Blake Walsh

20 Best Things to Do in Oswego, IL

  • Published 2023/03/09

Oswego is a fast-growing village approximately 45 miles west of Chicago.

It’s on the gorgeous banks of the Fox River and offers numerous parks with distinctive features.

There are also various restaurant establishments worth visiting where you may appreciate and relish multiple cuisines.

After restorations, the downtown is now a charming retail and dining district with magnificent brick buildings.

Here are the best things to do in Oswego, IL:

Visit the Hudson Crossing Park

Welcome sign of Hudson Crossing Park

Brian Kapp /

Hudson was an earlier title for Oswego.

Generations of Native Americans and early Euro-American immigrants crossed the Fox River through this area.

The arch at the main entrance, supported by local limestone pillars, alludes to this bygone period.

The waters of Hudson Crossing Park

Jauerback, CC BY-SA 3.0, via Wikimedia Commons

Find illuminated paths, an accessible children’s playground, a sand play area, a canoe and kayak dock, and a sculpture garden at Hudson Crossing Park.

Hudson Crossing Park is a public park in Oswego’s downtown district that hosts public programs.

The grounds of Hudson Crossing Park

Jauerback, CC BY-SA 3.0, via Wikimedia Commons

Check Out the Fox Valley Winery

The Fox Valley Winery is well-known for its wines, many of which are made from Illinois grapes grown in single vineyards.

You have the opportunity to taste the superb wines of Illinois in the Fox River Valley.

Taste their wines and decide whether you favor red, white, dry, or a bottle of sweet wine.

The tasting room is open seven days a week, with extended hours on Friday and Saturday.

You can also find local artists’ work there.

Stop by their lovely Fox River Valley site on Main Street in Oswego, Illinois.

Grab Fresh Produce at Keller’s Farmstand

Are you looking for a place to grab healthy fresh foods?

Keller’s Farmstand first opened its doors to the public in 1991.

Grab a rotating selection of fresh fruit in the summer, including tomatoes, zucchini, spicy and sweet peppers, onions, and Illinois classics like melons and peaches.

Planters, hanging baskets, wildflowers, seasonal flowers, herbs, fruits, and veggies are available in the spring.

Then, in the fall, choose a variety of apples and pumpkins.

Celebrate at Venue 5126

Venue 5126 is a beautiful rustic rural barn ideal for your wedding and other special occasions.

They provide unique seven acres of lovely countryside in their barn and outdoor event settings.

Their land features beautiful countryside, perfect for first views, wedding photographs, and guest selfies.

Whether you choose to marry inside their beautiful barn or on the pergola facing a 500-acre farm, your ceremony at Venue 5126 will be breathtaking.

The stunning environment and exquisite barn offer a pleasant crew that will treat guests like family.

They go beyond to give your wedding or grand celebration a day to remember.

Learn Local History at the Little White School Museum

Exterior of the Little White School Museum

Jordano53, CC0, via Wikimedia Commons

The Little White School Museum retains the community’s rich history and represents the character of its early citizens.

The Oswegoland Heritage Association runs the museum in collaboration with the Oswegoland Park District.

Built as a church in 1850 and later becoming a school until the mid-1960s, the building is now a public community museum and repository of local Oswegoland history.

The museum has gotten a lot of acknowledgment for showcasing the community’s history using thousands of objects.

This tourist attraction offers a variety of events, such as history tours and children’s storytime, as well as a treasure hunt to keep youngsters entertained.

Learn more about history at this Oswego tourist attraction.

Try an Italian Beef Sandwich at Portillo’s

Have you ever tried Portillo’s?

Portillo’s Hot Dogs is recognized for its iconic Chicago-style hot dogs, Italian beef sandwiches, salad, fries, and chocolate cake shake.

The wide variety of menu in Portillo’s attracts visitors.

Grab finely sliced Italian beef, roasted for hours and slapped onto a freshly baked French baguette.

Then they dunk the whole concoction in hot gravy with its spice combination perfected over 50 years.

Grab a Chicago-style hot dog, or Italian beef dipped in sweet or spicy peppers and see what the fuss is about.

Add Flavored Syrup to Your Drinks at the Village Grind

Try freshly baked goods, meals, and a large selection of coffee beverages, iced drinks, teas, and smoothies at the Village Grind Coffee & Tea Co.

