Above: The Baraboo Bluffs at Spirit Lake in Fall.

Embrace the Essence of Fall: Baraboo Events September 2023

Step aside, summer shorts – it’s time cozy up in our hoodies, wear that light jacket that only gets used for about 6 weeks a year, and spark up the debate of pumpkin-versus-apple for the Queen of Fall flavors. We’re here to spill the cider and let you in on the juiciest secrets of the season events. Hint: Oktoberfest isn’t in October… Yay!

As the warmth of summer gradually fades, Baraboo, Wisconsin, comes alive with the vibrant hues and crisp air of fall. A town known for its timeless charm, Baraboo offers a quintessential Midwestern autumn experience that captures the hearts of locals and visitors alike. This September, as we celebrate the changing seasons, discover the enchanting fall activities that define Baraboo’s picturesque town and make it an autumn destination like no other.

Embracing Fall in Classic Baraboo Style

Nestled amid rolling hills, Baraboo seems tailor-made for the magic of autumn. The streets are adorned with colorful leaves, the scent of pumpkin spice rolling out of the Downtown cafes, and for goodness sake… Fall is the most comfy season of the year! #WeSaidWhatWeSaid

This year, the inaugural launch of The GPOE Monthly Event Blog adds an exciting twist to Baraboo’s fall festivities. Your go-to source for local event information, the blog brings the best of Baraboo’s happenings right to your fingertips.

GPOE on Tour at Ski Hi Fruit Farm petting zoo

Above: Ski-Hi. Baraboo Events September 2023.

An Oktoberfest fellow holding many large beers in a crowd of Oktoberfest goers.

Best Activities for a Memorable Fall

As the calendar flips to September, Baraboo beckons with open arms, inviting you to savor the simple joys of fall. From festive markets to invigorating hikes, this charming town promises an unforgettable autumn experience that captures the essence of the season. And with The GPOE Monthly Event Blog, your ultimate guide to local events, discovering the best of Baraboo’s September 2023 festivities has never been easier.

1. Farmers Markets and Harvest Festivals: As the fields yield their bountiful harvest, Baraboo’s farmers markets burst with an array of fresh produce, artisanal goods, and local crafts. Stroll through the stands, indulge in homemade treats, and discover unique treasures that embody the spirit of the season. September offers the BYP Baraboo Night Market. See our highlights below!

2. Scenic Fall Foliage Drives: Baraboo’s surroundings transform into a tapestry of reds, oranges, and yellows during fall. Embark on a scenic drive through the countryside, relishing the breathtaking fall foliage that lines the roads and offers picturesque views at every turn. 

3. Pumpkin Patches, Apple Orchards and Corn Mazes: Embrace the whimsy of fall by visiting one of Baraboo’s pumpkin patches, apple orchards, or corn mazes. Our favorite spot is Ski-Hi. The official start to the season was August 28th and we are SO excited! The sunsets are spectacular, the cider donuts are delicious, the giftshop is unique, and the apples are the shining star. Be sure to pour a craft beverage or cider at a picnic table – inside or on the porch – it’s a great place to hang out with friends.

4. Hiking and Nature Walks: Baraboo’s natural beauty truly shines in the fall. Lace up your hiking boots and explore the town’s trails, forests, and parks, reveling in the crisp air and the rustling leaves underfoot. West Bluff Trail at Devil’s Lake State Park is certainly a show-stopper but we love Balanced Rock Trail as our iconic, Fall, Baraboo Hike. If you’re ready for a grind, sign up for a tri-athalon! See our highlights below.

5. Autumn Art and Culture: Immerse yourself in Baraboo’s vibrant arts scene by attending local galleries, theater performances, and cultural events. Fall provides the perfect backdrop for artistic inspiration and creative exploration. One of the year’s best cultural celebrations is Oktoberfest! Learn more below in our highlights section.

Prepare for the anticipation of our upcoming blog posts as we gear up to honor more GPOE Friday heroes and unveil a thrilling new community initiative. Plus, don’t miss out on the chance to be the first to know about our inaugural Forward in the Field event coming this September—join our email list today!

Baraboo Community
Event Calendar

Receive #TheGPOE monthly Baraboo Events List right to your email! As always, we respect your privacy. So, we won’t fill up your inbox or share your info.

