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Many Exciting Events Planned for Spring and Summer 2019 in Highland Park

This article refers to events held in 2019. Please note that due to COVID-19, Food Truck Thursdays, along with other large summer events, has been canceled for summer 2020. More information is available in the cancellation announcement.

May 2, 2019 -- Highland Park is known for its bustling downtown, pristine beaches, great parks, unique shopping and dining experiences, and renowned special events that celebrate the vibrant energy of the community. Join your family, friends, and neighbors at the upcoming spring and summer events listed below to experience first-hand, a community that lives with heart and leads with passion. All events are free, family-friendly, and open to the public.

Night of Italian Songs – A Sister Cities Foundation Event
Wednesday, April 10 at 7 PM at the Highland Park Library, 494 Laurel Ave.
Celebrate our Italian Community and Highland Park's 150th Anniversary with an evening of Italian songs, performed by tenor Gianni Coletta and Linda Iovino, accordion.

Highland Park’s Voice of the Past
Saturday, April 13 at 11 AM & 2 PM at the Highland Park Library, 494 Laurel Ave.
In honor of Highland Park's Sesquicentennial Celebration, East on Central and Highland Park Poetry teamed up on the HP150 Persona Poetry Project, telling the community story through verse. Witness Highland Park history from the perspective of those who lived it in these two special performances by ARTicuLIT Readers Theatre.

 Arbor Day Celebration
Saturday, April 27 from 9 AM to 12 PM at Jens Jensen Park, 486 Roger Williams Avenue.
More than a dozen local businesses and sustainability organizations will offer activities and projects focused on planting and caring for trees, shrubs, and flowers. On a first come, first serve basis, the City will give away 500 free tree seedlings ready for planting while supplies last. The event will also feature live raptor talks, free paper shredding, and a touch-a-truck exhibit.

Highland Park HP150 Bus Tours
Saturday, May 11.
The HP150 Architecture Committee has coordinated three exciting Highland Park Tours on May 11: Highland Park Architecture Tour, Hollywood in Highland Park Tour, and Art Tour. Tour Tickets are available at City Hall, 1707 St. Johns Ave. for $15.

Highland Park Uncorked Wine Stroll
Thursday, May 16 in Downtown Highland Park.
Wine lovers and foodies can sip, savor and stroll through the eclectic businesses of downtown Highland Park while enjoying fine wines and delicious small bites at the Highland Park Chamber’s Uncorked spring wine stroll!

Bitter Jester Music Festival
Fridays May 31, June 7, June 14, and June at 7 PM at Port Clinton Square and Thursday, July 4 at Wolters Field.
Enjoy a variety of music as bands perform four consecutive Fridays beginning May 31.  Winning bands are selected by professional and celebrity judges and then eight semi-finalist bands compete against each other on the 4th of July for over $20,000 in cash and other prizes and the chance to be named the 2019 Grand Champion!  Food and drink vendors are on hand all night long.

Ravinia Farmers Market
Wednesdays from June 5- October 23 at 7 AM - 1 PM on Dean Avenue between St. Johns and Roger Williams.
Fresh produce, flowers and other artisanal items are available for purchase.

Ravinia District’s Food Truck Thursdays
Thursdays from June 6 – September 12 from 4:30 PM - dusk at Jens Jensen Park (St. Johns and Roger Williams Avenues).
Food Truck Thursdays features delicious food and drink from local restaurants and more than a dozen food trucks offering an array of delectable options. Paired with a rotating list of live bands and musicians, Food Truck Thursdays makes for a fun weekly outing with family and friends in the Ravinia Business District.

The Art Center – Highland Park Festival of Fine Arts
June 22-23 from 10:00 AM - 5:00 PM at Sheridan Road and Central Avenue.
The Art Center Festival of Fine Arts showcases the work of over 100 juried artists from around the world in a variety of mediums. In addition to the incredible artwork available for purchase, attendees will be able to interact with artists. Live music and kid-friendly activities will be available for visitors to enjoy.

 4th of July Parade, Big Bash, and Evening Fireworks
Wednesday, July 4.
The celebration kicks off with the annual 4th of July Parade at 10 AM hosted by the City and Park District. The parade features floats, marching bands, dignitaries, novelty groups, community entries and other special entertainment. The parade route has changed this year. The parade begins at the intersection of Laurel Avenue and St. Johns Avenue, proceeding on St. Johns to Elm Place, west on Elm Place, immediate south on First Street, west along Central Avenue, ending at Sunset Woods Park.

After the parade, the entire City is invited to celebrate the City's 150th birthday at the Big Bash with cake, entertainment, dancing, and family-friendly games and activities. In conjunction with Fourth Fest, the Big Bash will be the biggest 150th Anniversary celebration of the year. The first 1000 attendees will receive a free HP150 canvas bag.   

The 4th of July festivities will culminate with a special HP150 firework show which can be viewed at dusk from Wolters Field.

Highland Park Sidewalk Sale
Thursday, July 25, Friday, July 26 and Saturday, July 27 in Downtown Highland Park.
Coordinated by the Highland Park Chamber of Commerce, more than 80 merchants in Highland Park’s lively Central Business District move their merchandise outdoors for this shopping extravaganza. Check out the trendy goods and great deals at this annual event.

National Night Out
Tuesday, August 6 from 6 PM – 8:30 PM City Hall Front Lawn, 1707 St. Johns Avenue.
Coordinated by the City of Highland Park Police Department, National Night Out will offer entertainment and activities that promote safety, health and civic mindfulness. This event brings the community and public safety personnel together for a fun and interactive afternoon of activities.  

North Shore Venetian Night
Saturday, August 17 at Park Avenue Boating Facility.
This traditional Venetian Night event, coordinated by the North Shore Yacht Club (NSYC), will feature an evening parade of themed boats decorated with festive lights that can be viewed from Park Avenue Boating Facility. Registration to be in the parade is open to anyone with a (US Coast Guard compliant) boat.

Port Clinton Art Festival
August 24 & 25 from 10 AM – 6 PM in Downtown Highland Park.
Amdur Productions coordinates this well renowned juried art festival that attracts more than 250,000 art enthusiasts from around the globe. More than 300 of the world’s most celebrated artists come together to showcase their work over the course of the weekend, creating an atmosphere brimming with artistic creativity.

The events above are sponsored by the City of Highland Park. The City’s Sister Governments including the Park District of Highland Park and the Highland Park Public Library, along with private entities such as Ravinia Festival and other private organizations and businesses host a number of other notable events throughout the spring and summer in the City. Please check the Community Calendar on the City’s website at or the respective organizations’ websites to find other exciting reasons to visit Highland Park.