PM (4 PM Sun). twentydirtyhands.com.

iLuminate
Oct 19 @ Five Flags Arena

Named “Best New Act in America” by America’s Got Talent, “Best Date Show” by the Best of Vegas Awards, and “Best New Production” at the Best of Las Vegas Awards, each scene in iLuminate takes the audience on a dazzling journey where an exhilarating blend of music, dance, illusion, technology and comedy.

The Tappening
Oct 21 @ Five Flags Arena

This Saturday afternoon event will bring local breweries together with one common interest: the finest crafted brews in the Tri-State area. Come see for yourself–the variety of craft samples will satisfy your drinking pleasure. Plus a Tri-State Bags Tournament! Noon–4 PM.

Haunting on Lincoln Ave
Oct 21 @ Mathias Ham Historic

Historic activities included with the tour will be family-friendly, between 11 AM and 4 PM! Spooky, fun activities include crafts, games, fortune-telling, and a witch’s cave! Apple cider and snacks are also available! And special spooky evening tours at 6 & 7:30 PM.

The Music of Billy Joel & Elton John with Michael Cavanaugh
Oct 21 @ University of Dubuque Heritage Center

Grammy and Tony-nominated vocalist and pianist Michael Cavanaugh is a charismatic performer and musician famous for his piano/lead vocals in the Broadway musical Movin’ Out. Handpicked by Billy Joel to star. Billboard called him “The New Voice of the American Rock and Roll Songbook,”

JDIFF Halloween “Boo” Parade
Oct 21 @ Main St Parade Route

Ghosts and goblins of all ages will converge once again for perhaps the most popular parade of the year in Dubuque. The parade follows the usual parade route, starting at Jackson Park and ending at Washington Park. Scores of groups come out in full costumed madness for a super-fun hour in the streets of Dubuque. Prizes for best float, walking group and marching band. 7 PM. julienfilmfest.com.

Galena’s Halloween Parade & Festival
Oct 28 @ Main St, Galena, IL

The legendary parade literally lights up Galena’s historic Main Street for the 43rd year in one of the Midwest’s largest Halloween celebrations, featuring spectacular floats, local marching bands, hot air balloons breathing fire, costumed participants and plenty of sweet treats. $5 shuttle from Walmart after 3 PM. 6–8:30 PM.

Mad Scientist Party
Oct 29 @ National Mississippi River Museum & Aquarium

Join River Museum for their annual family Halloween event! Everyone is welcome to come in costume (not just kids!) Trick-or-treating and other activities–games, science experiments, music, and all of the regular daily programming will be available throughout the day. Discount admission can be purchase online. 9 AM–5 PM. rivermuseum.org/events.

Steely Dane
Nov 3 @ Grand Opera House

Steely Dane is dedicated to not only faithfully reproducing the Steely Dan and Donald Fagen songbook but to bringing an energetic live-show experience to the crowd featuring 14 of the Midwest’s best jazz and rock musicians.

45th Annual National Farm Toy Show
Nov 3–5 @ Dyersville, IA

Filling Beckman High School, The National Farm Toy Museum, and the Commercial Club Park, highlights include a Collectors Dinner on Saturday at Royal Lanes, a sanctioned Micro-Mini Pull at Commercial Club Park in South Building on Saturday at 11 AM and Sunday at 9 AM plus the National Farm Toy Show Auction at 10 AM Saturday at Beckman Auditorium (1325 9th St. SE.). The granddaddy of farm toy shows draws about 6,000 people each year. toyfarmer.com.

Dubuque Winter Farmers Market
Sat: Nov 4–April 27 @ Kennedy Mall

An all-volunteer driven market, focusing on supporting our regional food system, eating from our food shed year-round and providing annual funding to farmers through our grant program. Homemade and baked goods, plus meat, cheese, eggs and, yes, vegetables! 9 AM–Noon.
wintermarketdbq.com.

Blippi: The Wonderful World Tour
Nov 9 @ Five Flags Arena

Dance, sing, and learn with Blippi and special guest Meekah as they discover what makes different cities unique and special. Will there be monster trucks, excavators, and garbage trucks galore? You bet! So get ready to shake those wiggles out and OJ Twist your way through this brand-new musical party!

The Struts
Nov 11 @ Diamond Jo Casino Mississippi Moon Bar

This high energy British rock band has amassed a giant following off hits like “Should Have Been Me” and toured with the biggest acts in music from the Stones to the Foo Fighters and Guns N’ Roses. This is their second visit to the Moon Bar.

