Escape to Woodstock this September

A Little Summer. A Little Fall.

September in Woodstock brings a little bit of everything! There’s art to explore, apples to pick, local brews to enjoy, coffee stops to discover, and live shows to catch. In other words, plenty of reasons to get out and enjoy Woodstock as the seasons start to change.

Make Room For Art

Find Your Way Into Woodstock's Creative Side

September is a great time to explore Woodstock's Art Scene. Wander through the Autumn Art Tour, discover local artists and makers, catch Arterrafest, and find more creative stops around town. We've rounded up some of the best ways to experience art in Woodstock this fall!

Explore the Art Guide

Fiesta in the Heart of Woodstock

Mexican Independence Fiesta

Sunday, September 13

Celebrate Mexican culture, traditions, and community during Woodstock's 10th Annual Mexican Independence Fiesta Celebration! Spend the day on the Square enjoying live music and dance, authentic Mexican food, family activities, cultural displays, artisan vendors, and more. This free, family-friendly celebration brings Woodstock's community together for a lively day of food, music, and fun.

Celebrate the Fiesta

September Side Trips

Apple Season is Calling

Think of a warm, sugar-covered cinnamon doughnut paired with a sip of crisp, tart apple cider! That screams September, doesn't it? We are on the cusp of fall and apple picking time is prime! Pick your own apples, explore the pumpkin patch, and tackle the Dolly Parton-themed corn maze at All Seasons Orchard. Then discover the quieter side of fall at Homestead Orchard, with 23 varieties of apples, pears, pie cherries, and a charming historic farm store. Two orchards, one very good fall day.

Not Your Average Coffee Stop

National Coffee Day | Sept. 29

In Woodstock, grabbing a cup of coffee can be part of the experience! Celebrate this special holiday and sip your morning brew while browsing books at Read Between the Lynes, admiring handmade ceramics at Wheelhouse Pottery & Coffee, or satisfying your sweet tooth with handmade chocolates and coffee at Ethereal. You can even grab a breakfast treat or deli sandwich at Cesaroni's. These aren't your average coffee stops, and that's exactly what makes them worth a visit!

Prost to September!

Oktoberfest Season Has Arrived

Two chances to raise a stein this month! Kishwaukee Brewing Company Oktoberfest, September 4–6, kicks things off, followed by BratHaus Oktoberfest on September 26. German-inspired food, local beer, live entertainment, and plenty of reasons to say prost!

BratHaus Oktoberfest

Kishwaukee Brewing Co. Oktoberfest

Take Your Seat at the Woodstock Opera House

Fall brings a brand-new season to the Woodstock Opera House, with a lineup that mixes beloved favorites with some seriously fun new acts. From comedy and dance to family shows and live performances, there’s plenty to look forward to as the curtains open on another season in one of Woodstock’s most iconic spaces.