Make it a REAL holiday weekend! Memorial Day in Woodstock brings together long-standing events, great food and fun experiences worth the trip, all set in our charming, historic community. We've put together a full weekend itinerary to help you make the most of it, from meaningful traditions to summer kickoff moments. Come for the day, stay for the weekend. You're always welcome!

 

Friday: Live Music and Late-Night Bites

 

Kick off the weekend with live music at Open Mic Night on the Woodstock Square, a favorite local event featuring original songwriters, poets, storytellers, and composers. These evenings showcase local and regional talent in a warm, welcoming setting. 

After the show, keep the evening going with a glass of wine at Winestock, a crafted cocktail at the Emerson & Oliver speakeasy or grab a bite and drink at Squire on the Square! 

 

Saturday: From Sunrise to Sunset

 

Start your Saturday off on the right foot (bring sneakers!) with the Melissa O’Leary Memorial Splash Bash and Family Water Run (registration required). Choose between a timed 5K or a one-mile family-friendly walk, then stick around for swimming, refreshments, and a lively, community atmosphere that celebrates the start of summer.

From there, head to the Woodstock Farmers Market on the Square, one of the area’s favorite producer-only markets. Browse fresh produce, baked goods, coffee, and artisan items while exploring the shops and boutiques.

As the afternoon unfolds, make your way to the Lost Lagoon Backlot Bash. This free event features vendors, tattoo flash, a chopper show, an art raffle, and a beer tent, bringing together art, community, and a little edge.

When evening arrives, unwind with some delicious nosh and seasonal cocktails at Sofie's Whiskey & Wine, where spring flavors like peach cosmos, French martinis, and sangria set the tone for a memorable night.

 

Sunday: Outdoor Fun & Local Favorites

 

Ease into Sunday with a hearty breakfast at Isabel's Family Restaurant, a hometown favorite serving up fresh dishes made with ingredients straight from their garden. Think omelets, skillets, waffles and more.

Then head to Emricson Park to spend some time immersed in nature! Stroll the scenic Woods Walk Trail, play a round of disc golf or pickleball and enjoy the fresh air! If you want to cool off, head to Woodstock Water Works for opening weekend and splash into summer with a little poolside relaxation.

Later, catch a hot new movie at Classic Cinemas Woodstock Theatre. Grab your fresh popcorn, settle into a reclining seat and enjoy the show! 

Wrap up the night with hot, cheesy pizza from Rosati's Pizza or Napoli's Pizza, then head to Kishwaukee Brewing Company for locally brewed, award-winning beers and a perfect sunset! 

 

Monday: Memorial Day Traditions

 

Start your Memorial Day on the Woodstock Square with a coffee and a pastry from Ethereal or Wheelhouse Pottery and Coffee. Head down the Park in the Square for Woodstock's beloved Memorial Day Ceremony and Parade, a meaningful tradition honoring those who served! 

Spend the rest of the day exploring Woodstock's public art scene. Visit the Pride Steps, the North Benton Street Mural, the Woodstock Movie Mural and the brand new Prairie Roots installation at the Woodstock Public Library...all perfect for capturing those Instagram-worthy moments.