Village Grind offers a variety of flavored syrups to customize your drink.

They also offer arts and crafts, so stop in for a drink or food and stay to do some shopping.

For those one-of-a-kind personalized gifts, they engage with some of Oswego’s local artists and artisans at the Village Grind.

Browse jewelry, scarves, seasonal things like fragrant candles, and fresh honey from local farms.

Stop in for a drink, brunch, or lunch, and give your special someone a present.

Grab a Beer at Tap House Grill

Tap House Grill is a laid-back hangout that serves inventive American pub cuisine and a rotating list of specialty beers.

Tap House Grill is the realization of a concept that began in the fall of 2005.

The restaurant brings together fresh, made-from-scratch addictive food with a vast range of local unique handcrafted and exclusive beers on tap.

You can find bar nibbles, appetizers, flatbreads, burgers, sandwiches, wraps, soups, desserts, and more on their menu.

Grab the Tap House Grill’s “Enjoyable Food” and “Original Brews” fresh daily.

Walk down the Streets of Downtown Oswego

People sitting on a street at Downtown Oswego during a festival

Jauerback, CC BY-SA 3.0, via Wikimedia Commons

Downtown Oswego began an initiative to revitalize the region.

The project involved improvements to the street, sidewalks, landscaping, ornamental lighting, and seats.

The cityscape has been improved, and old architecture has been preserved, attracting independent companies to this region.

The road of Downtown Oswego

Jauerback, CC BY-SA 3.0, via Wikimedia Commons

Find designer homewares, natural foods, antiques, cycling gear, flowers, and tuxedo rentals within a few blocks.

Likewise, check out a craft brewery, a doughnut shop, and a sprinkling of Mexican, modern Mexican American, and pub grub eateries.

Dining, shopping, and historical sites and residences may all be found in the downtown area.

Marvel at the View at Emerson Creek Pottery & Tea Room

The business, housed in a 100-year-old mansion, sells more than ceramics.

The shop includes handcrafted candles, artisan spreads & preserves, home décor, and fashion items, in addition to exclusive, handcrafted ceramics.

A tearoom also features a weekly lunch menu produced using local foods.

Emerson Creek enjoys providing a warm welcome, outstanding service, and tasty fresh food.

During their wedding season, from May to early November, Emerson Creek provides a gorgeous environment maintained to provide you with picture-perfect surroundings.

They also have a unique “Bridal Coop” for wedding day final touches and a restored barn that runs into a triple peak event tent lit by chandeliers.

Drink Local Craft Beers at Oswego Brewing Company

Do you enjoy local craft beers and wish to spend time with friends and family while drinking?

The Oswego Brewing Company is a local craft brewery with a competent crew under a former chemistry teacher.

Five year-round flagship beers are available in the taproom, in addition to a host of creative seasonal brews and unique series.

Have a blast with pals at Oswego Brewing!

Enjoy Outdoor Activities at Prairie Point Community Park

Prairie Point Community Park offers a diverse range of activities.

Play soccer, football, basketball, softball, baseball, and beach volleyball at the 66-acre park.

Likewise, you can check out a skate park, shelter, walking trail, splash pad, and sledding hill.

In addition, the 7,900-square-foot concrete skate park will delight people who like skating and want to enjoy some outside activities.

You can also do ice skating, but only if the weather permits.

Read a Book at Oswego Public Library

Exterior of Oswego Public Library

Jauerback, CC BY-SA 3.0, via Wikimedia Commons

Do you want to read a book in solitude and enjoy your own company?

Come to the Oswego Public Library if you want to enjoy your passion for reading books.

There are several publications to choose from that book enthusiasts will undoubtedly like.

The mission of the Oswego Public Library Area is to offer a high-quality library service that meets the informational, educational, and recreational requirements of district residents of all ages.

It focuses on delivering popular resources, offering a reference service, and aiding students of all ages with their educational needs.

Reading fascinating and instructive books is always fun and educational.

Order Japanese at Sakamoto Japanese Grill and Sushi

Sakamoto Japanese Grill and Sushi in Oswego, Illinois, provides great dining for locals and tourists.

Their sushi restaurant is recognized for its innovative take on classic meals and commitment to using only the highest quality fresh ingredients.

