Killington keeps the party going all season with stacked events lineup

Including can’t-miss performances by Young the Giant, Mix Master Mike, 220 KID and Matisyahu at the Stifel Killington Cup

Vermont’s Killington Resort, the largest ski and snowboard resort in Eastern North America and a POWDR company, is ready for winter with a jam-packed event series kicking off with the Loaded Turkey Rail Jam on November 18 and concluding with VT Green Up Day on May 4.  After that, Killington’s lifts will continue to spin as long as the snow lasts, with eyes on a multi-sport Memorial Day weekend and June skiing and riding. 

On November 24-26, Killington Resort will host the biggest event of the year, The Stifel Killington Cup, with performances by nationally touring acts Young the Giant, Matisyahu, Mix Master Mike and 220 KID. Double brit-nominated, multi-platinum-selling songwriter and producer 220 KID will play Friday evening as part of the athlete bib presentation and fireworks display, and again on Saturday night at the Wobbly Barn. 

Grammy-award-winning DJ Mix Master Mike brings his skillful, hard-hitting scratch work to the Beast between runs on Nov. 25, and headlining on Saturday after the race is the critically-acclaimed, multi-platinum selling artist Young the Giant. The music wraps up with a set by Grammy-nominated singer, songwriter, rapper, and alternative rock musician Matisyahu before the best female Giant Slalom skiers in the world take their final run on Sunday.

“There’s never a dull moment during the longest season in the East,” says Michael Sutcliffe, Events & Sponsorship Manager at Killington Resort. “The Killington Cup music lineup is not to be missed and a great way to get warmed up for classics such as Subaru Winterfest, Mini Shred Madness and the Bear Mountain Mogul Challenge. We are also thrilled to celebrate the 10th anniversary of Slash and Berm!” 

2023-24 Winter Events Lineup (subject to change) 

November 18: Loaded Turkey Rail Jam 

The kick-off to the freestyle season brings the best skiers and riders from around New England to compete on a custom set-up by the Woodward Parks crew. 

November 24-26: Stifel Killington Cup 

Witness the best female alpine skier racers in the world compete at break-neck speeds, enjoy live music from national acts and so much more. 

December 2: Hike & Hang 3.0 

Ski and socialize with Alex Hackel in the early season Woodward Mountain Park on Reason.  

December 9: Vermont Holiday Festival

Experience the indoor Christmas forest of trees, purchased and decorated by local businesses and individuals and bid for your chance to take them home. 

December 9-10 Ski Sauvage Demo

Your chance to try out the latest gear from Black Crows. 

December 13:  Michelob ULTRA Ski Bum Registration Party 

The locals gather at Moguls for a party to start the weekly Ski Bum race series right.  

December 31: New Year’s Eve Celebration at K-1 Lodge

Bring the kids for this celebration featuring fireworks to welcome in 2024. 

January 3 - March 13: Michelob ULTRA Ski Bum Race Series (Wednesdays) 

Every Wednesday, serious and not-so-serious racers vie for the fastest time on Highline. 

January 6: Mini Shred Madness at Killington

A gathering of groms to learn the ins and outs of park competition.  

January 11 – March 14: Michelob ULTRA Pico Race World (Thursdays)

The Thursday fun run race series returns to the slopes of Pico.

February 3: Park Affair 

All-female snowboard camp open to ladies of all ages teaching the fundamentals of park riding.

February 3-4: Subaru WinterFest  

A one-of-a-kind music and mountain lifestyle festival that invites everyone and their dogs to bask in their love of winter adventure. 

February 18: Tell A Friend Tour 

The social (media) event of the season, full of friends and cool tricks.  

February 23: Pico Hiko 

Go uphill with demos, clinics and more at Pico Mountain.  

February 24: Mini Shred Madness at Pico Mountain  

The groms go to Pico for the second stop of our kids’ gatherings in the park.  

March 1-2: Slash & Berm Banked Slalom 

The 10th annual race through The Stash, one of our Woodward Mountain Parks, presented by Burton and Darkside Snowboards.  

March 3: Slash & Berm Grom Slalom

The conclusion to Slash & Berm weekend featuring groms cruising through the Lil’ Stash.

March 8: Get the Girls Out!

A day where women and girls “support, challenge, mentor and inspire” each other with community-wide activations to benefit SheJumps. 

March 8-9: Ski Vermont Specialty Food Day 

Sample the foods that make Vermont unique.  

March 8-10: Red Bull Slide-in Tour 

Top pro snowboarders spend three days at The Beast and invite you to come along for the party.  

March 16: Vertical Challenge at Pico Mountain  

A free ski and snowboard race open to skiers and riders of all abilities.  

March 31: Easter Sunrise Service & Egg Hunt 

Start Easter Sunday at the Peak Lodge with a non-denominational service, then let the kids search for the treats hidden by the Easter Bunny himself.  

April 6: Bear Mountain Mogul Challenge 

The ultimate spring celebration of mogul mayhem. One of our biggest parties of the year! 

April 13: Woodward Wind Down 

A thank you celebration of the Woodward Mountain Parks and their crew with a fun competition open to all.  

April 13: Pond Skim 

The triumphant return of this spring spectacle—try not to get wet! 

April 20: Dazed & Defrosted  

Celebrate spring with soft bumps, cold brews and great live music. 

May 4: VT Green Up Day 

Grab a bag and do your part to help keep the Green Mountains green.  

For more information about the 2023-24 full events lineup, please visit and stay tuned to for the latest terrain status. 

About Killington Resort  

Killington Resort is a four-season destination sitting on 3,000 acres in the heart of Central Vermont’s Green Mountains. The Beast of the East boasts 92 miles of diverse snow sports terrain spread across six peaks including Pico Mountain, served by the most expansive lift network and snowmaking system in Eastern North America. After the snow melts, Killington features an 18-hole championship golf course, the family-friendly Snowshed Adventure Center, 35 miles of mountain biking trails with expansion underway with Gravity Logic, plus 15 miles of hiking trails. The seemingly infinite après, dining, and lodging options have made Killington a world-class destination for East Coast skiers and riders for over 60 years. Killington is part of the POWDR portfolio. Visit for more information and be social with #beast365.  

Source: 11.7.2023. Killington Resort