Monthly Business Owners & Leaders Connection (formerly B.O.M.)

Local Business Owners & Leaders Connection (formerly B.O.M.) hosted by the City with Chamber of Commerce to bring local Business Owners & Leaders together monthly to share information and discuss issues affecting the Woodstock business community.

Opera House Community Room

Valentine's Day Family Bingo

 LOVE IS IN THE AIR… AND BINGO IS ON THE CARD!  Bring the whole family and fall in love with Family Bingo Night!  Tuesday February 10th  6-7:30 PM  Kingston Lanes  Sweet prizes  Lots of laughs  Great vibes  Quality family time Whether you’re winning BI......More

 LOVE IS IN THE AIR… AND BINGO IS ON THE CARD!  Bring the whole family and fall in love with Family Bingo Night!  Tuesday February 10th  6-7:30 PM  Kingston Lanes  Sweet prizes  Lots of laughs  Great vibes  Quality family time Whether you’re winning BINGO or just cheering each other on, it’s a night full of love, laughter, and a little friendly competition.  Because the best Valentine is family.   Spots are limited — call to reserve your table! 815-338-2105

Kingtson Lanes

Making Connections: A Business Networking Lunch with a Twist

Looking to grow your network without the awkward elevator pitches? Join the Woodstock Chamber for Making Connections, a fun and engaging networking lunch designed to spark real conversations and meaningful connections. This isn’t your typical networking scramble. In......More

Looking to grow your network without the awkward elevator pitches? Join the Woodstock Chamber for Making Connections, a fun and engaging networking lunch designed to spark real conversations and meaningful connections. This isn’t your typical networking scramble. Instead, each table will feature a conversation topic to guide discussion and break the ice. Making it easier to connect, share ideas, and learn from fellow professionals in a relaxed, welcoming setting. You’ll still have plenty of time to exchange business cards, promote your business, and build new relationships, just in a more natural and enjoyable way. Sample table topics may include: Find Your Common Ground Your Favorite Thing About What You Do The Best Advice You’ve Ever Received in Business Whether you’re a seasoned networker or attending your first Chamber event, Making Connections offers a fresh, low-pressure way to connect with others while enjoying lunch.  Date: Wednesday, February 11, 2026  Time: 11:30 AM – 1:00 PM  Location: Woodstock Community Room  Cost: $25 Members | $35 Non-Members  Lunch provided Come ready to connect, collaborate, and have a little fun while doing it!

Woodstock Opera House Community Room

Paws on the Patio

Join us for a delightful evening on the patio at Squire on the Square, where great food and drinks meet a great cause! A portion of the evening's proceeds will benefit Helping Paws Animal Shelter, supporting our mission to provide shelter, food, medical care, and com......More

Join us for a delightful evening on the patio at Squire on the Square, where great food and drinks meet a great cause! A portion of the evening's proceeds will benefit Helping Paws Animal Shelter, supporting our mission to provide shelter, food, medical care, and comfort to abandoned, neglected, and abused animals until they find loving homes. Something for your pup to enjoy, a Sniff & Snack special: rice bowl with choice of beef or chicken along with a Pup Cup for dessert all for only $10. Enjoy the patio with your favorite drink, savor delicious bites, and enjoy the company of fellow animal lovers?all while making a difference in the lives of animals in need. Volunteers will be out with a few of our available pups as well.

Squire on the Square 101 N. Johnson St. Woodstock, IL 60098

Xtreme Bar Bingo at Kingston Lanes

Thursdays are for Bingo! Free to Play! New and progressive prizes each week!

Kingston Lanes

Regular Open Mic

Two songs or 10 minutes.   Sound system provided

Stage Left Cafe, adjacent to the Opera House Woodstock IL

Valentine's Day Dog Event

Get a picture of your dog, taken with a cute Valentine’s Day backdrop with Nicole Sutton Photography. Plus,K9s4U will represent and you can find out more about helping our furry friends thrive! Sunshine Canine Training will do nail trims too. Stop by and see us here on ......More

Get a picture of your dog, taken with a cute Valentine’s Day backdrop with Nicole Sutton Photography. Plus,K9s4U will represent and you can find out more about helping our furry friends thrive! Sunshine Canine Training will do nail trims too. Stop by and see us here on Green Street!

