If art, handmade finds and discovering something a little different are your idea of a good fall day, you’ll want to keep an eye on Woodstock this season.

From immersive art experiences and local artists to juried shows, handmade goods and a fall drive filled with creative finds, there are plenty of reasons to make Woodstock part of your fall plans.

Here are five dates worth saving:
 

ArterraFest | September 4–5

Woodstock’s fall arts season gets started with ArterraFest, a community-powered celebration of creativity, music, art, ideas and shared experiences throughout downtown Woodstock.

Over two days, artists, musicians, performers and community members come together for live performances, artist conversations, interactive experiences and plenty of opportunities to see creativity happening all around you.

The weekend includes collaborative music on the Square, an artist panel at WheelHouse Pottery & Coffee, pop-up artistic encounters at Arterra on the Square and a special immersive installation at the Woodstock Opera House.

Saturday evening brings Square Notes to the Opera House, featuring original music, poetry, storytelling, dance, theater and visual art inspired by Woodstock itself.

 

Autumn Art Tour | September 12

See Woodstock through the eyes of local and regional artists during the Autumn Art Tour, presented by the Woodstock Professional & Business Women.

This free, self-guided experience takes you throughout historic downtown Woodstock, where artists showcase pottery, paintings, jewelry, photography, glass, mixed media and more.

Meet the artists, watch live demonstrations and explore at your own pace. Pick up a map and make your way through the tour while enjoying the shops, restaurants and other downtown stops along the way.

And there’s a good reason to feel even better about spending the day exploring. Proceeds from the event support scholarships for local women pursuing higher education and trade school opportunities.
 

Art Fair on the Square | October 3–4

Then the art takes over the Square.

Art Fair on the Square, presented by Amdur Productions, brings more than 60 original artists to downtown Woodstock for a weekend of artwork, live music and hands-on creative experiences.

Browse original pieces, watch artists at work during live demonstrations or try your hand at a live painting class. Younger visitors can get creative in the Kids Art Zone with activities including spin art, sand sculpture, drawing and more. There’s even a face painting tent where you can become part of the artwork.

Admission is free, parking is easy and the festival is walkable, making it easy to spend a few hours at the fair and planning for coffee, lunch, boutique shopping or a drink!

 

Fall Diddley Craft Show | October 10–11

If your idea of art includes beautifully made things by artisans and crafters, keep Fall Diddley on the calendar!

The 41st Annual Fall Diddley Craft Show returns to the McHenry County Fairgrounds with a juried collection of artisans and makers offering handcrafted gifts, home décor, seasonal favorites, jewelry, specialty foods and more.

It’s a great place to start thinking about holiday gifts, find something for your home or simply discover something you didn’t know you needed.

There’s also a bigger reason to shop! One hundred percent of the event’s net proceeds benefit 13 McHenry County agencies that provide mental health services.

 

Autumn Drive | October 16–18

If you like your creative finds with a little fresh air and fall scenery, keep reading!

Autumn Drive takes place October 16–18 in rural Woodstock and beyond, bringing together local farms, crafters, antique dealers and plenty of classic fall activities.

Look for pottery, jewelry, soaps, specialty foods, refurbished furniture and vintage finds. Pick your own apples or pumpkins, explore barn and garage sales, and stop along the way for tractor rides, hayrides, petting zoos and pumpkin and apple launchers.

It’s not your traditional art fair, but if you love handmade goods, vintage treasures and finding something unexpected, it’s a pretty good way to spend a classic fall weekend.

 

More Ways to Experience the Arts

The big events aren’t the only way to experience the arts in Woodstock. From hands-on classes to local exhibits and creative gatherings, there are plenty of ways to keep exploring all season long.

A Night Out: Sip & Carve — On the first Friday of each month (September would be the second Friday due to Labor Day weekend), learn the art of sgraffito with the Clayworkers' Guild of Illinois - Artisans on Main while creating your own ceramic platter. Perfect for a date night, girls’ night or solo creative adventure.

Absurd Arts Social Club — On the second Wednesday of each month at Records Department, bring your doodles, paintings, collages or half-finished projects and create alongside other creative folks.

Community Night at Ethereal — Stop by on the third Friday of each month for a new local art exhibit, a featured small business and free music from Jazz on the Square.

Intro to Clay — Get your hands dirty on the third Thursday of each month and learn hand-building pottery techniques while creating your own functional pieces.

Saturday Art Workshops at Warp Corps — Young creatives ages 24 and under can make a new craft each week, with past projects ranging from acrylic pours and shrinky-dinks to jewelry making.

Art Exhibits at the Woodstock Opera House — Discover rotating exhibits throughout the year, including September’s immersive STAGE RIGHT: Shared Connections installation by Bert Leveille and John Hegner.

 

Make A Day or Weekend of It

Come for the art. Stay for the rest! Spend some time exploring the charm that is Woodstock, grab lunch or dinner (throw in a cocktail too!), browse local shops and find a few more reasons to stick around!

Making a weekend of it? Find lodging in Woodstock and start planning your stay. Find Places to Stay in Woodstock