Admin

Why did we choose Oswego, Illinois?

By
Real Estate Agent with Wayne M Martin

This is my entry to the April challenge hosted by Carol Williams and Margaret Rome Baltimore 410-530-2400.

Oswego, Illinois is approximately 50 miles west of Chicago and is the largest city in Kendall County. It was settled in 1833 as Hudson, renamed to Oswego in 1835 after Oswego, NY and incorporated in 1852. It sets along the Fox River and even today as the largest city in Kendall County maintains its small town charm.

The locally owned Main Street restaurant is famous for its breakfast "Blockbuster and other omelettes". Come hungry and be prepared to leave with leftovers. And true to its old town charm, cash only. Need a haircut? Two storefronts away, Ron the barber, also a local who has been cutting hair for over 58 years, is ready to be of service, no appointment necessary or taken. No Internet presence. And to keep it simple, cash only. Want a sandwich or a burger with a cold ice tea or draft beer? The Oswego Inn, founded in 1933 and still under family ownership has you covered. A limited number of sandwiches, onion rings and burgers are delicious, no French fries. Like you morning coffee with friends? A couple of coffee shops are ready to serve you, one on Main Street and the other just off. If you are a senior, one of them offers a donut free with your coffee purchase.

Why did we pick Oswego? The kitchen pure and simple. After years of living downtown in the sky with a small kitchen things had to change. And, the rest of the place fulfilled most of the rest of our needs. Not perfect but damn close.

Now for the rest of the story. The townhome is about a mile from downtown Main Street and about a mile the other way from modern day shopping and conveniences along the main highway that also runs through the downtown and crosses the Fox River.

So it is a location in the middle between living in a small town and yet having all the modern conveniences. Yes, we have national chain grocery stores including Aldi's and a soon to open Trader Joe's. We visit them all because of the kitchen.

Now you know why Oswego! Thanks to Carol Williams and Margaret Rome Baltimore 410-530-2400 for hosting this month's challenge. 

Comments(13)

Show All Comments Sort:
Ed Silva, 203-206-0754
203-206-0754 - Waterbury, CT
Retired Real Estate Broker

Oswego, Ill seems to have taken a page from other times and blended some modern as well, Wayne Martin .  A barber than only takes cash and obviously knows how to make change.

Apr 29, 2026 04:23 PM
Wayne Martin

Very few need change Ed Silva, 203-206-0754.nWith Ron you give the exact amount plus tip. The tip goes in one drawer and the haircut cost in another. The restaurant rounds everything to the nearest dollar and that's to make it easy.  

Apr 30, 2026 03:59 AM
Roy Kelley
Retired - Gaithersburg, MD

Thank you very much, Wayne. for telling us about the area. 

Enjoy your home community. You will love the new Trader Joe's store.

Aldi is also one of my regular shopping destinations.

Apr 30, 2026 04:34 AM
Wayne Martin

It is nice to have the old town preserved but having all the modern conveniences, shopping and medical nearby

Apr 30, 2026 06:02 AM
Nina Hollander, Broker
Coldwell Banker Realty - Charlotte, NC
Your Greater Charlotte Real Estate Broker

Good morning again, Wayne. I'm packing my bags as I write this! Oswego sounds charming and wonderfully livable. Hopefully, there is a bank in town... I'm notorious for not carrying cash... so I'd need to get into the habit of getting cash regularly! :)

Apr 30, 2026 04:51 AM
Wayne Martin

A local bank in the downtown area and the national ones near the shopping district.We are ready for you

May 01, 2026 06:32 AM
Carol Williams
Although I'm retired, I enjoy sharing my knowledge and learning from other real estate industry professionals. - Wenatchee, WA
Author, Golfer, Traveler, Retired, Wenatchee, WA

Hi Wayne,
Oswego sounds like my kind of place. Let's just hope the push for a cashless society dies. 

Apr 30, 2026 05:26 AM
Wayne Martin

Cash is still king in downtown Oswego. The local restaurant and Ron have signs on their doors. Ron had one the said "NO CASH, NO SERVICE" but took it down for "CASH ONLY".

