Apple Fest Lincoln Square: 2025 In-Depth Guide

Nestled in the heart of Chicago’s North Side, the Lincoln Square Apple Fest transforms Lincoln Avenue between Lawrence and Sunnyside into a bustling harvest marketplace. Over 80 local vendors, live music stages, and activity booths line the streets, inviting attendees to immerse themselves in the flavors and sights of the fall season. This charming neighborhood in Chicago blends tradition and excitement, making it an ideal destination for both first-time visitors and returning fans.

Mark Your Calendar for a Juicy Weekend

Apple lovers, rejoice—this isn’t your average fall fest. Two days of caramel-drizzled joy and crisp air fun await.

Mark your calendar for October 4th and 5th, 2025—when Lincoln Square comes alive with the 38th Annual Apple Fest. The festivities run on Saturday, October 4th, and Sunday, October 5th, from 9am-6pm, offering two full days of orchard-inspired fun. A $5 suggested donation at entry supports local beautification projects and community non-profits, enhancing the neighborhood’s charm.

Family Fun and Festive Cheer for All

The Apple Fest is designed with families in mind, featuring a dedicated Kid Zone (located in the parking lot at 4513 N Lincoln) packed with engaging activities, including:

• Craft stations: Kids can create beaded keychains, paint rocks, mold beeswax, or engage in apple-themed sensory play.
• Interactive performances: Enjoy musicians, jugglers, and sing-a-longs, with performers like Wiggleworms bringing energy to the crowd.
• Instrument petting zoo: Hosted by the Old Town School of Folk Music, where children can explore musical instruments.
• Games and activities: From hand-woven jump ropes to balance boards, organizations like Fit City Kids, Chicago Waldorf School, and Spark Montessori offer age-appropriate fun.

It’s an event where kids can giggle over caramel apples while parents sip warm cider or apple-flavored beer. Couples, solo adventurers, and foodies will also find plenty to enjoy, making this a truly inclusive celebration of community, flavor, and fall.

Why This Apple Fest Is the Core of Chicago Autumn

Wondering why locals treat this event like a seasonal rite of passage? It’s more than apples—it’s about community, connection, and celebrating all things cozy.

What sets this Apple Fest apart? Its authenticity. More than just a street fair, it’s a tradition passed down through generations in Lincoln Square. Guests can savor locally grown apples, homemade pies, and the sounds of live bluegrass bands echoing through the streets. The event’s friendly, relaxed atmosphere, combined with its focus on community, makes it a standout Chicago event for October.

Savor the Flavors of Fall

Indulge in a wide array of apple-inspired treats from over 80 local vendors and restaurants. Classic favorites include:

• Candy apples
• Fresh baked apple pies
• Hot apple cider
• Unique offerings elevate the experience, such as:
• Apple-stuffed tamales
• Apple doughnuts
• Apple pizza
• Apple and cinnamon empanadas
• Apple-stuffed grilled cheese

Quench your thirst with apple-flavored beer or non-alcoholic cider, perfect for toasting the season. Beyond food, vendors offer fall essentials like scarves, hats, and fresh bushels of apples, creating a vibrant marketplace.

Live Music and More

Enjoy live music performances by local musicians throughout the weekend, with stages set up in areas of the fest. From soulful bluegrass bands to family-friendly acts like Wiggleworms, there’s something for every musical taste. The marketplace also features artisanal goods, from handmade crafts to seasonal decor, ensuring a feast for the senses.

Community Impact and Safety

The Apple Fest is organized by the Lincoln Square Ravenswood Chamber of Commerce, with proceeds supporting local beautification projects and non-profits. While specific security details are not outlined, the event’s family-friendly nature and community focus suggest a safe, welcoming environment for all attendees.

Make Fall Magic Happen with Tripster

Don’t just attend the fest—make a weekend of it. Tripster lets you pair apple-filled fun with Chicago’s best attractions and stress-free planning.

We make it easy to turn a weekend in Lincoln Square into a full-blown fall adventure. Browse cozy, family-friendly lodging nearby, complete vackation packages, and craft the perfect autumn itinerary—all in one spot.

With exclusive deals, no hidden fees, and a smooth booking experience, Tripster helps you focus on making memories, not managing logistics. Book your Chicago fall escape with Tripster today—and let the season of cozy, cider-filled fun begin!