28 Mile Distilling Company

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes <a href="https://www.28miledistilling.com" rel="nofollow noopener" target="_blank">28 Mile Distilling</a>’s<a href="https://www.28miledistilling.com/live-music/" rel="nofollow noopener" target="_blank">Rock the Rails</a>. This first-of-its-kind music showcase celebrates the connection between independent artists and independent venues along the Metra rail line from Chicago to Kenosha; bringing you intimate performances and exclusive artist access. 28 Mile, located just steps from the Highwood train station, will feature incredible talent from across the country. From rising artists on the verge of breaking out to nationally recognized performers like Jimmie Allen, Mims, Bubba Sparxxx, and Michael Winslow, the initial Rock the Rails Music Series kicks off June 12 through the end of summer, every Friday night at 8 PM, with shows ending before the last train departs.
The concept of Rock the Rails is built around original artists, authentic performances, and songs that connect audiences. 28 Mile Distilling Co. will serve as a first stop “along the rails” for artists on larger tours craving intimacy along the way that larger venues just don’t provide.From country and rock to hip-hop and high-energy entertainment, every Friday night will deliver a one-of-a-kind experience just steps from the Metra line at 28 Mile Distilling Co.Rapper <a href="https://www.instagram.com/bubbamathis/?hl=en" rel="nofollow noopener" target="_blank">Bubba Sparxxx</a>, known for his chart-topping singles “Ugly” and “Ms. New Booty,” brings critically acclaimed sound to the 28 Mile stage.

Local Event: Rock The Rails - Bubba Sparxxx 

Lake County

Highwood

Illinois

Rock The Rails - Bubba Sparxxx 

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’sRock...

Danny Cunniff Park

<h3>The Most Exciting Experience In Pickleball&nbsp;</h3>
There's nothing like seeing the world's best pickleball players compete in person.
Feel the energy of Championship Court, witness lightning-fast rallies, impossible saves, and match points that bring the crowd to its feet. From rising stars to the biggest names in professional pickleball, every match delivers elite competition, unforgettable moments, and the electric atmosphere that has made pickleball America's fastest-growing sport.
Whether you're a lifelong fan, a weekend player, or simply looking for an exciting day out with friends and family, an APP Tour event is an experience you won't find anywhere else.

Local Event: 2026 APP Vlasic Classic Chicago Benefiting Shriners Children's

Highland Park

2026 APP Vlasic Classic Chicago Benefiting...

The Most Exciting Experience In Pickleball 
There's nothing like seeing the world's best pickleball players compete in...

2026 APP Vlasic Classic Chicago Benefiting Shriners Children's

Everts Park

The intoxicating scent of garlic and the promise of a stinking good time will once again bring the crowds back to Celebrate Highwood’s 15th annual Garlic Fest on Wednesday, August 12th,
from 4:30-9 PM in Everts Park (111 North Avenue).Held in conjunction with Highwood’s Evening Gourmet Market, this foodie fest showcases a plethora of dishes with the ever-popular taste (and scent) of garlic, with a garlic trivia contest, live music, and plenty of family-friendly activities to entertain all evening long.Not to worry, there will be plenty of mints on hand!
Known for its culinary and medicinal purposes, attendees will have the opportunity to sample various garlic creations from out-of-the-ordinary garlic-infused chocolate, cookies, ice cream, fudge, and cocktails, to the classic, savory options like pizza, sandwiches, sauces, and spreads, and vote for their favorite!
<a href="https://celebratehighwood.org/" rel="nofollow noopener" target="_blank">Celebrate Highwood</a>’s smelliest event will recognize the beloved flavor of garlic with a competition for the best Sweet and Savory Garlic Creations in the People’s Choice and Judge’s Competitions.

Local Event: Highwood's 15th Annual Garlic Fest

Highwood's 15th Annual Garlic Fest

The intoxicating scent of garlic and the promise of a stinking good time will once again bring the crowds back to Celebrate...

