· Local event
September Sweat Fitness Challenge Begins
Sachs Recreation Center · Deerfield
Free month-long cardio challenge; check registration details.
Organizer information: September Sweat Fitness Challenge Begins · Link to listing
Things to do in the North Shore this week.
Use this North Shore Chicago events calendar to find upcoming family activities, local events, and Chicago Bears games. Browse the month at a glance, then open the official event page for current details.
North Shore eventBears game
Event details by date
No listings match this date range. Try the weekend guide for more outing ideas, or choose All dates.
All 99 calendar listings, including past dates. Dates below are the listed dates, not live availability. Times and multi-day notes are preserved as supplied; use the organizer’s page to confirm time zones, changes and booking details.
September 2026
· Local event
Food Truck Thursdays
Jens Jensen Park · Highland Park
Food trucks, local restaurants, live music, and family-friendly fun.
Organizer information: Food Truck Thursdays · Link to listing
· Local event
Roger That — Summer Concert Series
Jewett Park Pavilion · Deerfield
Pack a picnic for an evening of live music.
Organizer information: Roger That — Summer Concert Series · Link to listing
· Local event
Sounds of Summer — The Jolly Ringwolds
Village Green · Wilmette
Free live music, 7–8:30 PM.
Organizer information: Sounds of Summer — The Jolly Ringwolds · Link to listing
· Local event
Thursday Night Market
Fountain Square · Evanston
Artists, makers, and retailers from the regional community.
Organizer information: Thursday Night Market · Link to listing
· Local event
Downtown Concert — Nashville Nosh
Port Clinton Square · Highland Park
Family-friendly concert, food, and activities, 6–8 PM.
Organizer information: Downtown Concert — Nashville Nosh · Link to listing
· Local event
Nashwood Labor Day Weekend
Downtown Highwood
Country, southern blues, rock, food, and live performances through Sep 6.
Organizer information: Nashwood Labor Day Weekend · Link to listing
· Local event
Sounds of Summer — Funky Enough
Village Green · Wilmette
Free live music, 6–8 PM.
Organizer information: Sounds of Summer — Funky Enough · Link to listing
· Local event
Wilmette French Market
722 Green Bay Road · Wilmette
Fresh flowers, artisan foods, and Saturday market shopping.
Organizer information: Wilmette French Market · Link to listing
· Local event
Winnetka-Northfield-Glencoe Chamber Farmers’ Market — September 5
Winnetka Metra Station · Winnetka
Saturday farmers market, 7:30 AM–12:30 PM.
Organizer information: Winnetka-Northfield-Glencoe Chamber Farmers’ Market — September 5 · Link to listing
· Local event
Braeside Outdoor Farmers Market
Braeside Market Green Space
Local growers, bakeries, artisans, and small businesses.
An organizer link is not yet available for this listing. · Link to listing
· Local event
Quack ’N Splash: Duck Derby
Centennial Family Aquatic Center · Wilmette
Family duck race, 1–1:20 PM.
Organizer information: Quack ’N Splash: Duck Derby · Link to listing
· Local event
Public Art Program Open House
Deerfield Public Library · Deerfield
Meet the featured artists and learn about their work, 6–8 PM.
Organizer information: Public Art Program Open House · Link to listing
· Local event
Ravinia Farmers Market — September 9
Jens Jensen Park · Highland Park
Farmers market with local vendors and live performances, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — September 9 · Link to listing
· Local event
Sounds of Summer — The Yacht Rock-ettes
Wallace Bowl · Wilmette
Free live music, 7–8:30 PM.
Organizer information: Sounds of Summer — The Yacht Rock-ettes · Link to listing
· Local event
Downtown Concert — Notte Italiana
Port Clinton Square · Highland Park
Italian food, live music, and cultural performances, 6–8 PM.
Organizer information: Downtown Concert — Notte Italiana · Link to listing
· Local event
Downtown Concerts at Port Clinton
Port Clinton Square · Highland Park
Free Friday night concert series.
Organizer information: Downtown Concerts at Port Clinton · Link to listing
· Local event
First Friday in Hubbard Woods
Hubbard Woods · Winnetka
Local shopping and community evening, 4–7 PM.
