- Spring and Fall Wine Festivals
- Valentine’s Day Dinner
- Family Paint Nights
- Easter Brunch and Egg Hunt
- Summer Pool Parties
- Members’ Car Show on the Valley Golf Course
- Cooking Classes
- Winemaker and Beer Dinners
| - Castlewood’s Halloween Howl
- Thanksgiving at the Club
- Mother’s Day Brunch and Dinner
- Brunch with Santa
- Father’s Day Pancake Breakfast and Fishing Derby
- Annual Castlewood Food Drive
- Holiday Sing-A-Longs
- New Year’s Eve Gala
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