Timeless Vermont: Antiques and Artisans from Woodstock to Windsor

Vermont’s blend of history, craftsmanship, and beauty is best experienced on a scenic drive through its most charming towns. On this driving tour, I’ll take you along picture-perfect roads, over historic covered bridges, and into the heart of the region’s artistic culture.

The tour begins at the Pizza Chef of Woodstock, in what’s often called one of the most beautiful small towns in America. You’ll set off towards Quechee, passing through Taftsville to see its striking red covered bridge, one of the most attractive in Vermont. From there, you’ll have a chance to browse a bounty of antiques, vintage finds, and fine art at Vermont Antique Mall and BF Southgate & Company.

You’ll follow a historic route to Windsor, affectionately known as the “Birthplace of Vermont", that parallels the Connecticut River. I’ll show you the Cornish-Windsor Covered Bridge, the longest wooden covered bridge in the United States, before you make your way back to Woodstock via West Windsor and South Woodstock’s beautiful farm and horse country.

Along the way, you’ll have a chance to:

• Marvel at Quechee Gorge, Vermont’s deepest, a breathtaking natural wonder referred to as “Vermont’s Little Grand Canyon“
• Enjoy driving through rolling hayfields alongside Ascutney Mountain West Windsor, Vermont
• Stop at Simon Pearce Glassblowing and watch skilled artisans handcraft elegant glassware and pottery, blending traditional techniques with contemporary designs
• Savor locally brewed craft beers, small-batch spirits, and delicious pub fare at Harpoon Brewery & Silo Distillery
• Wander through a peaceful outdoor sculpture park at the Path of Life Garden
• Stroll through Woodstock with its charming village green, historic architecture, and boutique shops

This tour is perfect for anyone looking to experience Vermont’s charm at their own pace, without stops it'll take you three hours. Whether you’re interested in searching for antiques, admiring artisan craftsmanship, or simply soaking in the breathtaking scenery, this tour offers a one-of-a-kind glimpse into Vermont’s history and creativity.