Trail ride Events and Things to do in Westchester, IL

Consider the Wildflowers 1M 5K 10K 13.1 26.2
Sun, Mar 1, 1:00 PM
Chicago · Chicago
Consider the Wildflowers 1M 5K 10K 13.1 26.2
Sun, Mar 1, 1:00 PM
Chicago · Chicago
Memorial Day 1M 5K 10K 13.1 26.2
Mon, May 25, 1:00 PM
Chicago · Chicago
Memorial Day 1M 5K 10K 13.1 26.2
Mon, May 25, 1:00 PM
Chicago · Chicago
Sales end soon
Downtown Mount Prospect Progressive Dinner
Wednesday at 6:00 PM
Mount Prospect · Village Of Mount Prospect
Sales end soon
Downtown Mount Prospect Progressive Dinner
Wednesday at 6:00 PM
Mount Prospect · Village Of Mount Prospect
MEGAWOOF AMERICA - CHICAGO - RIDE ME !
Sat, Apr 11, 9:00 PM
Chicago · Jackhammer
MEGAWOOF AMERICA - CHICAGO - RIDE ME !
Sat, Apr 11, 9:00 PM
Chicago · Jackhammer
Mend in Public day with Chicago Textile Center
Sun, Apr 26, 12:00 PM
Chicago · The WasteShed
Mend in Public day with Chicago Textile Center
Sun, Apr 26, 12:00 PM
Chicago · The WasteShed
Going fast
Eat the Neighborhood Ramp Foraging Walk and Lunch: Carnivore Oak Park
Sun, Apr 26, 11:00 AM
Oak Park · Carnivore Meats and Seafood
Going fast
Eat the Neighborhood Ramp Foraging Walk and Lunch: Carnivore Oak Park
Sun, Apr 26, 11:00 AM
Oak Park · Carnivore Meats and Seafood
Fleet Feet South Loop: Karhu Demo Run
Mon, Apr 27, 6:00 PM
Chicago · Fleet Feet South Loop
Fleet Feet South Loop: Karhu Demo Run
Mon, Apr 27, 6:00 PM
Chicago · Fleet Feet South Loop
Nature Walk at Hammel Woods - Shorewood
Thu, Apr 23, 5:30 PM
Shorewood · Hammal Woods
Nature Walk at Hammel Woods - Shorewood
Thu, Apr 23, 5:30 PM
Shorewood · Hammal Woods
2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE
Sun, Feb 15, 1:00 PM
Chicago · Chicago
2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE
Sun, Feb 15, 1:00 PM
Chicago · Chicago
Naperville Food Truck Festival
Sat, May 9, 12:00 PM
Naperville · Naper Settlement
Naperville Food Truck Festival
Sat, May 9, 12:00 PM
Naperville · Naper Settlement
The Sunday Recharge
Sun, Jun 21, 11:30 AM + 3 more
Chicago · Chicago
The Sunday Recharge
Sun, Jun 21, 11:30 AM + 3 more
Chicago · Chicago
League of American Bicyclists - League Cycling Advocate Workshop - Chicago
Thu, Sep 17, 8:30 AM
Chicago · Illinois Medical District
League of American Bicyclists - League Cycling Advocate Workshop - Chicago
Thu, Sep 17, 8:30 AM
Chicago · Illinois Medical District
2026 He is Risen 1M 5K 10K 13.1 26.2- Benefitting Easter Seals
Sun, Apr 5, 1:00 PM
Chicago · Chicago
2026 He is Risen 1M 5K 10K 13.1 26.2- Benefitting Easter Seals
Sun, Apr 5, 1:00 PM
Chicago · Chicago
Sales end soon
The Drag Queen Party Bus Columbus - The Ultimate Drag Experience
Friday at 8:00 PM + 394 more
Columbus · Drag Queen Party Bus Columbus
Sales end soon
The Drag Queen Party Bus Columbus - The Ultimate Drag Experience
Friday at 8:00 PM + 394 more
Columbus · Drag Queen Party Bus Columbus
Saturday Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo
Sat, May 2, 6:30 PM
Chicago · Lincoln Park Zoo
Saturday Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo
Sat, May 2, 6:30 PM
Chicago · Lincoln Park Zoo
FREESTYLE FRIDAY @Puerto Rican Festival Chicago
Fri, Jun 12, 3:00 PM
Chicago · Humboldt Park, 2800 W Division St, Chicago, IL, USA
FREESTYLE FRIDAY @Puerto Rican Festival Chicago
Fri, Jun 12, 3:00 PM
Chicago · Humboldt Park, 2800 W Division St, Chicago, IL, USA
Earth Day 5K Virtual Race 2026
Sun, Apr 19, 1:00 PM
Chicago · Chicago
Earth Day 5K Virtual Race 2026
Sun, Apr 19, 1:00 PM
Chicago · Chicago
2026 Born to Be a Princess 1M 5K 10K 13.1 26.2 - Now Only $16!
Sun, Nov 1, 1:00 PM
Chicago · Chicago
2026 Born to Be a Princess 1M 5K 10K 13.1 26.2 - Now Only $16!
Sun, Nov 1, 1:00 PM
Chicago · Chicago
Terrapin Flyer: Grateful Dead Tribute
Sat, Jun 6, 6:30 PM
Lemont · The Forge Adventure Park & Ziplines
Terrapin Flyer: Grateful Dead Tribute
Sat, Jun 6, 6:30 PM
Lemont · The Forge Adventure Park & Ziplines

