Date Night in Castle Rock
Romantic restaurants, wine bars, and entertainment for the perfect evening out.
Castle Rock has transformed into a culinary destination with romantic restaurants, intimate wine bars, and unique entertainment options perfect for couples.
Wine & Small Plates
Start your evening at Siena Wine Bar & Small Plates on Perry Street. This intimate spot offers an extensive wine selection paired with thoughtfully crafted small plates—perfect for sharing and conversation.
Farm-to-Table Dining
Union American Bistro is Castle Rock's go-to for creative, seasonal American fare. Their handcrafted cocktails and warm atmosphere make it ideal for special occasions. Pro tip: make reservations for weekend evenings.
Historic Charm
For a truly unique experience, dine at Scileppi's at The Old Stone Church. This Italian restaurant is housed in a beautifully restored 1888 church—the ambiance alone makes it worth the visit.
After-Dinner Adventures
Continue your evening with a show at Theatre of Dreams, featuring world-class magicians and variety acts in an intimate 74-seat setting. It's entertainment you won't find anywhere else in Colorado.
Dessert & Coffee
End the night with coffee and treats at Lost Coffee downtown, or stroll through the charming downtown streets and window shop at the boutiques.