Highwood IL

Evening Gourmet Market

Highwood, IL Calendar

Garlic Fest

Highland Park Library

PJ Storytime

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’s Rock the Rails. This first-of-its-kind music showcase celebrates the connection between independent artists and independent venues along the Metra rail line from Chicago to Kenosha; bringing you intimate performances and exclusive artist access. 28 Mile, located just steps from the Highwood train station, will feature incredible talent from across the country. From rising artists on the verge of breaking out to nationally recognized performers like Jimmie Allen, Mims, Bubba Sparxxx, and Michael Winslow, the initial Rock the Rails Music Series kicks off June 12 through the end of summer, every Friday night at 8 PM, with shows ending before the last train departs.
The concept of Rock the Rails is built around original artists, authentic performances, and songs that connect audiences. 28 Mile Distilling Co. will serve as a first stop “along the rails” for artists on larger tours craving intimacy along the way that larger venues just don’t provide. From country and rock to hip-hop and high-energy entertainment, every Friday night will deliver a one-of-a-kind experience just steps from the Metra line at 28 Mile Distilling Co.
Michael Winslow, godfather of Beatbox and famous for his roles in Cheech and Chong, Spaceballs, and Police Academy, brings a show of comedy and music to the stage.

Local Event: Rock The Rails: Michael Winslow

Rock The Rails: Michael Winslow

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’s Rock...

&nbsp;Celebrate Highwood is thrilled to announce its beloved <a href="https://www.celebratehighwood.org/bloody-mary-fest/" rel="nofollow noopener" target="_blank">Bloody Mary Fest</a> will take place Sunday, August 16 from 10 AM – 5 PM in Everts Park (111 North Ave). In its sixteenth year, mixologists from bars and restaurants will have the opportunity 
to shake up their unique concoctions in competition for the title of ‘Best Bloody Mary in the Midwest’. 

The Bloody Mary Fest competition includes a ‘People’s Choice Award,’ as well as formal judging on the ‘Best Bloody Mary’, ‘Best Garnish’ and ‘Most Creative’ by some of Chicago’s leading media personalities, and food and beverage experts. Contestants will be evaluated on taste, presentation, spice, color, texture and garnish.
While the formal battle for the Best Bloody Mary starts at 2 PM when the judges will evaluate each contestant’s take on the classic drink, attendees will be able to cast their vote in the People’s Choice award using the QR code sponsored by <a href="https://www.highlandparkbank.com/locations/il/highland-park/highland-park-bank-trust.html?cid=organic:yext:yext-referral-traffic:LFBT9198:202201" rel="nofollow noopener" target="_blank">Highland Park Bank &amp; Trust/Bank of Highwood-Fort Sheridan</a>until 4 PM. All winners will be announced from the bandshell at 4:30 PM, and rewarded with a trophy, recognition throughout the local media, and bragging rights for the entire year!

Local Event: Highwood's 16th Annual Bloody Mary Fest

Highwood's 16th Annual Bloody Mary Fest

 Celebrate Highwood is thrilled to announce its beloved Bloody Mary Fest will take place Sunday, August 16 from 10 AM – 5 PM in...

Bloody Mary Fest

Highwood Evening Gourmet Market

CELEBRATE HIGHWOOD WITH RAILHEART! — Life Rhythms

Tamales Mexican Restaurant | Highland Park

Connect. Collaborate. Grow.
<a href="https://forms.gle/mWeaoKQnTxkaNXUz5" rel="nofollow noopener" target="_blank">EVENT REGISTRATION HERE</a>
<a href="https://forms.gle/mWeaoKQnTxkaNXUz5" target="_blank" rel="nofollow noopener">RSVP for Event!</a>
​​You're Invited: Health &amp; Wellness Membership Interest Event 
We're hosting a Health &amp; Wellness Membership Interest Event on August 20th in Highland Park, IL.
This event is a great opportunity to connect with other healthcare professionals, learn how our referral network works, and explore ways to grow your practice through trusted referrals.
We'd love to have you join us.&nbsp;​ 
We'd be happy to see you there! 
<a href="https://forms.gle/mWeaoKQnTxkaNXUz5" target="_blank" rel="nofollow noopener">EVENT&nbsp;REGISTER HERE</a>
During this event, you will:
<ul><li>Learn how the WellConnect Network referral model works.</li><li>Discover the benefits of membership.</li><li>Meet like-minded health and wellness professionals.</li><li>Explore opportunities to build trusted referral partnerships.</li><li>Ask questions and determine if WellConnect is the right fit for you and your business.</li></ul>
Whether you are a physician, nurse, therapist, dietitian, health coach, fitness professional, chiropractor, pharmacist, or another wellness expert, this event is an opportunity to connect with professionals who share your commitment to improving lives while growing successful practices.
Join us and discover how collaboration can create healthier communities and stronger businesses.
<a href="https://forms.gle/mWeaoKQnTxkaNXUz5" rel="nofollow noopener" target="_blank">EVENT&nbsp;REGISTER HERE</a>

Local Event: WellConnect Network Membership Interest Event

WellConnect Network Membership Interest Event

Connect. Collaborate. Grow.
EVENT REGISTRATION HERE
RSVP for Event!
​​You're Invited: Health & Wellness Membership Interest...

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’s Rock the Rails. This first-of-its-kind music showcase celebrates the connection between independent artists and independent venues along the Metra rail line from Chicago to Kenosha; bringing you intimate performances and exclusive artist access. 28 Mile, located just steps from the Highwood train station, will feature incredible talent from across the country. From rising artists on the verge of breaking out to nationally recognized performers like Jimmie Allen, Mims, Bubba Sparxxx, and Michael Winslow, the initial Rock the Rails Music Series kicks off June 12 through the end of summer, every Friday night at 8 PM, with shows ending before the last train departs.
The concept of Rock the Rails is built around original artists, authentic performances, and songs that connect audiences. 28 Mile Distilling Co. will serve as a first stop “along the rails” for artists on larger tours craving intimacy along the way that larger venues just don’t provide. From country and rock to hip-hop and high-energy entertainment, every Friday night will deliver a one-of-a-kind experience just steps from the Metra line at 28 Mile Distilling Co.
Country Music Association’s New Artist of the Year in 2021, Jimmie Allen’s genre bending performance honors country’s storytelling while leaning into today’s pop-forward energy.

Local Event: Rock The Rails - Jimmie Allen

Rock The Rails - Jimmie Allen

Jimmie Allen -LIVE

28 Mile Distillery, 454 Sheridan Road, Highwood, IL

From the founder of Celebrate Highwood’s ever popular Nashwood and Great Highwood Pumpkin Fest comes 28 Mile Distilling’s Rock the Rails. This first-of-its-kind music showcase celebrates the connection between independent artists and independent venues along the Metra rail line from Chicago to Kenosha; bringing you intimate performances and exclusive artist access. 28 Mile, located just steps from the Highwood train station, will feature incredible talent from across the country. From rising artists on the verge of breaking out to nationally recognized performers like Jimmie Allen, Mims, Bubba Sparxxx, and Michael Winslow, the initial Rock the Rails Music Series kicks off June 12 through the end of summer, every Friday night at 8 PM, with shows ending before the last train departs.
The concept of Rock the Rails is built around original artists, authentic performances, and songs that connect audiences. 28 Mile Distilling Co. will serve as a first stop “along the rails” for artists on larger tours craving intimacy along the way that larger venues just don’t provide. From country and rock to hip-hop and high-energy entertainment, every Friday night will deliver a one-of-a-kind experience just steps from the Metra line at 28 Mile Distilling Co.
Country/southern rock darling Erin Stroll brings her authentic storytelling and electrifying stage presence to Highwood, as the last stop on the summer Rock the Rails tour.

Local Event: Rock The Rails - Erin Stroll

Rock The Rails - Erin Stroll

Space 900

Beth Shadur's paintings are inspired by Antelope Canyon Tribal Park, and can be seen from Sept 4-27. Artist's receptions, Sept 4, 4-8pm and Sept 5, 11-5pm. Open hours, weekends, Fridays, 11-4; Saturdays 11-5, and Sundays, 12-4.

Local Event: Wondrous Strange, paintings by Beth Shadur

Wondrous Strange, paintings by Beth Shadur

Beth Shadur's paintings are inspired by Antelope Canyon Tribal Park, and can be seen from Sept 4-27. Artist's receptions, Sept...