Organizer information: First Friday in Hubbard Woods · Link to listing
· Local event
Sounds of Summer — Jeff Julian
Village Green · Wilmette
Free live music, 6–8 PM.
Organizer information: Sounds of Summer — Jeff Julian · Link to listing
· Local event
Go Green Winnetka Fall Native Plant Sale
Winnetka · Winnetka
Native plant sale hosted by Go Green Winnetka, 9–11 AM.
Organizer information: Go Green Winnetka Fall Native Plant Sale · Link to listing
· Local event
Main Beach Clean-Up
Gillson Beach · Wilmette
Community beach cleanup, 9–11 AM.
Organizer information: Main Beach Clean-Up · Link to listing
· Local event
Pool Member Appreciation Event
Centennial Family Aquatic Center · Wilmette
End-of-season community gathering, 10–11:30 AM.
Organizer information: Pool Member Appreciation Event · Link to listing
· Bears game
Chicago Bears vs. Carolina Panthers
Chicago Bears · 2026 regular season
12:00 PM · FOX · Away
Final: W · Bears 59, opponent 37
Organizer information: Chicago Bears vs. Carolina Panthers · Link to listing
· Local event
Go Green Wilmette Bird Habitat Workday
Gillson Park · Wilmette
Volunteer stewardship workday, 9–11 AM.
Organizer information: Go Green Wilmette Bird Habitat Workday · Link to listing
· Local event
Sounds of Summer — Animal Husbandry
Village Green · Wilmette
Free live music, 7–8:30 PM.
Organizer information: Sounds of Summer — Animal Husbandry · Link to listing
· Local event
Go Green Wilmette Mallinckrodt Park Workday
Mallinckrodt Park · Wilmette
Volunteer habitat workday, 9–11 AM.
Organizer information: Go Green Wilmette Mallinckrodt Park Workday · Link to listing
· Local event
Downtown Concert — Sabor de Libertad
Port Clinton Square · Highland Park
Mexican food, salsa, and live music, 6–8 PM.
Organizer information: Downtown Concert — Sabor de Libertad · Link to listing
· Local event
Downtown Concerts at Port Clinton
Port Clinton Square · Highland Park
Free Friday night concert series.
Organizer information: Downtown Concerts at Port Clinton · Link to listing
· Local event
Sounds of Summer — Louie Zagoras
Village Green · Wilmette
Free live music, 6–8 PM.
Organizer information: Sounds of Summer — Louie Zagoras · Link to listing
· Local event
Deerfield Harvest Fest
Deerfield
Food, cars, music, community, and fireworks.
Organizer information: Deerfield Harvest Fest · Link to listing
· Local event
Northbrook Brewfest
Downtown Northbrook · Northbrook
Local breweries, food, and live entertainment, 5–8 PM; 21+.
Organizer information: Northbrook Brewfest · Link to listing
· Local event
Solar Power Hour
Winnetka Public Library · Winnetka
Community solar education program, 1–3 PM.
· Bears game
Chicago Bears vs. Minnesota Vikings
Chicago Bears · 2026 regular season
12:00 PM · Soldier Field · Home
Final: L · Bears 3, opponent 9
Organizer information: Chicago Bears vs. Minnesota Vikings · Link to listing
· Local event
Evanston Cars & Coffee
Downtown Evanston
Vintage classics, muscle cars, exotics, and unique daily drivers.
Organizer information: Evanston Cars & Coffee · Link to listing
· Local event
HP Community Fall Fest
Highland Park
Food, outdoor activities, and family fun.
Organizer information: HP Community Fall Fest · Link to listing
· Local event
Ravinia Farmers Market — September 23
Jens Jensen Park · Highland Park
Farmers market with local vendors and live performances, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — September 23 · Link to listing
· Local event
Friends of Elmwood Dunes Workday
Elmwood Dunes Preserve · Wilmette
Volunteer stewardship workday, 9–11 AM.
Organizer information: Friends of Elmwood Dunes Workday · Link to listing
· Local event
Sounds of Summer — Are You Ready For It
Wallace Bowl · Wilmette
Free live music, 7–8:30 PM.
Organizer information: Sounds of Summer — Are You Ready For It · Link to listing
· Local event
Downtown Concert — Finale & Scarecrow Trail
Port Clinton Square · Highland Park
Family fall celebration with music, food, pumpkins, and scarecrows, 4–8 PM.
