15 Best Things to Do in Oswego (IL)

The fast-growing village of Oswego, about 45 miles west of downtown Chicago, has doubled in size since 2000.

Oswego is on the idyllic banks of the Fox River, and has several beautiful waterfront parks where you can relax, launch a canoe or kayak or follow the long-distance Fox River Trail.

As the village has grown, the downtown has been completely revitalized, and is now an endearing shopping and dining area with attractive brick buildings.

Oswego is also within minutes of some excellent family attractions, like the largest waterpark in Illinois or the quaint Keller’s Farmstand, which offers all kinds of fun in the fall.

1. Downtown Oswego

Although Oswego’s population has skyrocketed over the last two decades, the village has been around for 170+ years, and nowhere is this more visible than downtown.

A lot of careful work has been done improving the streetscape, preserving historic architecture and attracting independent businesses to this district.

Downtown is also the setting for exciting events, like Oswego Beats & Eats, the Country Market, Brew at the Bridge, Wine on the Fox and the much-loved Christmas Walk.

In the space of a few blocks are specialty stores for designer homewares, health food, collectibles, bicycle gear, flowers and prom rentals, as well as a craft brewery, a donut shop and a smattering of eateries for Mexican, contemporary American and pub grub.

2. Hudson Crossing Park

An early name for Oswego was Hudson, and this location was where generations of Native Americans, and then early Euro-American settlers, forded the Fox River.

At the main entrance, the arch, held up by pillars of local limestone, refers to those times. Hudson Crossing Park is one of a handful of local parks on the Fox River Trail, which crosses the river here on a pedestrian bridge previously used by the Aurora, Elgin and Chicago interurban trolley line, with historic limestone piers that date to 1867.

Elsewhere Hudson Crossing Park has lighted walkways, an accessible children’s playground, a sand play area, a launch for canoes and kayaks, a picnic area with grills, a sculpture garden and concert area.

3. Raging Waves Waterpark

The largest waterpark in Illinois is little more than 15 minutes from downtown Oswego. Most towns in the Chicago suburbs have a waterpark, but the Aussie-themed Raging Waves is on another level.

In 45 acres, with abundant greenery all around, this place has a massive wave pool, a lazy river more than a quarter mile long and no fewer than 20 water slides.

Among the headliners is Aussie Mat Dash, a six-lane “rallyRACER”, and one of only three rides of its kind in the world. Also outstanding is Wonambi, a four-person raft ride from a height of 68 feet, with a 720° downward spiral.

Raging Waves has several kiddie areas, like the four-story water playground, Kangaroo Falls, and toddler-oriented Koala Kove, with a minimal depth pool and safe slides.

4. Little White School Museum

Oswego’s local history museum is housed in a church-turned-schoolhouse dating back to 1850. This predates Oswego’s incorporation by two years, and is Kendall County’s oldest public building still to have a public use.

The church was converted into a school in 1915 and after closing in 1964 was saved from demolition in the 1970s and eventually handed over to the local park district in 2010.

The museum inside has received a lot of plaudits, recounting the history of the community, calling on many thousands of artifacts.

This attraction organizes lots of interesting programs, like history walks and children’s storytime, and helps keep kids’ occupied during a visit with a scavenger hunt.

5. Sugar Grove Family Fun Center

It’s no exaggeration to say that this family fun center close to Raging Waves in Sugar Grove has something for everyone. Surely the top attraction here is the pair of go-kart tracks, both with smooth concrete surfaces.

Sugar Grove Speedway is a ¼ mile circuit for up to 16 karts, and with two-seaters available so kids can join their parents.

A little more serious is the adult-only Wrangler, with turns specially designed for drifting. Some of the other attractions at the center include bumper boats, a special water fight area, 18 holes of mini golf, a driving range and golf center.

6. Keller’s Farmstand

Out in the farmland to the south of the town is a classic farmstand, open late April through May, and then opening again from mid-July to the last weekend of October.

In spring you can visit for planters, hanging baskets and all kinds of perennials, bedding flowers, herbs, fruits and vegetables.

A changing variety of fresh produce is available throughout the summer, from tomatoes to zucchini, hot and sweet peppers, onions and Illinois favorites like watermelon and peaches. Then in fall you can come to pick a wide variety of apples, as well as pumpkins.

On weekends in September and October the farm has a lot going on, like an animal barn, 10-acre corn maze, wagon rides, and great food like kettle corn, apple cider donuts and homemade fudge.

7. Phillips Park Zoo

It will take you around ten minutes to reach this public zoo in neighboring Aurora. The Phillips Park Zoo has a history going back to 1915 and, unlike many attractions of its kind, is open daily all year round.

Here you can view the wild species native to the Midwest. Several of these, like the mountain lion or gray wolf, can no longer be found in the wild, or exist only in scarce numbers.

