Castillo's Hillside Shire Winery is a private estate winery set into the hills of Morgan Hill, at the southern end of Santa Clara County. The property is built around an Italianate villa that looks out over terraced formal gardens: a stone fountain and twin staircases descending to an ornamental courtyard, clipped hedges and flowering hedgerows laid out in symmetry, and vineyard slopes rising behind the house. Below the gardens, a covered stone pavilion with a balustrade sits above the pond, shaded by mature willows and redwoods. Because the estate is a private event venue rather than a public park or tasting room you can simply walk into, a proposal here is booked with the winery in advance, and the setting is genuinely yours for the occasion.
Why Propose Here
- The architecture does the work that a beach or park setting can never do: a villa facade, stone staircases, a fountain courtyard, and formal terraced gardens give you a backdrop with structure and grandeur, and photographs that look composed from almost any angle.
- The covered pavilion above the pond is the most popular setup spot on the estate. The stone balustrade and columns frame a floral arch beautifully, the roof means the setup is unaffected by sun or a passing shower, and the water and mature trees sit directly behind you in every photo.
- It is a private venue, so there are no crowds to work around and no passers-by wandering into the frame; once the date is booked, the gardens and pavilion are yours, which is difficult to guarantee at any public location in the South Bay.
Venue Details
Best Time
Midday through mid-afternoon, within the winery's opening hours, which end earlier than most outdoor venues and shift with the season; spring and early autumn for the fullest garden colour
Getting There
Morgan Hill is roughly thirty minutes south of San Jose off Highway 101, with parking on the estate itself. As a private venue, access is arranged as part of your booking
This is a private estate, so the date has to be reserved with the winery before anything else is planned. Yes Moment can put you in touch with the venue directly and handle the setup around whatever time slot you are given. Confirm the closing time for your date when you book, as the winery closes earlier than most outdoor venues and the hours vary by day and by season. An afternoon slot leaves plenty of light on the gardens and time to walk the grounds together afterwards.