Highwood Metra Station

Celebrate Highwood is thrilled to announce Highwood Days and the Taste of Highwood! Kicking off Friday, July 17 through Sunday, July 19, the Highwood Days Carnival will take place in the Downtown Highwood Metra Station parking lot, with the Taste of Highwood and live music in Everts Park. Additionally, the Highwood 5K Family Run, Walk &amp; Stroll will take place on Saturday, July 18 at 9 AM.Combined with the 59th Annual Highwood Days, the City’s most celebrated event in its history, the 3-day festival will be complete with carnival rides and games. Come on out, sample some of Highwood’s great ‘tastes”, enjoy a cocktail, and listen to some great music!Highwood Days and Taste of Highwood will take place in rain or shine. Taste of Highwood hours areFriday 5–9 PM, Saturday 1–9 PM and Sunday 1–7 PM. The 59th
Annual Highwood Days Carnival hours are Friday 5–10 PM, Saturday 1–10 PM and Sunday 1–8 PM.For information on all-you-can-ride wristbands times and costs visit 
<a href="https://www.celebratehighwood.org/taste-of-highwood-and-highwood-days/" rel="nofollow noopener" target="_blank">https://www.celebratehighwood.org/taste-of-highwood-and-highwood-days/</a>.

Local Event: Highwood Days with Taste of Highwood

Lake County

Highwood

Illinois

Highwood Days with Taste of Highwood

Celebrate Highwood is thrilled to announce Highwood Days and the Taste of Highwood! Kicking off Friday, July 17 through Sunday,...

Port Clinton Square

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Eastern Europe is the theme this week, with Slavic Sounds from the Paul Strolia and Volodymyr Okilko complimented by delightful European cuisine from Cafe Dacha to savor, alongside Steep Ravine offering a selection of craft beer.

Local Event: Port Clinton Concert Series: Slavic Savor

Highland Park

Port Clinton Concert Series: Slavic Savor

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the...

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.

Local Event: Rock The Rails - Alex Key

Rock The Rails - Alex Key

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

Sheridan Road & Clay Avenue

The public is invited to put on their sneakers, grab their family, friends, strollers, and pets and join the fun on Saturday, July 18 at 9 AM in Downtown Highwood. The course starts and finishes at the corner of Sheridan Rd &amp; Clay Ave. and will guide participants along the beautiful lake front trail and through historic Fort Sheridan and then back again. This year’s run embraces a special "Superhero" theme, encouraging participants to come dressed as their favorite superhero. “Celebrate Highwood is thrilled to partner with Oak Terrace and align with their ‘Be a Superhero in Your Community’ theme,” says Celebrate Highwood president, Jess Ortega. “Oak Terrace’s platform on community mindedness goes hand in hand with our mission with Celebrate Highwood!”
Proceeds from the 2026 Celebrate Highwood 5K will directly benefit the Oak Terrace PTO, a non-profit organization committed to developing closer connections between home and school.
Runners and walkers can sign up <a href="https://www.CelebrateHighwood.org" rel="nofollow noopener" target="_blank">HERE</a>&nbsp;or at www.CelebrateHighwood.org now through midnight on Saturday, July 18. The 5K Run, Walk &amp; Stroll registration fee is $45 per participant, and includes a run t-shirt (must be registered by Monday, July 6 to guarantee a shirt and size). The one-mile walk fee is $25 and does not include a t-shirt. Participants aged 21 and older, will receive a coupon for an alcoholic beverage to enjoy at the Celebrate Highwood bar located at the Taste of Highwood in Everts Park, or the Celebrate Highwood bar at Highwood Days, held at the Highwood Metra Station parking lot, through Sunday, July 19.
Race Day Schedule &amp; Logistics: 8:00 AM: Race Day Registration and Packet Pick Up opens (Intersection of Sheridan Rd &amp; Clay Ave) 9:00 AM: 5K Race Start 10:00 AM: Age Group Awards Ceremony (or when the last participant crosses the finish line)
Age Group Awards: Celebrate Highwood will recognize the 1st, 2nd, and 3rd place Male and Female finishers in two age groups: 16 &amp; under, and 17 &amp; over.

