World Cup Watch Party at Cesaroni’s Deli
World Cup Watch Party at Cesaroni's Deli
Woodstock Wine Walk 2023
The Woodstock Wine Walk returns
Woodstock PrideFest Rainbow Run 2023
Color, Color everywhere!
Woodstock PrideFest Pub Crawl 2023
We're going on a Pub Crawl
Woodstock Pride Promenade 2023
Woodstock is Bursting with Pride
Woodstock Pride Fest 2023
Woodstock is Bursting with Pride
Woodstock Moose Lodge #1329 Sunday Groundhog Day Breakfast
Woodstock Moose Lodge #1329 Sunday Groundhog Day Breakfast
Woodstock Fourth of July Fireworks 2023
Woodstock Fourth of July Fireworks
Woodstock Folk Festival
Woodstock Folk Festival
Woodstock Community Choir “Greatest Hits” Concert
Woodstock Community Choir "Greatest Hits" Concert
Wine with Willie
Wine with Willie
Wheels North – Live Jammin Bluegrass – FREE
Wheels North - Live Jammin Bluegrass - FREE
Wheels North – Live Jammin Bluegrass – FREE
Wheels North - Live Jammin Bluegrass - FREE
WACM Saturday Morning Children March Show
WACM Saturday Morning Children Shows
WACM Saturday Morning Children January Show
WACM Saturday Morning Children Shows
WACM Saturday Morning Children February Show
WACM Saturday Morning Children Shows
Vintage Shop Hop Spring 2023
The Vintage Shop Hop is a self-guided day of vintage & boutique shopping held twice a year.
Ugly Sweater Party and Contest at Holzlager Brewing
Ugly Sweater Party and Contest
Treasure Island – A Participation Play for Children
Treasure Island - A Participation Play for Children
The Woolly Buggers – LIVE MUSIC – Free Show
The Woolly Buggers - LIVE MUSIC - Free Show
The Rockets Band at Kingston Lanes
The Rockets Band at Kingston Lanes
The Hogmires – Live Music Event – FREE
The Hogmires - Live Music Event - FREE
The Creation of South Pacific – Charles Troy
The Creation of South Pacific - Charles Troy
The Creation of King and I – Charles Troy
The Creation of King and I - Charles Troy
The Creation of Funny Girl – Charles Troy
The Creation of Funny Girl - Charles Troy
The Creation of Camelot – Charles Troy
The Creation of Camelot - Charles Troy
The Comedy Zone – Simon Taylor
The Comedy Zone - Simon Taylor
The Comedy Zone – Johnny Beehner and J Tyler Menz
The Comedy Zone - Johnny Beehner and J Tyler Menz
The Blue Shield Band – FREE EVENT
The Blue Shield Band - FREE EVENT
The Blue Shied Band – Free Event at Holzlager Brewing
The Blue Shied Band - Free Event
The Blooze Brothers
The Blooze Brothers
Thank You For Being a Friend: An Afternoon with The Golden Girls
Thank You For Being a Friend: An Afternoon with The Golden Girls
Tea & D: Night Before Christmas
Tea & D: Night Before Christmas
SUPER ROLL Pins For Independence
SUPER ROLL Pins For Independence
Stage Left Cafe – Trivia Night
Pub Trivia USA at Stage Left Cafe
Stage Left Cafe – 2023 Trivia Night
Pub Trivia USA at Stage Left Cafe
St. Mary School Merry Little Market Craft Show and Bake Shoppe
St. Mary School Merry Little Market Craft Show and Bake Shoppe
Sparkling Wine Dinner at Emerson & Olivers
Sparkling Wine Dinner at Emerson & Olivers
Solo piano man show at Sofie’s
Solo piano man at Sofie's
SING-O at Offsides 2023
SING-O at Offsides
Sausage Fest 2022 at Holzlager Brewing
Sausage Fest 2022
Santa Visits in the Rotary Club Christmas Hut
Santa Returns to the Hut!
Rockturnal Band at Kingston Lanes
Rockturnal Band at Kingston Lanes
Rock N’ Roll and Philly Cheese Steak Party at Holzlager Brewing
Rock N' Roll and Philly Cheese Steak Party
Red Corvette – A Prince Tribute Band
Red Corvette - A Prince Tribute Band
Rail Fest 2023
Model train enthusiasts and families looking for some weekend fun are sure to enjoy our third Woodstock Rail Fest event
Puzzle Palooza – Groundhog Days
Puzzle Palooza - Groundhog Days
Puppy Pals – Comedic Dog Stunt Show
Puppy Pals - Comedic Dog Stunt Show
Parenting in a Digital Age
Parenting in a Digital Age
Opera House Tours
Opera House Tours
Open Mic Night at Stage Left Cafe
Open Mic Night at Stage Left Cafe
of Books & Blues Band at Kingston Lanes
of Books & Blues Band at Kingston Lanes
of Books & Blues Band at Kingston Lanes
of Books & Blues Band at Kingston Lanes
New Year’s Eve Bowling and Karaoke
New Year's Eve Bowling and Karaoke
Neil Rose Band at Kingston Lanes
Neil Rose Band at Kingston Lanes
Miss Woodstock 2023 Scholarship Pageant
Join us for the 74th Annual Scholarship Pageant as we crown our 2023 Queens.
