The Okemo Valley is a cluster of picturesque mountain towns — Ludlow, Chester, Windsor, Grafton, Proctorsville, Plymouth Notch — along or near Route 100, also called Vermont Skiers Highway, in south-central Vermont. View Map
Be advised: there is plenty of wintertime fun here even for people who don’t do snow sports or who don’t especially like winter temps. Are you not up for downhill skiing or snowboarding? Try snow tubing – a sport where gravity does all the workd –ice skating, and Snow Cat excursions at the Okemo ski area.
Go shopping for art, antiques, and gifts; eat delicious meals at Vermont-proud farm-to-table restaurants. Or just walk and take photos in these picturesque towns. Learn more.
Food and drink for fun
Artisans Park at 71 Artisans Way in Windsor is a cluster of eight unique Vermont businesses that includes Great River Outfitters and the completely unique Path of Life Sculpture Garden. Dining and socializing is tasty and cheerful at Harpoon Brewery, SILO Distillery, Harpoon Brewery, SILO Distillery, Vermont Farmstead Cheese Company, Artisan Eats, and Blake Hill Preserves
Country Girl Diner in Chester serves the wholesome, fresh food that its name implies for breakfast and lunch every day. Pies and baked goods rotate daily. Vermont is dairy country, so expect delicious cheeses and ice cream.
Homestyle Hostel in Ludlow is an inn with a very welcoming restaurant. Cocktails are unique and delicious. Menu is varied and has something for everyone.
Mojo Café in Ludlow rocks the Tex-Mex, Cajun, and barbeque flavors with its tacos, burritos and blackened catfish. Cool your throat with Vermont craft beers.
Big Eyes Bakery in Ludlow. Baked goods include a savory sausage roll made with Vermont sausage and puff pastry. Ethnic? You bet: Irish soda bread, Irish wheaten bread, scones; Finnish coffee cake, chocolate babka, Italian wedding cookies, Venetian rainbow cookies, Guinness Stout chocolate cake and cannoli.
Massage therapy. A phrase that makes many of us react with an “ahh-h-h-h.” Find a refreshing massage at Castle Hill Resort & Spa at Routes 103 and 131 in Proctorsville, located in a former carriage house on the grounds of the Castle Hill Resort. Also, Calm Moments Massage Therapy at 101 Main Street in Ludlow can hook you up with hot stone, deep tissue, and sports massage. In-home massage is available, too.
DaVallia Gallery and DaVallia Art Boutique in Chester DaVallia are run by owners who choose jewelry, art, furniture, home décor, and garden sculpture works from dozens of local and national artists.
Blue Sky Trading Company in Ludlow makes it easy to draft back home with affordable jewelry, pottery, candles, maple syrup, greeting cards, scarves, purses, accessories and many types of Vermont souvenirs.
It goes without saying that there is plenty of outdoor sport in the area. A good place to start if you need ideas, gear, or simply a snowy playground is Grafton Trails and Outdoor Center in Grafton. Directly behind it are wooded hills with groomed trails for cross-country skiing, snowshoeing, and fat biking in winter. There’s a snow tubing hill.