Local Event: Highwood 5K Family Run, Walk & Stroll

Highwood 5K Family Run, Walk & Stroll

The public is invited to put on their sneakers, grab their family, friends, strollers, and pets and join the fun on Saturday,...

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/mimslife/?hl=en" rel="nofollow noopener" target="_blank">MIMS</a>, best known for his chart topper “This is why I’m Hot” joins the Rock the Rails line up with a special with bourbon launch!

Local Event: Rock The Rails - MIMS

Rock The Rails - MIMS

Everts Park

– <a href="https://celebratehighwood.org/" rel="nofollow noopener" target="_blank">Celebrate Highwood</a> is proud to announce the return of its themed Margarita Night on July 29 from 4:30 - 9 PM during its Wednesday Evening Gourmet Market. This festive theme night invites attendees to dress in their favorite Jimmy Buffett-style, Parrothead and Hawaiian gear to party to the sounds of <a href="https://www.facebook.com/SouthOfDisorderBand/" rel="nofollow noopener" target="_blank">South of Disorder</a>, a Jimmy Buffett tribute band, from 6 – 9 PM. There will be beach balls, flamingos, margaritas, tropical food, key lime treats, and more!Margarita Night would not be complete without a plethora of the classic cocktail that combines tequila, lime, and triple sec for ultimate refreshment. Attendees can choose from a variety of creative twists on the traditional margarita from fruit flavors to creative smokey and spicy options, and more.Encouraging the community to “make a night of it,” Highwood’s Evening Gourmet Market showcases a wide range of local produce, gourmet snacks, homemade breads and pastries, an array of ethnic delicacies and local artisan wares. Guests can enjoy dinner and cocktails while exploring the market, catching up with friends, and listening to different live music acts each week. To view vendors and entertainment line-up and to purchase tickets to the Historical Highwood Cocktail Tours, visit <a href="https://www.celebratehighwood.org/" rel="nofollow noopener" target="_blank">www.celebratehighwood.org</a>.
A special thanks to Celebrate Highwood sponsors of Margarita Night: <a href="https://www.windowworks-il.com/ghl/index.cfm?ctid=2585&amp;chid=695&amp;gad_source=1&amp;gad_campaignid=19581063779&amp;gbraid=0AAAAADgGCkv97IJA5hOVHHQUvxPBlVmx7&amp;gclid=Cj0KCQjwof_QBhCgARIsADaMzOfNTcMWvrh63Ri9UhjEO-NPd0YVGpHP990WGt0QT--dbPMrl-BibTgaAoL9EALw_wcB" rel="nofollow noopener" target="_blank">Window Works</a>, and the Budnik Family, who sponsored the live music.For more information on Margarita Night, please visit <a href="https://www.celebratehighwood.org/margarita-night/" rel="nofollow noopener" target="_blank">https://www.celebratehighwood.org/margarita-night/</a>. For more information on Celebrate Highwood’s 2026 series of family friendly festivals and events, please visit <a href="https://www.celebratehighwood.org/" rel="nofollow noopener" target="_blank">www.celebratehighwood.org</a> or Celebrate Highwood on <a href="https://www.facebook.com/celebratehighwood" rel="nofollow noopener" target="_blank">Facebook</a>.

Local Event: Margarita Night

Margarita Night

– Celebrate Highwood is proud to announce the return of its themed Margarita Night on July 29 from 4:30 - 9 PM during its...

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Get ready for a Taste of Thailand with cuisine from Ruby of Siam, wine from Lynfred Winery, and entertainment provided by Thai dancers and The Muzik Engine.

