September 3, 2021 – Get ready for Labor Day, the last official weekend of summer. Make the most of it with these fun events.

Freewheelin’ Bike the Drive

Imagine bicycling on Lake Shore Drive without having to dodge cars. It’s Chicago’s annual Bike the Drive that lets you ride on a 30-mile course that stretches from the North Side to the South Side.

Take a spin on the popular lakefront while it’s completely closed to cars for 4.5 hours. Ride as little or as much as you want. The course opens at 5:30 a.m. and you can join from one of five designated entry points.

Proceeds benefit the Active Transportation Alliance, a nonprofit organization working to improve conditions for pedestrians and cyclists in Chicago. Cost: $50, kids $18.

Sunday, September 5 – 5:30 a.m.

 More info: Bike the Drive

Chow Down at Roscoe Village Burger Fest Fire up the grills for the Midwest’s best Patty Party!

More than a dozen Chicago eateries will join in for the tastiest weekend in town. Get your burgers on and tune into two stages of rockin’ music, arts and crafts, and a family-friendly Kids Zone. Here’s your chance to vote for Chicago’s Best Burger. $10 suggested fest donation.

September 4-5

Fellger Playlot Park, 2000 West Belmont Avenue

 More info: Lakeview Roscoe Village Chamber of Commerce

Get Your Kicks on Route 66 Did you know the famous Route 66 actually starts in Chicago? From downtown, the route winds its way out of Chicago on a long journey to California.

Walk the beginning of America’s main highway on a guided walking tour through Chicago’s downtown. Discover art, architecture, and history of the road with legends and stories galore.

Monday, September 6

12:00 – 1:30 p.m.

Start at the Route 66 sign at Adams & Michigan. Additional Dates: September 5, 8, 10 (and more dates).

 More info: Route 66 Chicago

Rosé Fest on the Beach Relax...and no more whining! Taste a variety of sweet rosé wines while hanging out at Shore Club on North Avenue Beach.

A perfect way to enjoy one of the last days of summer, with perfect views of the lake. Tickets include different rosé tastings, giveaways, and more.

Monday, September 6

6:00 – 9:00 p.m.

Shore Club, 1603 North Lake Shore Drive

 More info: River North Fests

Hip Hop to the North Coast Music Festival The electronic dance, hip hop, and rock music North Coast Music Festival opens for Labor Day weekend at the SeatGeek Stadium in nearby Bridgeview, Illinois.

The three-day festival will feature sets from Kaskade, Griz, and Zeds Dead, as well as appearances from Diesel (Shaq’s DJ alter ego), Whethan, and San Holo.

Friday, September 3 – Sunday, September 5

 More info: North Coast Music Festival