Trombone Shorty & Orleans Avenue will bring New Orleans brass-funk to downtown Winnetka on Juneteenth itself, as the Winnetka Music Festival kicks off its 10th anniversary weekend.
Official Juneteenth-specific programming on the North Shore is limited this year to one event. Here's that celebration, plus four more ways to fill the long weekend.
1. Catch Trombone Shorty on Juneteenth at the Winnetka Music Festival
Troy Andrews, the Black musician and bandleader from New Orleans' Tremé neighborhood known as Trombone Shorty, headlines Friday, June 19, at Lincoln Avenue and Pine Street in downtown Winnetka. Father John Misty takes the stage Saturday, June 20. More than 25 acts perform across both days, including Grace Potter, Petey USA, Ben Kweller, and Futurebirds.
Co-founder Val Haller called the festival "a comfortable, destination fest in the suburbs that feels like a downtown festival."
The festival draws about 7,000 people per day, according to the Evanston Roundtable. Single-day general admission tickets are $94.03 (fees included) at winnetkamusicfestival.com. Two-day passes are sold out. Children under 12 get in free; ages 12-16 pay half-price. The venue is two blocks from Lake Michigan and steps from the Winnetka Metra station. Co-presented by Evanston's SPACE and Val Haller's music discovery platform Valslist.
2. Bring the kids to the free family stage Saturday morning
A dedicated free family stage runs 11 a.m. to 3 p.m. Saturday, June 20, at the Winnetka Music Festival. No tickets required. The lineup includes the Rock and Roll Playhouse playing the music of Taylor Swift, plus crafts and activities for children.
3. Head to the DuSable Museum's free Juneteenth celebration
For North Shore residents willing to make the trip south, the DuSable Black History Museum and Education Center (740 E. 56th Place, Hyde Park) hosts its annual Juneteenth celebration Friday, June 19, from 10 a.m. to 8 p.m. The free event features live performances, DJs, spoken word, wellness activities, educational programming, and local vendors. Hosts are Shermann "Dilla" Thomas and Zion Ali.
Shuttle buses run between the Obama Presidential Center and the museum grounds from 11 a.m. to 3 p.m. The Obama Presidential Center opens to the public on Friday, June 19; grounds are free and open 6 a.m. to 9 p.m., though museum tickets ($23-$30) are sold out for opening weekend.
4. Visit the Chicago Botanic Garden's "Shimmering Summer" exhibit in Glencoe
The Chicago Botanic Garden, a short drive north of the festival site, is running its "Shimmering Summer" exhibit through Sunday, September 20. The centerpiece "Evanescent" installation features monumental iridescent bubble sculptures by Australian art duo Atelier Sisu set among summer blooms. Summer hours are 10 a.m. to 8 p.m. daily. Admission is $22.95 for Cook County adult residents, $24.95 for non-residents.
5. See "Leopoldstadt" at Writers Theatre in Glencoe
Writers Theatre (325 Tudor Court, Glencoe) is staging Tom Stoppard's final play, "Leopoldstadt," through Sunday, August 9. The production follows a Jewish family in Vienna from 1899 to 1955 and asks: Who is a citizen? Who gets to belong? It's one of the largest productions in the theater's 35-year history, with a 24-person ensemble. Tickets are $35-$95 at writerstheatre.org.