Local Event: Port Clinton Concert Series:Treasures of Thailand

Port Clinton Concert Series:Treasures of Thailand

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.Country double bill <a href="https://www.kendalltuckermusic.com/" rel="nofollow noopener" target="_blank">Kendal Tucker</a> and <a href="https://www.instagram.com/carsonleeofficial/" rel="nofollow noopener" target="_blank">Carson Lee</a> bring their love of all genres into their country vibe.

Local Event: Rock The Rails - Kendal Tucker | Carson Lee

Rock The Rails - Kendal Tucker | Carson Lee

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10. Celebrate our great American melting pot with a variety of menu options from BWB Shakes and beverage selection from Steep Ravine Brewing Company, while enjoying some classic music and covers spanning every genre from Uptown Shakedown.

Local Event: Port Clinton Concert Series:American Melting Pot

Port Clinton Concert Series:American Melting Pot

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 

Rock The Rails - Bubba Sparxxx 

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Bringing in a bit of France, attendees will enjoy flavors from That Little French Guy, wines from Lynfred Winery, and music by Lush Life providing the jazz to complete the evening.

Local Event: Port Clinton Concert Series: Bon AppetEAT 

Port Clinton Concert Series: Bon AppetEAT 

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...

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Downtown darlings Indus Progressive Indian are bringing their authentic Indian fare to compliment Bollywood dancers and music from Manmeet Kaur.

Local Event: Port Clinton Concert Series: Bollywood Beats + Eats 

Port Clinton Concert Series: Bollywood Beats +...

Port Clinton Concert Series: Bollywood Beats + Eats 

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

A community favorite returns to Downtown Highland Park! The City of Highland Park’s 5th annual Vintage Car Show is slated for Saturday, August 22, from 12 PM - 4 PM. Up to 150 classic &amp; custom vehicles, vintage motorcycles, and an electric vehicle showcase will be displayed at the North St. Johns parking lot (525 Central Ave.), between Central Avenue and Elm Place, and along St. Johns Avenue, between Central and Park Avenues in downtown Highland Park.
This free, all-ages event promises an exciting afternoon spent perusing a variety of vintage cars while enjoying music from DJ Big Cat, radio personalities from MeTV 87.7, kid-friendly activities, giveaways, plus bites and beverages from Highland Park favorites!
Attendees can expect to see a diverse lineup of cars dating from the early 1900s to 1984, ranging from vintage models to unique classics, local Highland Park commercial vehicles, muscle cars, hot rods, and more.
In the spirit of this being an all-ages event, The Art Center Highland Park will be offering a free craft making opportunity at their booth onsite. Kids can decorate their very own wooden car craft to take home as a souvenir.
New for 2026: Enjoy even more vintage, classic, and antique vehicles with an expanded event footprint! Plus, get a glimpse into the future of automobiles with a brand new EV showcase featuring a number of electric and hybrid vehicles.
Onsite food and drink vendors include BWB Shakes, Harmony Coffee Bar, Las Torres Mexican Restaurant, Michael’s Grill &amp; Salad Bar, and Steep Ravine Brewing Company. Libations will be available for those 21 and older.

Local Event: Vintage Car Show

Vintage Car Show

A community favorite returns to Downtown Highland Park! The City of Highland Park’s 5th annual Vintage Car Show is slated for...

The Shops on Elm Place will host its first-ever ‘End of Summer Party’ on Wednesday, August 26, celebrating 10-years of smiles
with<a href="https://gilbert-ortho.com/" rel="nofollow noopener" target="_blank">Gilbert Orthodontics</a>
and 5-years of sparkles with <a href="https://www.abcdesignjewelers.com/" rel="nofollow noopener" target="_blank">ABC Design Jewelers</a>! Hosted by <a href="https://gilbert-ortho.com/" rel="nofollow noopener" target="_blank">Gilbert Orthodontics</a>, and fellow businesses at The Shops on Elm Place, the free community event will feature a live DJ and dancing, food, family-friendly activities, and prize giveaways from 3 - 5:30 PM. The celebration will continue from 6 - 8 PM with an adult-only after-party hosted by <a href="https://www.abcdesignjewelers.com/" rel="nofollow noopener" target="_blank">ABC Design Jewelers</a>, and supported by <a href="https://gabriellawhite.com/pages/stores/chicago" rel="nofollow noopener" target="_blank">Gabby &amp; Summer Classics</a>, featuring bites and beverages.
The End of Summer celebration is designed to bring the community together while showcasing the businesses that make The Shops on Elm Place a unique local destination. Attendees will enjoy free activities such as a bounce house, face painting, balloon art, free samples from The BBQ Pit, and more.

