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  • Santa Shuffle 5k

    Ottawa Township High School Visitor Parking Lot 216 E Main St, Ottawa, IL, United States

    Kick off the holiday season with a festive fun run in downtown Ottawa! Join us on Sunday, November 30 for the First Annual Santa Shuffle, a spirited event for runners, walkers, families, and friends of all ages. Start Time: 9:30 AM (Check-in begins at 7:00 AM) Location: Ottawa Township High School Visitor Parking Lot Registration: […]

  • Family Photos with Santa

    Cat's Eye Wine Bar 724 LaSalle Street, Ottawa, IL, United States

    Capture the magic of the season with a professional family photo session with Santa at CatsEye, right in the heart of downtown Ottawa. What’s included:-A 10-minute photo session with Santa and Brickstreet Studios-3 professionally edited photos delivered in your personal client gallery-A built-in print shop & holiday card ordering system right inside your gallery—making it […]

  • 2nd Annual Krampus Cookie Crawl

    Downtown Ottawa

    Join us for the Second Annual Krampus Cookie Crawl as part of Ottawa’s enchanting Chris Kringle Market on Saturday, December 13! This unique, adults-only holiday experience invites guests to follow Krampus’ mischievous path through historic downtown Ottawa, stopping at nine festive locations. Along the way, you'll collect 6 deliciously decadent cookies and confections crafted to […]

  • Donuts with Santa

    Floret Plants and Provisions 610 Court Street, Ottawa, IL, United States

    Kick off a sweet holiday morning with Santa himself! Join us at Floret (610 Court Street) on Sunday, December 14 for Donuts with Santa — a fun and festive experience for kids. Each 45-minute session (9 AM or 10 AM) includes a delicious donut, a hands-on holiday craft, and special time with Santa to share […]

  • Plaid-urday!

    Downtown Ottawa

    Pull out your plaid and join the fun! Saturday, December 20, is Plaidurday at the Chris Kringle Market — a community day dedicated to flannel, fun, and festive spirit. Come cozy and colorful as you stroll the market, shop local vendors, and enjoy Christmas ambiance on every corner! Let’s make downtown Ottawa plaid and proud […]

  • 2nd Annual Sweet Stroll

    Downtown Ottawa

    Indulge your sweet tooth and create lasting memories at the Downtown Ottawa Sweet Stroll! Join us on Saturday, February 7, from 11 am-2 pm for an afternoon of delicious fun the whole family will love. Stroll through charming downtown Ottawa and visit a variety of local businesses, each offering a unique confection or cookie for you to collect. Your ticket […]

  • Coldest Night of the Year

    Jordan Block 101 W Main St, Ottawa, Illinois

    Walk + Fundraise February 28, 2026 The Coldest Night of the Year (CNOY) is a family-friendly winter walk that raises vital funds for local organizations serving people experiencing homelessness, hunger, and hardship. When you join CNOY, you’re not just walking - you’re fundraising to help your neighbors find warmth, safety, and support. Each February, thousands […]

  • Restaurant Week

    Downtown Ottawa

    Don’t forget to pick up your Restaurant Week Passport at the Ottawa Visitors Center before the festivities begin. During Restaurant Weeks, collect a stamp at each participating location you visit, the more stamps you earn, the better your chances of winning!This year’s Restaurant Week drawing prize is now over $200 in gift cardsOnce you’ve collected […]

  • Pack the Place at the Lone Buffalo!

    The Lone Buffalo 808 - 812 LaSalle St., Ottawa, IL, United States

    Join us for a Pack the Place fundraising night supporting the Ottawa Downtown Association! On March 11, The Lone Buffalo will donate 10% of all sales from 5–9 PM to the Ottawa Downtown Association, an organization dedicated to supporting local businesses, events, and the continued growth of downtown Ottawa. Enjoy great food, craft beer, and […]

  • Startup Starved Rock Lunch and Learn: Realtors and Property Owners

    IVCC Ottawa Center 321 W Main St, Ottawa, IL, United States

    Realtors and Downtown Storefront Property Owners: Join us for a Lunch & Learn on our new Business Incubator Program: StartUp Starved Rock! Sponsored by the Ottawa Area Chamber of Commerce and the Ottawa Downtown Association, the StartUp Starved Rock Incubator Program is designed to support new and early-stage businesses in Ottawa, Illinois by providing seed […]