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Downtown Oswego

With an eye to the future and firm roots dating back to the 1833 arrival of its first settlers, the Oswego community today combines progressive economic vision, a burgeoning business community and quintessential American charm.

Just 50 miles southwest of downtown Chicago, Oswego boasts hundreds of stores, more than 70 restaurants and easy access to entertainment venues in town and throughout the nearby metropolitan area. The community is fast becoming an employment hub for manufacturing, engineering and companies representing multiple market sectors. As the largest community in rapidly growing Kendall County, Oswego is home to a number of national retailers, big box stores, service providers, entrepreneurs, restaurants and small businesses.

While the area’s bustling shopping hub is located along the busy Route 34 corridor and Orchard Road, Oswego’s downtown serves as an icon of community pride and plays frequent host to popular community events including Wine on the Fox, and the Beats & Eats celebrations promoting music, art, food and culture, as well as a plethora of seasonal and holiday festivals. An annual antiques fest, farmers market with locally grown produce, fall festival, cookie walk, bunny hop, and antique car and tractor shows are among the popular and varied downtown events.

“Downtown Oswego is the heart and center of the community,” said Angie Hibben, President & CEO, Oswego Chamber of Commerce. “Since the early 1800s the area has been the site for gatherings, commerce, and a community focal point. That same sense of community is alive today!”

Located along the scenic Fox River, historic downtown Oswego includes shops, restaurants, the Oswego Public Library with its new addition and the iconic Little White School Museum known for classic mid-19th century Greek Revival-style church architecture.

Many downtown shops are housed in historically significant buildings, with QR codes visible in windows and storefronts, attesting to the structure’s historical prominence. Local history of Oswego dates to 1835, when the village was first platted by Lewis B. Judson and Levi F. Arnold. The waves of growth that have occurred in the village from its origin to the present have led to the development of an architecturally diverse urban area.

Centered along Main Street, older historic buildings, pedestrian-oriented streets, parks and the Fox River generate a charming atmosphere for downtown Oswego’s eclectic mix of restaurants and cultural/entertainment facilities, taking advantage of both the waterfront setting and historic character.

Founded in 1899 when the Nineteenth Century Women’s Club started with a market basket full of books carried to each meeting, the expanded Oswego Public Library is a downtown landmark drawing patrons from the surrounding Oswego, Montgomery, Plainfield, and Bristol and Wheatland Townships

When strolling Main Street, curious visitors and locals frequently stop to enjoy a quick visit, lazy morning or relaxing afternoon at the Village Grind Coffee & Tea Co. (19 S. Main). The Grind offers handcrafted drinks, homemade pastries, soups and sandwiches. The quaint establishment oozes both character and hometown charm while serving as a local favorite. Longtime loyal customers rave about homemade pastries including bumbleberry pie or the holy cow pie (every fruit all in one), caramel macchiato, blackberry chai tea served with a dollop of whipped cream, and other specialty coffees, soups, sandwiches, box lunches and fresh roasted coffee beans.

“Many of our loyal customers shop locally and enjoy dropping by for conversation and a bite to eat,” said Jodi Behrens, who together with husband, Dave, encourages visitors to “come feel our warmth.” The Grind was established in 1996 and many village events help draw new friends and customers, many who return again and again, Behrens noted.

Tap House Grill, the Oswego Inn, and Firehouse Pizza and Pub also are popular downtown Oswego eateries.

Located close to the Oswego Farmers Market and several restaurants and shops is Hudson Crossing Park, a popular family-friendly destination with shade trees, benches, children’s activities and a perfect picnic location along the banks of the Fox River.

Hoping to tap into your artistic side? Classes in painting, jewelry design, fused glass and glass blowing, pottery, music lessons, dance, photography, and more are available at downtown Oswego establishments including the Fox River Academy of Music & Art, Inc., Studio 60, Fox River Studios and others.

Those with more energetic outdoor tastes will want to visit the Oswego Cyclery and rent a bike for scenic touring along the Fox River bike path, or sign up for a guided group ride. Owner Art Black is one of a core group of founding downtown Oswego business owners quick to recognize Oswego’s business potential. Founded in 2004 under the brand Mill Race Cyclery in Geneva, Oswego Cyclery is housed in the 14,000-square-foot former Oswego Fire Station (59 Main St.), in a building dating back to the 1950s. The shop provides a complete bicycle shopping experience, sales and service. Black hopes to expand operations in 2016 with a vision to create a healthplex type facility, possibly incorporating a yoga studio, fitness and training gym, or renting space to a canoe and kayak business to take advantage of the site’s proximity to the Fox River.

Shopping enthusiasts throughout the region will find unique items of all varieties ranging from organic garden novelties at the Garden Faire to spices, herbs and supplies at Sage Spice Shop, gourmet popcorn at Page’s Popcorn & Flavors, and healthy dog, cat and bird food, toys and accessories at Go Dog Go.

