Things to do in Oswego, Illinois

Shop & Dine in downtown Oswego

Home to an eclectic collection of boutique and antique shops, downtown Oswego has established itself as a bustling destination for visitors to shop, dine, and enjoy the historic charm of the district's limestone and brick main street buildings.

Enjoy a day browsing antiques and vintage at Happenstance Goods, visit a curated lifestyle boutique at Hudson Design House, and try on the latest fashions at Bella-Gia. Dining destinations in downtown Oswego include new American fare at 113 Main and authentic Mexican cuisine in an upbeat casual environment at La Marimba. Sip award winning Illinois wines at Fox Valley Winery, where visitors can enjoy the casual ambiance and live entertainment at the winery's new downtown location.

Discover some of Chicagoland's top wedding venues in Oswego

A trio of highly-rated rustic-chic venues for weddings and events can be found in Oswego, Illinois, including Venue 5126 (formerly Emerson Creek), Northfork Farm, and Arranmore Farm + Polo Club. Each of these distinctive venues offer upscale elegance combined with rich, rural scenery less than an hour from O'Hare and Midway. 

Outdoor adventure in Oswego, Illinois

The Oswegoland Park District maintains more than 40 miles of trails in Oswego that connect up and down the river and throughout the Fox Valley. Saw Wee Kee Park is a hidden gem for mountain bikers, who can gear up at independent bike shop Oswego Cyclery, and trail runners, who descend on the wooded riverside nature park by the hundreds four times a year for the seasonal Saw Wee Kee Park Trail Run. 

Paddlers can enjoy a scenic stretch of the Fox River in Oswego. Violet Patch Park offers a picturesque spot for picnics and rest, while Hudson Crossing Park is the perfect put-in or take-out just steps away from it all in downtown Oswego. 

Shop farm fresh produce, pick apples from a heritage orchard, and enjoy the pumpkin patch and corn maze at Keller's Farmstand. Keller's is proudly family owned, with multiple generations of Kellers putting in the work to make their Oswego farmstand one of Chicagoland's top agritourism destinations.