Fall Festivals Near Ludlow, VT: Your 2026 Okemo Valley Events Guide
The best fall festivals near Ludlow, VT in 2026 - from the Chester Festival to Okemo's Fall Into Winter. Plan your Okemo Valley foliage weekend at The Governor's Inn.
Fall Festivals Near Ludlow, VT: Your 2026 Okemo Valley Events Guide
There is a particular kind of magic to autumn in the Okemo Valley. The maples along Route 100 start to turn, the air gets that crisp apple-cider snap, and nearly every village green fills up with artisans, live music, and the smell of something delicious on a griddle. Fall is festival season in southern Vermont, and here at The Governor's Inn in downtown Ludlow, you are perfectly placed to enjoy all of it - most of these events are a 30-minute drive or less.
Here is your guide to the best fall festivals near Ludlow this September and October, all within an hour of your room.
First weekend of September: three festivals, one valley
The season kicks off strong on Saturday, September 5. Just 25 minutes south in the storybook village of Grafton, the Grafton Historical Society hosts its Food & Antique Tractor Show - a wonderfully Vermont mix of vintage machinery, local food, and small-town charm.
The same day, Wellwood Orchards in nearby Springfield throws its annual Harvest Festival. Pick your own apples, wander the farm, and load up on cider donuts (trust us on the donuts).
Then, on September 5 and 6, the Plymouth Folk & Blues Festival brings two days of soulful live music to Plymouth, about 20 minutes north near the Calvin Coolidge Historic Site. It is an easy, atmospheric way to spend a foliage-season afternoon.
Mid-September: gravel grinding in Plymouth
If your idea of leaf-peeping involves a little more effort, the TriQuest Gravel Triathlon rolls into Plymouth on September 12. It is a great one to watch or, for the ambitious, to enter - Vermont's back roads are at their most spectacular this time of year.
The main event: the 52nd Annual Chester Festival
Circle this one. On September 19 and 20, the beloved Chester Festival returns for its 52nd year - and this year it moves to a roomy new home at Gateway Field, next to the Chester American Legion at 637 Vermont Route 103S, just 20 minutes from the Inn.
Entry is free, and you will find 100-plus juried New England artisans, live music, local food, and family entertainment across the weekend. Hours are Saturday 9 a.m. to 5 p.m. and Sunday 9 a.m. to 4 p.m. It is genuinely one of the best fall craft festivals in Vermont, and it lands right as the foliage is peaking - which also makes it one of the busiest weekends of the season. If you want a room, book early.
Looking ahead to October
The fun does not stop when the calendar flips. On October 10, Ludlow itself hosts the Ludlow Rotary Club Chili Cook-Off - a hometown favorite where local restaurants and home cooks battle for chili supremacy, and you get to taste your way through it. That same day, Wellwood Orchards rolls out its Annual Car Show back in Springfield.
Then, on October 11, Okemo Mountain caps the season with its Fall Into Winter Festival - live music, food, and family activities as the resort transitions from foliage to first snow. You can find the full local lineup on the Okemo Valley Regional Chamber's events calendar.
Make it a foliage weekend
The beauty of basing yourself in Ludlow is that a festival is only ever part of the day. Pair the Chester Festival with a drive along scenic Route 100, lace up for a fall hike in the Okemo Valley, or simply enjoy a leisurely dinner at one of Ludlow's excellent local restaurants. After a full day of leaf-peeping and festival-hopping, there is nothing better than returning to a warm, welcoming room right in the heart of the village.
Your fall home base in Ludlow
Foliage weekends are the busiest - and most beautiful - of the Vermont year, and rooms near these festivals fill up fast. Skip the long drive and stay steps from the fun.
Book your Okemo Valley fall getaway today at thegovernorsinn.com - and let The Governor's Inn be your home base for the best of autumn in Vermont.
