Ravinia Festival

Large outdoor crowd seated on lawn chairs at a park event during late afternoon.

Ravinia Festival has been a cornerstone of North Shore summers for more than a century.

Photo courtesy of Ravinia

Dates: June 3-Sept. 23

Boasting an updated and redesigned Hunter Pavilion, Ravinia Park’s iconic festival returns with a season of outdoor performances spanning classical, pop and contemporary music, with artists including Paul Simon, Brandi Carlile and Chance the Rapper alongside the Chicago Symphony Orchestra, marking its 90th anniversary at the festival. 200 Ravinia Park Road, Highland Park

Leopoldstadt

Dates: June 4-July 19

This Midwest premiere brings celebrated playwright Tom Stoppard’s 2023 Tony Award–winning play to Writers Theatre, tracing the lives of a Jewish family in Vienna across the first half of the 20th century. Spanning decades of cultural change and upheaval, the production explores identity, memory and the lasting impact of history through an intimate yet sweeping narrative. 325 Tudor Court, Glencoe

June 14-15

Lurie Children’s Pro-Am & Dinner on the Bluff

Outdoor event with people socializing near a large white tent by the water and trees.

The Founders’ Board of Lurie Children’s hosts its 66th annual event at Onwentsia Club, pairing 200 amateur golfers with professionals from 50 clubs across the country. Festivities begin the evening prior with a dinner, paddle raise and live auction at Shoreacres in Lake Bluff, with proceeds supporting the board’s $3.5 million commitment to the Lurie Children’s Center for Cancer and Blood Disorders. Shoreacres, 1601 Shoreacres Road, Lake Bluff; Onwentsia Club, 300 N. Green Bay Road, Lake Forest

Evanston Plein Air Festival

Woman smiling next to easel with painting and blue ribbon at outdoor art event on city street.

Chicago-based artist Christina Body was among the winners at last year’s Evanston Plein Air Festival.

Photo by Liz Cramer

Dates: July 11-19

This weeklong, citywide celebration of outdoor art invites artists to capture Evanston’s landscapes, architecture and everyday scenes through plein air painting, with neighborhood paint-outs, live competitions and a festival finale featuring an open-air market, music and local vendors. Downtown Evanston

Wilmette French Market

Fresh blueberries, cherries, and raspberries displayed in green cartons on a checkered table at a market.

Dates: Through Oct. 31

Held on Saturdays from spring through fall, the Wilmette French Market draws a lively crowd with its ever-changing mix of farm-fresh produce, gourmet provisions, artisanal baked goods, seasonal offerings and unique finds from local vendors. 722 Green Bay Road, Wilmette