Other inhabitants include North American river otters, American elk, a wide array of turtles and snakes in the Reptile House, and birds of prey like the red tail hawk, bald eagle, Harris hawk, Cooper’s hawk and peregrine falcon.

8. Prairie Point Community Park

The main public park in Oswego for active recreation is this 66-acre space surrounding the Oswegoland Park District headquarters.

To sum up, Prairie Point Community Park has 18 acres of soccer fields, a large concrete skate park, two full basketball courts and four lighted baseball/softball fields. In winter families love the sledding hill and there’s an outdoor skating rink, depending on the conditions.

The park is in a natural mesic-wet prairie basin, and is home to Oswego’s pantry garden, annually producing more than 1,000 lb of fresh produce for families in need.

Last but not least, one of the top attractions is the splash pad on the south side, treasured by families in the summer months.

9. Fox Valley Winery

When we put this list together this multi award-winning boutique winery was planning on moving its tasting room to the heart of downtown Oswego.

The Fox Valley Winery has a high reputation for its wine, many of which are produced from single-vineyard Illinois grapes.

The winery’s range covers the gamut from red to white, and palates from sweet to dry. You can sample and purchase varietals like Chardonnay, Seyval Blanc, Syrah, Petite Sirah, Merlot and Cabernet Sauvignon, as well as a choice of carefully balanced blends.

The tasting room is open seven days, with longer hours on Friday and Saturday, and features the work of talented local artists.

10. Oswego Brewing Company

With a talented brewing team led by a former chemistry teacher, the Oswego Brewing Company is a burgeoning local craft brewery.

As well as a slew of imaginative seasonal beers and special series, there are five year-round flagship beers, always available at the taproom.

These are Station 1 (IPA), Oswego Lager (Vienna-style lager), Stone Skipper (Hefeweizen), Old Firehouse (Cream Ale) and Hay’z for Horsez (New England IPA).

The friendly taproom and beer garden is right in the middle of downtown Oswego and stays open to 11 pm on Friday and Saturday. The local eatery, 113 on Main, brings food right to the taproom, and there’s always a food truck outside on weekends.

11. Saw Wee Kee Park

A little wilder than the riverside parks in town, this 135-acre park has been part of the Oswegoland Park District for half a century.

This stretch of riverside is the site of a strip-mined gravel pit that has been carefully restored and is now a habitat for deer and bald eagles.

Weaving through the forest is a system of color-coded trails for hiking, horseback riding, BMX biking and cross-country skiing. You can also launch your canoe or kayak here in the summer, or go fishing from the riverbank (catch and release only).

12. Violet Patch Park

Another lovely place to spend some time by the Fox River, Violet Patch Park is on the east side of the Violet Patch Bridge, for pedestrians and cyclists.

This is another place where you can launch a canoe or kayak for a paddle on the Fox River, and if you just want to relax, there are picnic tables, grills and shelters, all with ample cover from the tall mature trees on the river bank.

Parallel to Violet Patch Park, across IL 25, is Eagle Ridge Park, known for its 18-hole disc golf course, and accessible via the 3.2-mile Waubonsie Trail, which will take you through quiet residential areas as far as Jaycee Park in Boulder Hill.

13. Fox Bend Golf Course

This beautiful public course in Oswego welcomes visitors and has very affordable rates. The course is on the banks of Waubonsie Creek, which serves as a water hazard on several holes.

Though always fun, Fox Bend is not an easy course. On deceptively hilly terrain, the holes have narrow, often dogleg fairways fringed by deep woodland, as well as a lot of strategically positioned bunkers.

The greens roll firm and fast, so you’ll need to be on top of all aspects of your game. For a bit of pre-round practice there’s an excellent driving range, as well as two putting greens, a short game area and practice bunker.

14. Altitude Trampoline Park

Perfect for energetic kids, but also grownups looking for a new workout, Altitude Trampoline Park offers a range of attractions in one 30,000-square-foot facility.

The main space is Main Court, which has wall-to-wall trampolines, but you’ve also got a battle beam, giant stunt bag, larger “super trampolines”, special performance trampolines, a dodgeball court, wipeout area, foam pit, rock wall and much more.

There’s a separate area, just for smaller jumpers at the Kids Court, with trampolines and a foam pit. You can buy all-access passes for anything from 60 to 120 minutes. This is a great option for children’s birthdays, from toddlers to teens.

15. Movies in the Park

Every summer, the Oswego Entertainment Venue at 1010 Station Drive hosts a popular season of outdoor movie screenings.

Beginning in early June, Movies in the Park runs until the end of August. The year we wrote this article, you could stay in your car for a drive-in experience, or bring a picnic blanket or lawn chair.

There are no food trucks on hand, but you’re free to bring your own food and drink. Movies on the schedule at the time of writing included The Greatest Showman, Trolls World Tour, Raya and the Last Dragon and The Croods: A New Age.