The holidays may look a little different for us all this year, but there’s still so much holiday fun to be had! Enjoy holiday happenings and activities in Downtown Oshkosh all season long. We can’t wait for you to join us in celebrating the holidays downtown and supporting local this holiday season! Thank you to our lead sponsor of Downtown for the Holidays – Oshkosh Corporation.

November 20th: Light Up Downtown Sponsored by the JEK Foundation
Thanks to the generous support of the JEK Foundation and other private donors, our Opera House Square will be beautifully lit this year and for years to come! Downtown businesses will join us in lighting up our downtown at 6:30pm. Mayor Palmeri will lead the countdown to our virtual tree lighting, and our Holiday Square will be revealed right on Facebook! Grab a bite to eat at a downtown restaurant, shop locally at our downtown businesses and enjoy our holiday décor every night all season long! More details coming soon.

November 28th: Opening of Santa Sightings, Coloring Book Contest and Letters to Santa (see details below)

November 28th: Small Business Saturday
Shopping local is more important than ever this holiday season! Join us downtown on Saturday, November 28th in supporting our amazing downtown businesses. Share your finds, meals and experiences on social and tag @downtownoshkosh for a chance to win a variety of downtown goodies and gift cards!

December 10th: Holiday Virtual Shop Hop
Join us virtually on Facebook Thursday, December 10th from 6-8pm for our Holiday Virtual Shop Hop event! Our downtown stores are coming together to bring you a fun night of online holiday shopping, special offers, giveaways and more! Find the perfect gifts for the loved ones in your life right from the comfort of home. More details coming soon!

December 11th-13th: Shop Local Rewards Weekend
Spend over $100 at our downtown businesses December 11th-13th and upload your receipt on our website! We’ll send you a $10 Downtown Oshkosh gift card just for shopping local! Redeem here:

December 6th-12th: Letters to Seniors Week
Drop off letters/Christmas cards to Santa’s mailbox in Opera House Square by December 12th. 

During the week of December 6th-12th, the Downtown Oshkosh BID will be collecting letters to seniors/holiday cards from our Letters to Santa mailbox in Opera House Square. We encourage our Oshkosh community to write letters or create artwork or holiday cards for those in our community who may be limited in having visitors and seeing their family and friends this holiday season.

Print our Downtown Oshkosh holiday card or make your own!

-Letters should be legible and handwritten.
-Avoid religion and politics. Your letter should resonate with anyone.
-Exclude the date.
-Embrace your creativity! Personalize your letters as much as you can – you could include drawings, coloring pages, etc!
-Please envelope your cards/letters but leave the envelope unsealed.
-Snap a photo and tag us @downtownoshkosh to help us promote our campaign to connect the community with our elderly in isolation this holiday season! Sharing acts of kindness is a great way to promote others to do the same!

A special thanks to our friends at Miravida Living and the Oshkosh Senior Center for helping us connect the community this holiday season!

December 12th-19th: Downtown Scavenger Hunt
Santa’s helpers have hidden special ornaments in storefronts throughout Downtown Oshkosh – can you find them all?! Join the fun downtown December 12th-19th.

Grab a ballot from Fire Escape, Escape Oshkosh or Adventure Games & Hobby or print the list of participating businesses and start your search!
Return your completed ballots to Santa’s mailbox in Opera House Square and a winner of a $100 Downtown Oshkosh gift card will be selected LIVE on Facebook on December 19th. Good luck!

December 16th: Coloring Books Due
Drop off in Santa’s mailbox in Opera House Square (see details below)




Letters to Santa Sponsored by the Oshkosh Area Community Foundation
Write a letter to Santa and deliver it to Santa’s Mailbox in Holiday Square at any time during the holiday season! (Don’t forget to address it to 321 Santa Claus Lane!) From December 6th-12th we will also be collecting Letters to Seniors that will be handed out by our friends at Miravida Living, Evergreen Retirement Community and the Oshkosh Senior Center. More details coming soon!

Downtown Coloring Contest Sponsored by City Center
Grab a Downtown Coloring Book from participating downtown businesses and get started! Complete the coloring book and deliver it to Santa’s mailbox in Opera House Square by December 16th. Winners will be announced December 23rd!

Coloring Book Pickup Spots:
-The Roxy Supper Club
-Planet Perk Cafe
-Caramel Crisp Cafe
-Brinkley’s Boutique
-Wagner Market
-Bar 430


Santa Sightings Sponsored by Visit Oshkosh
Santa Claus is coming to (Down)town! Can you find him?! Beginning November 28th, Santa (murals) will be hiding in fun spots throughout Downtown Oshkosh. Santa’s Nice List with locations:

…. and eat local, shop local & be merry all season long!

More holiday activities and happenings will be announced throughout the holiday season.

All activities have been planned and designed to promote social distancing so our community can safely experience the magic of the holiday season!

Continue to follow along on social (Facebook/Instagram) and check this page on our website for updates! 



A special thank you to our wonderful Downtown for the Holidays sponsors!


Title Sponsor


Holiday Square Sponsor


Letters to Santa Sponsor


Santa Sightings Sponsor


Downtown Coloring Book Sponsor