Wintergreen’s Oktoberfest weekend pairs the resort’s biggest fall celebration with near-peak seasonal foliage, making it one of the busiest and best weekends of the year on the mountain.
Alongside the festival, you’ll find the Colors of Fall Chair Lift Rides, The Nature Foundation Living With Nature hike, and a Fall Watercolor Workshop. It’s the perfect weekend to experience mountain and resort life firsthand.
What is Wintergreen Oktoberfest, and when is it?
Wintergreen Oktoberfest is the resort’s marquee fall event, drawing visitors from across central Virginia and beyond. The 4th Annual Oktoberfest will be held Saturday, October 17, 2026. Expect a day packed with scenic views, local brews, traditional music, delicious food, and some good-natured competitions.
Learn more and purchase tickets
Why is this the busiest weekend on the mountain?
Timing. The festival lands right as the foliage peaks, and that overlap is why lodging fills early and the mountain feels alive. For visitors it’s a great weekend. For anyone watching the local market, it’s a vivid illustration of how much demand this mountain draws in the fall.
What does a weekend like this tell a buyer – or an investor?
If you’ve ever tried to book a Wintergreen rental on Oktoberfest weekend, you already understand the investment case. Peak weekends like this drive strong occupancy and premium nightly rates consistently, year over year. For a second-home buyer, it’s the lifestyle you’re buying into; for an investor, it’s income potential you can see with your own eyes.
Frequently asked questions
Curious what a property that pays for itself on weekends like this looks like? On the higher end, 83 Fortunes Ridge Drive is a super-traditional mountain cabin, with tons of space and rental appeal.
If you prefer a condo, 332 Dobie is a rare ski in/ski out opportunity (and the mid-mod fire pit is to die for!). You may also like 413 Three Ridges, impressively updated at a very comfortable entry point.
Contact WRE and let’s talk through the numbers.
Wintergreen Real Estate, established 1974, is the exclusive real estate partner for Wintergreen Resort, and part of the original Wintergreen developers. Last updated July, 2026.