Micro Wrestling 2023 at Porkies
Get in on the action at Porkies
Mexican Independence Day Celebration
Sixth annual Mexican Independence Day Celebration this year in the Historic Woodstock Square!
Mardi Gras Party 2023 – All Day Event at Holzlager
Mardi Gras Party 2023 - All Day Event
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Makers Market – Sunday Funday – Live Music at Holzlager
Makers Market - Sunday Funday - Live Music
Lucky Pickers LIVE at the Holzlager Maker’s Market
Lucky Pickers LIVE at the Holzlager Maker's Market
Live Tunes & Great Eats with The Been Reals & Smash’D Burgers Saturday
Live Tunes & Great Eats with The Been Reals & Smash’D Burgers Saturday
Lighting of the Square 2023
Visit the beautiful and historic Square on the Friday after Thanksgiving and watch the flip of the switch
Lighting of the Square
Visit the beautiful and historic Square on the Friday after Thanksgiving and watch the flip of the switch
Lighting of The Cabin
Lighting of The Cabin
Ladies Nite Out 2023
Ladies Nite Out in Woodstock is a long standing tradition started years ago to celebrate you ladies who selflessly work to make the Holidays special
Karaoke with Sundowner Entertainment at Kingston Lanes
Karaoke with Sundowner Entertainment
Karaoke Night with DJHarps at Kingston Lanes
Karaoke Night with DJHarps
John McGivern’s Main Streets Free Sneak Peek at The Woodstock Opera House
John McGivern's Main Streets Free Sneak Peek at The Woodstock Opera House
Jesse Fuller – LIVE – Free Show
Jesse Fuller - LIVE - Free Show
Jesse Fuller – LIVE – Free Show
Jesse Fuller - LIVE - Free Show
Houseplants & Tea
Houseplants & Tea
Hometowns to Hollywood: The Women who Built Hollywood
Hometowns to Hollywood: The Women who Built Hollywood
Hometowns to Hollywood: Icons of Fashion
Hometowns to Hollywood: Icons of Fashion
Hometowns to Hollywood: Fred & Ginger
Hometowns to Hollywood: Fred & Ginger
Hometowns to Hollywood: Dynamic Duos
Hometowns to Hollywood: Dynamic Duos
Holidaze Maker’s Market
Holidaze Maker's Market
Holiday Market on the Square
Holiday Market on the Square
Helping Paws Grinchmas Party at Kishwaukee Brewing
Helping Paws Grinchmas Party at Kishwaukee Brewing
Groundhog Days Pop Up Bar at Stage Left Cafe Woodstock Square
Groundhog Days Pop Up Bar at Stage Left Cafe Woodstock Square
Groundhog Days B&B Tours
Groundhog Days B&B Tours
Groundhog Day Complimentary Photo Booth from Westward 360
Groundhog Day Complimentary Photo Booth from Westward 360
Groundhog Day Celebration at Isabel’s Family Restaurant
Groundhog Day Celebration at Isabel's Family Restaurant
Groundhog Day Breakfast at Ethereal
Groundhog Day Breakfast
Groundhog Day 30th Anniversary Tip Top Cafe Breakfast
Groundhog Day 30th Anniversary Tip Top Cafe Breakfast
Groundhog Breakfast Buffet at Main Street Pour House
Groundhog Breakfast Buffet at Main Street Pour House
Girl Named Tom
Girl Named Tom
Gingerbread Make & Take
Gingerbread Make & Take
Free Taproom Trivia every Wednesday Night at Kishwaukee Brewing
Free Taproom Trivia every Wednesday Night
Free Bar Bingo at Kingston Lanes
Free Bar Bingo
Football – Smash Burger – Beer Special Party
Football - Smash Burger - Beer Special Party
First Annual Dog Show and BarkBQ!
First Annual Dog Show and BarkBQ!