Apr 30, 2026 06:07 AM
Gwen Fowler SC Lakes & Mountains 864-710-4518
Gwen Fowler Real Estate, Inc - Walhalla, SC
Gwen Fowler Real Estate, Inc.

This is a great example of how a place becomes home for very personal reasons. It is not always about finding something perfect, it is about finding what fits your lifestyle.

I like how you tied it back to everyday living. The mix of small-town character and convenient access is what so many buyers are looking for right now. And sometimes, it really does come down to something as simple as the kitchen.

Apr 30, 2026 05:44 AM
Wayne Martin

Great kitchen = happy wife! What more can I say?

Apr 30, 2026 06:08 AM
Kat Palmiotti
eXp Commercial, Referral Divison - Kalispell, MT
Helping your Montana dreams take root

The kitchen is definitely reason enough to make a move - I'm glad to hear Oswego fit the bill!

Apr 30, 2026 05:45 AM
Wayne Martin

After viewing many homes the kitchen sealed the deal. 

Apr 30, 2026 06:09 AM
Michael Jacobs
Pasadena, CA
Pasadena And Southern California 818.516.4393

Hello Wayne - I like learning about the history of communities along with the evolution of names plus remembrances of many sorts that remain in existence today.   Oswego Illinois sounds like an ideal match for you.  

Apr 30, 2026 06:03 AM
Wayne Martin

We were not sure initially but as we explored a bit the more we thought we made the right decision. 

Apr 30, 2026 06:12 AM
Margaret Rome Baltimore 410-530-2400
HomeRome Realty 410-530-2400 - Pikesville, MD
Sell Your Home With Margaret Rome

Wayne Martin , Please continue to enjoy your town!

Thanks for your entry! It's clear why you love living in Oswego. The town combines small-town charm with modern conveniences. I like that local shops accept cash and that the services have a friendly, hometown feel. The welcoming atmosphere makes it feel like home.

Apr 30, 2026 07:09 AM
Wayne Martin

The small town atmosphere downtown gives you a warm feeling. It amazes me how many know each other since grade school. Ron has been a barber for 58 years, Katy at the Oswego in has been there 37 years and the restaurant has been owned by the same family for many years.

May 01, 2026 06:36 AM
Brian England
Ambrose Realty Management LLC - Gilbert, AZ
MBA, GRI, REALTOR® Real Estate in East Valley AZ

Since kitchens seem to be a big deal in your world, I am not surprised at all that it caused you to move, haha.  It's good to know that you have found a good local watering hole as well, haha.

Apr 30, 2026 07:58 AM
Wayne Martin

The local watering hole still features pint drafts of a Chicago favorite, Old Style, for $2.00 tax included. 

May 01, 2026 06:38 AM
Kathy Streib
Cypress, TX
Retired Home Stager/Redesign

Hi Wayne- This sounds idyllic...the best of both worlds. And yes, the kitchen would be a key item for me. I'm so used to using my Apple watch or a card to pay for something that I rarely have much in the way of cash on hand. You forgot to add onother reason why you moved to Oswego...it's not Chicago.

Apr 30, 2026 11:43 AM
Wayne Martin

Yep, you are right,  I voted with my feet and beat it!

May 01, 2026 06:39 AM
John Pusa
Glendale, CA

Hello Wayne Martin  Oswego, Illinois brought great memories to me. I remember Oswego was a small excellent farming town. Have a great weekend.

May 01, 2026 08:18 PM
Leanne Smith
Dirt Road Real Estate - Golden Valley, AZ
The Grit and Gratitude Agent

Having been to Oswego, I concur this is hometown living with a return to the main street experience. Love cash only businesses. Thanks for sharing your why you moved. 

May 02, 2026 06:51 AM
Patricia Feager
Appraisal Review Board, Denton County, TX - Flower Mound, TX
Licensed to April 2027

Wayne Martin - After all my family history in Chicago, I never visited Kendell County. It sounds wonderful! I like that hometown feeling of belonging. And a bigger kitchen is something everyone should consider. Oswego - a charming down off the beaten path far enough away from downtown Chicago with a magical charm of its own. Where you live is truly unique and charming too!

May 25, 2026 10:22 AM