Get Away for Fall Fun at Virginia’s Wintergreen Resort

Despite the season mentioned in the property’s eponymous name and the fact it’s a paradise for skiers, snowboarders and tubers, Wintergreen Resort in Virginia is actually perfect any time of year for family travelers. Autumn offers leaf-peeping opportunities aplenty, both from the resort’s many overlooks or nearby Shenandoah National Park. You’ll also find lots of other seasonal activities right now in this destination, located three hours from Washington, D.C., and 90 minutes from Richmond and Raleigh.

Here’s a three-day itinerary for a fabulous fall family getaway at Wintergreen Resort:

Day 1

Check into your room at The Mountain Inn, Timbers or one of the condos. All accommodations at Wintergreen are individually owned, meaning you’ll find a variety of configurations, design and décor to suit the size of your family or group. Rooms in The Mountain Inn and Timbers are centrally located to restaurants, shops and slopes, and feature a kitchenette and either studio or separate living area. You’ll find one- to five-bedroom condos in the Blackrock and Devils Knob areas, with views of the woods, golf course, slopes or valley; they’re either a short walk, drive or shuttle ride to all the action.

Grab a casual dinner of wings, loaded tots and burgers at The Edge, the resort’s casual slope-side restaurant, or get pizza delivered to your room or condo while you settle in.

Oktoberfest © Courtesy of Wintergreen Resort

After dark, brave Wintergreen’s brand-new Haunted Chairlift Rides, offered Thursday–Saturday evenings the last weekend in October and first weekend in November. During the journey down Blue Ridge Express chairlift, you’ll encounter spooky, holiday-themed scenes. At the end, warm up around a campfire at Checkerberry Cabin and partake in Halloween activities, treats and drinks like pumpkin bowling and different Halloween flicks each evening, including The Nightmare Before Christmas and Hocus Pocus. Costumes are optional, but encouraged.

Day 2

Fuel up with a buffet breakfast at Copper Mine, adjacent to The Mountain Inn, then sign up for a family pickleball lesson at one of the indoor or outdoor courts at Devils Knob Racquet Sports Center.

© Courtesy of Wintergreen Resort

Purchase provisions for lunch from The Market, which sells made-to-order sandwiches, salads, desserts and more, as well as snacks and drinks to take back and enjoy in your room or condo. Hike to The Plunge, a short-but-challenging, out-and-back hike with rock scrambles and a decent descent leading to a dramatic vista. If your brood includes small children or anyone with a fear of heights, a better option is Upper Shamokin Falls Trail, a moderate, family favorite with a waterfall and stream. Both offer great family photo opps and a place to have a picnic.

If your visit coincides with Wintergreen’s second annual Oktoberfest Oct. 19, cheer on the participants in ax- or keg-throwing competitions; enjoy live music; take scenic lift rides; try your hand at polka dance lessons; and sample seasonal beers, brats and pretzels.

You can also hang back at the resort to relax by the indoor or outdoor pools, soak in the Jacuzzis or settle into an Adirondack chair by the slopes with a book.

© Ryan Magyarics

At dusk, don some dressier duds and drive or take the shuttle to Raven’s Roost Overlook for killer sunset views and a family portrait. Afterwards, dine at a table overlooking the golf course at Devils Grill, Wintergreen’s fine-dining restaurant.

After dinner, change into warm clothes, tote a blanket and thermos and stargaze at Blue Ridge Overlook on Devils Knob Loop. Wintergreen Resort is already rated highly on the Bortle Scale (which measures light pollution) and residents are committed to keeping it to the minimum. On a clear night when a low percentage of the moon is visible, you can see planets, tons of stars and the Milky Way. High Country Park is also a great place to spot constellations and celestial objects. Occasionally, the resort offers guided stargazing through The Nature Foundation.

Day 3

Before checking out, get breakfast sandwiches, pastries or yogurt parfaits to go from The Market for your room or condo. If the kids are old enough, let them sleep in while you indulge in one of seven seasonal treatments at The Spa at Wintergreen. Options include a pumpkin spice facial and peel; warm pumpkin honey wrap; and a body scrub with orange, ginger and essential oils. If you can’t decide, do the seasonal sampler, with three 25-minute treatments. All come with a complimentary apple cider mimosa or glass of sparkling wine.