Calendar
What’s Happening?
There’s always something to see or do in Highland Park! Check out our calendar to plan your next visit.
Note: The sponsoring organization for each event is included in the event listing. The City does not sponsor or endorse events listed on the calendar except those attributed to the City of Highland Park. Please direct any questions to the sponsoring organization.
To have your Highland Park event featured, please email Marketing Coordinator Diane Larson.
Individual Event Listings
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
July 18 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
JULY 18 LINEUP
Entertainment
Urban Roots Band | Reggae
Food & Beverage
Yana’s Speakeasy
Fluffy Bunny
Yellow Duck Truck
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 1 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 1 LINEUP
Entertainment
Kaleidoscope Eyes | Beatles Tribute Band
Food & Beverage
Indus Progressive Indian
Steep Ravine Brewing Company
Fluffy Bunny
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 8 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 8 LINEUP
Entertainment
Michelle Hallman Band | Classic Rock & Pop
Food & Beverage
Indus Progressive Indian
Steep Ravine Brewing Company
Fluffy Bunny
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 15 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 15 LINEUP
Entertainment
Guy King | Vocal Jazz Classics
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 29 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 29 LINEUP
Entertainment
Guitarra Azul | Flamenco
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 5 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 5 LINEUP
Entertainment
Radio Free Honduras | Latin Rock
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 12 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 12 LINEUP
Entertainment
Don Stiernberg Quartet, Feat. Petra van Nuis | Jazz
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 19 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 19 LINEUP
Entertainment
Dave Specter | Chicago Blues
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yana’s Speakeasy
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
July 11 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
JULY 11 LINEUP
Entertainment
The Oh Yeahs | Acoustic Vocal Trio
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
Bitter Jester Music Festival Grand Finale
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Grand Finale
June 28 | 2 PM - 10:30 PM
Second St. from Central Ave. to Laurel Ave.
Looking for something fun to do on the weekend? How about live music near you…
The Grand Finale concert will be co-emceed by NPR's Peter Sagal (host of "Wait Wait... Don't Tell Me!") and Bitter Jester's Nicolas DeGrazia (Emmy-winning Producer/Director). Come out and meet Peter in person while you discover your next favorite band! Twelve musical acts from half a dozen states will be featured.
Eight musical acts from half a dozen states compete alongside four Showcase Artists. Kick back with a cool drink from Steep Ravine Brewing Company or a great bite to eat from Judy’s Pizza, BWB Shakes, or Curt’s Cafe while you enjoy this FREE, vibrant, and family-friendly show. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
FINALE LINEUP
In Competition:
Cabin Fever (NY)
Charlieboy (WI)
Exit 122 (IL)
Meera Raphael (RI)
Patches & Albo (IL)
Platinum Moon (NY)
Tikimen of Berlin (MI)
Zeke Rowan (MI)
Featured Showcases:
Crowd Vulture (IL)
North Grove (IL)
The Orchids (IL)
Rae (TN)
Bitter Jester Music Festival Preliminary Concert - Night 4
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 4
June 14 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 4 LINEUP:
• Belle Vista (Showcase)
• Cabin Fever
• Control the Sound (Showcase)
• Crowd Vulture
• Elle of the Wilds (Guest Artist)
• Exit 122
• The Orchids
• Party Hat Club
• rae
• TUMI (Guest Artist)
Bitter Jester Music Festival Preliminary Concert - Night 3
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 3
June 13 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 3 LINEUP:
• Candy Cigarette (Showcase)
• Christine Compall (Guest Artist)
• Floryence (Guest Artist)
• Lackadays
• Monica James (Guest Artist)
• Plastic Summer
• Platinum Moon
• The Regulars
• Sierra Sikora
• STARLESS (Showcase)
• ZEKE ROWAN
Bitter Jester Music Festival Preliminary Concert - Night 2
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 2
June 7 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 2 LINEUP:
• The 1-800s
• The Broken Vinyls
• Claire-Mckenna
• Holden Garcia (Guest Artist)
• NewClearFusion (Showcase)
• Nikki Rodrigues (Guest Artist)
• Patches & Albo
• Superimposed
• Tikimen of Berlin
• Trial and Error (Showcase)
• Violet Clare (Guest Artist)
Bitter Jester Music Festival Preliminary Concert - Night 1
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 1
June 6 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 1 LINEUP:
• Ayden Holt (Guest Artist)
• BYRON (Guest Artist)
• Charlieboy
• The Coves
• Earl Hester (Showcase)
• Holden Garcia (Guest Artist)
• Meera Raphael
• North Grove
• The Reys
• Silver October (Guest Artist, MUSIC @ 5:15pm)
• Speedbump
• State of Youth (Showcase)
Brand New Day Cabaret
Uptown Music Theatre of Highland Park presents its third annual cabaret - "Brand New Day." This performance of Broadway songs celebrates family, friends, community, and inspiration. Performers from Highland Park, including HPHS alumni, and surrounding communities share their musical talents in a one-night-only show. Audience members are required to wear masks and provide proof of vaccination.
For tickets, visit www.umthp.org.