Spend Autumn in Woodstock

Falling for Woodstock this October? We can't blame you!

Art-filled weekends around town. Scenic drives through the countryside. Pumpkins flying through the air. Spooky trails! Whatever it is, there is plenty of autumn fun in Woodstock and we guarantee you don't want to miss out! So grab your hoodie, round up your favorite people, and come see why October in Woodstock is the place to be!

Art Fair on the Square Returns

A Weekend Made for Artful Wandering

Saturday & Sunday, October 3 & 4

10 AM - 5 PM

Seventy original artists, live music, creative activities, and two days to wander Woodstock! Come browse the Woodstock Art Fair on the Square for one-of-a-kind finds, meet the artists behind the work, and let the kids make some art of their own! Free to attend, easy to explore, and a pretty good excuse to spend a fall weekend downtown.

*Please note the Woodstock Farmers Market will be located at McHenry County College on Saturday, October 3 from 8 AM - 1 PM!

Spend a Day with Art

Hit the Road

Two Great Reasons to Get Out to Woodstock and Explore

Fall Diddley Craft Show

Saturday & Sunday, October 10 & 11

Spend a fall weekend browsing a juried collection of talented artisans and makers at the 41st Annual Fall Diddley Craft Show. Discover handcrafted gifts, home décor, seasonal finds, jewelry, specialty foods, and plenty of one-of-a-kind treasures along the way!

One hundred percent of the event's net proceeds benefit 13 McHenry County agencies providing mental health services!

Discover Fall Diddley

Autumn Drive

Friday-Sunday, October 16-18

Head out into the countryside for a beautiful fall weekend filled with farms, fresh produce, handmade goods, antiques, and plenty of unexpected finds with the 38th Annual Autumn Drive!

Stop for pumpkins, apples, honey, jams, and homemade treats, then keep exploring for hayrides, tractor rides, petting zoos, pumpkin launchers, local crafters, and barn sales. It's the quintessential fall weekend!

Take the Drive

All Aboard for Rail Fest

October 10 & 11

Rail Fest rolls into downtown Woodstock October 10–11! Explore more than a dozen local businesses featuring model train displays, interactive family activities, and special offers as you wander the Square.

Why drive when you can arrive by train? Hop on Metra, ride the rails into Woodstock, and make your trip to Rail Fest part of the adventure.

Explore Rail Fest

The Haunted Trail Has Two Sides

Sweet First, Scary Later

October 17

At Emricson Park, the Haunted Trail has a little something for everyone, from candy to creepy! The Candy Walk, 3–6 PM, is made for younger trick-or-treaters, with a family-friendly trail and plenty of treats along the way. Then, after dark, the Zombie Walk, 7–10 PM, turns up the scares with plenty of tricks and thrills. Both begin at the Hilltop Pavilion, and admission is free!

Choose Your Fright

Next Stop: Woodstock

A Real Woodstock Podcast

What Makes Woodstock Worth the Stop?

The Conversation Drops October 7

Join Heather Arnold and Jason Ryan Lovett as they get curious about the local people, unique businesses, unexpected places and stories that make Woodstock worth discovering in this new podcast and video series Next Stop: Woodstock. Each episode uncovers something you may not know, introduces you to the people making things happen and gives you another reason to explore your own backyard or plan your next visit.

Save the Date & Meet Us On YouTube

A Meg Ryan Fall in Woodstock

You've Got Mail meets When Harry Met Sally in Woodstock

Woodstock's history with movies runs deep! And while our favorite Meg Ryan rom-coms weren't filmed here, we can absolutely envision what a weekend would look like if they were!

As Sally would say, “I’ll have what she’s having.”

Think pie. Coffee. Bookstores.And your very own movie-worthy fall.

We took a few cues from two of our favorite rom-coms and imagined a Meg Ryan weekend in Woodstock, complete with a fall itinerary you can follow!

Check Out the Itinerary

This Season at the Woodstock Opera House

Dinner on the Square. A drink before the show. Then take your seat inside one of Illinois’ most historic theaters. The Woodstock Opera House makes it easy to turn an evening downtown into a whole night out.