What to See
Destinations
Plan the perfect family vacation to Wintergreen Resort
man walking across a bridge overlooking a forest
What to See
Destinations
Plan the perfect family vacation to Wintergreen Resort
man walking across a bridge overlooking a forest

Explore the best outdoor spots near Wintergreen Resort

Whether you go to a new place or take a repeat trip to a favorite locale, you want to take in the famous sights and see something new, try new foods, and have fresh adventures. While Wintergreen Resort may be a main attraction in the central Virginia area, it’s far from being the only thing this beautiful area has to offer.

By exploring the area, you can find a wide range of activities for year-round adventures. Your options range from bungee trampoline parks to canoeing, kayaking, brewery and cidery experiences, distilleries, hiking trails, live music, ski resorts, and much more. Of course, a wintertime trip into the Blue Ridge Mountains offers skiing, snow tubing, snowboarding, and all manner of winter sports. It’s also the home of the Devils Backbone Brewing Company, a famed local craft brewery.

Stay a few nights with friends or family in a two-bedroom apartment or three-bedroom home with features like video libraries, cable TV, and free Wi-Fi while you explore central Virginia to your heart’s content. Check out some incredibly cool destinations just a short drive from Wintergreen.

Sunrise hikes along the Blue Ridge Mountains

View of woman sees sunset

The Blue Ridge Mountains are filled with amazing views. Hikers can explore miles upon miles of hiking trails surrounded by stunning sights. These include the Appalachian Trail, the Plunge, Humpback Rocks, and many others. Additionally, The Nature Foundation started over 40 years ago as a conservation passion project among Wintergreen locals. They manage over 30 miles of trails within and around the resort and have handy guides for enjoying the trails while respecting the ecosystem.

If you prefer not to get out of the car, plenty of driving trails through the Shenandoah Valley are available as well, such as Skyline Drive, where you’ll find plenty of gas stations and EV charging stations, emergency phones, and stunning scenery that is sure to capture the imagination. Snap some photos of the breathtaking views to wow your social media followers.

Beautiful lakes

Few things are as wondrous as a lakeshore vacation where you can go hiking, biking, kayaking, canoeing, and swimming. Wintergreen Resort is just a stone’s throw from many gorgeous lakes like Lake Monocan and Lake Sherando and just steps away from the Stoney Creek Golf Course.

A Nelson County trip through Washington National Forest will lead you to the stunning Crabtree Falls, with five major cascades and several smaller ones trailing over 1,200 feet. Crabtree Falls must not be missed if you want an unspoiled natural overlook with clear, clean water and staggering views.

 
   
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Nearby cities

Wintergreen Resort is just three hours from Washington, D.C., making it an ideal day trip to see our nation’s capital. Even closer, you can see many other spots like Charlottesville, Waynesboro, Lynchburg, Nelson County, Rockfish Valley, Roseland, Staunton, Afton, and others. These towns, cities, and recreation areas are filled with history, food, scenery, drinks, and more.

Charlottesville

A trip from Wintergreen to Monticello to see the home of Founding Father Thomas Jefferson takes only about one hour along the Blue Ridge Parkway. Few places in the nation are filled with as much of our country’s history and culture as the home of the man who wrote the Declaration of Independence, Thomas Jefferson, who was a Founding Father, avid spokesperson for democracy, and the country’s third president from 1801 to 1809. Here you can see thousands of blooming tulips and take several tours to see the beautiful gardens and explore Jefferson’s living quarters and library. There is even a digital scavenger hunt included with the price of admission that will keep your kids engaged as they explore and take photos!

Charlottesville is also home to the University of Virginia, the Carter Mountain Orchard and Country Store, the Virginia Discovery Museum, the Paramount Theater, and the historic Michie Tavern, founded circa 1784. Shenandoah National Park is also located just 32 miles from Charlottesville and offers even more stunning vistas for you and your family to enjoy.

Waynesboro

Waynesboro is at the intersection of Skyline Drive, the Blue Ridge Parkway, and the Appalachian Trail. Here, you can enjoy almost every adventure, from fly fishing to scenic drives, a walkable downtown filled with independent shops, the vaudeville-era Wayne Theatre, art galleries, restaurants, and murals. Hit up places like Luke’s Hobbies, Make Waynesboro Clay Studio, Rockfish Gap Outfitters, and Cross Stitch Station for shopping.

