Explore Vermont’s charm on a scenic drive from Woodstock to Windsor, featuring historic bridges, antique treasures, and artistic culture.
Explore Vermont’s charm on a scenic drive from Woodstock to Windsor, featuring historic bridges, antique treasures, and artistic culture.
- Taftsville Covered Bridge - The tour will take you past the historic Taftsville Covered Bridge, one of the oldest in Vermont, celebrated for its unique red color and charming wooden design.
- Quechee Gorge - Enjoy a view of Quechee Gorge, often referred to as “Vermont’s Little Grand Canyon,” featuring breathtaking vistas and impressive cliffs…
- Taftsville Covered Bridge - The tour will take you past the historic Taftsville Covered Bridge, one of the oldest in Vermont, celebrated for its unique red color and charming wooden design.
- Quechee Gorge - Enjoy a view of Quechee Gorge, often referred to as “Vermont’s Little Grand Canyon,” featuring breathtaking vistas and impressive cliffs sculpted by the Ottauquechee River. Please note that any expenses for visiting the area are not included in this tour.
- Vermont Antique Mall - The tour includes a drive by the Vermont Antique Mall, a haven for vintage treasures and local curiosities. Please be aware that any expenses for visiting the mall are not included in this tour.
- Simon Pearce - The tour will pass by Simon Pearce, a renowned glassblowing studio and shop famous for its exquisite handcrafted glassware. Please note that any expenses for visiting the business are not included in this tour.
- Cornish-Windsor Covered Bridge - The tour crosses the historic Cornish-Windsor Covered Bridge, the longest covered bridge in the United States, which spans the Connecticut River between New Hampshire and Vermont. Please be aware that any expenses for visiting the area are not included in this tour.
- SILO Distillery - The tour will pass by SILO Distillery, a local craft distillery celebrated for its small-batch spirits and tasting room. Please note that any expenses for visiting the distillery are not included in this tour.

- Lifetime access to this tour in English before your booking date and after it
- Offline access to audio, maps, and geodata
- App for Android and iOS
- Flexibility to explore at your own pace with a self-guided GPS tour
- Directions to the starting point so that when you’re in the right place, the tour will start
- Lifetime access to this tour in English before your booking date and after it
- Offline access to audio, maps, and geodata
- App for Android and iOS
- Flexibility to explore at your own pace with a self-guided GPS tour
- Directions to the starting point so that when you’re in the right place, the tour will start
- Smartphone and headphones
- Smartphone and headphones
Vermont offers a delightful mix of history, craftsmanship, and natural beauty, best appreciated on a scenic drive through its most picturesque towns. This self-guided driving tour takes travelers along idyllic roads, across historic covered bridges, and into the vibrant heart of the region’s artistic culture.
The journey begins in Woodstock, often hailed…
Vermont offers a delightful mix of history, craftsmanship, and natural beauty, best appreciated on a scenic drive through its most picturesque towns. This self-guided driving tour takes travelers along idyllic roads, across historic covered bridges, and into the vibrant heart of the region’s artistic culture.
The journey begins in Woodstock, often hailed as one of the most beautiful small towns in America. Travelers will head towards Quechee, passing through Taftsville to admire its stunning red covered bridge, one of Vermont’s most charming. Along the way, there are opportunities to explore a wealth of antiques, vintage treasures, and fine art at Vermont Antique Mall and BF Southgate & Company.
The route continues to Windsor, running parallel to the Connecticut River, affectionately known as the “Birthplace of Vermont.” The tour highlights the Cornish-Windsor Covered Bridge, the longest wooden covered bridge in the United States, before returning to Woodstock via West Windsor and South Woodstock.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.