Ski Towns: Okemo Valley, Vermont

Ludlow, Chester, Windsor, Grafton,
Proctorsville, & Plymouth Notch

The Okemo Valley is a cluster of picturesque mountain towns scattered along or near scenic Route 100 in south-central Vermont.

This very beautiful road, part of Vermont’s Skiers Highway, connects major ski resorts including Magic Mountain in Londonderry, VT and Okemo in Ludlow, VT. The geographical center is near the town of Ludlow.

All the mountains are major East Coast destinations for year-round outdoor recreation. But you don’t need to be a skier to love these towns in winter! Apart from skiing and snowboarding, you can try snow tubing, ice skating, and Snow Cat excursions at the Okemo ski area. Visitors enjoy the abundant off-mountain pleasures of Ludlow and neighboring Chester, Windsor, Proctorsville, Plymouth Notch, and Grafton, VT. These include shopping for art, antiques, books, and gifts; fine dining at farm-to-table restaurants in a land of producers of cheese and other foods; and simple strolling and picture-taking in lovely, restful towns embraced by snowy mountains. - Area Map

Downtown Chester, VT Winter Shops - Photo Credit Okemo Valley Chamber

Boutique Shopping in the Okemo Valley

  • DaVallia Gallery on Main Street in Chester, VT, and their DaVallia Art Boutique on South Main Street, are the place to exercise your love for artful living and artful gift-giving. The owners curate works from dozens of local and national artists in jewelry, local art, furniture, home décor, ad garden sculpture. Inspiring and creative designs spark your imagination and make your home beautiful.
  • Blue Sky Trading Company in Ludlow, VT - A fun and very useful source for vacationers and local folks, where you can find affordable jewelry, pottery, candles, Vermont-made goods, souvenirs from your visit to the Green Mountain state’s ski region, maple syrup, greeting cards and gifts. Also, beautiful scarves, purses, and accessories.

Food and Drink Adventures

Artisans Park in Windsor, VT: This charming retail community is a collection of eight unique Vermont businesses all located in the same park. Included among them are:

  • Harpoon Brewery is a wonderful place to enjoy a craft beer surrounded by the mountains. This Boston-born brewer added a second brewery in Windsor, VT to keep up with the growing demand.
  • SILO Distillery is the adventure zone if unique spirits is your taste. The company uses Vermont all Vermont grains and ingredients and offers a full tasting, tour and cocktail experience.
  • Vermont Farmstead Cheese Company, Artisan Eats (in the summer), and Blake Hill Preserves are your Artisan Park locations to slake any hunger. Vermont-sourced ingredients create tasty cheeses, toothsome pizzas, and other fresh, healthful meals and treats.


  • Castle Hill Resort & Spa in Proctorsville, VT. The Aveda Concept Spa at Castle Hill emphasizes the importance of physical, emotion, and mental wellness. The only full-service spa in the Okemo/Ludlow region, its features six private treatment rooms in the historic carriage house on the grounds of the Castle Hill Resort. A Wide range of treatments is designed to relax and rejuvenate people in need of some expert care.
  • Calm Moments Massage Therapy in Ludlow, VT. Calm Moments is a sweet getaway on any vacation, whether you are achy from outdoor sports – or not! Irene Berry, CMT offers quality massage therapy, including hot stone, deep tissue, and sports massage. Gift cards and in-home massage are available.


  • Fletcher Farm School for the Arts and Crafts in Ludlow, VT. While the outdoor sports enthusiasts in your family are flying down the nearby ski mountains, sign up for a short learning vacation at this rustic farm setting. Browse through classes in jewelry making, textile arts, wood working and more for a short immersion into these arts, taught by experts. Classes vary from one to seven days and are taught by working artists.
  • Plymouth Artisan Cheese in Plymouth Notch, VT. The Plymouth Cheese Factory occupies the same building it did when it was built in 1890 John Coolidge, father of President Calvin Coolidge, who used same exacting recipe that settlers brought from Europe. Jesse Werner, owner and cheese maker, has revived that recipe. The Plymouth store is open daily, offering free samples and a self-guided tour through the Plymouth Cheese Factory building. Big windows overlook the cheese-making rooms. Large groups may organize a tour. Call ahead to learn cheese-making schedule.

