Upcoming Special Events

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May

 Experience our Illuminated Concert Series! This special intimate acoustic music series by candlelight will have limited tickets, a local dining/drinking establishment to host the reception and different themes per performance. With every ticket, comes a dining voucher for a Downtown Glen Ellyn Restaurant. 

Tickets will be on sale April 1, 2025

 Friday, May 16

 Taylor Swift cover band, Shake It Off 

5:00pm Start setting up chairs. 

6:00 - 9:45 Live Music - Two bands

Experience the best Chicagoland bands at our FREE Family Friendly Friday Summer Concert Series. Dine and drink from local restaurants.   No outside food or drink allowed. Restaurants will be serving specials just for you!  

 FREE

  May

Guests will meet at Park & Oak where the scene will be set. Groups will be divided and escorted by an actor detective into 5 different storefronts finding clues and interviewing suspects before all meet up for the big reveal finding the answer to the question “Who’s done it?”.

Tickets will be on sale April 1, 2025

June thru July

In partnership with the Bookstore of Glen Ellyn, and the Glen Ellyn Public Library, participate in the Summer Scavenger Hunt. For the entire months of June and July, challenge yourself to find all the clues downtown to complete your scavenger hunt card for a prize and join us for the wrap-up party hosted by the library!

FREE

  Friday, June 6

Semple, Rock cover band

5:00pm Start setting up chairs. 

6:00 - 9:45 Live Music - Two bands

Experience the best Chicagoland bands at our FREE Family Friendly Friday Summer Concert Series. Dine and drink from local restaurants.   No outside food or drink allowed. Restaurants will be serving specials just for you!  

 FREE

Saturday, June 14

Nothing will be nicer than a beautiful afternoon Wine Walk! Sipping on fine wine and bites, strolling through unique shops, award-winning home décor designers and gorgeous boutiques to find one-of-a-kind treasures.

Tickets go on sale May 1, 2025 

  Friday, July 4th

The Glen Ellyn 4th of July Committee is thrilled to announce the return of the Glen Ellyn 4th of July Parade to its historic downtown location. 

After two years of extensive construction and revitalization efforts, the heart of Glen Ellyn is ready to once again host this beloved community tradition to honor the nation’s birthday. FREE

 Saturday, July 12 

This is the premiere jazz festival of DuPage County bringing an afternoon line-up of the best jazz in the Midwest by collaborating with local partners such as 90.9fm WDCB Home of Chicago Jazz, Fareed Haque, and Bellas Artes School of Music.

FREE

July 18-20

Everyone is always excited for the long awaited 3-day Summer Sidewalk Sales. Find bargains and treasures for this annual highly anticipated event! Main street is closed only Friday-Saturday.

FREE

Friday, September 5

 Hillybilly Rockstarz, Country Night

5:00pm Start setting up chairs. 

6:00 - 9:45 Live Music - Two bands

Experience the best Chicagoland bands at our FREE Family Friendly Friday Summer Concert Series. Dine and drink from local restaurants.   No outside food or drink allowed. Restaurants will be serving specials just for you!  

 FREE

September

 Experience our Illuminated Concert Series! This special intimate acoustic music series by candlelight will have limited tickets, a local dining/drinking establishment to host the reception and different themes per performance. With every ticket, comes a dining voucher for a Downtown Glen Ellyn Restaurant. 

Tickets will be on sale August 1, 2025

Sept 18-20

 Grab your Lederhosen and join us for the Glen Ellyn Oktoberfest with Live Music, Activities, and a mouthwatering array of German-themed food and beer at Two Hound Red Brewing Co.

FREE to Enter

 Thursdays November 6 & 13

Join us for the highly anticipated Ladies Night Out in Downtown Glen Ellyn!  Grab your friends and spend the evening strolling through the cutest shops and boutiques finding the best gifts on your holiday list.    Don't miss the many discounts and specials while enjoying wine and treats along the way! 

Tickets go on sale October 1, 2025  

Through December

Downtown Glen Ellyn offers the perfect picturesque holiday shopping experience for the season. Our charming historic downtown is home to trendiest boutiques and locally owned shops each brimming with treasures for everyone on your holiday list. Find our favorite 2025 gift ideas in our Downtown Glen Ellyn Holiday Shopping Guide.

FREE

Through December

Light Up Glen Ellyn!  Who on your block is the Clark Griswold of Holiday Lights? Show off your home in all its holiday splendor! Categories:

• Best Overall
• Most traditional
• Most whimsical
• The Clark Griswold Award

Registration available November 1, 2025

November 27 - December 15

 Glen Ellyn's very own Santa mailbox will return on the northeast corner of Main Street and Crescent Boulevard. Letters “mailed” by Monday, December 15 will receive a response from Santa, along with a signed photo. Please make sure letters include a legible return address so that Santa can reply. The mailbox will return to the North Pole on Monday, December 16 until next Christmas! 

FREE

November 26 - December 25

Grab a cocoa and walk through Downtown Glen Ellyn this holiday Season for the pure magic of it all. Witness the creativity, inspiration and imagination of the holidays. A beautifully decorated window can make even the coldest of days feel a bit warmer.

FREE

Saturdays & Sundays

November 29 - Dec 21 

10:30am - 12:30pm   

(times may vary)

 Ho Ho Ho, Santa Claus is coming to town! Don’t miss your chance to snap a photo with Santa and share your Christmas wishes. Visit with Santa at his Glen Ellyn weekend House off Main St. Don't miss out on this new tradition while you shop & dine in Downtown Glen Ellyn.

FREE

Thursdays December 4, 11 & 18

  What’s the best way to get into the holiday spirit? Hop aboard our classic Victorian trolley for a 30-min narrated tour of our festive Downtown and see the best decked-out homes in a warm trolley. This ride will include a little Glen Ellyn History, local holiday lights with a few jokes in between. Check in is at 515 Crescent @The North Pole, where all are welcome to warm up with hot cocoa, get your picture with Santa and much more!

Thank you to our Trolley Sponsor @properties Christie's International Real Estate.

Tickets go on sale November 1, 2025

Wednesday, December 10

 Jingle, mingle, and enjoy discounted nibbles and nog at participating restaurants while sporting your best festive attire.

Choose your first stop to check in, grab your light up necklace and program. Then the night is free to roam to all the restaurants and see friends and family along the way. 

Tickets go on sale November 1, 2025