Vienna Boys Choir
Nov 17 @ University of Dubuque Heritage Center

Dubuque Arts Council presents the rich 500 year history of the Vienna Boys Choir, which has been associated with many of the world’s greatest composers like Mozart. Today, there are 100 choristers between the ages of 10 and 14 from 31 nations, divided into four touring groups.

39th Annual Galena Nouveau Wine Weekend
Nov 17 @ Galena, IL

Celebrate the new vintage with wine-inspired lunches, dinners, and tastings in Galena, IL. The official release of the Le Beaujolais Nouveau wine is delivered by Galena Cellars Vineyard & Winery delivers their Nouveau wine via horse-drawn wagon. Galena comes alive with a multitude of offerings: vineyard tours, wine dinners, wine tasting, lodging, shopping, and spa specials.
nouveauweekend.com.

A Christmas Carol
Nov 24–Dec 3 @ Grand Opera House

This thrilling adaptation by Patrick Barlow uses only five actors and nothing more than some simple props, fresh physicality, and the power of imagination to bring some of Dickens’ most beloved characters to life and convey this timeless story of redemption.

Reflections in the Park
Nov 24–Jan 2 @ Louis Murphy Park

Hillcrest Family Services’ annual lights festival celebrates their 28th anniversary. Visitors will see many new displays and have the option to participate in the featured “Memory Lane,” an opportunity to remember your loved one(s) in a special way at Reflections in the Park. Admission is $12 per vehicle at the gate, Santa Claus will visit on Mondays 5–8 PM in December. 5-10 PM. hillcrest-fs.org.

Christmas on the Square
Nov 25 @ Cable Car Square

Hundreds of luminaries will line Bluff and 4th Streets lighting the way as families gather at the foot of the famed Fenelon Place Elevator waiting for the Jolly ol’ Elf himself along with the Missus to ride the last cable car trip of the year! This is an amazing event for kids of all ages. 5–8 PM.

A Doublewide, Texas Christmas
Dec 1–17 @ Bell Tower Theater

Somewhere in the Texas heartland, lies the brand new town of Doublewide–Population, 10. It’s Christmas time, and it’s beginning to look a lot like trouble.

A Merry Millwork Market
Dec 1–2 @ Dubuque Millwork District

A unique holiday shopping experience featuring the best of local crafts, sips and bites benefiting nonprofits of the Dubuque Millwork Collective.

DSO Holiday Concerts
Dec 2–3 @ Five Flags Theater

The DSO is joined by vocalist Jeff Liebow, the Dubuque Chorale and members of the Heartland Ballet in an enchanting collection of holiday favorites for two shows! A one hour kid-friendly matinee is also offered on Saturday. dubuquesymphony.org.

Million Dollar Quartet Christmas
Dec 8 @ Five Flags Arena

Rock ‘n’ roll newcomers, and soon to be legends, Johnny Cash, Jerry Lee Lewis, Carl Perkins and Elvis Presley come together again to celebrate the holidays. Inspired by the true story of their December 1956 homecoming at Sun Records including nostalgic holiday hits including “Run Rudolph Run,” “Jingle Bell Rock,” “I’ll Be Home For Christmas.”

The Dubuque City Youth Ballet: The Nutcracker
Dec 9–17 @ Grand Opera House

An Annual Dubuque Christmas Tradition! Clara and her enchanted Nutcracker battle the dreadful Mouse King in a nightmare that becomes a beautiful dream in this classic ballet featuring the music of Tchaikovsk and performed by the Dubuque City Youth Ballet. New design elements for 2023 inspired by Dubuque. thegrandoperahouse.com.

Night of the Luminaria & Living Windows
Dec 9 @ Main Street, Galena, IL

More than 5,000 candlelit luminaries line the streets, steps, and sidewalks, and store windows come alive. Plus, store windows come alive with holiday-inspired animation. 4-7 PM. visitgalena.org

Toys For Tots Kids’ Christmas Party
Dec 10 @ Five Flags Arena

Date is tentative. One gigantic and completely FREE Christmas bash hosted by Toys For Tots, The Dubuque Police Department, and 365ink and sponsored by Theisen’s, The Community Foundation of Greater Dubuque, and Paramount Ambulance. Hundreds of local kids enjoy music, dancing, inflatable rides, treats, plus photos with Santa as well as Frozen and Star Wars characters. Noon–3 PM.

