Trail ride Events and Things to do in Westchester, IL

St. Sava Academy's 3rd Annual Beneficiary Event
Mon, Apr 27, 6:30 PM
Burr Ridge · Topaz Café
St. Sava Academy's 3rd Annual Beneficiary Event
Mon, Apr 27, 6:30 PM
Burr Ridge · Topaz Café
Walk MS with 3G Realty Group: Join Our Team for the MS Walk
Sun, May 17, 9:00 AM
Orland Park · Orland Park 153rd Street Metra Station
Walk MS with 3G Realty Group: Join Our Team for the MS Walk
Sun, May 17, 9:00 AM
Orland Park · Orland Park 153rd Street Metra Station
Chicago Fight For Air Climb
Sun, Apr 12, 8:00 AM
Chicago · Prudential Plaza
Chicago Fight For Air Climb
Sun, Apr 12, 8:00 AM
Chicago · Prudential Plaza
2026 Day of the Dead 1M 5K 10K 13.1 26.2
Sat, Mar 14, 1:00 PM
Chicago · Chicago
2026 Day of the Dead 1M 5K 10K 13.1 26.2
Sat, Mar 14, 1:00 PM
Chicago · Chicago
First Sunday Walking Tour at Pullman National Historical Park - May 2026
Sun, May 3, 1:00 PM
Chicago · Pullman Exhibit Hall
First Sunday Walking Tour at Pullman National Historical Park - May 2026
Sun, May 3, 1:00 PM
Chicago · Pullman Exhibit Hall
Bike Night at The Chill House Arklight Live on the Outdoor Stage
Fri, May 15, 6:00 PM
Frankfort · 7905 W Lincoln Hwy
Bike Night at The Chill House Arklight Live on the Outdoor Stage
Fri, May 15, 6:00 PM
Frankfort · 7905 W Lincoln Hwy
250 Miles for America's 250th Birthday Running and WalkingChallenge
Tue, Feb 3, 1:00 PM
Chicago · Chicago
250 Miles for America's 250th Birthday Running and WalkingChallenge
Tue, Feb 3, 1:00 PM
Chicago · Chicago
2026 Full Armor of God 1M, 5K, 10K, 13.1, 26.2
Sat, Feb 7, 1:00 PM
Chicago · Chicago
2026 Full Armor of God 1M, 5K, 10K, 13.1, 26.2
Sat, Feb 7, 1:00 PM
Chicago · Chicago
2026 Capy "Happy" Birthday To Me 2026
Sat, Jan 31, 1:00 PM
Chicago · ILLINOIS VIRTUAL
2026 Capy "Happy" Birthday To Me 2026
Sat, Jan 31, 1:00 PM
Chicago · ILLINOIS VIRTUAL
2026 Be Brave 1M 5K 10K 13.1 26.2
Sat, Mar 7, 1:00 PM
Chicago · Chicago
2026 Be Brave 1M 5K 10K 13.1 26.2
Sat, Mar 7, 1:00 PM
Chicago · Chicago
Joliet Eat the Neighborhood Foraging Walk: Route 66 Park
Sat, Jun 13, 2:00 PM
Joliet · Route 66 Park
Joliet Eat the Neighborhood Foraging Walk: Route 66 Park
Sat, Jun 13, 2:00 PM
Joliet · Route 66 Park
Explore Haunted Stories at St Charles Walking Ghost Tour.
Fri, May 15, 8:00 PM + 4 more
St. Charles · Riverside Pizza & Pub - St. Charles
Explore Haunted Stories at St Charles Walking Ghost Tour.
Fri, May 15, 8:00 PM + 4 more
St. Charles · Riverside Pizza & Pub - St. Charles
Just added
Chicago River Day 2026 - Dammrich Rowing Center ~On the Water~
Sat, May 9, 9:00 AM
Skokie · Dammrich Rowing Center
Just added
Chicago River Day 2026 - Dammrich Rowing Center ~On the Water~
Sat, May 9, 9:00 AM
Skokie · Dammrich Rowing Center
Just added
Chicago River Day 2026- Lincolnwood Centennial Park
Sat, May 9, 9:00 AM
Lincolnwood · Lincolnwood Centennial Park Sculpture Walk
Just added
Chicago River Day 2026- Lincolnwood Centennial Park
Sat, May 9, 9:00 AM
Lincolnwood · Lincolnwood Centennial Park Sculpture Walk
Fleet Feet Running Club: Fleet Feet Lincoln Square
Mon, Mar 30, 6:00 PM + 39 more
Chicago · Fleet Feet Lincoln Square
Fleet Feet Running Club: Fleet Feet Lincoln Square
Mon, Mar 30, 6:00 PM + 39 more
Chicago · Fleet Feet Lincoln Square
Sales end soon
Chicago: Millennium Park Self-Guided Walking Audio Tour
Today at 7:00 PM + 475 more
Chicago · Millennium Park Welcome Center
Sales end soon
Chicago: Millennium Park Self-Guided Walking Audio Tour
Today at 7:00 PM + 475 more
Chicago · Millennium Park Welcome Center
Customizable Scenic Chicago Driving Tour
Today at 9:30 AM + 427 more
chicago · Downtown Chicago
Customizable Scenic Chicago Driving Tour
Today at 9:30 AM + 427 more
chicago · Downtown Chicago
Fleet Feet Health Fair with Altra, Athletico, Orange Theory and SPRINTS
Wed, Apr 1, 6:30 PM
Algonquin · Scorched Earth Brewing Company
Fleet Feet Health Fair with Altra, Athletico, Orange Theory and SPRINTS
Wed, Apr 1, 6:30 PM
Algonquin · Scorched Earth Brewing Company
Wine Crawl - RSVP for Our Next Experience in the South Suburbs
Sun, May 24, 2:00 PM
Naperville · TBD
Wine Crawl - RSVP for Our Next Experience in the South Suburbs
Sun, May 24, 2:00 PM
Naperville · TBD
Sales end soon
Fleet Feet Running Club: Fleet Feet Algonquin
Tomorrow at 6:00 PM + 7 more
Algonquin · Fleet Feet Algonquin
Sales end soon
Fleet Feet Running Club: Fleet Feet Algonquin
Tomorrow at 6:00 PM + 7 more
Algonquin · Fleet Feet Algonquin