Organizer information: Downtown Concert — Finale & Scarecrow Trail · Link to listing
· Local event
Downtown Concerts at Port Clinton
Port Clinton Square · Highland Park
Free Friday night concert series.
Organizer information: Downtown Concerts at Port Clinton · Link to listing
· Local event
Sounds of Summer — Surfing Bird
Village Green · Wilmette
Free live music, 6–8 PM.
Organizer information: Sounds of Summer — Surfing Bird · Link to listing
· Local event
Bike Winnetka
Winnetka · Winnetka
Community bike event, 3:30–5 PM.
· Local event
Community Garage Sale
Centennial Parking Lot · Wilmette
Community sale, 8:30 AM–noon.
Organizer information: Community Garage Sale · Link to listing
· Local event
Fall Fest
Winnetka Park District · Winnetka
Family fall festival, 4–7 PM.
· Local event
Main Beach Clean-Up
Gillson Beach · Wilmette
Community beach cleanup, 9–11 AM.
Organizer information: Main Beach Clean-Up · Link to listing
· Local event
Oktoberfest
Jens Jensen Park · Highland Park
Community Oktoberfest with food and live entertainment, 4–8 PM.
· Local event
Lake Forest Then & Now Auto Show
Lake Forest
A community auto show for classic and modern car fans.
Organizer information: Lake Forest Then & Now Auto Show · Link to listing
· Local event
Sounds of Summer — The Petty Kings
Hibbard Park · Wilmette
Free live music, 4–5:30 PM.
Organizer information: Sounds of Summer — The Petty Kings · Link to listing
· Bears game
Chicago Bears vs. Philadelphia Eagles
Chicago Bears · 2026 regular season
7:15 PM · Soldier Field · Home
Final: W · Bears 27, opponent 7
Organizer information: Chicago Bears vs. Philadelphia Eagles · Link to listing
October 2026
· Local event
Sounds of Summer — Scott & Sara
Village Green · Wilmette
Free live music, 6–8 PM.
Organizer information: Sounds of Summer — Scott & Sara · Link to listing
· Local event
Wilmette Sounds of Summer
Village Green · Wilmette
Live music, 6–8 PM.
Organizer information: Wilmette Sounds of Summer · Link to listing
· Local event
Fire Department Open House
Northbrook · Northbrook
Public safety open house with the Northbrook Fire Department.
Organizer information: Fire Department Open House · Link to listing
· Bears game
Chicago Bears vs. New York Jets
Chicago Bears · 2026 regular season
12:00 PM · Soldier Field · Home
Final: W · Bears 23, opponent 12
Organizer information: Chicago Bears vs. New York Jets · Link to listing
· Local event
Go Green Wilmette Bird Habitat Workday & Family Day
Gillson Park · Wilmette
Autumn habitat stewardship workday and family seed-gathering activity, 9–11 AM.
Organizer information: Go Green Wilmette Bird Habitat Workday & Family Day · Link to listing
· Local event
Great Highwood Pumpkin Fest
Downtown Highwood
Pumpkin carving, carnival rides, music, and family activities.
Organizer information: Great Highwood Pumpkin Fest · Link to listing
· Local event
Ravinia Farmers Market — October 7
Jens Jensen Park · Highland Park
Wednesday farmers market with local vendors and live performances, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — October 7 · Link to listing
· Local event
Charcuterie Board Painting
Patty Turner Center · Deerfield
Guided painting workshop with supplies included, 6:30–8 PM.
Organizer information: Charcuterie Board Painting · Link to listing
· Local event
Moonlight Movie + Campfire
Winnetka Park District · Winnetka
Outdoor movie and campfire, 6–8:30 PM.
Organizer information: Moonlight Movie + Campfire · Link to listing
· Local event
Fall Tree Planting Workshop
Mallinckrodt Center · Wilmette
Hands-on fall tree planting and overwintering basics.
Organizer information: Fall Tree Planting Workshop · Link to listing
· Local event
Main Beach Clean-Up 10/10
Gillson Beach · Wilmette
Community beach cleanup, 9–11 AM.
