If you’ve spent any time on Erie Street, you know that Downtown Willoughby isn't just a historic district—it’s the social heart of Northeast Ohio. As the weather warms up, our calendar fills up with festivals, concerts, and markets that bring thousands of visitors to the 44094.

At Paramount Properties Group, our office is right in the thick of the action on Erie St. We’ve scoured the local listings from the City of Willoughby, the DTW Bar & Restaurant Association, and the Heart of Willoughby to bring you the definitive guide to Spring and Summer 2026.

Grab your calendar and get ready to experience the best of DTW!

🛍️ The Heart of Willoughby Outdoor Market

• When: Every Saturday, May 2 – October 31 | 8:00 AM – 12:00 PM

• Where: City Hall Parking Lot (1 Public Square)

• The Vibe: Kick off your weekend with fresh produce, local honey, and handmade crafts. It’s the perfect Saturday morning stroll before heading over to Erie St. for brunch.

🍖 The 13th Annual Marous DTW Rib Burn Off

• When: Saturday, May 16 (12 PM – 10 PM) & Sunday, May 17 (12 PM – 8 PM)

• Where: Erie Street, Downtown Willoughby

• The Vibe: This is the signature event of the season! National rib vendors, local food, and multiple stages of live music. It’s a free, family-friendly event that defines the DTW summer spirit.

🎸 2026 Summer Concert Series (Gazebo & DTW)

The city is bringing live music back to the streets! While Osborne Park has Wednesday shows, the Thursday night DTW series is a local favorite.

• June 18: Hair Supply (70s Soft Rock / 80s Pop)

• June 25: Motor City Gold (Motown / Oldies)

• July 2: Ace Molar (Classic Rock)

• July 9: Van Sailin’ (Yacht Rock)

• July 16: Yosemite Slim (Nashville Country)

• July 23: Swamps of Jersey (Bruce Springsteen Tribute)

• July 30: Burning River Band (Rock)

• August 6: China Grove (Doobie Brothers Tribute)

• August 13: Dirty Deeds (AC/DC Tribute)

• All DTW concerts are Thursdays from 6:30 PM – 8:30 PM.

🏎️ Downtown Willoughby Car Cruise-In

• When: Saturday, June 20 | 4:00 PM – 10:00 PM

• Where: Erie Street

• The Vibe: Hundreds of classic cars and trucks line the streets. It’s a nostalgic trip through automotive history right in our historic downtown.

🎨 Willoughby ArtsFest 2026

• When: Saturday, July 18 | 10:00 AM – 5:00 PM

• Where: Throughout Downtown Willoughby

• The Vibe: Organized by the Willoughby Arts Collaborative, this event brings over 100 juried artists to town. Expect live demonstrations, unique finds, and incredible creativity.

🤠 NashWill: Music Fest

• When: Saturday, August 1 | 1:00 PM – 9:00 PM

• Where: Participating DTW Bars & Restaurants

• The Vibe: DTW transforms into a mini-Nashville. Grab your boots and enjoy live country music across the district’s best venues.

🚂 Last Stop Willoughby Festival & Parade

• When: Saturday, August 8 | 10:00 AM – 4:00 PM

• Where: Downtown Willoughby & Wes Point Park

• The Vibe: Celebrating our railroad history! The day features a parade (starting at 2 PM), the "Stop at Willoughby" screenings at the library, and the 6th Annual ChalkFest.