Trends in Westchester

Explore more trends

St. Sava Academy's 3rd Annual Beneficiary Event

St. Sava Academy's 3rd Annual Beneficiary Event

Walk MS with 3G Realty Group: Join Our Team for the MS Walk

Walk MS with 3G Realty Group: Join Our Team for the MS Walk

Chicago Fight For Air Climb

Chicago Fight For Air Climb

2026 Day of the Dead 1M 5K 10K 13.1 26.2

2026 Day of the Dead 1M 5K 10K 13.1 26.2

First Sunday Walking Tour at Pullman National Historical Park - May 2026

First Sunday Walking Tour at Pullman National Historical Park - May 2026

Bike Night at The Chill House Arklight Live on the Outdoor Stage

Bike Night at The Chill House Arklight Live on the Outdoor Stage

250 Miles for America's 250th Birthday Running and WalkingChallenge

250 Miles for America's 250th Birthday Running and WalkingChallenge

2026 Full Armor of God 1M, 5K, 10K, 13.1, 26.2

2026 Full Armor of God 1M, 5K, 10K, 13.1, 26.2

2026 Capy "Happy" Birthday To Me 2026

2026 Capy "Happy" Birthday To Me 2026

2026 Be Brave 1M 5K 10K 13.1 26.2

2026 Be Brave 1M 5K 10K 13.1 26.2

Joliet Eat the Neighborhood Foraging Walk: Route 66 Park

Joliet Eat the Neighborhood Foraging Walk: Route 66 Park

Explore Haunted Stories at St Charles Walking Ghost Tour.

Explore Haunted Stories at St Charles Walking Ghost Tour.

Chicago River Day 2026 - Dammrich Rowing Center ~On the Water~

Chicago River Day 2026 - Dammrich Rowing Center ~On the Water~

Chicago River Day 2026- Lincolnwood Centennial Park

Chicago River Day 2026- Lincolnwood Centennial Park

Fleet Feet Running Club: Fleet Feet Lincoln Square

Fleet Feet Running Club: Fleet Feet Lincoln Square

Chicago: Millennium Park Self-Guided Walking Audio Tour

Chicago: Millennium Park Self-Guided Walking Audio Tour

Customizable Scenic Chicago Driving Tour

Customizable Scenic Chicago Driving Tour

Fleet Feet Health Fair with Altra, Athletico, Orange Theory and SPRINTS

Fleet Feet Health Fair with Altra, Athletico, Orange Theory and SPRINTS

Wine Crawl - RSVP for Our Next Experience in the South Suburbs

Wine Crawl - RSVP for Our Next Experience in the South Suburbs

Fleet Feet Running Club: Fleet Feet Algonquin

Fleet Feet Running Club: Fleet Feet Algonquin

Things to do around Westchester

Trends in Westchester

1. Craft fairs

2. Randb

3. Free paper shredding

4. Silent party

5. Randb sunday brunch

6. Day party

7. Children activities

8. Brunch

9. Easter events

10. Chicago st patricks day

11. Trivia

12. St patrick day