Organizer information: Main Beach Clean-Up 10/10 · Link to listing
· Local event
Stews & Brews
Port Clinton Square · Highland Park
Comfort food, beverages, fire pits, and live music.
· Bears game
Chicago Bears at Green Bay Packers
Chicago Bears · 2026 regular season
3:25 PM · Away
Final: L · Bears 7, opponent 31
Organizer information: Chicago Bears at Green Bay Packers · Link to listing
· Local event
Ravinia Farmers Market — October 14
Jens Jensen Park · Highland Park
Wednesday farmers market with local vendors and live performances, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — October 14 · Link to listing
· Local event
Halloween Hoopla Family Fun Fest
Sachs Recreation Center · Deerfield
Family trick-or-treat trail, DJ, and seasonal activities, 5:30–7:30 PM.
Organizer information: Halloween Hoopla Family Fun Fest · Link to listing
· Local event
Wicked Wilmette
Gillson Park · Wilmette
A family Halloween event with activities for kids.
· Bears game
Chicago Bears at Atlanta Falcons
Chicago Bears · 2026 regular season
12:00 PM · Away
Final: W · Bears 31, opponent 23
Organizer information: Chicago Bears at Atlanta Falcons · Link to listing
· Local event
Charming Charcuterie
Patty Turner Center · Deerfield
Hands-on charcuterie workshop with refreshments, 6:30–7:30 PM.
Organizer information: Charming Charcuterie · Link to listing
· Local event
Ravinia Farmers Market — October 21
Jens Jensen Park · Highland Park
Wednesday farmers market with local vendors and live performances, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — October 21 · Link to listing
· Bears game
Chicago Bears vs. New England Patriots
Chicago Bears · 2026 regular season
7:15 PM · Soldier Field · Home
Organizer information: Chicago Bears vs. New England Patriots · Link to listing
· Local event
Glow Workout
Patty Turner Center · Deerfield
Neon-themed all-level fitness class with music and refreshments, 6:30–8:30 PM.
· Local event
Pumpkins in the Woods
Winnetka Park District · Winnetka
Family pumpkin event, 4–6 PM.
Organizer information: Pumpkins in the Woods · Link to listing
· Local event
Ravinia District Halloween Candy Stroll
Ravinia District · Highland Park
Family trick-or-treating with participating local businesses.
Organizer information: Ravinia District Halloween Candy Stroll · Link to listing
· Local event
Gillson Beach Cleanup
Gillson Beach · Wilmette
Community beach cleanup, 9–11 AM.
Organizer information: Gillson Beach Cleanup · Link to listing
· Local event
Main Beach Clean-Up 10/24
Gillson Beach · Wilmette
Community beach cleanup, 9–11 AM.
Organizer information: Main Beach Clean-Up 10/24 · Link to listing
· Local event
PTC Community Band Concert: Autumn Winds
Patty Turner Center · Deerfield
Deerfield Community Band concert, 1–2 PM.
Organizer information: PTC Community Band Concert: Autumn Winds · Link to listing
· Local event
Puzzling for Prizes — Halloween Edition
Patty Turner Center · Deerfield
Team puzzle competition with costumes and prizes, 6:30–8:30 PM.
Organizer information: Puzzling for Prizes — Halloween Edition · Link to listing
· Local event
Ravinia Farmers Market — October 28
Jens Jensen Park · Highland Park
Final Wednesday farmers market of the 2026 season, 7 AM–1 PM.
Organizer information: Ravinia Farmers Market — October 28 · Link to listing
· Local event
Spooky Skate
Centennial Ice Rinks · Wilmette
Family Halloween skating event, 1–2:30 PM.
· Local event
Wilmette Children’s Theater: Mary Poppins Jr.
Community Recreation Center · Wilmette
Fall production opening weekend.
Organizer information: Wilmette Children’s Theater: Mary Poppins Jr. · Link to listing
November 2026
· Bears game
Chicago Bears at Seattle Seahawks
Chicago Bears · 2026 regular season
7:15 PM · Away
Organizer information: Chicago Bears at Seattle Seahawks · Link to listing
· Local event
First Fridays MainStreet Libertyville
Downtown Libertyville · Libertyville
Recurring First Friday community evening; confirm the 2026 program and hours.
