Fall in the Okemo Valley
There is something special about fall in the Okemo Valley. Crisp mornings, mountainsides filled with color and the return of favorite harvest traditions make this one of the best times of year to explore our corner of Vermont.
Whether you are spending a weekend here, settling into your seasonal home or simply looking for a scenic fall drive, these local orchards, farm stores and upcoming events belong on your autumn list.
Pick Your Own Apples
Alyson’s Orchard | Walpole, New Hampshire
Alyson’s Orchard is well worth the drive across the Connecticut River. Set among rolling hills and ponds in Walpole, the orchard has more than 50 acres of fruit-bearing trees and grows over 50 varieties of apples, including heirloom varieties.
In addition to pick-your-own apples, the farm store offers fresh fruit and homemade pies. Weekend hayrides provide an especially scenic way to enjoy the orchard and its surrounding landscape. Alyson’s annual harvest celebration is planned for Sunday, September 20.
Alyson’s Orchard is located at 57 Alyson’s Lane in Walpole, New Hampshire.
Wellwood Orchards | Springfield, Vermont
Wellwood Orchards is a longstanding local favorite for apple picking and an easy outing from the Okemo Valley. During September and October, visitors can find apples, pears, plums, grapes, squash and pumpkins, with available varieties changing throughout the season.
The orchard also has a farm store, picnic tables and a petting zoo. Wellwood is currently open daily from 8:00 a.m. to 5:00 p.m. through November 1, although it is always wise to call ahead for picking conditions and current varieties.
Wellwood Orchards is located at 529 Wellwood Orchard Road in Springfield.
More Local Stops for Fall Flavors
Apple picking may get most of the attention, but some of our favorite fall finds come from the area’s farm stands and general stores.
Allen Brothers Farm Market | Westminster, Vermont
Located just off Interstate 91, Allen Brothers is an ideal stop on the way to or from the Okemo Valley. This family-owned market has been part of Westminster since 1956 and offers Vermont-grown apples and seasonal produce alongside a bakery, deli, greenhouse and gift shop.
It is a convenient place to pick up cider, baked goods, local products or everything needed for an easy fall meal. The deli serves breakfast, lunch and dinner, making Allen Brothers much more than a traditional roadside farm stand.
Allen Brothers Farm Market is located at 6023 US Route 5 in Westminster.
Singleton’s General Store | Proctorsville, Vermont
Singleton’s is a true Vermont general store and one of the area’s most distinctive shopping stops. Known for its full-service butcher counter, smoked meats, cheeses and specialty foods, the store also carries local products, seasonal produce, clothing and an assortment of items you may not expect to find under one roof.
Stop in for something to put on the grill, local cheese for a fall gathering or simply the experience of browsing a classic country store. Singleton’s is located at 356 Main Street in Proctorsville.
Plew Farm | Mount Holly, Vermont
For authentic Vermont maple products, meat and other farm-raised goods, take a drive to Plew Farm in Mount Holly. The family farm produces pure Vermont maple syrup in small batches over a wood fire and operates an on-site farm store offering maple products, meat, eggs and other seasonal selections.
The trip along the back roads of Mount Holly is especially beautiful during foliage season. Because farm-store hours can vary, check with Plew Farm before making a special trip.
Plew Farm is located at 1966 Healdville Road in Mount Holly.
Upcoming Fall Events
Chester Festival
September 19–20, 2026
More than 100 artisans and food vendors will gather for the 52nd annual Chester Festival. Visitors can browse handcrafted Vermont and New England goods, enjoy local food and spend a day surrounded by fall color. This year’s festival will be held at its new location at Gateway Field, 637 VT Route 103 North in Chester. Hours are 9:00 a.m.–5:00 p.m. Saturday and 9:00 a.m.–4:00 p.m. Sunday. View festival details.
Okemo Valley Fall Foliage Train & Pop-Up Fall Festival
October 3–4, 2026
New this year, the Okemo Valley Fall Foliage Train will depart from Ludlow for a nearly hour-long ride aboard a vintage railcar. Six departures are planned each day, accompanied by a pop-up festival featuring local food, Vermont artisans and seasonal treats. This promises to be a memorable new way to experience foliage season in the Okemo Valley. Learn more about the new fall train.
Ludlow Rotary Chili Cook-Off
October 10, 2026 | 11:00 a.m.–2:00 p.m.
Downtown Ludlow will once again fill with the aromas of creative chili recipes during the Ludlow Rotary Club’s 35th annual Chili Cook-Off. Sample the entries, vote for your favorite and support the Ludlow Area Rotary Charitable Fund. The event takes place along Main and Depot Streets. Find event information.
Belmont Cider Days | Mount Holly
Belmont Cider Days is one of the area’s most beloved fall traditions. Held during Indigenous Peoples’ Day weekend, the celebration centers around cider pressed on the Belmont Green using an antique hydraulic press. The weekend traditionally includes homemade apple desserts, food, music, local crafts and activities throughout the village. Watch for the final 2026 schedule from the Mount Holly Community Association.
Okemo’s Fall Into Winter Celebration
October 11, 2026 | 11:00 a.m.–3:00 p.m.
Celebrate the transition from foliage season to ski season at Jackson Gore. Okemo’s annual Fall Into Winter event is scheduled to include hayrides, live music, an apple cider bar, Okemo barbecue, pumpkin decorating and other seasonal activities. View Okemo’s event details.
Make a Day of It
One of the best things about fall in the Okemo Valley is that no elaborate itinerary is required. Choose an orchard, add a stop at a local farm store and leave time to wander through Ludlow, Proctorsville, Mount Holly or Chester along the way.
Orchard conditions, farm-store hours and event schedules can change with the weather and the harvest, so confirm current information before heading out. Then bring an extra bag for apples, maple syrup, local cheese and all the other things that make a Vermont fall taste as good as it looks.
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