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November in Woodstock: A Quiet Season at The Jackson

November in Woodstock is Vermont at its most peaceful — the streets are quieter, the air is brisk, and the first traces of snow dust the Green Mountains. At The Jackson, this in-between season is a time to slow down, explore locally, and settle into small-town rhythm before ski season begins.

Start your mornings with a walk along the Ottauquechee River or a hike up Mount Tom, where you’ll likely have the trails to yourself and can catch the late-autumn light over the valley. Afterward, wander downtown — browse the shelves at Yankee Bookshop, sample local cheeses at Woodstock Farmers’ Market, and stop in for a pint at Long Trail Brewery just down the road.

November is also the perfect month to experience Vermont’s makers and markets. Pop into Simon Pearce in nearby Quechee to watch glassblowers at work, or check out local holiday craft fairs that begin appearing throughout the region. As evening sets in, retreat to The Jackson — warm lighting, soft bedding, and the kind of quiet that only comes this time of year.

It’s a different kind of getaway — calm, restorative, and authentically Vermont. November might just be Woodstock’s best-kept secret.

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