Things to Do Near Ludlow, VT: Your October 3-4 Weekend Guide to the Okemo Valley
A harvest fair on Main Street, a vintage foliage train, Oktoberfest, and a scarecrow festival. Here's your Oct 3-4, 2026 weekend guide near Ludlow, Vermont.Things to Do Near Ludlow, VT: Your October 3-4 Weekend Guide to the Okemo Valley
Things to Do Near Ludlow, VT: Your October 3-4 Weekend Guide to the Okemo Valley
The first weekend of October is the one Vermonters quietly circle on the calendar. Vermont's own state historic sites describe Plymouth Notch as a place "where fall foliage traditionally reaches peak colors in the first week of October," and the hillsides around Okemo run on roughly the same clock. Add a harvest fair on Main Street, a vintage train, and a free Oktoberfest, and October 3-4 becomes the kind of weekend that fills a whole trip without a single long drive.
Here's how to spend it, starting right outside our door at 86 Main Street.
Saturday Starts on Main Street
The 42nd Annual Ludlow Harvest Fair and Fire Department Safety Fair takes over downtown Ludlow on Saturday, October 3, from 10 a.m. to 4 p.m. at 45 Main Street. It's free, it's been running for four decades, and it benefits the Ludlow Elementary School PTG. Expect food trucks, dozens of local vendors, games for the kids, and a fire department safety demonstration that our younger guests reliably rank above anything happening on the mountain.
For our guests, this one is a walk, not a drive. Leave the car in our lot, stroll two blocks, and you're in it.
All Aboard the Okemo Valley Foliage Train
Also both days: the Okemo Valley Fall Foliage Train and Pop-Up Fall Festival, hosted by the Okemo Valley Regional Chamber of Commerce. A vintage train carries you on a roughly hour-long run through the valley, with departures at 9 a.m., 10:30 a.m., noon, 1:30 p.m., 3 p.m., and 4:30 p.m. on Saturday and Sunday.
Trains leave from the Blue Lot at 75-77 Witalec Road in Ludlow, about five minutes from the Inn. Before or after your ride, the pop-up festival brings food trucks, Vermont artisans, and seasonal treats. Tickets are sold through SimpleTix and top out around $35. Two things worth knowing: seating is first come, first served in the vintage cars, so groups aren't guaranteed to sit together, and this ride sold out fast last season. Book before you arrive.
Oktoberfest at the Base of the Access Road
Saturday afternoon and evening belong to the Second Annual Okemo Valley Oktoberfest at Off The Rails, 64 Pond Street, from noon to 8 p.m. It's free to attend, with no tickets required.
The lineup: craft beer, cocktails from Killington Distillery, classic Oktoberfest food, lawn games, and live music from LimeWired, a high-energy cover band running through the 80s, 90s, and 2000s. Sponsors this year include Black River Produce, Lawson's Finest Liquids, and New England Cider Donuts. Off The Rails doesn't take reservations, so arrive early if you want a table on the patio.
Scarecrows and Free Music in Chester
Twelve minutes down Route 103, the Chester Scarecrow Festival fills the Chester Green both Saturday and Sunday, 9 a.m. to 4:30 p.m. More than 27 scarecrows go on display, and visitors vote for a favorite. There's food, live music, and local vendors, all free.
Stay into the evening for the Kinhaven Music School Fall Concert Series, also free. Saturday's 5 p.m. concert is at Walker Farm in Weston; Sunday's 5 p.m. concert is at Chester Town Hall, 556 Elm Street, which pairs perfectly with a scarecrow-filled afternoon.
Farms, Presidents, and Cider Presses
Saturday is a remarkable day for farm events. The Fall Festival and Chicken BBQ at the Calvin Coolidge State Historic Site in Plymouth Notch runs 10 a.m. to 4 p.m., with wagon rides, heritage apple tasting, a craft station, and cider pressing demonstrations, all included with museum admission. The Plymouth Fire Department serves BBQ chicken dinners as their annual fundraiser.
Closer to home, Abundance Acres in Andover hosts its free Annual Harvest Celebration from 1 to 4 p.m., built around a chili, cornbread, and pie cook-off (entries by 2 p.m., tasting 2 to 3, prizes at 3:30). And in Woodstock, Billings Farm & Museum runs its Harvest Celebration both days, 10 a.m. to 5 p.m., with wagon rides, pumpkin bowling, and natural dyeing demonstrations.
If You Just Want the Views
The Sunburst Six scenic chairlift at Okemo runs Thursday through Sunday, 10 a.m. to 5 p.m., with free parking at 501 Mountain Road. The Ride & Dine bundle adds an entree, a beverage, and an ice cream sundae at the summit lodge. It's the fastest way to see how far the color has come.
Prefer browsing to hiking? October 3-4 is also Vermont Fall Open Studio Weekend, when artists across the state open their doors from 10 a.m. to 5 p.m.
Make It a Weekend
This is the weekend the Okemo Valley shows off, and rooms go first. Book your room at thegovernorsinn.com and wake up two blocks from the harvest fair, five minutes from the train, and a short drive from every cider press in the county.
