BERWYN RT66 CAR SHOW; FLATWATER CLASSIC

Send off summer with a pair of transportive events: Relive retro road trips when a convoy of hot rods rolls into Berwyn; then hit the Chicago River’s North Branch for an adventurous end-of-season paddle.

DETAILS:

9/10 Where Chicago ends, the spirit of the open road begins: More than 300 classic cars, trucks, and motorcycles line suburban Berwyn, just a few miles from the starting point of the famed Route 66. Sat 9–dusk. Ogden and Oak Park, Berwyn. berwynrt66.com.

9/18 This year’s paddlepalooza relocates to the North Branch of the Chicago River for a six-and-a-half-mile canoe/kayak; for landlubbers, a 16-mile cycle skirts the Skokie Lagoons and the Chicago Botanic Garden before heading south along the North Branch Trail. Both routes convene at a party in Morton Grove’s Linne Woods. Sat 10–4. $17 (under 18) to $35. Chicago River at Willow Road Dam, Willow and Lagoon, Winnetka. chicagoriver.org.

Photograph: schlol/istockphoto

HYDE PARK JAZZ FESTIVAL

A rollicking September bookend to Labor Day weekend’s Chicago Jazz Festival, this free South Side affair bops harder with each passing year. On the bill for year 5, three capital W’s: Willie Pickens, Corey Wilkes (right), and a hopping set at Wright’s Robie House.

DETAILS:

9/24–25 Why did we declare this now-two-day affair the city’s best neighborhood music fest in Chicago’s August issue? Foremost, for staging top-notch local acts, such as the pianist Willie Pickens, the drummer Paul Wertico, the trumpeter Corey Wilkes, and dozens more in venues of all shapes and sizes (the DuSable Museum, the Midway Plaisance, a midnight jam session at Mandel Hall) across the South Side enclave. A rent party at Wright’s Robie House? Count us in. Schedule, locations: hydeparkjazzfestival.org.

Photograph: Marc Monaghan

HIDEOUT BLOCK PARTY

Hooray for the revival of this anti–street fest, a traditionally laid-back gig that nonetheless should raise a few pulses with its 2011 headliners: Mavis Staples and Andrew Bird.

DETAILS:

9/24 The blue-collar tavern and grassroots community center revives its end-of-summer blowout in grand fashion for its 15th birthday. On deck: the orchestral-pop violinist Andrew Bird, the gospel-rock icon Mavis Staples, the legendary B3 noodler Booker T Jones, the one-man juggernaut Jon Langford with a backing 40-man chorus, and more—all for a mere $25. Sat noon–10. The Hideout, 1354 W Wabansia. hideoutchicago.com.

Photograph: Ryan Robinson

BERTRAND GOLDBERG

As of presstime, the fate of his 1975 Prentice Women’s Hospital was in preservation limbo. Show your support for the Chicago architect’s would-be landmark by visiting two exhibits, at the Art Institute and the Arts Club, devoted to his singular space-age style. Also? Call Rahm’s office.

DETAILS:

Opening 9/16 Bertrand Goldberg: Reflections. A companion to the Art Institute’s new show, this exhibit focuses on the architect’s personal photos, selections from his own art collection, and samples of his lesser-known jewelry and furniture designs. 201 E Ontario. artsclubchicago.org.

Opening 9/17 Bertrand Goldberg: Architecture of Invention. Click here for more info. 111 S Michigan. artinstitutechicago.org.

Photograph: Heather Charles/Chicago Tribune

RED

A prediction: If you don’t snap up tickets now to John Logan’s six-time Tony winner about the artist Mark Rothko, making its Chicago debut at Goodman, you’ll be seeing—well, you know.

DETAILS:

9/17–10/23 It’s difficult to reduce John Logan’s Tony-winning exploration of the artist Mark Rothko to blurb length. But if you want a sense of the piece, Google some of the art referenced therein: Caravaggio’s The Conversion of Saul, Matisse’s The Red Studio, and Rembrandt’s Belshazzar’s Feast. Or don’t. Red has the power to thrill all, Rothko expert and art history dropout alike. Previews 9/17–26. All tickets $25–$89. Goodman Theatre, 170 N Dearborn. goodmantheatre.org.

Photograph: Courtesy of Goodman Theatre