A pleasant mix of rural town charm and the amenities of a fast-growing suburb
Red barns, manufacturing buildings. Crop-lined country roads, cul-de-sacs. Mom-and-pop shops, newly-opened chain stores. Although Oswego was a largely rural community until fairly recently, it’s now considered a far west suburb, near Aurora and other fast-growing towns like Plainfield and Yorkville. Rather than fading and trading one part of its character for another, this village of more than 30,000 residents — double the population of 20 years ago — effectively balances its newer suburban character with its country roots.
That’s good news not just for those with longtime ties to the town and those who want to settle there now, but for others who visit Oswego for things to see and do, ranging from barn parties and festivals to craft beer tastings and 10K races — not to mention easy access to the Fox River and all the great outdoors has to offer.
As they say in some circles in Oswego, here “we go” to see what’s going on in this Kendall County town.
Get to the Heart of It
Go find Main Street USA — it’s right here in downtown Oswego and it’s lined with quaint shops and places to grab a bite or your favorite libation.
Support local artisans, bakers and even candle makers . . . at The Village Grind Coffee & Tea Co. In addition to signature drinks, this cozy spot serves up tasty homemade baked goods and lunches. It also sells a host of locally made items including jewelry, pottery, artworks, honey and more. Driving the point home is a sign reading, “Remember, the big stores don’t do a little jig when they make a sale. Make someone jig this year.”
Say cheers . . . at the Oswego Inn, a neighborhood place where everyone knows everyone else’s name — and there’s room for new faces. The bar and grill dates to the early 1930s and also serves up hand-formed burgers that have earned local raves.
Order sunny-side-up . . . at the Oswego Family Restaurant, known for home-style cooking, including hearty breakfasts.
Step into the cute cottage . . . that looks right out of a fairy tale for some just-from-the-oven baked goods at My Sister’s Lil Donut Shoppe.
DIY to your heart’s content . . . at A Lady and Her Tools, a woodworking workshop with next-level make-and-take projects that range from a basic blanket ladder all the way to a kitchen island. Take a brush to it at DIY painting events and workshops at other places in downtown Oswego, like Happenstance Goods. And check out Stonehouse Market, a charming boutique featuring a mix of antique and vintage finds as well as offering upholstery fabrics and services.
Browse everything . . . from baubles to blouses, knickknacks to knitted hats, at a variety of gift, accessory, clothing and hobby stores in downtown Oswego, including The Marmalade Tree, Forever After Finds, Prairie Stitches Quilt Shoppe, Velvet Grace and others. Don’t forget your fur baby — check out goods for your animal buddies at Bentley’s Pet Stuff.
Deck out your home . . . at Hudson Design House, a home accents boutique where you’ll find timeless furniture, home decor, clothing and vintage and specialty goods from local artisans.
Ride like the wind . . . after a visit to Oswego Cyclery, which offers bikes, gear and service for cyclers of all levels and ages. Those mountain bikes will speed you along the many paths and trails that cut through Oswego.
Remember those who served . . . by taking some moments at the Veterans Historical Walk in the downtown area near the public library.
Bookend your visit . . . to downtown Oswego that perhaps started with a cup of coffee with a visit to the Oswego Public Library. In addition to its myriad resources, the library hosts an annual Oswego Literary Festival with the local cultural arts commission at the Oswego Village Hall.
Experience the upside of suburban sprawl at a plethora of stores in other shopping areas within Oswego, including Centennial Plaza, Douglas Square, Mason Square, Orchard Grove, Orchard Way, Orchard Woods, Oswego Commons, Oswego Junction, Oswego Plaza, Prairie Market, Townes Crossing and Washington Square. Here, you’ll find a host of chain stores, from Bed Bath & Beyond to Wal-Mart, as well as locally owned business like Purcell ACE Hardware and The Popcorn Store, among dozens of others.
Find the best produce . . . at the weekly Country Market in downtown Oswego. Browse seasonal produce, locally sourced eggs, cheeses and meats and artisan-made specialty foods ranging from popcorn to honey. Alas, you’ll have to wait until June.
Pick your own pumpkins and apples . . . in the fields and orchards at Keller’s Farmstand, where you can also maneuver through a 10-acre cornstalk maze and savor homemade apple cider doughnuts this fall.
Make Time to Dine
Did we mention that Oswego is home to more than 70 restaurants? There are too many to name them all here, but suffice it to say that you’ll find fast food, fast-casual, fine dining and snacks and sweets galore. Say you’re in the mood for blackberry cheesecake in a Mason jar — you can find it at Steve Buresh’s Cheesecake Store and Sandwich Shop. Or maybe you’re hankering for a Berlin curry bratwurst, which you can order at The Landing. Craving sashimi? Get on a roll at Sakamoto Japanese Grill and Sushi. See what’s smoking at Piggy’s BBQ, where you can sample all of the house-made barbecue goodies on the Piggy Platter. Enjoy a post-canoe trip meal or brews at the Tap House Grill near Hudson Crossing Park.
