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Labor Day Weekend

Friday - Monday, September 2 - 5, 2022

Bid farewell to summer, and pack in as much summertime fun as you can at Wintergreen Resort!

Here's what is going down on Labor Day Weekend:

Activities & Events

Discovery Ridge Adventure Center: Friday, Sept 2 10am-5pm, Saturday, September 3 - Sunday, September 4 10am-3pm

Adventures abounds at DRAC including the Ninja Warrior Course, mini golf, disc golf, summer tubing, and gem mining. Fees Apply.

Lake Monocan: Friday - Monday, September 2 - 5; 11am-6pm Friday & Saturday // 11am - 5pm Sunday & Monday

Bring your beach bag, lounge chair, or blanket, and jump in the refreshing water at Lake Monocan. Saturday, September 3rd, the lake is only open to Resort Lodging Guests and Wintergreen Club Members. 

Summer's End Cabin Jam: Saturday, September 3; Noon - 7pm

  • Scenic Chairlift Rides: Take in the beautiful Blue Ridge Mountains on a scenic chairlift ride aboard the Blue Ridge Express. This is one of the only times you will get to ride the lift outside of ski season. Complimentary for Wintergreen Club Members; Resort Lodging Guests $5 each; General Public $10/adult 13+ // $5/children 6-12
  • Food, Fun & Games at Checkerberry Cabin:  Arriving down at Checkerberry Cabin via chairlift, you'll be greeted by live music, artisan vendors, face painting, family games, and hot food and cold drinks to send off summer with one last celebration on the Mountain!
  • Ax Throwing: Saturday Sep 3rd 2:00pm - 4:00pm Come throw some axes, knives and throwing stars with us! Whether you're an axepert or never held an axe, you are guaranteed to have a good time. Instruction will be given before you throw.
    12 years or older. Children under 18 must be accompanied by an adult.
    Closed Toe Shoes Required!

Live Music at Checkerberry Cabin

12pm-2pm - Don't Look Up

Don’t Look Up is a central Virginia group of musicians that was formed from their connection to the Central Virginia Blues Society (CVBS). The band has over 150 years of combined music experience and they have all performed with multiple local and regional acts throughout their careers. Dave Sherman – Guitar, Vocals, Rob Martin – Guitar Vocals, Andy Burdetsky - Bass, Vocals, Lance Foster – Drums, Vocals. They perform many styles of music, but this band focuses on traditional Chicago and Delta blues along with a vintage Rock N Roll sound. Get your dancing shoes on, because these guys will get you off your seat and moving.

2:30pm-4pm - Gypsy Town

GypsyTown is a multi-genre four piece hailing from the Shenandoah Valley & Charlottesville areas. This band features soulful guitar, rhythm & vocals, playing unexpected covers & original music ... From Stevie Wonder to Adele to the Tedeschi Trucks Band, GypsyTown has something for everyone!

5pm-7pm - Gentlemen & Their Lady

Formed in 1960, The Gentlemen and Their Lady has brought its patented brand of infectious energy to countless events in its generation-spanning career. Performing in major venues in Las Vegas, Atlantic City, New York, Montreal, Nova Scotia, Toronto, Quebec, Puerto Rico, Aruba, Bermuda, Japan, and the Bahamas, The Gentlemen and Their Lady continues to bridge the generation gap each night by performing a catalog of hits for partygoers of all ages. The concept of the generation gap has added meaning for this ensemble. When the time came for the founding members to pass the baton to a younger generation, they handpicked musicians for their talents, their dedication to the band’s longstanding tradition of performing a wide variety of great music, and for their commitment to the band’s high standards of friendly customer service. Marcus Carr - the “Lady” in the band for more than twenty years - provides continuity and leadership for the new generation of the band. Though performers in the band have changed since 1960, the principles and standards set then are as alive today as ever.


Delectable Dining Options

What's a celebration without delicious food and festive drinks!?

Checkerberry Cabin

The Checkerberry Cabin grill will be fired up on Saturday, September 3rd from Noon to 7pm with classic cook-out cuisine - burgers, dogs, cold beer, and more! 

The Market

Stop by Wintergreen's mountain store, open daily, for your basic food staples, hot breakfast sandwiches, the best selection of over-stuffed hot and cold sandwiches and healthy salads, fresh baked goods and fresh hot pizza (by the pie or by the slice). Drool over the menu here.

The Edge

The Edge will be open Friday through Monday. Come for the food and stay for the live music, and spectacular views! The Edge offers a casual family-friendly menu to please all palates and our wide selection of craft beer and ciders will quench your thirst. Offering indoor dining and takeout. Call 434.325.8080 to place your order.

Devils Grill

The dining experience at Devils Grill is as elevated as its location on top of the mountain. Featuring lunch and dinner menus with sophisticated and carefully curated ingredients, you'll be pleasantly surprised from soup to nuts. Limited indoor and outdoor seating exclusively for Wintergreen Club Members and Resort Lodging Guests along with takeout. Reservations recommended, call 434.325.8100

Terrace Café

THE place to grab a Starbucks© drink, hot breakfast or lunch sandwich, or something to satisfy your sweet tooth!