September Baraboo Event Highlights

“The Gem City Sideshow is a three piece rock cover band. The idea of getting out of our houses to play music on the weekends sounded like a great way to break up the monotony of everyday life. It is three friends who simply want to spread joy to those around them through playing the songs we love. Thank you for being part of that journey! We love to play a variety of rock covers ranging from Dolly Parton to Foo Fighters. We truly love to see people singing along or dancing, and enjoy the joy that our music brings to others!” – Gem City Sideshow

Saturday, September 2, 2023 4:00 PM 6:30 PM Balanced Rock Winery 1065 Walnut Street Baraboo, WI, 53913 United


Sips & Swings poster


“The area’s only golf outing of its kind is back! We’ve combined nighttime glow-in-the-dark golf with a beer and wine walk for this can’t-miss event.

Join the Baraboo Young Professionals at Fairfield Hills Golf Course in Baraboo, Wisconsin, for a one-of-a-kind golf outing on Friday, September 8! Shotgun start is at 6pm, ensuring golfers play a few holes while it’s still light out before breaking out the LED balls once the sun starts to go down. Each hole also has tastings of a featured beer or wine. Registration of $80 per person includes 12 holes of golf (four person scramble format), three LED balls, beer and wine tastings, food, and the 13th Hole Post-Party.

Experience golf like you’ve never done before at the BYP Sips & Swings Golf Outing! All proceeds benefit BYP and The Boys & Girls Club of West Central Wisconsin – Baraboo/Sauk County. Please note, this is a walking outing for safety reasons. Golf at night and driving carts around don’t mix. All golfers must be 21+.

If you’re interested in golfing but don’t have a full foursome please email barabooyoungprofessionals@gmail.com.

Note: Eventbrite fees are added on to registrations that pay with a credit card. If you’re interested in paying offline via check to save on those fees, we will provide you a code to comp your online registration. Please email barabooyoungprofessionals@gmail.com to make payment this way.” – BYP

Click here to purchase tickets.

** Celebrate Your September Birthday Bash at Baraboo Bluff Winery! **

The fine folks at Baraboo Bluff Winery are rolling out the red carpet for all you September babies! If your special day falls in the month of September, get ready for a celebration like no other.

Join us for live music from 1 PM to 4 PM, where local winemaker extraordinaire, Fred, will take the stage in the name of his ongoing midlife crisis. Expect some musical antics, and who knows, you might even witness the birth of the next rock sensation (or not).

Got a September birthday? Fred’s got you covered – he’ll raise a glass in your honor and treat you to a drink on the house. But here’s the kicker: if you’re musically inclined and bring your own instrument, you’re in for an extra treat. Fred will not only buy you a drink but also provide the soundtrack to your jamming session.

Don’t worry; Fred won’t be going solo on this musical journey. His trusty sidekick, Bob McNurlen, will be there to add some musical magic to the mix.

So, mark your calendars, grab your instruments (if you’ve got ’em), and get ready for a September birthday bash like never before. Sip, celebrate, and create unforgettable memories at Baraboo Bluff Winery.

Remember, our doors swing open daily at 11 AM. Join us at E9120 Terrytown Road, Baraboo, and let’s make this birthday celebration one for the books! Visit our website at www.baraboobluffwinery.com for more details. 🎉🍷🎶

** Get Ready to Jam at the 2nd Annual BaraBlues Music Festival & Jam! **

The stage is set, the amps are humming, and the blues are calling your name! Join us at the 2nd Annual BaraBlues Music Festival & Jam, hosted by the Friends of Charles and Henry Ringling Estate from 1PM – 9PM.

This year, they’re turning up the bluesy heat with not one, not two, but three incredible regional blues bands! Get ready to groove to the soulful rhythms of Dead Henry, rock out to the electrifying sounds of The Dave Potter Band, and let loose to the melodic tunes of Maple Road Blues Band.

While you soak in the tunes, don’t forget to wet your whistle at their cash bar, where wine and beer will be flowing. And to satisfy those blues-inspired cravings, we’ve got one, or possibly two, mouthwatering food trucks ready to serve up delicious bites.

So mark your calendars, gather your fellow blues enthusiasts, and prepare for a jammin’ good time at the BaraBlues Music Festival & Jam. Stay tuned for more updates as we get ready to make this event a bluesy sensation you won’t want to miss!

Pay at the door.  $5 entry fee – OR – a non-perishable food item that will be donated to the Baraboo Food Pantry.