1218 N. Green Street, McHenry, Illinois 60050, McHenry, IL

Mystic Menagerie

Hosted by Our Happy Space at the Woodstock Square Mall 110 S Johnson Street, Woodstock IL, 60098 Saturday February 14th, 2026 FREE TO THE PUBLIC! Shop among local readers, mystics and spooky small businesses! This event will feature spooky goods, crystals, and han......More

Hosted by Our Happy Space at the Woodstock Square Mall 110 S Johnson Street, Woodstock IL, 60098 Saturday February 14th, 2026 FREE TO THE PUBLIC! Shop among local readers, mystics and spooky small businesses! This event will feature spooky goods, crystals, and handcrafted witchy tools amongst many curios and oddities.  MARKET | 12 PM - 4 PM PARANORMAL INVESTIGATION | 6 PM - 8 PM Sign up in advance for the paranormal investigation of the Woodstock Square Mall. Learn about the history of the mall, and see different types of tools and communication strategies used by professional ghost hunters. Sign up here through EventBrite: https://www.eventbrite.com/e/woodstock-mall-paranormal-investigation-tickets-1980124529772?utm-campaign=social&utm-content=attendeeshare&utm-medium=discovery&utm-term=listing&utm-source=cp&aff=ebdsshcopyurl 

The Woodstock Square Mall

Woodstock Square Mall Paranormal Investigation

This night of mystical exploration will include communication with the spirits that reside at the Woodstock Square Mall as well as any other spirits that may wander in from the historic Woodstock Square. During this time you will learn a breif history of the space, as ......More

This night of mystical exploration will include communication with the spirits that reside at the Woodstock Square Mall as well as any other spirits that may wander in from the historic Woodstock Square. During this time you will learn a breif history of the space, as well as how to use equipment used by professional paranormal investigators. Ditch the roses this Valentines Day and take your partner to venture through a space filled with secrets to be discovered. Whether you're a skeptic or a believer, this event promises to be an unforgettable experience.

The Woodstock Square Mall

Valentine's Paint & Sip! (Woodstock Studio)

Join us to paint this Valentine's Day at our Woodstock Studio! Great event for date night or girl's night out. Register here at link: https://www.eventbrite.com/e/1981339536891   Our Paint & Sip events are a fun......More

Join us to paint this Valentine's Day at our Woodstock Studio! Great event for date night or girl's night out. Register here at link: https://www.eventbrite.com/e/1981339536891   Our Paint & Sip events are a fun creative art party atmosphere, and by the end, you'll create your beautiful work of art to take home. Choose to create your painting from our inspiration packets and Alicia will guide you step by step through the process. It’s fun to see the different paintings people create! All ages welcome :-) What are we painting: Valentine's Themed packets will be provided to choose a picture from to create your painting to take home. We will be painting on canvases using acrylic paint. You will learn basic painting skills and build confidence in your newly created art. What's Provided: All painting supplies are provided. Food & Drink: Feel free to bring your favorite drinks and snacks. Adults BYOB. Prerequisites: None - all levels and ages welcome. Location: 10016 Bull Valley Road

Location: 10016 Bull Valley Road, Woodstock, IL 60098

Bites & Business at 3Brothers

Good food. Great connections. Thursday, February 19 12:00–1:30 PM 3 Brothers Restaurant 1220 S. Eastwood Dr, Woodstock, IL Bites & Business is a casual, come-as-you-are networking lunch designed to make building relationships easy. There’s no agenda and no pre......More

Good food. Great connections. Thursday, February 19 12:00–1:30 PM 3 Brothers Restaurant 1220 S. Eastwood Dr, Woodstock, IL Bites & Business is a casual, come-as-you-are networking lunch designed to make building relationships easy. There’s no agenda and no pressure, just good food, great conversation, and the chance to connect with fellow local business owners and professionals. Grab a seat, order lunch, and enjoy natural conversations in a relaxed setting. Whether you’re new to the Chamber, a longtime member, or simply looking to expand your network, Bites & Business offers a welcoming way to stay connected. ✔ Open to members and non-members ✔ Order and pay on your own ✔ Come for the full lunch or stop by when you can Held monthly, Bites & Business is your go-to midday opportunity to connect, catch up, and build meaningful business relationships.

3 Brothers Restaurant 1220 S. Eastwood Dr, Woodstock, IL