2025 Events

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Chocolate Walk for Charity*

February 8 

Downtown Bunny Hop* Buy tickets Here

April 12

Charming Oswego* Buy tickets Here

May 3

Memorial Day Parade

May 26

Country Market

Sundays June through September 9am-1pm

Sidewalk Sales

July 

Fall Fox Fest*

Sunday, October 5th (9 am – 3 pm) – Join us for the Annual Fall event in downtown Oswego.  Live music, Food Trucks, handcrafted market, farmers market vendors, sponsor booths, kids activities and more.

Trick or Treat

October 25 (10 am – 2 pm)- No Registration required.  Maps will come out with participating stores October 21st.  Kids can Visit the participating stores and trick or treat.  

Holiday Open House

November  – Join us the see the stores in their holiday glory and start your Christmas Shopping.  Shop Small Season starts the 7th.  Watch for details on the chances to win downtown dollars from November 1st through December 14th.

Coffee/Cocoa Crawl*

November 8, (10 am – 2 pm) Tickets are on sale.  Check out this new event for downtown!  Visit the participating stores to get a coffee/cocoa treat.  While you are in the stores – check out their amazing products and do some Christmas shopping.

Black Friday/Shop Small Saturday*

November 28th & 29th – Watch for details on Shop Small Season promotion.  Shop Small/Shop local and support the businesses of downtown Oswego.

Christmas Walk*

December 5 – (4:30 – 8:30 pm)  Contact the Village of Oswego for booth and sponsorship opportunities.

Cookie Walk*

December67  (10 am – 2pm) –  Join us for this annual event in downtown Oswego.  You must buy this years tin to participate!  Thank you Byline Bank for being the tin sponsor.

Jingle Bell Jog

December 13th (9am)- Sponsorship opportunities and Registration will be opening soon.  Join us for this new event.  Every runner will receive a long sleeve Tech type shirt and jingle bells.  Wear your Santa Hat and your bells and jog from Old Traughber down to the chamber office, over to Byline, then almost to Eastview and back around to Traughber.  No timing, no awards – just pure holiday fun.  Bring off some Christmas cookies and stress then visit with Santa after the jog and enjoy Cocoa & Cookies.  After the jog, head downtown to eat lunch and finish your Christmas Shopping.