Downtown Oswego is a winter wonderland for holiday shoppers—complete with reindeer! Here's what to expect when you #GoOswego this holiday season: independent shopping at an eclectic collection of boutiques and one of the region's most unique Christmas festivals in a friendly and forward-thinking village. 

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Holiday Events in Oswego, Illinois

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Backroads Holiday Vintage Market 

When: Saturday, November 10 to Sunday, November 11, 10:00 AM – 4:00 PM
Where: Emerson Creek Pottery & Tearoom
Join us for a vibrant vintage market curated with care. November 10th and 11th from 10:00am – 4:00pm. We will have over 60 vendors that will Holiday Decor, Vintage & Handmade and so much more! It is $10 per car entrance fee. There will be lunch items available in our Barn. Tearoom Seating by Reservation Only. We hope you can join us! It will be our last Vintage Market of the season! You won’t want to miss it.

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Gobbler Hobbler 10K & Mashed Potato Mile

When: Sunday, November 11, 7:00 AM
Where: Fox Chase Elementary School 
Celebrate fall with a chip-timed 10K run down the Fox River and through scenic Oswego, or enjoy the Mashed Potato Mile just for fun! The USATF certified course begins and ends at Fox Chase Elementary School. Volunteers provide two water stations on the course and split times at every mile. All pre-registered runners are guaranteed a hoodie sweatshirt, refreshments, and participation ribbon. Athletes are invited to enjoy complimentary walking pancakes after the run. This 10K qualifies for the Oswego Triple Race Series.

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Oswego's Christmas Walk

When: Friday, November 30, 4:00 to 8:00 PM 
Where: Downtown Oswego
Come home for the holidays for the Oswego Christmas Walk, a memorable and cherished community holiday event that brings thousands of families to downtown Oswego for a magical start to the holiday season. Help light the Village’s official tree and save it from the Grinch, take a ride on a horse-drawn carriage, ride the Toyland Train through downtown, and welcome Santa to Oswego during the Silent Light Parade!

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Downtown Oswego Cookie Walk

When: Saturday, December 1, 10:00 AM
Where: Downtown Oswego 
Join downtown Oswego businesses for the annual Cookie Walk, an Oswego tradition! Buy a Cookie Walk tins are available for $10 (cash only) at Floral Expressions, Page’s Popcorn, and Hudson Design House, then visit participating downtown businesses to fill your commemorative holiday tin with one freshly baked cookie from each shop. Purchase your Cookie Walk tin in advance — limited supplies available.

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Oswego Holiday Express

When: Thursday, December 6 through Sunday, December 9, 4:00 to 8:00 PM 
Where: South Point Park
Take a magical journey to the North Pole! Don your pajamas and board the trolley at Santa Station as you head to the top of the world. Warm up in Mrs. Claus’s Cookie House, enjoy hot cocoa from the Village Grind, meet real reindeer and the man of the hour – Santa Claus!


Holiday Shopping in Oswego, Illinois

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Oswego is where you can shop for everyone on your list, from weekend warriors and fashionistas to amateur gourmands. Go shop, dine, and play with a getaway in Oswego, Illinois. Visit to plan your visit now.