Trends in Westchester

Explore more trends

Consider the Wildflowers 1M 5K 10K 13.1 26.2

Consider the Wildflowers 1M 5K 10K 13.1 26.2

Memorial Day 1M 5K 10K 13.1 26.2

Memorial Day 1M 5K 10K 13.1 26.2

Downtown Mount Prospect Progressive Dinner

Downtown Mount Prospect Progressive Dinner

MEGAWOOF AMERICA - CHICAGO - RIDE ME !

MEGAWOOF AMERICA - CHICAGO - RIDE ME !

Mend in Public day with Chicago Textile Center

Mend in Public day with Chicago Textile Center

Eat the Neighborhood Ramp Foraging Walk and Lunch: Carnivore Oak Park

Eat the Neighborhood Ramp Foraging Walk and Lunch: Carnivore Oak Park

Fleet Feet South Loop: Karhu Demo Run

Fleet Feet South Loop: Karhu Demo Run

Nature Walk at Hammel Woods - Shorewood

Nature Walk at Hammel Woods - Shorewood

2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE

2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE

Naperville Food Truck Festival

Naperville Food Truck Festival

The Sunday Recharge

The Sunday Recharge

League of American Bicyclists - League Cycling Advocate Workshop - Chicago

League of American Bicyclists - League Cycling Advocate Workshop - Chicago

2026 He is Risen 1M 5K 10K 13.1 26.2- Benefitting Easter Seals

2026 He is Risen 1M 5K 10K 13.1 26.2- Benefitting Easter Seals

The Drag Queen Party Bus Columbus - The Ultimate Drag Experience

The Drag Queen Party Bus Columbus - The Ultimate Drag Experience

Saturday Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo

Saturday Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo

FREESTYLE FRIDAY @Puerto Rican Festival Chicago

FREESTYLE FRIDAY @Puerto Rican Festival Chicago

Earth Day 5K Virtual Race 2026

Earth Day 5K Virtual Race 2026

2026 Born to Be a Princess 1M 5K 10K 13.1 26.2 - Now Only $16!

2026 Born to Be a Princess 1M 5K 10K 13.1 26.2 - Now Only $16!

Terrapin Flyer: Grateful Dead Tribute

Terrapin Flyer: Grateful Dead Tribute

Things to do around Westchester

Trends in Westchester

1. Free paper shredding

2. Craft fairs

3. Randb

4. Silent party

5. Randb sunday brunch

6. Day party

7. Children activities

8. Brunch

9. Chicago st patricks day

10. Trivia

11. St patrick day

12. Jardin