Country Walks

The Path of Life Sculpture Garden at 36 Park Road in Windsor, VT consists of 14 acres of woods and meadows dotted with 18 large sculptures that illustrate the stages of human life. It makes a peaceful and contemplative walk in all seasons. In warmer seasons, the garden has been known of host celebrations and the occasional bonfire. The sculpture garden is managed by Great River Outfitters, an outdoor adventure company that host a broad range of adventurous outdoor activities all year long, including dog sledding and snowshoeing.


  • Grafton Trails and Outdoor Center in Grafton, VT - This busy facility for outdoor place is a resource all year for people of all ages. The outdoor center has a warming shack with a wood stove and equipment rentals and maps and experts to guide you. Directly behind it are wooded hills with access to miles of groomed trails used for cross-country skiing, snowshoeing, and fat biking in winter. There’s a snow tubing hill.
  • Snowmobile Vermont in Plymouth, VT - Here’s a snow sport that’s perfect for people who love to simply sit, and watch the wintry world fly past. You can enjoy the excitement of snowmobiling with the state’s most experienced snowmobile tour. A range of tours and riding options is tailors for everyone from the beginner to the most advanced rider.
  • Tubing, Skating, and Snowcat Tours: Okemo Mountain Resort in Ludlow, VT has plenty of outdoor winter play options, even for people who have little taste for skimming down a mountainside with their feet buckled to slick boards. The snow tubing park, near the courtyard at Jackson Gore, is open to anyone who’s at least 42 inches tall. It takes little athleticism to whirl down scooped lanes wedged into big inner tube, and it’s great fun. Or, get up on your feet at Okemo’s roofed hockey rink and recreational ice skating pavilion at the Ice House and mimic your favorite figure skater


  • Homestyle Hostel in Ludlow, VT - Very welcoming atmosphere and good service at this inn and attached restaurant. The chef has turned the hostel into a foodie destination in southern Vermont. Diners praise the cornmeal crusted artichokes, curry cauliflower, arugula salad and lemon poppy seed ice cream and lemongrass sorbet. Cocktails are handcrafted, unique and delicious. Menu is varied and has something for everyone.
  • Country Girl Dinerin Chester. The Country Girl Diner serves breakfast and lunch every day, and you are 100 percent certain of getting fresh foods, sourced at nearby Vermont farms (pure maple syrup harvested within state borders comes out with your pancakes, of course). The building is a Silk City silver dining car built in New Jersey in 1944. The pies and baked goods change daily. Vermont is dairy farming country, so expect delicious cheeses and ice cream. Doors open at 7am.
  • Mojo Café in Ludlow, VT. Mojo Cafe brings on the flavors of more-southern places, like Tex-Mex, Cajun, barbecue and others. Visitors love the poblanos, the tacos, burritos and blackened catfish. Cool down with Vermont craft beers – that goes without saying.
Okemo Mountain Resort - Ludlow, VT
Okemo Mountain Resort

77 Okemo Ridge Road Ludlow, VT, 05149 Phone: 802-228-1600

Skiing & Snowboarding: Located in southern Vermont, Okemo Mountain Resort is a family-operated, four-season, playground. Owners Tim and Diane Mueller also operate Crested Butte Mountain Resort, in Colorado, and Mount Sunapee Resort in N.H. Winter sports enthusiasts love southern Vermont's highest vertical drop and vast trail network over five alpine areas. Terrain features include Okemo Superpipe, The Zone, Tomahawk Park, Hot Dog Hill Terrain Park, OMS Crazy Train Progression Park, Robbins' Nest, Bounder Park, Broken Arrow, and NASTAR Race Arena. There also is Nordic skiing, snowshoeing, ice skating, a mountain coaster attraction and snow tubing.
Everything Else: Accommodations include slope-side condos, the Jackson Gore Inn, Adams House, Bixby House and other area lodging. The mountain has six places to dine. There is a Ski + Ride School and racing programs.