Take a grown-up field trip in Oswego, which offers plenty of over-21 spots where you can imbibe and have fun.
Enjoy a cold one . . . at Oswego Brewing Company, where there are beers for all tastes on tap, including the seasonal Oktoberfest and Frozen Fields. There are brews that give a nod to Oswego, like Go Man-Go and PrairieFest Ale. Come for special events, too, like music bingo and food trucks. Recharge with Detox/Retox power yoga classes on Sunday mornings in the taproom, where a 10-oz. beer is served up after class — cheers and Namaste!
Take a flight . . . or enjoy your favorite vintage at Fox Valley Winery, a family-owned winery along Route 34 that makes a range of dry, reserve, semi-sweet, sweet and dessert wines available for sampling in the tasting room. Tour the winery to see how the magic happens or take a load off after a long work week with a glass of vino and wood-fired pizza on Wine-d Down Friday, which also features live music.
Be festive . . . with special events centered on wine and beer at Oswego’s annual Wine on the Fox, a wine tasting festival held in May at Village Square Park, and Brew at the Bridge, a craft beer fest put on in September by Oswegoland Park District at Prairie Point Community Park.
Barnstorm the Area
Get your Chip-and-Joanna vibe on or just have fun shopping, eating and roaming around the beautiful grounds of Emerson Creek, a seven-acre site on scenic farmland run by a family that wanted to share the beauty of their surroundings and celebrate country life.
Order lunch . . . in the café that features locally-famous Flower Pot Salad and peach-blackberry cobbler, among other homemade menu items.
Hunt for gifts or home accents . . . in the Country View Shop inside the farmhouse. In the warmer months, check out the monthly Vintage Market held on the grounds and inside the renovated barn. The last one of this season is Oct. 9.
Planning a wedding . . . or any event? See why Emerson’s Creek barn is such a popular and Instagram-worthy venue.
Hang Outs and Happenings
Get in on the good times at any or all of the special events in Oswego.
Watch an international polo match . . . or simply seek peace and fitness at sunset yoga or enjoy a concert at Arranmore Farm and Polo Club, a privately owned farm that hosts a variety of public events throughout the year. Welcome fall and celebrate craft beers with Solemn Oath at the Farm, a “bring your own party” event on Oct. 5 featuring new and cellared S.O.B. beers, food and live entertainment.
Mingle with the supernatural . . . at the Witches & Warlock Ball on Oct. 12 to support childhood cancer awareness. Scare up Halloween fun at a zombie fest, “Park After Dark: Outbreak,” on Oct. 19 at the Civic Center. Take the younger set to the Monster Mash Bash on Oct. 26 at Oswego High School. Dare to take part in the Oswego Cemetery Walk on Oct. 3, put on by Oswegoland Park District and the Oswegoland Heritage Association.
Round out autumn . . . with other noteworthy community events, including the Gobbler Hobbler 10K and Mashed Potato Mile walk on Nov. 10.
Put some jolly in the holidays . . . at the annual Oswego Christmas Walk on Dec. 6, complete with horse-drawn wagon rides and tree lighting ceremony. There’s a Cookie Walk on Dec. 7 and Holiday Express trolley rides on Dec. 12 –15.
Take in a play . . . staged by the Limelight Theatre Company that’s part of the Oswegoland Park District, including entertaining radio plays like “The Black Eyes of the Crow” on Oct. 26 and “Miracle on 34th Street” on Dec. 7 and 8.
Save the dates . . . for Oswego events that return in 2020, including a Chocolate Walk in February, a Bunny Hop for kids (and a Bloody Mary social and separate egg hunt for adults) around Easter, a Memorial Day Parade in May, and the big community party, PrairieFest, on Father’s Day weekend in June.
A River Runs Through It
Channel your inner explorer and get back to nature in Oswegoland’s 1,000-plus acres of open lands, parks, and trails. The park district operates 65 parks and more than 40 miles of trails.
Float your boat . . . — or, as it may be, your kayak or canoe — at any of the launch sites in Oswego along the scenic Fox River that flows through the community. Spot eagles soaring above the Fox, as they tend to do. Cast a line for sport fish including bass, walleye and others. Bike the banks along five miles of single-track trails that you can pick up at Saw Wee Kee Park in Oswego Township.
Take a stroll . . . through Hudson Crossing Park, near a ford where stagecoach travelers once crossed the Fox River. Today that park includes a playground, picnic area, fishing area, trail head, festival grounds and even a sculpture garden.
Score an eagle . . . and maybe see an eagle flying overhead, at the scenic Fox Bend Golf Course, run by Oswegoland Park District. Play the par-72 course and grab a bite at Pearce’s Pub and Grill.
Get a dose of local history . . . at the Little White Schoolhouse museum, which was once a church and later served as a school. Now operated by Oswegoland Park District with the Oswegoland Heritage Foundation, the museum hosts events and rotating displays throughout the year, including a “Remember Our Veterans” special exhibit during the month of November.