Downtown Concerts at Port Clinton: Notte Italiana

SEPT. 11 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

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One of Highland Park’s newest restaurants, Nico Trattoria & Pizzeria will share your favorite Italian cuisine and cocktails while Steep Ravine Brewing Company serves craft beer. Rat Pack-inspired entertainment from the Diva Montell & Jeorge Holmes Duo  will provide the perfect romantic atmosphere for the evening.

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Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

SEPTEMBER 4 | NASHVILLE NOSH

Nothing makes you feel like family quite like Southern hospitality! Enjoy a family-friendly Nashville-inspired evening with The Barn Steakhouse, County Line String Band (featuring a Dolly Parton frontwoman), Line Dancing with Heather, and a “Fearless”-Era Taylor Swift impersonator. Kids will enjoy chalk, bubbles, ring toss, and tic-tac-toe in the plaza.

Downtown Concerts at Port Clinton: Nashville Nosh

SEPT. 4 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

Vintage Car Show

AUG. 22 | 12 PM - 4 PM
St. Johns North Parking Lot | 525 Central Ave.

Step back in time and experience the golden age of automobiles… and take a look at the future with a brand new EV showcase. Mark your calendars for 2026’s Vintage Car Show: Saturday, August 22.

Admire the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, August 22 from 12 PM - 4 PM. Head to the St. John’s North Lot (525 Central Ave.) and peruse a fabulous array of vintage vehicles, all while enjoying DJ Big Cat spinning your favorite tunes, kid-friendly activities, plus delicious food and ice cold beverages from local Highland Park restaurants. Additionally, 87.7 MeTV-FM will be onsite with station reps giving out swag. Whether you’re a seasoned collector or simply curious, you will definitely enjoy this journey through automotive excellence. Expect to see a diverse lineup of cars featuring vintage and antique models, unique classics, muscle cars, hot rods, motorcycles, and more.

Get ready for more cars, more food, and more fun in 2026!

New for 2026: Enjoy even MORE cars with an expanded event footprint, extending onto St. Johns Avenue between Central Avenue and Park Avenue. Plus, take a look at how sustainable the future can be with a brand new electric vehicle showcase.

AUGUST 21 | BOLLYWOOD BEATS & EATS

Eat to the Bollywood Beat with elevated Indian cuisine from the award-winning Indus Progressive Indian. Bollywood dancers and music from Manmeet Kaur will be the evening’s entertainment. Kids will enjoy chalk, ring toss, and tic-tac-toe, plus bubbles courtesy of Civil Tech.

Downtown Concerts at Port Clinton: Bollywood Beats & Eats

AUG. 21 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

Food Truck Thursdays - 90s Theme Night

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

Downtown Concerts at Port Clinton: Bon AppétEAT

AUG. 14 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

AUGUST 14 | BON APPÉT-EAT

This week will make you think that you’re enjoying a warm summer evening in Montmartre. Enjoy authentic French flavors from That Little French Guy and curated wines from Lynfred Winery. Jazz ensemble Lush Life will provide the perfect Parisian ambiance. Kids will enjoy chalk, bubbles, ring toss, a meet & greet with Belle from Beauty & the Beast, a French mime, and movie trivia presented by Wayfarer Theaters.

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

America250 at Ravinia Festival - This Land: America in Song

AUG. 8 | 1:30 PM
Ravinia Festival | Bennett Gordon Hall

Ravinia Festival’s Steans Institute performance-study fellowship program for emerging professional classical singers presents an afternoon concert featuring a kaleidoscope of musical impressions of America from diverse times, places, and viewpoints, including music by Ives, Weill, Puccini, Britten, Montsalvatge, Dvořák, and Rameau.

AUGUST 7 | AMERICAN MELTING POT

America is truly a melting pot, a delicious melting pot! Savor the flavors and fusions that have shaped American cuisine with BWB Shakes during AMERICAN MELTING POT night on August 7. Steep Ravine Brewing Company will also offer a selection of craft beers for those 21+. In addition to sidewalk chalk, bubbles, and bean bag tic tac toe for the kids, entertainment will include music from Uptown Shakedown and trivia from Wayfarer Theaters.

Downtown Concerts at Port Clinton: American Melting Pot

AUG. 7 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

America250 at Ravinia Festival - This Land: America in Song

AUG. 2 | 5 PM
Ravinia Festival | Hunter Pavilion

Ted Sperling hosts and conducts “This Land,” traversing two centuries-plus of popular music across U.S. history with the Chicago Symphony Orchestra—Stephen Foster gems, Sam Cooke and Bob Dylan anthems, songs from stage and screen, and more.

America250 at Ravinia Festival - Emanuel Ax with Chicago Symphony Orchestra: John Adams & Rachmaninoff

AUG. 1 | 7:30 PM
Ravinia Festival | Hunter Pavilion

Emanuel Ax guests with the Chicago Symphony Orchestra, playing the new Piano Concerto written for him by John Williams. Chief Conductor Marin Alsop also leads music by John Adams and Rachmaninoff’s Symphonic Dances, written shortly before he became an American citizen. 

America250 at Ravinia Festival - Chicago Symphony Orchestra: Carlos Simon’s Good News Mass

JUL. 31 | 7:30 PM
Ravinia Festival | Hunter Pavilion

Chief Conductor Marin Alsop leads the Chicago Symphony Orchestra in Carlos Simon’s Good News Mass, combining African American spirituality and classical music tradition, and dovetails to the American-heartland inspirations in Dvořák’s “New World” Symphony. 

Get ready for a Taste of Thailand with cuisine from Ruby of Siam and perfectly paired wine selections from Lynfred Winery. In addition to sidewalk chalk, bubbles, and bean bag tic tac toe for the kids, entertainment will include music from The Muzik Engine, Thai dancers, and trivia from Wayfarer Theaters & J. Blanton Plumbing.

Downtown Concerts at Port Clinton: Treasures of Thailand

JUL. 31 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

America250 at Ravinia Festival - Chanticleer: Our American Journey

JUL. 26 | 1:30 PM
Ravinia Festival | Martin Theater

The Grammy-winning ensemble Chanticleer traces centuries of musical heritage, exploring spirituals, shape-note songs, barbershop, and vocal jazz alongside bluegrass, folksong, and more as blueprints of contemporary classics. 

America250 at Ravinia Festival - On the Movies with the Chicago Symphony Orchestra

JUL. 24 | 8 PM
Ravinia Festival | Hunter Pavilion

Chief Conductor Marin Alsop and composer Laura Karpman rack focus on one of America’s leading features in global culture—the movies!—for an evening with the Chicago Symphony Orchestra that illuminates film-music perspectives by and about women. 

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.

Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.

Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

Downtown Concerts at Port Clinton: Slavic Savor

JUL. 17 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.

Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

JUL. 17 | SLAVIC SAVOR

We're headed to Eastern Europe this week with SLAVIC SAVOR. Cafe Dacha will be serving up all your Eastern European favorites and Steep Ravine Brewing Company will offer a selection of craft beers for those 21+. In addition to sidewalk chalk, bubbles, and bean bag tic tac toe for the kids, entertainment will include music from Paul Strolia and Volodymyr Okilko, Ukrainian dancers, and trivia from Wayfarer Theaters & J. Blanton Plumbing.