December 2018 View more

Get ready to dine, shop, and play in this riverside town

Naperville’s neighbor to the southwest holds the title of the largest and fastest-growing municipality located entirely in Kendall County. Where Waubonsie Creek meets the Fox River, Oswego’s downtown district hosts antique shops, restaurants, and the tail end of the Fox River Trail. Whether you plan to visit in the winter or after the thaw, there are plenty of ways to keep busy indoors and out.


Waa Kee Sha Park
Cross-country ski or snowshoe during the winter at this 22-acre park or picnic and play at the handicap-accessible playground come spring.
4700 Reservation Road

Planet Fun
This entertainment center for kids offers myriad indoor entertainment, including mini golf, arcade games,
and bounce houses, plus a gigantic slide for good measure.
1505 Mitchell Drive, 630.800.3958

A Lady and Her Tools
Sign up for a class at this DIY workshop to make and take home your choice of woodworking projects, from a rustic bench to a blanket ladder. Workshops and private parties are offered.
61 South Madison Street, 331.425.4381

Fox Valley Winery
Visit the tasting room to sample this winery’s array of wines and hard cider. To take a tour of the winemaking operations during your visit, call ahead for an appointment. Enjoy live jazz at free bimonthly Wine Down Friday events.
5600 U.S. Route 34, 630.554.0404

Dine & Drink

Steve Buresh’s Cheesecake Store & Sandwich Shop
Fare: Soups, sandwiches, salads and owner Steve Buresh’s signature cheesecakes, served in Mason jars
Good for: Weekday lunch or a sweet treat anytime
Must try: Cheesecake in fun flavors such as maple bacon, chocolate hazelnut, and horchata
1019 Station Drive, 630.636.7209


My Sister’s Lil Donut Shoppe
Fare: Freshly made doughnuts, from cake to bismarcks to Long Johns
Good for: A morning pick-me-up
Must try: The latest seasonal doughnut special, whether it be pineapple-
coconut or triple chocolate
25 South Madison Street


Emerson Creek Tea Room & Events
Fare: Hearty soups, salads, sammies and strudels served in a century-old farmhouse that also operates as a picturesque wedding venue
Good for: Warm weather lunches (open May to October)
Must try: The Flower Pot salad served in pottery made onsite
5126 Stephens Road, 630.554.7100

Fare: Japanese hibachi-grilled meats and seafood, plus classical
and contemporary sushi
Good for: Workday lunch or takeout night at home
Must try: Drunken Salmon maki with mango, sweet onion, ikura roe, and daikon radish sprouts
2984 U.S. Route 34, 630.554.2388

Tuscan Tavern
Fare: Classic Italian entrees—think veal Marsala and chicken limone—plus pizza and pasta to boot
Good for: Weekend family dinners or date night
Must try: Oysters fiorentino with bacon, spinach, and sambucca-spiked hollandaise; meatball and ricotta pizza; oven-roasted half chicken
4571 Route 71, 630.554.9600


Bella-gia Boutique
Shop the latest women’s clothing trends—think velvet tops, distressed denim and embroidery—at this fashion-minded boutique. In the same storefront, the Prom Shoppe is a destination for those seeking dresses or tuxedos for high school dances.
27 South Main Street
630.554.3265, bella-gia.com

Hudson Design House
If you dig the farmhouse-chic look, you’ll love the chalkboard signs,
vintage furniture, and holiday
accessories at this boutique featuring
goods from local artisans.
76 Main Street

Marmalade Tree
Still searching for just the right gift for those on your holiday shopping list? The shelves here are stocked with everything from photo frames to funky socks to whimsical toys.
79 Main Street, 630.554.7550


DeMont Guitars
This indie shop specializes in guitar sales (including custom designs), repairs, and lessons.
61A Stone Hill Road, 347.433.6668


More Fun on the Way

Oswego is on its way to becoming a entertainment district: In addition to annual events like Prairie Fest (above), and venues like Planet Fun, two new family-oriented spots are in the works. Gravity 34, due to open soon in a former Lowe’s store space (2408 Route 34), will have a climbing wall, bumper cars, a ropes course, laser tag, arcade games, and go-carts. And Altitude Trampoline Park has announced that an Oswego location (1600 Douglas Road) is under construction as of presstime.