Castle Rock Car Show Weekend Kickoff Concert 2026

The 18th Annual Classic Rock Cruise In Car Show Weekend takes over downtown Castle Rock at Wilcox Square (4th & Wilcox Street) on June 19-20, 2026. Free admission, family-friendly, and one of the largest classic car shows in Douglas County.

Schedule

Friday June 19 — Kickoff Cruise & Concert (6:00–9:00 PM)
Free outdoor concert with Shelvis and the Roustabouts on the main stage at Wilcox Square. 50+ classic cars on display from The Vintage Car Club of Castle Rock.

Saturday June 20 — Main Car Show (10:00 AM–3:00 PM)
Streets of historic Downtown Castle Rock shut down for 300+ classic cars, hot rods, trucks, and specialty vehicles. Live music lineup: Steve and the Cruisers (10:00 AM–12:30 PM), then 6202 (12:30–3:00 PM).

Free Kid Attractions (Saturday)

• Bounce houses
• Face painters
• Rock wall
• Ice cream and live music

Food Trucks

Both days: Glacier Homemade Ice Cream & Gelato, Eggroll Parker, Berliner Haus, La Chaparrita Sabor de Mex, Mondal's, Woodhill BBQ, El Cubanaso. Friday only: Granny's Pantry. Saturday only: Bailey's Bites, Bebo's Mini Donuts.

Beverage Providers

Molly Brown Spirits, Purgatory Cellars Winery, Bear'L Cellars, Alidade Brewing, Wild Blue Yonder Brewing Co., 105 West Brewing Company, Woods Boss Brewing Company, Platt Park Brewing Co., Dos Santos.

Parking

Encore Parking Garage, Philip & Jerry Miller Library, Douglas County Garage, Douglas County School District Parking Lot. See the Downtown Parking Map on the Downtown Castle Rock Alliance site.

Hosted by: Castle Rock Downtown Alliance.