Sinatra and Friends New Year’s Eve
Dec 31 @ Grand Opera House

Spend New Year’s Eve with Bryan Anthony’s Sinatra and Friends. Featuring Hunter Fuerste’s American Vintage Orchestra and the music of Dean Martin, Sammy Davis Jr., Nat King Cole, Bobby Darin, and Old Blue Eyes himself.

Special Olympics Iowa Winter Games
Jan 8–9 @ Various Locations in Dubuque

More than 200 athletes with intellectual disabilities from across the state compete in Alpine and Nordic skiing, figure skating, snowshoeing, speed skating, and more. The Grand River Center, Sundown Ski Area, Albrecht Acres, and Dubuque Ice Center will host the competitions and activities.

Harlem Globetrotters
Jan 9 @ Five Flags Arena

Get ready for a slam-dunk extravaganza as the world-famous Harlem Globetrotters make their triumphant return! This is your chance to witness the record-breaking stars of basketball live as they bring an unforgettable blend of dribbling, spinning, and dunking to the court, taking on their fierce rivals, the Washington Generals.

DSO: Ultimate Rock Hits
Jan 12–13 @ Diamond Jo Casino Mississippi Moon Bar

The DSO joins with local rock bands to present an amazing symphonic rock experience! Members from local bands will join the DSO for a rocking good time. dubuquesymphony.org.

IceFest
Jan 13-14 @ National Mississippi River Museum & Aquarium

The National Mississippi River Museum & Aquarium will present special winter-related programs daily throughout IceFest including historic ice harvesting on the river, winter crafts, snow sculptures, and more. Featured activities include professional snow sculpting, outdoor winter games, live animal programs, winter safety demonstrations, and more. rivermuseum.org/events.

Winter Iowa Games
Jan 26–28 @ Various Locations

The Winter Iowa Games is held annually late January and early February, mainly in Dubuque, offering over 20 sports and 4,000 athletes.

An Evening with Marty Stuart & His Fabulous Superlatives
Jan 27 @ University of Dubuque Heritage Center

Country music hall of famer, five-time Grammy Award winner, and AMA Lifetime Achievement honoree Marty Stuart has released more than 20 major label albums and scored platinum sales, hit singles, and just about every honor the industry could bestow along the way.

Baggage
Feb 9–25 @ Bell Tower Theater

Two demanding, single strangers get their luggage mixed up at the airport. After a disastrous first meeting, they decide to force a friendship to help each other heal their past heartbreaks. These two are too difficult for everyone else to date, but are they perfect for each other?

Almost Maine
Feb 23–March 3 @ Grand Opera House

Sweet, poignant, and witty… Almost, Maine is a beautifully structured play, with nifty surprise endings (most but not all of them happy).

Dubuque on Ice Brewfest
Feb 24 @ Grand River Center

Tri-State beer lovers, mark your calendars! Dubuque on Ice Brewfest will feature beer from 30+ breweries, plus wine, spirits, specialty cheeses, sausage and chocolates, and live music. 1–4 PM. dubuquebrewfest.com.

365 Impact Awards
Feb 27 @ Diamond Jo Casino Mississippi Moon Bar

The 365 Impact Awards, sponsored by Premier Bank and the Community Foundation of Greater Dubuque, return to the Mississippi Moon Bar at the Diamond Jo Casino. The 365ink Impact Award is for those who choose to make an effort to impact the world around them 365 days a year. It’s meant for those who believe in our community and are willing to do something to make it better for everyone. The event is FREE (must be 21). 7 PM. dubuque365.com.

Galena Whiskey Weekend
March 9 @ Turner Hall (Galena, IL)

Sip your way through winter with the extensive collection of bourbons and whiskeys. Cheers to over 200+ whiskey offerings. galenawhiskeyweekend.com.

Dyersville St. Patrick’s Day Parade
March 16 @ Dyersville, IA

Ancient Order of Hibernians—Dubuque County #1 presents Dyersville’s Annual St. Patrick’s Day Parade and Mass. A church celebration at 10:30 AM at St. Francis Xavier Basilica is followed by the huge parade which starts at 1 PM downtown.

BestFest 2024
March 21 @ Grand River Center

A benefit to support Hospice of Dubuque is just as it sounds, a celebration of the best Dubuque has to offer, as voted on by you, the people of Dubuque. Winners will gather and give away samples of their best products. Voting happens by ballot in the Dubuque Advertiser as the event nears. It always sells out in advance, so get your tickets early. 5–7:30 PM