Local eateries include three breweries along the Shenandoah Beerwerks Trail, the Blue Ridge Bucha kombucha taproom, and many others. You can enjoy the Veritas Vineyard and Winery, Afton Mountain Vineyards, Silverback Distillery, and Stable Craft Brewing Company. Locals enjoy hitting the Farmhaus Coffee Co., E&J’s Deli Pub, Willy’s Ice Cream, Sam’s Hot Dogs, and Bottles.

Nellysford

Nellysford offers golf opportunities at world-class locations just minutes away from Wintergreen, such as the Stoney Creek Golf Course and Devils Knob Golf Course. You can also head for Bold Rock Hard Cider or the Hill Top Berry Farm & Winery to enjoy a craft beverage in the great outdoors.

Go biking or soar with zip lines through the resort!

Biking trails and zip lines run through Wintergreen Resort for a wide range of exciting adventures. The Zip, as it’s called, races over 900 feet at speeds of up to 40 miles per hour. You’ll traverse the entire distance in under 30 seconds of pulse-pounding thrills. Kids under 18 must have a signed risk agreement from their parents.

The great thing about the attractions within Wintergreen Resort is that you do not have to stay at the resort to take advantage of them. You can buy a pass to enter the resort and experience all the attractions available at the Discovery Ridge Adventure Center while enjoying one of our private two- or three-bedroom rental properties with views overlooking Devils Knob Golf Course.

Outdoors not your style? Try some shopping

An hour or less away from the resort area, you can find several unique shopping destinations, including thrift shops, antique stores, and small independent shops. You can also find malls and department stores to satisfy your shopping needs. Some of the most enjoyable spots include the Rockfish Gap Country Store, Country Connections, the Tuckahoe Antique Mall, the Waynesboro Bargains Store, and the Mountain House Trading Company.

See the Blue Ridges Mountains from Devil’s Knob Overlook

If you’re not into hiking or biking but still want breathtaking sunrise or sunset views to light up your Instagram feed, it’s hard to beat Devil’s Knob Overlook. This gorgeous attraction is accessible by car — just drive up the mountain to see one of the most colorful and stunningly beautiful sunsets you’ve ever seen. It’s a perfect spot for a few quiet minutes with your loved one, for proposals or anniversaries, or to soak in the skies bathed in red, orange, and purple as the lush valleys stretch out endlessly before you.

Step outside and prepare for adventure!

Devil's Knob hiking trail

The Blue Ridge Mountains and Wintergreen Resort offer a world of adventure and excitement, so much so that you can’t see it all in one trip. There is no reason to restrict yourself to the resort area. Just check out our rental properties with features like heated bathroom floors, cable TV, in-unit laundry facilities, fully-equipped kitchens, and all the privacy you could ever want with the comfort of your home right at your fingertips. Book your vacation and get started on building memories that are sure to last a lifetime.

Customer Reviews

What guests say

  • Quenzelle
    October 13, 2023
    Erik and Lisa are awesome host! No issues what so ever! Great place!! Great location! Great views!!! Definitely would stay again!!!!
  • Nick
    August 13, 2023
    Was looking for somewhere to bring our kids to so we could enjoy some time away from work. We found a good deal with this chalet and decided to try it out. Was pleasantly surprised to find this beautiful place….
  • Michael
    August 12, 2023
    Our family loved staying here. It is a lovely home in a very peaceful setting. The host was super responsive and helpful. Would love to stay here again.
  • Megan
    July 13, 2023
    Erik and Lia’s place was lovely! Very friendly and communicative hosts. The condo was clearly well taken care of and located a walk away from a restaurant and some nice trails. Would highly recommend!
  • Michael
    July 11, 2023
    Owners were very accommodating. The property was very comfortable and provided a great getaway opportunity for me and my family. Would definitely book again!!
  • Amy
    July 11, 2023
    Chalet on the Green was the perfect place for our weekend away! Beautifully renovated, great location, hosts quick to communicate. We would definitely stay there again!
  • Keith
    June 13, 2023
    Still feeling refreshed. We booked last minute for a weekend getaway and our hosts were amazing. 5 stars!!!
  • Mike
    June 12, 2023
    Nice place! We loved opening up all the windows and feeling the cool mountain air. It was 10° cooler at the top of the mountain than it was in the valley.
  • Kristen
    May 13, 2023
    We enjoyed our stay! There is a great trail from the condo that follows along the road. It was so nice to be able to go for a run in nature right outside of Erik and Lia’s place.
  • Brett
    April 13, 2023
    First of all, our previous reservation fell through literally when we arrived at Wintergreen, but we were able to find this beautiful place and book it via phone phone. Within a half an hour, Eric and Lia had c…