Top Vermont Cultural Tours

This tour is built just for you! You provide what you'd love to see and do (scenery, farms, photography, food, artisans, etc.) and what you'd rather skip and I'll create a customized itinerary for your day. We'll travel in a built-for-back roads Bronco, with a (weather permitting) top-down, open air experience you won't soon forget! As much as possible, we keep off the main routes and stick to dirt roads where traffic doesn't exist, the scenery is breathtaking, and hidden views abound. There will be plenty of opportunities to pause and take it all in. Be sure to check out the Vermont Wayfinders website for more information on tours and availability, including add-on options like heading to the top of Killington or going for a horse-drawn carriage ride. The places provided listed here are just the start; this truly is a signature tour, tailored to you and your small group.

Vermont’s blend of history, craftsmanship, and beauty is best experienced on a scenic drive through its most charming towns. On this self-guided driving tour, you'll journey along picture-perfect roads, over historic covered bridges, and into the heart of the region’s artistic culture. The tour starts in 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 that parallels the Connecticut River, affectionately known as the “Birthplace of Vermont.“ 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.

This 7-hour tour begins with a trip to Montpelier, Vermont’s capital city—the smallest and least populous state capital in the nation. There, we will enjoy a guided tour of the Vermont State House*, led by a dedicated guide who will share its history and answer questions. *Guided tours in the Vermont State House are only available from early July through October. The building is closed for visitors on Saturdays and Sundays. Our weekend tours will therefore admire the state house from outside, then explore downtown Montpelier by foot. While in Montpelier, we will also visit the family-run Morse Farm Maple Sugarworks for a maple syrup tasting. Next we will drive scenic VT RT 100 to the villages of Waitsfield and Warren. Popular attractions include an 1833 covered bridge ("The Big Eddy") and Appalachian Gap. Lunch is available for purchase at the Warren Store, a uniquely Vermont experience with great local food. The Warren Store features its own deli, bakery, wine shop, and gift store.

This tour brings together two iconic Vermont features - craft beer and covered bridges. The pace is relaxing and easy going, with minimal walking required. Enjoy Vermont beer with a built-in designated driver! We'll travel in a built-for-back roads Bronco, with a (weather permitting) top-down, open air experience you won't soon forget! As much as possible, we keep off the main routes and stick to dirt roads where traffic doesn't exist, the scenery is breathtaking, and hidden views abound. There will be plenty of opportunities to pause and take it all in! Be sure to check out our website for more information on tours and availability! We'll stop at Long Trail and Harpoon but will tailor the route before, between and after to your preferences... some examples of what we suggest are provided for you. Just reach out after you book with any requests!

There’s nothing like fall in Vermont! The crisp air, the burst of color from maple leaves, and sunlight filtering through the trees make every back road feel like an adventure. Be sure to check out the Vermont Wayfinders website for more information on tours and availability, including add-on options like heading to the top of Killington or going for a horse-drawn carriage ride. Your curated tour takes you through the most scenic routes during foliage season. Whether you’re looking for panoramic views, covered bridges framed by colorful leaves, or charming villages bursting with fall vibes, we put together each itinerary to give you the ultimate Vermont fall experience. Tour Highlights: - Breathtaking foliage views from iconic overlooks and winding back roads - Visits to cozy Vermont towns - Stops at local farms, breweries and hidden vistas - Chances to wander near fields and forests and capture postcard-worthy photos