The Ultimate 2026 Bucket List: 26 Unforgettable Things to Do in the Okemo Valley
Whether you are planning a snowy family retreat for early '26, a summer lakeside escape, or are chasing the legendary foliage of autumn, the Okemo Valley is ready for you. While specific event dates for 2026 are still under wraps, the best the region has to offer is timeless. We’ve compiled the ultimate 26-item bucket list for your 2026 visit to the Okemo Valley.
Attend an Outdoor Summer Concert: Keep an eye on the 2026 Jackson Gore Summer Music Series schedule. These free, family-friendly lawn concerts on Friday nights are a community staple.
Shop the Ludlow Farmers Market: Grab local cheeses, artisan bread, crafts, and more on Depot Street. It is usually open Sundays from 9 am - 1 pm between Memorial Day and Indigenous Peoples' Weekend.
Take a Class with ‘Create Together at Fletcher Farm School’: Feeling creative? This renowned arts and crafts school in Ludlow offers varied workshops, ranging from quilting and pottery to jewelry making.
Catch a Show at the Weston Theater Company: Despite its small village location, Weston boasts professional, Broadway-caliber theater during its summer and fall seasons. It’s a cultural gem of the region.
Visit Alder Bakery & Eatery, opening in Chester: Starting on January 3, the former Heritage building will offer pastries, coffee, breakfast, and lunch.
Attend Okemo’s 70th Anniversary Celebration: Mark your calendars for Saturday, January 31, 2026. This mid-season bash features live music, food, and drinks to celebrate seven decades of mountain magic.
Test the Drink Luge at the Let It Glow Winter Ice Festival: On March 14, 2026, head to the Jackson Gore base area to marvel at professional ice carvings and grab a chilled beverage from the famous ice luge.
Support the Ludlow Fire Department at the Fire & Ice Fundraiser: On February 28, 2026, it’s a night of comedy and community spirit that locals look forward to all winter.
Take Advantage of the Epic Pass First Track Mornings: If you're a pass holder, set your alarm. Getting on the mountain before the general public for those crisp, untouched corduroy runs (or maybe even powder!) is the ultimate ski-day luxury.
Attend Nordic Nights at Viking Nordic Center: Experience the woods of Londonderry in a whole new light. These nighttime cross-country skiing events (scheduled for late Jan and Feb) turn the trails into a glowing winter wonderland.
Indulge in the Magic of Maple at Billings Farm & Museum: Take a short drive to Woodstock in late February (Feb 15–22) to learn about Vermont’s sugaring history and sample "sugar on snow."
Visit the Maple Open House Weekend: The biggest weekend in Vermont! On March 22–23, 2026, local sugar houses throw open their doors. Watch the steam rise from the evaporators and taste the freshest syrup you've ever had.
Eat a Maple Creemee from Green Mountain Sugar House: It’s a Route 100 rite of passage. No trip to the valley is complete without this iconic Vermont soft-serve.
Compete in the Okemo Slush Cup: On April 4, 2026, watch (or join) the brave souls attempting to skim across a pond of icy meltwater. It’s the splashiest way to end the ski season.
Take a Class at Edgar May Health & Rec Center: From "Ladies Who Lift" to floating "BOGA" yoga boards in the pool, this Springfield hub offers fantastic guest passes and community classes to keep you moving during the "mud season."
Visit the Hall Art Foundation in Reading: Reopening in May 2026, this former dairy farm houses world-class contemporary art in beautifully converted stone barns.
Taste New Flavors from the Ocreemo Ice Cream Tent: Look for this mobile super-premium ice cream cart at the Ludlow Farmers Market. Their small-batch, Vermont-ingredient scoops (like "Salted Caramel" or "Maple Walnut") are legendary.
Grab a Latte at the West River Coffee Barn: This Londonderry gem is the perfect place to fuel up. Grab an espresso and a local pastry before heading out on an adventure.
Grow a Garden with Starter Plants from Glebe Mountain Gardens: Planning your 2026 veggie patch? This Londonderry nursery is the place to find hardy, Northern-grown annuals and perennials that can handle the Vermont climate.
Book a Photoshoot with Riley Karl Photography: Whether it’s an engagement at the summit or a family portrait in the wildflower fields, Riley is known for capturing the "adventure lifestyle" of the valley perfectly.
Become a Cardholder at Fletcher Memorial Library: If you’re a resident or frequent visitor in Ludlow, Mt. Holly, or Plymouth, your library card gives you access to the "Homecard" system, unlocking 30+ libraries across the state.
Trunk or Treat at Benson’s Chevrolet: A Halloween staple! Local businesses line up with decorated car trunks to hand out candy in a safe, festive environment on October 31.
Join The INNdulgence Tour: Usually held in early December, this self-guided tour allows you to step inside up to ten of the valley’s most beautiful historic inns, all decked out in their holiday finest with treats at every stop.
Board the Okemo Valley Holiday Express: Located at the Chester Depot in late December. It’s a magical ride through the snowy landscape, complete with hot cocoa and a visit from Santa.
Book a Reservation for Rootin Tootin's Summer Farm Dinner Series : These are not just dinners—they are immersive, four-course culinary narratives. Held throughout the summer months (typically June through August), each event is a celebration of the season’s peak harvest.
Get a Home Value Assessment with William Raveis: Thinking of making your stay permanent? Reach out to the Vermont Properties Team in Ludlow for a home value assessment or to find your dream home.
We hope to see you around the Okemo Valley in 2026!
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