Organizer information: First Fridays MainStreet Libertyville · Link to listing
· Bears game
Chicago Bears vs. Tampa Bay Buccaneers
Chicago Bears · 2026 regular season
7:20 PM · Soldier Field · Home
Organizer information: Chicago Bears vs. Tampa Bay Buccaneers · Link to listing
· Local event
Veterans Day Observance
Highland Park · Highland Park
City of Highland Park annual observance, 11 AM.
Organizer information: Veterans Day Observance · Link to listing
· Local event
Let’s Play! Geological Exploration
Winnetka Park District · Winnetka
Family exploration program, 4–7 PM.
Organizer information: Let’s Play! Geological Exploration · Link to listing
· Local event
Northbrook Anniversary Open House
Northbrook · Northbrook
Community open house celebrating Northbrook’s anniversary.
Organizer information: Northbrook Anniversary Open House · Link to listing
· Local event
Northbrook 125th Anniversary
Village of Northbrook · Northbrook
Community anniversary programming marking Northbrook’s 125th year.
Organizer information: Northbrook 125th Anniversary · Link to listing
· Local event
Illuminate Northbrook
Downtown Northbrook · Northbrook
Northbrook holiday lighting celebration.
Organizer information: Illuminate Northbrook · Link to listing
· Local event
ArtWauk
Downtown Waukegan · Waukegan
Recurring third-Saturday arts event; confirm the 2026 program and venues.
· Bears game
Chicago Bears vs. New Orleans Saints
Chicago Bears · 2026 regular season
12:00 PM · Soldier Field · Home
Organizer information: Chicago Bears vs. New Orleans Saints · Link to listing
· Local event
Santa’s Mailbox Opens
Winnetka Park District · Winnetka
Seasonal Santa mailbox open November 25 through December 18.
Organizer information: Santa’s Mailbox Opens · Link to listing
· Bears game
Chicago Bears at Detroit Lions
Chicago Bears · 2026 regular season
12:00 PM · Thanksgiving · Away
Organizer information: Chicago Bears at Detroit Lions · Link to listing
December 2026
· Local event
First Fridays MainStreet Libertyville
Downtown Libertyville · Libertyville
Recurring First Friday community evening; confirm the 2026 program and hours.
Organizer information: First Fridays MainStreet Libertyville · Link to listing
· Bears game
Chicago Bears vs. Jacksonville Jaguars
Chicago Bears · 2026 regular season
12:00 PM · Soldier Field · Home
Organizer information: Chicago Bears vs. Jacksonville Jaguars · Link to listing
· Bears game
Chicago Bears at Miami Dolphins
Chicago Bears · 2026 regular season
12:00 PM · Away
Organizer information: Chicago Bears at Miami Dolphins · Link to listing
· Local event
ArtWauk
Downtown Waukegan · Waukegan
Recurring third-Saturday arts event; confirm the 2026 program and venues.
· Bears game
Chicago Bears at Buffalo Bills
Chicago Bears · 2026 regular season
7:20 PM · Away
Organizer information: Chicago Bears at Buffalo Bills · Link to listing
· Bears game
Chicago Bears vs. Green Bay Packers
Chicago Bears · 2026 regular season
12:00 PM · Christmas · Soldier Field · Home
Organizer information: Chicago Bears vs. Green Bay Packers · Link to listing
January 2027
· Bears game
Chicago Bears vs. Detroit Lions
Chicago Bears · 2026 regular season
3:25 PM · Soldier Field · Home
Organizer information: Chicago Bears vs. Detroit Lions · Link to listing
· Bears game
Chicago Bears at Minnesota Vikings
Chicago Bears · 2026 regular season
Time TBD · Away · Week 18
Organizer information: Chicago Bears at Minnesota Vikings · Link to listing
Plan the rest of the day
Find a nearby restaurant, pizza spot, youth activity, or practical service in the Loktin directory.
November & December plans
More holiday listings are published by local organizers throughout the fall. Check these official calendars for the newest dates before you go.
Plan a North Shore weekend
Use the calendar’s list view for upcoming events and official event details. Build a day around the schedule with local dining guides and restaurant websites.
Pizza restaurants · Fine dining · Italian restaurants · Search the full directory