Events & Festivals

The Plymouth Folk and Blues Festival 2026
Plymouth, VT
September 5-6, 2026 

• Free two-day music festival at the President Calvin Coolidge State Historic Site in Plymouth Notch

5th Annual Whoopie Pie Festival  
Rutland, VT
September 12, 2026 

• Whoopie Pie Samples & Voting 

• Whoopie Pie Mile Fun Run/Walk 

• Food Trucks 

• Caricature Artists / Face Painting 

• Magician and Hula Hooping

• Square Dancing 

• Street Entertainment 

• Live Music

• World’s Largest Whoopie Pie

VT Fairy Tale Festival  
Killington, VT
September 19, 2026 

• Dress up as your favorite fairy tale character and bring the whole family to support Vermont Public Libraries and all they do for their communities 

Spartan Weekend
Killington, VT
September 19-20, 2026 

• This legendary Killington course will push limits with brutal climbs, punishing descents, and relentless terrain. 

• Participate • Kids Race • Spectators

• Reminder: Pine Ridge has bike storage

Vermont Cheesemakers Festival Shelburne, VT
September 20, 2026

• Celebrate Vermont’s world-class cheese with tastings, demos, and pairings from dozens of local producers

20th Annual Killington Golf Classic
Killington, VT
September 25-26, 2026 

• Hosted by Foreplay Golf Company. Features 18-hole and 27-hole tournament tiers, plus a late-afternoon 9-hole option with shotgun starts

• Post-Tournament activities include an après-golf party and awards ceremony

Killington Brewfest
Killington, VT
September 26, 2026 

• Since 1995, the Brewfest has drawn craft beer enthusiasts to the stunning Green Mountains

• This year, the celebration returns to the picturesque Pico Mountain Base Area, blending the best of Vermont’s natural beauty with a love for exceptional craft beers

Pico Ski Club's Annual Ski & Snowboard Sale and Swap
Killington, VT
October 2-4, 2026 

• New and used skis, snowboards, clothing, snowshoes, and equipment for kids and adults, from the recreational snow sports enthusiast to the seasoned racer, will be available, along with local shops bringing great deals. 

Okemo Valley Foliage Train
Ludlow, VT
October 3 and 4, 2026

• Fall foliage train tour out of Ludlow offers a unique opportunity to take in the colors of fall

• This ride captures that magic in a way only a historic train can 

• > Get tickets

KSC Monster Ski & Bike
Sale and Swap
Killington, VT
October 9-11, 2026 

• Need some gear for this upcoming season? Or do you just have some gear you have been meaning to sell? 

• Come to Killington's Ramshead Base Lodge for Killington Ski Club's Monster Ski and Bike Sale & Swap!

Killington Harvest Faire
Killington, VT
October 10, 2026 

• Come and enjoy fall in the mountains at our Snowshed Base Area with amazing food, fun, and games for the whole family to enjoy!

Woodstock Apples & Crafts Fair Woodstock, VT
October 10-11, 2026 

• A fall favorite featuring handmade crafts, apple treats, and foliage views

Vintage Market Days of Vermont
Vermont State Fairgrounds
Rutland, VT
October 9-11, 2026 

• From vintage college collectibles to timeless home décor, you’ll find treasures around every corner at Vintage Market Days® of Vermont

Wassail Weekend
Woodstock, VT
December 11-13, 2026 

• Step into a Hallmark movie with horse-drawn carriages, carolers, and twinkling lights during this magical holiday celebration

Okemo Valley Holiday Express Train
Chester, VT
December 19 and 20, 2026

• Enjoy a beautiful hour-long holiday adventure through Vermont's winter wonderland!

• Sip hot cocoa and eat cookies, join in singing and caroling, and meet Santa and his elves on board the Holiday Express Train! 

• > Get tickets

Flow State Mountain Bike Festival
Brownsville, VT
July 24-26, 2026

• Three days of singletrack, live music, local food, Vermont beer, camping and community at Ascutney Trails, Vermont

• Ride by day, hang by night, and settle into a full weekend of peace, love and dirt

Okemo Mountain Taps & Tastes
Ludlow, VT
August 1, 2026

• 50+ craft beers from the region, live music from BoomBox, and food trucks!

For the Luv of Dogs Car Show!
Brandon, VT
August 15, 2026 

• A fun Car Show to benefit the Rutland County Humane Society!

Best of Vermont Summer Festival
Ludlow, VT
August 22–23, 2026 

• 100+ Vermont vendors: artisans, makers, specialty foods

• Food trucks & dining tent (including lobster rolls!)

• Beer & wine from regional producers

• Expanded Family Fun Zone: clown antics, face painting, games & hands‑on fun

• Agriculture demos & community displays

• Woodworkers, fine art, and more

Covered Bridges Half Marathon
Woodstock, VT
June 6, 2027

• Participate or cheer on runners as they pass through Woodstock’s iconic Covered Bridge 

Quechee Hot Air Balloon Festival Quechee, VT
June 19-21, 2026 

• New England’s most colorful Father’s Day tradition for more than 45 years

• Featuring hot air balloons, live music, family-friendly shows, food vendors, and unforgettable views under beautiful blue Vermont skies

• Great for families and photographers alike

Killington 250th 4th of July Parade Killington, VT
July 4, 2026 

• Parade, barbecue, games, pie-baking competition, fireworks, and more

July Fourth Celebration
at Plymouth Notch
Plymouth, VT
July 4, 2026 

• Celebrate the birth of our nation as well as the birth of our 30th president at President Calvin Coolidge State Historic Site

• Festivities include food, a naturalization ceremony, live performances, and horse-drawn carriage rides

Killington Uncorked
Killington, VT
July 17-18, 2026

• Annual event blends fine wines, craft spirits, refreshing nonalcoholic beverages, gourmet food, select artisan vendors, and stunning mountain views into an unforgettable weekend experience