Chicago North Shore Fall Festivals & Events Guide | Chicago North Shore Moms

The leaves are turning and Labor Day has come and gone, but that doesn’t mean festival season is over!  Here at Chicago North Shore Moms we think the best of the fest season is yet to come this fall!  These are the best bets to hit this fall along the North Shore and beyond.  Cheers!


Valslist Emerge Winnetka, September 11th
Hubbard Woods is host to this years festival presented by popular music guru Valslist!

Pitchfork Music Festival, September 10-12th 
Long standing music festival occupying Union Park, Chicago featuring everything from indie, nostalgic one hit wonders, rock, pop, and punk to rap and DJ sets.

Art in the Village, Winnetka’s Fine Art Fair
Fine art in Winnetka’s Hubbard Woods.

German-American Oktoberfest, September 10-12th 
Celebrating 100 years in Lincoln Square Chicago this year!  This family friendly festival is held in the quant square and never disappoints.

Festival of the Vine, September 10-12th 
Lake Geneva hosts a festival celebrating all things grown on the vine (hint, hint- wine.  LOTS of wine and great food!)

Lakeview East Festival of the Arts, September 11th  &12th 
A personal favorite art festival that runs down Broadway in Lakeview East Chicago and delivers great art in a great neighborhood- with great food and drink all around!

Renegade Craft Fair, September 18th & 19th 
This is one of the coolest craft + art street fests going!  Find everything from unique screen printed kids tees to fine jewelry along Division Street in Ukrainian Village, Chicago.

Bloody Mary Fest, September 19th
Eclectic Highwood hosts this street festival centered around brunch and weekend favorite, the Bloody Mary!

American Craft Exposition
Chicago Botanic Garden is host to this fine arts show and featuring more than 140 artists in a gorgeous setting.

Long Grove Apple Fest, September 24-26th 
Indulge in apple pies, donuts, caramel dipped and candied apples, apple wine, and more at this family (and dog friendly) festival!

Blocktoberfest Glenview, Oct 2nd 
Beer, bands, great food & a kid friendly section (with games, arts/crafts, prizes) in Glenview!

The Great Highwood Pumpkin Festival, October 11-13th 
We love this fun fall festival! Join in the fun carving a pumpkin to display or simply enjoy others skills!  Carnival rides, a 5k, music and food through the weekend! (Carving begins October 7th)

Chicago Pride Fest, October 1-3rd 
Colorful and bright with the happiest vibe, Chicago Pride Fest is a Chicago staple celebrating love.

Evanston Oktoberfest on Sunday, September 29
A full day of beer tasting, delicious local food, live music and traditional Oktoberfest fun in downtown Evanston!

Keep checking back for more events to be added between festivals!

Thank you to our sponsor of the Summer and Fall Festivals Guide, Kelli Gould with @properties!  We are so appreciative of her supporting not only Chicago North Shore Moms, but each and every festival here and their local vendors!

Considered selling in this non-stop hot market?  We know you’re starting to book your holiday card photo shoots, but don’t forget that this is also the critical time to shoot exterior house photos before winter!  If you’re looking to sell in the next 6 months or know someone who is, reach out to Kelli to book an outdoor photo session before the leaves fall!






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