Local Event: Shops on Elm Place: End of Summer Party

Shops on Elm Place: End of Summer Party

The Shops on Elm Place will host its first-ever ‘End of Summer Party’ on Wednesday, August 26, celebrating 10-years of...

The Shops on Elm Place will host its first-ever ‘End of Summer Party’ on Wednesday, August 26, celebrating 10-years of smiles with Gilbert Orthodontics and 5-years of sparkles with ABC Design Jewelers! Hosted by Gilbert Orthodontics, and fellow businesses at The Shops on Elm Place, the free community event will feature a live DJ and dancing, food, family-friendly activities, and prize giveaways from 3 - 5:30 PM. The celebration will continue from 6 - 8 PM with an adult-only after-party hosted by ABC Design Jewelers, and supported by Gabby &amp; Summer Classics, featuring bites and beverages.
The End of Summer celebration is designed to bring the community together while showcasing the businesses that make The Shops on Elm Place a unique local destination. Attendees will enjoy free activities such as a bounce house, face painting, balloon art, free samples from The BBQ Pit, and more. The public is invited to attend this free ‘End of Summer Party’ that will give attendees the chance to experience all that The Shops on Elm Place has to offer. From familiar favorites like The BBQ Pit and Love’s Yogurt, to businesses they may be discovering for the first time like ABC Design Jewelers, Joan Barry Hair Designers, The Custom Framer, and TREVI Longevity &amp; Aesthetics Institute, visitors can enjoy an afternoon of local shopping, activities and summer fun.

Local Event: Shops on Elm Place: End of Summer After Party

Shops on Elm Place: End of Summer After Party

The Shops on Elm Place will host its first-ever ‘End of Summer Party’ on Wednesday, August 26, celebrating 10-years of smiles...

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

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
New to Highland Park, The Barn Steakhouse will provide southern American fare while County Line String Band, along with line dancing and a Dolly Parton tribute artist to entertain the crowd.

Local Event: Port Clinton Concert Series: Nashville Nosh 

Port Clinton Concert Series: Nashville Nosh 

The City of Highland Park is thrilled to announce an eclectic line-up of coordinated entertainment and cuisine as part of the 2026 Downtown Concerts at Port Clinton series. Select Fridays, July 10 through September 25 at Port Clinton Square in Downtown Highland Park, the public is invited to take a trip around the world - without ever leaving Highland Park. Attendees will partake in global cuisine from a different onsite local Highland Park restaurant each week while enjoying accompanying world music and entertainment. No passport necessary.
Over the course of ten Friday evenings, attendees are encouraged to bring lawn chairs to Port Clinton Square and start their summer weekends with free live music for the entire family. Concerts will generally run from 6 PM - 8 PM. Please note there will be no concerts July 24 or August 28, and the July 10 concert will take place from 5 PM - 7 PM. The season finale on September 25 will be held from 4 PM – 8 PM and feature the return of the ever-popular Scarecrow Trail through Downtown Highland Park. Over one dozen Downtown businesses will decorate seasonal scarecrows in front of their shops, creating a fun and festive Scarecrow Trail. Attendees will be able to vote “best in show, with the winner being announced during Stews &amp; Brews on October 10.
Highland Park’s newest restaurant, Nico Trattoria &amp; Pizzeria, will share family friendly Italian favorites and classic cocktails, alongside Steep Ravine Brewing Company serving craft beer to compliment the Rat Pack entertainment by the Diva Montell &amp; Jeorge Holmes Duo this evening!