Highland Park Community House

The High&nbsp;Holidays are central to our Jewish living, not because they mark an historic event, but because they embody an essential Jewish process: intense personal and communal introspection held in play with boundless hope that our behavior will make a difference. In these difficult and painful times with so much division in our community and our country, we need to share in our Jewish journeys. That's why we invite you to participate this year, either in person or on Zoom. Information is available on our website: <a href="https://aitzhayim.org/" target="_blank" rel="nofollow noopener">https://www.aitzhayim.org</a>

Local Event: Aitz Hayim High Holiday services

Cook County

Winnetka-Glencoe

Aitz Hayim High Holiday services

The High Holidays are central to our Jewish living, not because they mark an historic event, but because they embody an...

Rachel Barnes

Chicago Metropolitan Area

Eric DeGrechie

Deerfield

Lake Forest-Lake Bluff

Northbrook

Vernon Hills

Buffalo Grove

Glenview

Amie Schaenzer

Libertyville

Wilmette-Kenilworth

Lake

Your New Favorite Yoga Studio,  Modern Yoga for Every Body

YogaSix Highland Park

At YogaSix Highland Park, we believe yoga should be accessible, empowering, and energizing for everybody. Our modern, welcoming studio offers a variety of heated and non-heated classes designed to meet you where you are—whether you’re brand new to yoga or looking to deepen your practice. From strength-building Power and Sculpt + Flow classes to restorative Slow Flow and Restore experiences, every class is designed to help you move, sweat, reset, and reconnect. More than just a workout, YogaSix Highland Park is a community-focused space where members can show up exactly as they are. Our experienced instructors create an inclusive environment that feels supportive, motivating, and approachable—without intimidation or pressure. We focus on movement that feels good, music that keeps the energy high, and experiences that leave you feeling stronger both physically and mentally. Located in the heart of Highland Park, our studio is proud to offer a consistent schedule of classes seven days a week, special workshops, wellness events, and opportunities to connect with others in the community. Whether you’re looking to build strength, reduce stress, improve flexibility, or simply carve out time for yourself, YogaSix Highland Park is here to support your goals. We’re more than a yoga studio—we’re a place to sweat, grow, breathe, and belong.

At YogaSix Highland Park, we believe yoga should be accessible, empowering, and energizing for everybody. Our modern, welcoming studio offers a...

Welcoming Spaces for your next meeting, celebration or event

Available rental spaces for your next event at Trinity Church

Looking for the perfect space for your next event, meeting, celebration, concert, class, or gathering? Trinity Episcopal Church offers beautiful, welcoming spaces in the heart of Highland Park for groups of all sizes. Historic charm with modern flexibility Perfect for celebrations, receptions, workshops &amp; community events Ideal spaces for concerts, performances &amp; gatherings Meeting rooms and office spaces available Whether you need a warm gathering space, performance venue, meeting room, office space, or a place to celebrate life's special moments, Trinity offers flexible spaces designed to bring people together. Go to our website to see our spaces. If you are interested in hosting an event or using office space on a consistent basis at Trinity, please email us at office@trinitychurchhp.org or call 847-432-6653 425 Laurel Avenue Highland Park, IL We would love to help bring your next event, meeting, or gathering to life.

Available rental spaces for your next event at...

Looking for the perfect space for your next event, meeting, celebration, concert, class, or gathering? Trinity Episcopal Church offers beautiful,...

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Events and Things to Do in Highwood, IL

Saturday, August 8

2026 APP Vlasic Classic Chicago Benefiting Shriners Children's

AUG

8

9:00 AM

Danny Cunniff Park, 2700 Trail Way, Highland Park, IL

Also around town...

Please confirm event details with the organizers before attending

Friday, August 7

Saturday, August 8

Wednesday, August 12

Thursday, August 13

Friday, August 14

Sunday, August 16

Wednesday, August 19

Thursday, August 20

Friday, August 21

Friday, August 28

Friday, September 4

Friday, September 11

2026 APP Vlasic Classic Chicago Benefiting Shriners Children's

YogaSix Highland Park

Available rental spaces for your next event at Trinity Church