Ed Hall’s Woodstock Guitar Night
Ed Hall's Woodstock Guitar Night
Eat, Shop + Be Merry Holiday Market at Kishwaukee Brewing
Eat, Shop + Be Merry Holiday Market at Kishwaukee Brewing
Despina & Cassie from The Fox Crossing String Band – FREE Show
Despina & Cassie from The Fox Crossing String Band - FREE Show
Customer Appreciation Day at Cesaroni’s Deli
World Cup Watch Party at Cesaroni's Deli
Cookies with Santa
Cookies with Santa
Cookies and Churros with Santa 2023
All are invited to this free event for the true belivers
Community Festival: Summer in The Park
Community Day at the Woodstock Recreation Center
Community Day at the Woodstock Recreation Center
Community Day at the Woodstock Recreation Center
Community Day at the Woodstock Recreation Center
Community Day at the Woodstock Recreation Center
Community Day at the Woodstock Recreation Center
Christmas Clearing House – 2022 Delivery Day!
Christmas Clearing House - Delivery Day!
Chill Murray Presents: Chicago Comedy Takeover 2023
Chill Murray Presents: Chicago Comedy Takeover
Chill Murray Presents: Chicago Comedy Takeover 2022
Chill Murray Presents: Chicago Comedy Takeover
Challenger Center Family Night Open House
Challenger Center Family Night Open House
CASA Information Session
CASA Information Session
Broken Arrow Band at Kingston Lanes
Broken Arrow Band at Kingston Lanes
Broken Arrow Band at Kingston Lanes
Broken Arrow Band at Kingston Lanes
Brewery Food Pop-Up – Uncle Cam’s Sandwich’s & Soups at Holzlager
Brewery Food Pop-Up - Uncle Cam's Sandwich's & Soups
Bowling with Santa
Bowling with Santa
Bourbon Country
Bourbon Country plays Sofie's
Bossy Dog at Kingston Lanes
Bossy Dog at Kingston Lanes
Black Wednesday at Kingston Lanes
Black Wednesday at Kingston Lanes
Black Friday Trim Party at Hempstock Pharm
Black Friday Trim Party at Hempstock Pharm
Benton Street Fests presents Shamrocked
Benton Street Fests presents Shamrocked
Author Event: Alyssa Wees
Author Event: Alyssa Wees
Artisans on Main / Clayworkers’ Guild 1st Anniversary Celebration
Artisans on Main / Clayworkers' Guild 1st Anniversary Celebration
An Evening With Jim Messina
An Evening With Jim Messina
All Ages Punk Show at Warp Corps
All Ages Punk Show at Warp Corps
All Ages EDM/Hip-Hop Show at Warp Corps
All Ages EDM/Hip-Hop Show at Warp Corps
Afternoon Tea: It’s a Date
Afternoon Tea: It's a Date
Afternoon Tea: It’ll All Workout
Afternoon Tea: It'll All Workout
Afternoon Tea: Holiday Comforts at Casting Whimsy
Afternoon Tea: Holiday Comforts at Casting Whimsy
Abominable Snow Race #StompOutHunger Event at Holzlager Brewing
Abominable Snow Race #StompOutHunger Event
65 North Pickers – St. Patrick’s Day Weekend Party at Holzlager
65 North Pickers - St. Patrick's Day Weekend Party at Holzlager
2023 Woodstock Square Easter Eggstravaganza
2023 Woodstock Square Easter Eggstravaganza
2023 Groundhog Days- Welcoming of the Groundhog
Join us to Welcome Woodstock Willie
2023 Groundhog Days- Guided Walking Tour
Join us for a guided walking tour of sites
2023 Groundhog Days- Danny Rubin Live
Join us to Welcome Woodstock Willie
2023 Groundhog Days – Pub Crawl
Who doesn't enjoy a pub crawl
2023 Groundhog Days – Prognostication
Join Woodstock Willie as they make their prediction for the winter.
2023 Groundhog Days – Official Groundhog Day Breakfast
The official Groundhog Day Breakfast is back
2023 Groundhog Days – Movie Memorabilia Open House
2023 Groundhog Days - Movie Memorabilia Open House
2023 Groundhog Days – Groundhog Day Trivia
Free GHD Trivia will be held in the Woodstock Opera House
2023 Groundhog Days – Groundhog Day the Movie
Enjoy our favorite movie on the big screen
2023 Groundhog Days – Drink to World Peace
We always drink to world peace
2023 Groundhog Days – Dinner & Dance at the Moose Lodge
Groundhog Days - Dinner & Dance at the Moose Lodge
2023 Groundhog Days – Bingo
GHD Bingo is back
2023 Groundhog Days – Bags Tournament
The Bags Tournament tradition continues at Ortmann's Red Iron Tavern
2023 Annual Woodstock Christmas Parade
Let's welcome the man in the red suit back to Woodstock
10th Annual Woodstock Ale Fest
Woodstock Ale Fest is back!