Don’t leave Woodstock without capturing these must-see spots! From colorful murals and quirky landmarks to historic icons that glow in every season, our Top 9 Instagram-Worthy Spots will have you snapping, tagging, and exploring the charm of the Square and beyond. Plan your photo adventure and make your visit unforgettable!
1. The Wings at The Backdrop
Step inside the boutique shop The Backdrop at 106 Cass St and find the vintage green door with mounted ivory wings—a perfect mix of charm and whimsy for photos.
📸 Pro Tip: Stand in the center and perfect a flawless face pose to match your angelic wings.
📍 106 Cass St., Woodstock, IL 60098
2. The Pride Steps
Located at the corner of Benton and Van Buren, leading down toward Jefferson St near Material Things, these rainbow-painted steps are a bold, colorful statement.
📸 Pro Tip: Shoot from down low for a dramatic view.
📍 Corner of Benton & Van Buren, Woodstock, IL
3. Woodstock Movie Mural
This iconic mural, designed by local artist Michael Stanard, celebrates our town’s cinematic history and offers a perfect mix of art and pop culture.
📸 Pro Tip: Capture the full mural with a wide-angle shot or stand at one end to get every detail. (thanks to @roadtrippinwithkaren for the inspo pic!)
📍231 Main St., Woodstock, IL 60098
4. In Front of the Opera House
The historic Woodstock Opera House at 121 W. Van Buren St. is a jewel of the town, built in 1889 with timeless charm.
📸 Pro Tip: Sunset is the golden hour here, perfect for glowing, cinematic shots.
📍 121 W Van Buren St., Woodstock, IL 60098
5. Kishwaukee Brewing Co. Wall
Kishwaukee Brewing Co. at 1900 Dillard Court combines inviting brewery vibes with a hand-painted wall mural perfect for casual or group photos.
📸 Pro Tip: Include your pint in the frame for a lifestyle shot that tells a story.
📍 1900 Dillard Ct., Woodstock, IL
6. Benton Street Mural
Created by nationally renowned artist Mauricio Ramirez, this vibrant mural celebrates Woodstock’s history and musical heritage, weaving in roses, patriotic elements, and subtle depictions of the Square.
📸 Pro Tip: Walk the span of the mural to show its full scale in your photo.
📍 North Benton St., Woodstock, IL
7. The Pink Chair at Rocket Fizz
Snap a photo on the iconic pink chair outside Rocket Fizz and channel the playful energy of this fun candy shop.
📸 Pro Tip: Grab some unique candy or a specialty soda to match the colorful vibe of the store.
📍 109 S. Benton St., Woodstock, IL
8. The Old Courthouse Center
At 101 N. Johnson Street, this historic building is a breathtaking backdrop, especially when lit up at night or during special holiday displays.
📸 Bonus Photo Op: Snap a pic at the judge’s bench in the Old Courthouse. Slip on a robe, grab the gavel, and strike your best “order in the court” pose!
📍 101 N. Johnson St., Woodstock, IL
9. The Cherry Tree Inn Bed & Breakfast
Step into cinematic history at the charming spot where Groundhog Day was filmed in Woodstock!
📸 Pro Tip: Recreate Bill Murray’s iconic view—snap a photo in front of the inn, or face the road to capture the view from his window.
📍 344 Fremont St., Woodstock, IL
Ready to explore Woodstock through your lens? These nine spots are just the beginning—wander the streets, find your favorite angles, and capture the charm that makes our town so special. Don’t forget to tag us on Instagram at @realwoodstockil and use #RealWoodstock so we can see and share your photos with our community!