Local Event: Port Clinton Concert Series: Notte Italiana

Port Clinton Concert Series: Notte Italiana

info

Rachel Barnes

Chicago Metropolitan Area

Eric DeGrechie

Deerfield

Cook County

Northbrook

Winnetka-Glencoe

Lake Forest-Lake Bluff

Glenview

Buffalo Grove

Vernon Hills

Wilmette-Kenilworth

Niles-Morton Grove

Amie Schaenzer

Libertyville

Today marks one more week until Family Night Out begins!! 🚗We will be hosting a "Road Trip" without the need to leave town for all families, with four unique nights of games, service projects, dinner, and workshops every night at the Kingswood Deerfield campus! Come to this multi-generational event when it fits your schedule and experience a faith-filled community! Sign up and learn more at the link below!

Local Event: Family Night Out

Family Night Out

Today marks one more week until Family Night Out begins!! 🚗We will be hosting a "Road Trip" without the need to leave town for...

Make a Day (or Two) of It in Downtown Highland Park!
The Highland Park Sidewalk Sale returns July 24 &amp; 25, inviting you to shop, dine, and explore everything downtown has to offer.
This FREE, family-friendly event features special sidewalk sales, unique finds, and outdoor shopping from your favorite local businesses. Between shopping stops, enjoy lunch or dinner at one of downtown's many restaurants, discover new local favorites, and let the kids enjoy family-friendly activities throughout the event.
Whether you're searching for great bargains or simply looking for a fun summer outing, the Highland Park Sidewalk Sale is the perfect way to experience the best of Downtown Highland Park while supporting the local businesses that make our community thrive.
FREE Admission Friday &amp; Saturday, July 24–25 10:00 AM–5:00 PM Downtown Highland Park

Local Event: Highland Park Sidewalk Sale

Highland Park Sidewalk Sale

Make a Day (or Two) of It in Downtown Highland Park!
The Highland Park Sidewalk Sale returns July 24 & 25, inviting you to...

Nearby Communities

State Edition

National Edition

Posting Activity

Highwood Days with Taste of Highwood

JUL

17

5:00 PM

Highwood Metra Station, 406 Sheridan Rd, Highwood, IL

Port Clinton Concert Series: Slavic Savor

JUL

17

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Rock The Rails - Alex Key

JUL

17

8:00 PM

454 Sheridan Rd, Highwood, IL

Highwood 5K Family Run, Walk & Stroll

JUL

18

9:00 AM

Highland Park, IL

Rock The Rails - MIMS

JUL

24

8:00 PM

28 Mile Distilling Company, 454 Sheridan Rd, Highwood, IL

Margarita Night

JUL

29

4:30 PM

Everts Park, 111 North Ave, Highwood, IL

Port Clinton Concert Series:Treasures of Thailand

JUL

31

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Rock The Rails - Kendal Tucker | Carson Lee

JUL

31

8:00 PM

28 Mile Distilling Company, 454 Sheridan Rd, Highwood, IL

Port Clinton Concert Series:American Melting Pot

AUG

7

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Rock The Rails - Bubba Sparxxx

AUG

7

8:00 PM

28 Mile Distilling Company, 454 Sheridan Rd, Highwood, IL

Port Clinton Concert Series: Bon AppetEAT

AUG

14

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Rock The Rails: Michael Winslow

AUG

14

8:00 PM

28 Mile Distilling Company, 454 Sheridan Rd, Highwood, IL

Port Clinton Concert Series: Bollywood Beats + Eats

AUG

21

6:00 PM

Port Clinton Square, 600-601 Central Ave, Highland Park, IL

Rock The Rails - Jimmie Allen

AUG

21

8:00 PM

28 Mile Distilling Company, 454 Sheridan Rd, Highwood, IL

Vintage Car Show

AUG

22

12:00 PM

525 Central Ave, Highland Park, IL

Shops on Elm Place: End of Summer Party