Sakamoto Japanese Grill and Sushi is a staple in the Oswego neighborhood, known for its exceptional sushi, attentive service, and welcoming staff.

This trendy eatery is available for sushi, tempura, grilled steaks, seafood, and vegetables.

If you’re searching for a location to eat Japanese food, this is the place to go.

Create Unforgettable Memories at Altitude Trampoline Park

Altitude Trampoline Park is ideal for enthusiastic kids and adults searching for a new workout routine.

You can buy all-access permits for one-to-two-hour sessions.

Main Court features wall-to-wall trampolines, but there’s also a battle beam, gigantic stunt bag, unique performance trampolines, a dodgeball area, wipeout zone, foam pit, rock wall, and much more.

The Kids Court has a separate section with trampolines and a foam pit for little jumpers.

This is a fantastic choice for birthday parties for kids of all ages.

Make the most of your holiday at Oswego.

Play a Round at Fox Bend Golf Course

Fox Bend Golf Course is a fantastic way to appreciate the simplicity of Oswego’s natural beauty.

Brimming with trees and surrounded by a couple of ponds, Fox Bend Golf Course is an exciting layout for experienced golfers because of its abundance of hazards.

The greenery is also well-maintained, making this one of the go-to golf courses within the area.

Besides that, Fox Bend Golf Course has a decent pro shop and a pretty famous restaurant, making this a great all-day activity for friends and family.

You can find this public golf course along Highway 34—a convenient spot to play golf.

Celebrate the PrairieFest Annual Festival

One of the most highly anticipated events in Oswego is its PrairieFest Annual Festival that’s typically held around summer, during the month of June.

Spanning several days, this is an exciting time in the city where you can do all sorts of fun activities with the locals.

One of the most prominent are the rides that are setup at the festival; it becomes a huge carnival that’s a must-see if you’re bringing children with you.

Besides that, there are a lot of concerts held at PrairieFest Annual Festival as well, along with an abundance of food and drinks.

The festival happens at PrairiePoint Community Park, utilizing its sprawling green spaces.

Experience Culinary Excellence at Asadoras Argentinas Burger

Asadoras Argentinas Burger is a must-try during your visit to Oswego, as it’s highly rated by both locals and visitors.

A Latin-inspired restaurant that fuses Latin flavors with Mexican cuisines, there’s a lot of novelty when trying their menu.

Their burgers here are some of the best you’ll taste in Illinois, as it’s packed full of flavor and has a unique taste to it when paired with their various dips.

Asadoras Argentinas Burger also has an abundance of other options besides their juicy burgers; they’re also known for fries that come in many dips, salsas, and beef empanadas.

You can’t go wrong ordering at Asadoras Argentinas Burger—visit them along Highway 71.

Take a Stroll at Stonegate Park

Stonegate Park is a quaint and tranquil spot that’s perfect for an afternoon walk.

Situated along North Madison Street, Stonegate Park also has access to the iconic Fox River that Oswego is known for.

The trees and shrubs here are abundant, giving this a serene charm that’s perfect for meditation or relaxation.

It got its name also because of its stone-laden entrance—a nice photo souvenir to take during your trip.

Whether you’re in search of an intimate spot or a place to simply relax, Stonegate Park is a great option for you.

Bike Along Waubonsie Trail

Waubonsie Trail is a paved biking path that runs several miles through Oswego and the neighboring community of Boulder Hill.

Tucked in the residential communities of the village, this is a perfect way to enjoy the countryside aesthetic and vibe of Oswego.

There are no cars that go through here considering it’s a greenway, so you’re guaranteed to enjoy this with no hazards.

This makes it an underrated activity with friends and family, so do bring a bike or rent one to experience it.

You can begin your adventure at Jaycee Park which is directly linked to Waubonsie Trail, located along Saugatuck Road.

Final Thoughts

Oswego, Illinois, is a fantastic weekend destination for the whole family.

There are several restaurants with relaxed and pleasant atmospheres.

Locals and travelers can enjoy the numerous parks, eat a delicious lunch at Emerson Creek Pottery and Tearoom, and then go shopping downtown afterward.

You can also visit a winery and sample some great Illinois wines.

It is a popular tourist destination with brilliant colors and a bustling community worth visiting.

Oswego may look like a typical tiny village at first sight, but as you start exploring it, you’ll discover that there’s more to this Illinois village.

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