When temperatures drop and a fresh layer of powder blankets the Green Mountain State, the Okemo Valley is a peak destination. Ludlow, a town of 2,100 along picturesque Route 100 in south-central Vermont, is home to Okemo Mountain Resort, ranked one of the best ski areas on the East Coast by SKI magazine. From Ludlow, Route 100 meanders south through a collection of towns that make up the Okemo Valley. These mountain villages — including Weston, Plymouth, Proctorsville and Chester — are rich in presidential history, year-round recreational opportunities, and two of the state’s signature treats: cheese and maple syrup.
If you want to visit Vermont’s Okemo Valley, here’s a suggested itinerary.
Note: Check websites to confirm business hours for the day you visit.
This resort, which draws nearly half a million visitors each year, offers more than 100 trails, 20 chairlifts, and plenty of beginner and intermediate terrain for skiers and snowboarders who would rather enjoy the breathtaking vistas than shred the pow. In the warmer months, chase thrills on the resort’s year-round roller coaster and mountain bike trails, accessible via lift, or de-stress with summit yoga, scenic chairlift rides and an al fresco summer concert series.
77 Okemo Ridge Rd., Ludlow
Inside this family-owned joint, you’ll find a bright orange 1963 Volkswagen bus, a lift chair, and seriously excellent wood-fired pizza and craft beer. Goodman’s welcomes your pups, too, as long as they’re on a leash.
5 Lamere Sq., Ludlow
The Calvin Coolidge homestead, the childhood home and resting place of America’s 30th president, is a time capsule from 1923, when Coolidge took the oath of office from his parlor. The site includes the Coolidge family estate, a 19th-century church and schoolhouse, a general store with a post office and dancehall, and historic barns. If dairy thrills you more than presidential history, check out the historic Plymouth Artisan Cheese factory (106 Messer Hill Rd., Plymouth), founded by Coolidge’s father, and sample some old-school American cheddar.
3780 Route 100A, Plymouth
A trip to Vermont isn’t complete without some form of maple syrup. Load up on all the sappy treats and gifts at the Green Mountain Sugar House, just off scenic Route 100. You can often see steam from the maple boilers rising above the red roof of the lakeside shop, open seven days a week year-round. The family-owned company uses some of its stock to make signature maple creemees.
820 Route 100, Ludlow
Calling this place a “general store” doesn’t quite do it justice. The Vermont Country Store, owned and operated by the Orton family since 1946, is an emporium of Americana with creaky wood floors and merchandise displays whose main aesthetic principle is a kind of glorious muchness — towers of cheese! Piles of lilac-scented soap! Rows upon rows of maple syrup! Jars upon jars of obscure penny candy! Flannel pajamas! Muumuus galore!
657 Main St., Weston
A staple of the region’s arts scene since the Great Depression and the first professional theater troupe in Vermont, Weston Theater Company presents musicals year-round, starring actors from Vermont and Broadway. Past productions include Pippin, Jersey Boys, Hair and Singin’ in the Rain, among other crowd-pleasers. Since the 2023 floods damaged the original Greek Revival playhouse, Weston has held performances at its modern Walker Farm venue, open since 2017.
705 Main St., Weston
Don’t be misled by the sign on the red clapboard façade, which advertises the Loft Tavern as the “Home of Warm Beer, Lousy Food, and Grumpy Owner.” This après-ski dive, across the road from one of the Okemo Mountain Resort parking lots, is beloved by tourists and locals alike for its hearty pub fare and down-to-earth vibes.
300 Mountain Rd., Ludlow