Illustration of felt figures in knitted sweaters and Santa hats playing guitar and fiddle beside a small Christmas tree (Oswego Coffee & Cocoa Crawl)
Christmas Parties

Oswego Coffee & Cocoa Crawl

2026 dates not announced yet. Details are from 2025.

Experience the warmth of the holiday season at the Oswego Coffee & Cocoa Crawl. This event invites visitors to explore downtown Oswego's charming shops, sampling delicious coffee and cocoa treats. It's the perfect opportunity to kick off Christmas shopping, enjoy festive activities like the Jingle Bell Jog and Cookie Walk, and soak in the holiday spirit.

All ages $

Plan Your Visit

Last year

Neighborhood

Downtown Oswego

Food & Drink

Coffee and cocoa treats available at participating stores.

Location

Downtown Oswego · 25 E Jackson St, Oswego, IL 60543 Get Directions

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 🎄 🎄 (5/5)

Best For

Holiday shoppers and families

Vibe

Festive and cozy

Energy Level

Low

Photo Friendly

📷 📷 📷 📷 📷 (4/5)

Weather Sensitivity

Medium

Tips & Advice

  • Purchase tickets in advance as they are on sale and this is a new, popular event.
  • Combine your crawl with other holiday events like the Christmas Walk or Cookie Walk for a full day of festive fun.
  • Wear comfortable shoes as you'll be walking between participating downtown businesses.
  • Check the event details closer to the date for a list of participating stores and their specific offerings.
  • This event is a great opportunity to discover unique local shops and find Christmas gifts.

Special Events & Promotions

  • Shop Small Season promotion runs from November 1st through December 14th.
  • Chances to win downtown dollars from November 1st through December 14th.
  • Black Friday/Shop Small Saturday promotions on November 28th & 29th.

Links & Contact

Run by Oswego Downtown Association

Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.

Frequently Asked Questions

What is the Oswego Coffee & Cocoa Crawl?

It's an event where visitors can purchase tickets to sample coffee and cocoa treats from various participating businesses in downtown Oswego.

When does the Coffee & Cocoa Crawl take place?

The event is scheduled for November 8th, from 10 am to 2 pm.

How do I participate in the Cookie Walk?

To participate in the Cookie Walk on December 6th, you must purchase this year's tin, which serves as your entry to collect cookies.

Are there other holiday events happening around this time?

Yes, the Oswego Downtown Association hosts several holiday events, including the Christmas Walk on December 5th and the Jingle Bell Jog on December 13th.

Can I shop for Christmas gifts during the crawl?

Absolutely! The event encourages visitors to explore the shops and start their Christmas shopping while enjoying the festive treats.

Browse Christmas in Oswego

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.

Contributors & Updates

Last checked: