Guide To 2019 Summer Festivals, Events In Highland Park, Highwood

With school out and summer kicking into gear on the North Shore, we've compiled a summer-long list of upcoming events in Highland Park and Highwood. There's family-friendly fun activities on offer across the area all summer long. Find schedules, events and registration deadlines below for festivals, fairs and markets set for summer 2019.

Highland Park

Food Truck Thursdays
The popular Ravinia District event returns for a third year. From 4:30 p.m. to dusk every Thursday until Sept. 12, the community is invited to stop by Dean Avenue between Roger Williams and St. Johns Avenue and Jens Jensen Park across from the Ravinia Metra station. A competitive cornhole league is new this year. A full schedule is available online.

Bitter Jester Music Festival
The professional music competition for young and emerging artists holds Friday night concerts at Port Clinton Square, 600 Central Ave., from 7 to 10:30 p.m. ahead of a grand finale among eight semifinalists on July 4 at Wolters Field and a Sept. 2 concert at Navy Pier in Chicago. More information about bands is available online.

Firecracker 5K Run and 2 Mile Walk for SMILE
The annual run-walk for the Parks Foundation of Highland Park takes place from 8 to 11 a.m. on June 30 at Sunset Woods Park, 1801 Sunset Road. The event offers free shirts and bags to all participants, and registration is available online.

Festival of Fine Arts
The Highland Park Art Center showcases close to 100 juried artists from around the world from 10 a.m. to 5 p.m. on Saturday, June 22, and Sunday, June 23, at 1957 Sheridan Road. The event will include live music and classes free classes on skills ranging from printmaking to portraiture.

Fourth Fest
The 2019 Independence Day celebrations in Highland Park will be heightened by the involvement of the city's "Big Bash" 150th anniversary celebrations. Festivities began at 9:30 a.m. with an HP150 parade leading into Sunset Woods Park for the Fourth Fest and Big Bash from 11 a.m. to 2 p.m. The event will offer carnival rides, bounce houses, local food and live music. The sesquicentennial celebrations include a pie-eating contest, a performance from the HP Pops and an all-community photo. Wristbands can be purchased at a discount from June 25 to July 3 at West Ridge Center, the Highland Park Rec Center and Highland Park Bank and Trust. From 4 p.m. to 9:30 p.m., the grand finale of the Bitter Jester Music Festival takes place at Wolters Field, 1080 Park Ave., ahead of the fireworks display at 9:30 p.m. Those wishing to relax at the pool while enjoying the show can also view the fireworks from Hidden Creek AquaPark, 1220 Fredrickson Place, from 8:15 to 10:15 p.m.

North Shore Amateur
The North Shore Amateur golf tournament returns to the renovated Sunset Valley Golf Club after a two-year hiatus on Saturday, July 20, and Sunday, July 21. Entries are due by July 13.

Highland Park Sidewalk Sale
More than 80 Highland Park merchants will bring their merchandise to the central business district from Thursday, July 25, to Saturday, July 27, for a discounted shopping extravaganza.

North Shore Venetian Night
The North Shore Yacht Club is coordinating a traditional evening on Saturday, Aug. 3, featuring themed boats decorated with festive lights parading in front of Park Avenue Beach.

Port Clinton Art Festival
More than 250,000 art fans are expected to drop by the central business district, where paintings, photography, sculpture, jewelry and more from over 260 artists will be showcased from 10 a.m. to 6 p.m. on Saturday, Aug. 24, and Sunday, Aug. 25. For youngsters, there is a youth art division to celebrate the work of those under 18 and scavenger hunts.

More: 2019 Ravinia Festival Complete Music Schedule

Highwood

Wednesday Evening Gourmet Market
For the 11th year, the evening market returns to Everts Park, 130 Highwood Ave., from 4:30 to 9:30 p.m. every Wednesday through Aug. 28, with live music, dancing, fresh food and cocktails. There's also a chance to shop for locally made prepared food and handmade goods. A full schedule is available online.

Inferno Fest
The festival of hot and spicy foods takes place from 4:30 to 9:30 p.m. in Everts Park during the weekly evening market. Described by organizers as "a test of taste buds and endurance for all those who dare to compete," the event will feature live music and a taquito-eating contest, which requires a waiver to participate.

Highwood Days-North Shore Taco Fest
The 51st edition of Highwood Days and the 4th annual North Shore Taco Fest takes place from Thursday, July 18, to Sunday, July 21, at the parking lot of the Highwood Metra station. It includes a wide range of tacos and other foods from local restaurants, caterers and food trucks. There will be carnival rides, live music and a 5K benefit run on Saturday morning. A full schedule of events is available online.

Bloody Mary Fest
The 10th annual cocktail-focused event takes place from 10 a.m. to 5 p.m. on Sunday, July 28, at Everts Park. Stiff competition to take the title of 'People's Choice' and 'Best Bloody Mary' is expected. According to organizers, the event attracted 10,000 attendees last year.

Garlic Fest
This sweet and savory celebration of the stinking rose takes place for the ninth consecutive year from 4:30 to 9:30 p.m. on Aug. 14 at Everts Park during the evening market. It will include the Garlic Royalty and Taste of Garlic competitions and feature garlic-infused culinary creations ranging from the usual to the unexpected.

Nashwood
The third annual celebration of country, blues and southern rock takes places from Friday, Aug. 30, to Sunday, Sept. 1, in downtown Highwood with 100 musical performances planned indoor and outdoor locations and more than 20 local bars and restaurants.

Got another North Shore summer event to add? Add it to the Patch calendar.