American Male & Co. (27 Main St.), is a family-owned and operated 25,000-square-foot shopping experience. The long-time Oswego retail operation has dressed many men and women for both work and play. Keeping up with trends and fashions, the American Male & Co. building also houses Bella-gia Boutique, clothes for the contemporary customer; the Prom Shoppe, one of the largest dress shops in the area with four rooms of dresses, tuxedos, and the newest addition, polished accessories to make the look complete.

“It’s all about knowing the individuality of our customers,” said Deena Graves, store manager and third-generation family member. Buyers also work the floor, providing one-on-one customer service. In business since 1905, American Male & Co. has been an Oswego landmark since 1978.

From new, vintage, and consignment home décor at Kimberly Ann Home Decorating Boutique, to floral arrangements and children’s clothing boutique items at Floral Expressions & Gifts, downtown Oswego has something to please even the most discriminating customers. Formal, upscale name brand wedding, prom, homecoming and formal attire can be found at De’ Zsa Vu – a formal & upscale consignment boutique, and antique lovers won’t want to miss Rejoyce, an antique store with trendy new merchandise. n

Downtown Businesses


Little White School Museum
Local Historical Society – Little White School Museum
P.O.Box 23
72 Polk St.
(630) 554-2999

Oswego Public Library
32 W. Jefferson St.
Oswego,IL 60543
Montgomery Branch located at
1111 Reading Dr.
Montgomery, IL 60538
(630) 554-3150

Raven Lodge – Masonic Hall
71 Main St.
Masonic Hall
(630) 277-1073


Firehouse Pizza & Pub
65 W. Washington St.
Pizza, burgers, wings, craft beers, spirits, catering, take-out, free delivery, dine in
(630) 551-0800

Oswego Inn
54 Main St.
(630) 554-9812

Tap House Grill
123 W. Washington St.
(630) 383-2020

The Village Grind Coffee & Tea Co.
19 N. Main St.
Gourmet coffee, expresso, tea, pastries, sandwiches and gifts
(630) 554-6678


American Male & Co.
(Editions/American Male/Bella-gia/Prom Shoppe – all in one building)
27 Main St.
Clothing and accessories
(630) 554-8661

De’ Zsa Vu A Formal & Upscale Consignment Boutique
56 Main St.
Formal & upscale boutique offering wedding, prom, homecoming, formal attire and name-brand items at bargain prices.
(630) 551-3033

Floral Expressions & Gifts, Inc. & Lil’Emm’s
27 Main St.
Florist & children’s clothing boutique
(630) 551-4438

Go Dog Go
100 Main St.
Healthy dog, cat and bird food, toys, collars & dishes

Kimberly Ann Home
Decorating Boutique
67 S. Main St.
New, vintage and consignment home decor
(630) 636-7441

Oswego Cyclery
59 Main St.
Bicycle retail sales, service and rentals
(630) 551-2300

Page’s Popcorn & Favors
108 Main St.
Gourmet popcorn, custom favors, fundraisers, gifts
(630) 215-4914

76 S. Main St.
Antique store with trendy new merchandise; chalk paint & classes
(630) 554-2995

Sage Spice Shop
74 W. Washington St.
Spices, herbs and supplies
(630) 554-7500

The Garden Faire
5 S. Madison St.
Organic garden boutique
(630) 636-9125

Arts & Entertainment

Fox River Academy of Music & Art, Inc.
26 W. Van Buren
Music and art instruction, musicians for hire, special events and community outreach
(630) 551-4321

Fox River Studios
64 S. Main St.
Photo and video studio, also classes and gallery showings
(630) 624-3269

Studio 60
12 W. Washington
Pinot & paint nights; art instruction studio & art gallery, open art nights, art classes, open houses, jewelry classes, fused glass classes, charity events; Pottery studio at 64 S. Main behind Fox River Studios
(630) 554-8885

Professional Services

American Quality Home Improvement
Home improvement services including roofing, siding, windows, gutters and gutter covers
10 Main St.
(630) 656-3406

Kettley Realtors
Greater Fox Valley real estate information for buyers and sellers in the Fox Valley
58 Chicago Rd.
(630) 554-8700

Oswego Dental Care
21 W. Jefferson St.
General dentistry
(630) 554-9100

Oswego Travel
103 Main St.
Travel for leisure, honeymoon, destination weddings
(630) 554-3777

Schoppe Design Associates
Landscape architecture
126 S. Main St.
(630) 551-3355

Stonehill Dental Family Dental
60C Main St.
(630) 554-7725

Tripp Insurance Agency, Inc.
5 Main St.
(630) 554-8831

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