RAPPtoberfest Returns to Wakefield School Oct. 17

RAPPtoberfest, the annual Oktoberfest celebration hosted by Wakefield Country Day School, takes place Saturday, October 17, 2026, bringing together authentic German food and beverages, live music, and an antique car show on the school's grounds. Proceeds benefit scholarships at Wakefield Country Day School, making it one of the more community-rooted fall gatherings on the Piedmont calendar.

• Date: Saturday, October 17, 2026
• Location: Wakefield Country Day School
• Organizer: Wakefield Country Day School
• Benefits: Wakefield Country Day School scholarships

What to Expect

True to its name, RAPPtoberfest leans into the German beer-hall tradition — expect authentic German fare and beverages alongside live music set against the school's grounds. The antique car show adds a second draw for the day, giving the gathering a dual identity as both a food-and-music festival and a classic-car outing, which tends to pull in a broader crowd than a tasting-room event alone.

Why It's Worth the Drive

Fall festivals in this part of the Piedmont tend to be tied to a specific place and a specific cause, and RAPPtoberfest is a clear example: it's a fundraiser first, built around the kind of unpretentious, family-friendly fun that doesn't require a reservation or a tasting fee. For visitors stacking a weekend in Rappahannock County, it's an easy anchor for a Saturday afternoon.

Making a Day of It

Because the festival runs on a Saturday, it pairs naturally with other stops in the surrounding counties. Travelers coming from the north might combine it with a stop at Jenkins Orchards in Woodville, where pick-your-own apples, peaches, and pumpkins are in season through October. Those staying overnight nearby might consider the log cabins at Lydia Mountain Lodge and Log Cabins in Stanardsville as a base for a fuller fall weekend in the region.

Planning Your Visit

• Event: RAPPtoberfest
• Date: Saturday, October 17, 2026
• Location: Wakefield Country Day School
• Organizer: Wakefield Country Day School (benefits student scholarships)