Happy Trails Chicago

We have some sad news to share- Happy Trails Chicago was in a bad accident yesterday. We are grateful the team was unharmed, but we are heartbroken that the trailer itself has been damaged beyond repair.

We have enjoyed every bit of this business and appreciate the friends we have made along the way. We are grateful to each of you that helped support our little business and trusted us with your events.

It’s too soon and we are too shaken up to say what’s next for Happy Trails….but we are certain we will meet again ❤️

Stay tuned friends…the comeback is always better than the setback, right?

I spy with my little eye….

Sweet Starbucks theme complete with tie dye Frappuccinos!

As we celebrate the greatest Dads today, our hearts ache for the greatest Dad that ever was. Oh how he would love this little mobile bar. The laughs he would have had! We hear his voice around us (swearing + all) as we straddle between celebrating life and loss and missing his physical presence.

Why Happy Trails?

Our dad was the best. We know lots of people feel that way about their dad, but our dad was for real the best. He was funny. Like p*e your pants kind of funny. He’d go to just about any length for a good laugh- even if that meant it was at someone else’s expense. He was the ultimate practical joker.

He loved his people. There is no doubt he loved his family more fiercely than we’ve ever known someone to love their family. He called us all day long- like 10+ times a day (that does not include the daily crank phone calls).

And nobody disliked a goodbye more than our Dad- whether it was in person or even just hanging up from a call, we’d never get a goodbye…rather "talk a while" or an alternative saying of “be wild tiger” or “see you later alligator."

And sometimes he’d sing (cue the loud, deep, obnoxious voice) “Happy Trails to you.... until we meet again.”

Our Dad passed away on March 13, 2020- the day the world shut down. Covid came (and never left!) and then Eric and Katie’s 11 year old son was diagnosed with Hodgkins Lymphoma.

Life was hard- like rock bottom kind of hard, for a really long time.

Our mobile bar idea was born from great loss. It started as a distraction from life. It gave us a focus and somewhere to place our energy. Colin went into remission in July (praise God!!) and a week later we discovered the abandoned trailer on a farm in southern Illinois.

So when it came time to name the business there was no doubt we needed to incorporate our Dad in some way. We were lucky enough to marry two people that share the same love and admiration for our Dad and miss him just as much as we do.

Happy Trails Chicago is much more than just a wandering bar: its an ode to the best Dad there ever was....until we meet again, Dad ❤️

Happy Father’s Day to the best of the best- our signature bartenders, master mixologists and our incredible craftsmen.

We love you- enjoy your day off ❤️

Let’s get this party started!

Ole’ girl needs a bath…

Wrapping up a full weekend on the Southside of Chicago.

Man oh man….you Southsiders know how to have a good time! A fun Friday in and wild Saturday in

Thanks for the fun, Chicago. Until we meet again ☘️

You can take the girls out of the Southside, but you can’t take the Southside out of the girls.

It felt good to be home ☘️

Welcome to summer, Chicago☀️

We look forward to lots of fun adventures!

HappyTrailsChicago on TikTok Welcome to Chicago’s newest Mobile Bar experience.

A year ago this weekend, we were deep in the throes of chemo and a cancer diagnosis that shook us to our core. Life was so incredibly hard. Kyle and the Elliestrong Forever foundation wrapped their arms around our family and rallied alongside the community of Lemont to support Colin. We are forever grateful for their support and for the work that they do to help families going through the unimaginable.

It felt so great, a year later, to see Colin help support the 1st annual Ellie Strong Pet Parade and to give back to the community that helped him through what was undoubtedly, the hardest year of his life.

Thank you for all that you do Kyle + team. We 💚 you!

Winnie + Charlotte are ready to serve up puppachinnos today in Lemont Downtown to celebrate Elliestrong Forever birthday 💚💚

Come out and see us, beginning at 4pm.

Come out tomorrow to help the Lemont community celebrate Ellie’s 18th birthday with a pet parade. Happy Trails will be bringing puppachinnos for all of our furry friends. Stop by and say hello 💚 We will be right in front of Next Mex.

Elliestrong Forever
Ruby Whiskers Animal Rescue
Lemont Downtown

It’s hot out there, Chicago ☀️Happy Trails Is busy getting ready for this weekends festivities, starting with our signature drinks. This weekend we are featuring a Pink Señorita and a Vodka Spritzer. And our mocktails were such a big hit over the last few weekends, we have also added a Classic Shirley Temple.

Cheers, friends! Get outside and enjoy your weekend!

And that’s a wrap, Hinsdale!

A huge thank you to J. Jordan Homes for inviting us out to your spectacular home. Not only is Julie beyond talented, she is so incredibly sweet and has been a joy to work with! Happy Trails hopes to partner again in the future ❤️

Lookin’ good Lemont!

Happy Trails Chicago enjoyed every minute spent celebrating the Lemont High School junior class as we helped send them off to prom ❤️

It’s almost prom weekend and Happy Trails Chicago is excited for their local debut.

We have two signature drinks on the menu: mocktails for the teens and well deserved cocktails for the parents.

AND….the forecast is looking good ☀️(please let it be 75 and sunny….)

What’s the best place for bourbon lovers? The bourbon capital of the world, of course.

Happy Trails Chicago is spending the day walking along bourbon trail. First stop: Heaven Hill Distilleries.

We are in bourbon heaven!

Todays Feature…

Happy Trails most popular package: Whiskey Wagon 🥃

Are you looking for a fun get together idea for the bourbon loving man in your life? Look no further- the Whiskey Wagon tasting is a guaranteed good time!

We have openings Thursdays, Fridays + Saturdays in April and May but are starting to book out in June.

Reach out for pricing and availability!

Let's talk about the weather, Chicago!

Spring has arrived in all its glory and the party planning is in full force. We have heard from so many of you over the last few days + look forward to collaborating on all of your celebrations soon!

DM us for pricing menu + availability.

Goodbye winter + hello to spring. Oh how we missed you 🥰

Looking forward to sunshine, outdoor celebrations, greenery, wedding season, warm evenings, graduations, street festivals, long walks with the pups and pool season.

Good weather is on the horizon + we are here for it!

Remember to move those clocks ahead tonight, friends.

Planning a golf outing this spring/summer?

Happy Trails will bring the fun + make your event Instagram worthy 📷

The best golf outings, especially those for fundraisers have some impressive features that keeps the non serious golfer coming back every year to support a good cause.

Happy Trails can be parked on a hole to make your special event unforgettable and stand out from the rest. It is fully equipped with running water, battery powered electricity, two refrigerators and a dual tap system.

Reach out for pricing and availability!

Let's talk about our signature drink menu.....

Happy Trails can help provide the perfect cocktails for your event!

You may have beer on tap and bottles of wine to boot- but the customized spirits makes the event unforgetable.

Need inspiration? We have over 25 signature drinks to choose from that range from refreshing and elegant aperol spritzs to classic whiskey sours.

You name it, we make it!

What is your favorite signature drink?

We have the best clients and appreciate the positive feedback 🖤

Thank you Lemon & Basil for trusting Happy Trails with your event. I think we had just as much fun as you did!

Who’s ready for prom season!?

Happy Trails is ready 👏🏻👏🏻

Send us a DM for pricing + availability.

Just over here trying to keep up with the latest information….