** Join the 50th Anniversary International Crane Foundation Celebration! 🎉 **

Mark your calendars for an unforgettable day on Saturday, Sept. 16, as we welcome you back to the incredible International Crane Foundation right here in Baraboo, Wisconsin. 🌍🌿 It’s a monumental occasion as we commemorate 50 glorious years of dedication to crane conservation! The festivities kick off with our exclusive Member Appreciation Day at our headquarters, where you can explore our remarkable work up close. But wait, there’s more! The real magic happens in the evening at the Kalahari Resorts and Conventions, where they’re throwing a truly inspirational 50th Anniversary Celebration. Hosted by none other than our Co-founder George Archibald and their esteemed President and CEO Rich Beilfuss, this event promises to be a night to remember. Don’t miss your chance to be a part of this incredible journey to save cranes. It’s a celebration you won’t want to miss!  
Date and Time
Saturday Sep 16, 2023 6:00 PM – 9:00 PM CDT
Saturday, September 16th, 2023 from 6 p.m. to 9:00 p.m. (check-in begins at 5:30)
Kalahari Resorts and Conventions, 1305 Kalahari Drive, Wisconsin Dells, WI 53965
$150 per person Purchase tickets here.

Get Ready to Groove with Mike Droho at Broken Bottle Winery!

We’ve got some fantastic news for all you music lovers out there. Please join us in welcoming the incredibly talented Mike Droho to the stage at Broken Bottle Winery. 🎶🍷

Mike is no stranger to our local music scene, and he’s a true favorite among the Baraboo crowd. We’re absolutely certain that you’ll fall in love with his music just as much as we have.

So, whether you’re a long-time fan of Mike or you’re looking to discover some incredible tunes, make your way to Broken Bottle Winery. The fun begins daily at 11 AM, and we’re ready to serve you some delightful wine while you soak in the sounds of Mike Droho.

Don’t miss out on this musical extravaganza! See you there!

📍 S2229 Timothy Lane, Baraboo
🌐 Visit the venue’s Website www.brokenbottlewinery.net

Be sure to Like Mike Droho on Faceboo to get updates on his shows and releases. https://www.facebook.com/mikedrohomusic/

** 🏊‍♂️🚴‍♀️🏃‍♂️ The Devil’s Challenge Triathlon: Unleash Your Inner Athlete! 🏊‍♂️🚴‍♀️🏃‍♂️ **

Triathlon enthusiasts and adventure seekers, mark your calendars for the Devil’s Challenge Triathlon! This thrilling sprint triathlon is the perfect way to wrap up your racing season in style.

Participants will kick off their journey with a refreshing 1/4-mile swim in the pristine waters of Devil’s Lake. Afterward, get ready for an adrenaline-pumping 15-mile bike ride, meandering through the breathtaking Baraboo bluffs – the scenic route alone is worth the ride! 🚵‍♀️🏞️

But the excitement doesn’t end there! Athletes will complete the challenge with a 5K run, winding through the serene park roads of Devil’s Lake State Park. 🏃‍♀️🍂

Don’t miss the opportunity to push your boundaries and conquer the Devil’s Challenge Triathlon. Are you ready for the challenge? 🏆🔥

Click here to visit their awesome website for further event details and registration information. This is an event that should not be missed! 📅💥

Above: Event swag via event website. 

** Lights, Flavors, Action: BYP Baraboo Night Market Is Back! **

Get ready to dive into a world of enchantment as the Baraboo Young Professionals (BYP) present the much-anticipated Baraboo Night Market. This evening extravaganza promises a vibrant fusion of lights, flavors, and all-around good vibes. It’s always one of our favorites of the year!

The Baraboo Night Market is where the heart of our community truly shines. You’ll discover a bustling marketplace filled with local artisans, talented crafters, and culinary wizards whipping up delectable treats. Whether you’re on the hunt for unique handcrafted goods or simply craving some mouthwatering delights, this market has it all.

And let’s not forget the live music that’ll be the soundtrack to your night. So grab your friends and family, bring your appetite, and make your way to the BYP Baraboo Night Market for an unforgettable evening of community, culture, and culinary delights.

The GPOE will see you there! Visit the BYP for more info.

Grab your lederhosen and dust off your dirndl because Baraboo Oktoberfest is back and brewing with excitement! This year, the town’s iconic Circus World Museum grounds will once again transform into a festive haven of bratwursts, pretzels, and oompah music. But wait, there’s more – the party’s getting a hoppy twist at the Al. Ringling Brewing Co., where a special event promises to pour on the fun like never before. So whether you’re pro-pretzel or pro-pumpkin (hey, it’s fall), this Oktoberfest extravaganza is set to tickle taste buds and delight dirndl enthusiasts alike.

Baraboo Oktobertest Event


Circus World grounds


Saturday, Sept. 23



Live Shows:

Griffy Jim and the Polka Dots will get things started for our headliner, Gold Dust Women.

Admission buttons cost $10 at the door, $7 in advance

Where to buy tickets:

Baraboo Area Chamber of Commerce Visitor Center (across from Festival Foods in West Baraboo)

*check the official event poster below for Al. Ringling Brewing Co. info

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