A Scenic Self-Guided Drive Through Vermont’s Charm: Woodstock to Windsor
Imagine cruising along quiet country roads, passing through charming small towns, crossing historic covered bridges, and discovering local artisans—all at your own pace. This Antiques and Artisans: A Woodstock to Windsor Self-Guided Drive offers just that, for a modest $19.99 per group (up to 15 people). With a duration of about 3 to 5 hours, it’s a relaxed way to soak up Vermont’s distinct character without the rigidity of a guided tour. You start in Woodstock, often called one of America’s prettiest small towns, then wind through scenic routes toward Windsor, the “Birthplace of Vermont,” encountering a treasure trove of vintage and artisan sights along the way.
We like how this tour combines classic Vermont sights—like the Taftsville Covered Bridge and Quechee Gorge—with the flexibility of exploring on your own schedule. Plus, the inclusion of lifetime access to the GPS-guided tour means you can revisit your favorite spots without feeling rushed. A key highlight for us was the chance to browse Vermont Antique Mall and see Simon Pearce glassworks at your own pace, adding a tangible layer of local craftsmanship.
However, a possible drawback is the reliance on internet connectivity. One reviewer pointed out that spotty Wi-Fi made it tricky to complete the tour’s full route. So, if you’re traveling in a remote area, downloading the map beforehand and ensuring your device is prepared can save some frustration. This experience suits travelers who enjoy independent exploration with a bit of guidance, especially those interested in Vermont’s scenic beauty and artisan culture.
Key Points

- Self-Guided Flexibility: Explore Vermont’s charming towns and sights at your own pace with GPS and offline access.
- Affordable Value: At just $19.99, it offers a low-cost way to discover notable landmarks like covered bridges and antique shops.
- Authentic Local Experiences: Highlights include browsing vintage shops and viewing handcrafted glassware.
- Scenic Highlights: Includes iconic sites such as Quechee Gorge and the longest covered bridge in the U.S.
- Connectivity Tip: Internet can be spotty, so plan ahead to download the tour materials.
- Designed for Independent Explorers: Ideal for those who prefer to customize their day and avoid large tour groups.
A Deep Dive into the Vermont Self-Guided Drive
When you consider what makes this tour appealing, it’s the chance to experience Vermont amid its most picturesque settings—without the rush or expense of a guided bus tour. For just under twenty dollars, you gain access to a carefully crafted GPS-driven route that guides you through some of Vermont’s most photogenic and historic spots. This approach makes it accessible for small groups or families who want the freedom to linger or skip certain stops.
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Starting Point: Woodstock’s Charm
Your journey begins in Woodstock, a town that exudes New England character with its well-preserved buildings, boutique shops, and welcoming atmosphere. It’s the perfect launchpad for a scenic drive. The tour’s directions start at Pizza Chef of Woodstock, ensuring you’re ready to go without fuss. From there, you’ll head toward Taftsville, crossing one of Vermont’s oldest covered bridges, recognizable for its vivid red color and quaint wooden structure. This bridge is not just pretty; it’s a snapshot of Vermont’s historical construction methods, dating back many decades.
The Route: Scenic, Historic, and Artisanal
As you drive along the route, you’ll pass Quechee Gorge, often called “Vermont’s Little Grand Canyon”. While the tour doesn’t include a paid visit inside the gorge, the views from the roadside are impressive and worth a quick stop for photos. You can expect panoramic cliffs carved by the Ottauquechee River, offering a scene straight out of a rural postcard.
Next, the tour takes you past the Vermont Antique Mall, a treasure chest for vintage lovers. Here, you can browse an eclectic mix of antiques, collectibles, and local curiosities. The tour doesn’t include entry costs, so be prepared for any personal expenses if you choose to shop or browse extensively.
Simon Pearce, a renowned glassblowing workshop, is also along the route. Though the tour doesn’t cover the cost of visiting, seeing artisans craft delicate glassware in a scenic setting adds a layer of authenticity to your Vermont experience.
The Iconic Covered Bridge: Cornish-Windsor
One of the highlight stops is the Cornish-Windsor Covered Bridge. This is the longest covered bridge in the United States, spanning the Connecticut River between New Hampshire and Vermont. As you cross, you’re not just passing a bridge—you’re being transported back in time, witnessing a piece of America’s rural engineering heritage.
After crossing into Windsor, the route continues through West Windsor and South Woodstock, offering additional scenic views and quiet backroads that are perfect for a relaxed, unhurried drive.
End Point: Back in Woodstock
Your tour concludes back in Woodstock at South Street, where you can extend your visit with a meal or further exploration. The accessibility of the starting and ending points makes this a convenient loop, especially for those staying in the area.
Authenticity and Practicality: What Travelers Say

One traveler mentioned that “the app worked perfectly,” and enjoyed the Vermont charm and covered bridges. This reinforces that for those with a decent smartphone and reliable GPS signal, the experience can be smooth and enjoyable. Conversely, another reviewer faced difficulties due to spotty Wi-Fi, which prevented completing the full route. This highlights the importance of pre-downloading the tour content and being prepared for limited connectivity in rural areas.
The price point is quite reasonable, especially considering you get lifetime access to the tour, meaning you can revisit parts of the journey or explore on different days. It’s a good fit for budget-conscious travelers who want to dip into Vermont’s scenic and artisanal culture without committing to more expensive guided tours or organized excursions.
Who Will Love This Tour?
This experience is best suited for independent travelers, small groups, or families who enjoy self-guided adventures. If you love scenic drives, historic bridges, antique shopping, or simply want a flexible way to explore a region famed for its natural beauty and craftsmanship, this tour offers a gentle, affordable introduction.
Final Thoughts: Is It Worth It?

For its price, this self-guided drive offers a genuine taste of Vermont’s landscape and heritage. The ability to explore at your own speed, combined with the scenic highlights like the Quechee Gorge and longest covered bridge, makes it a worthwhile addition to any Vermont itinerary. It’s especially appealing if you prefer independent planning over crowded tours or are looking for an inexpensive way to see multiple sights with minimal fuss.
However, the technical hiccups reported by one reviewer are worth noting—download the materials beforehand and plan for spotty connectivity in rural Vermont. It’s a small inconvenience for the chance to enjoy a peaceful drive through some of New England’s most picturesque settings.
In sum, this tour is a good option for adventurous souls eager to discover Vermont’s authentic beauty on their own terms, especially if you prioritize scenic views and local craftsmanship over guided commentary.
FAQs

What is included in this self-guided tour?
You get lifetime access to the GPS-guided route in English, with offline maps, audio, and directions so you can explore at your own pace.
How long does the tour take?
The tour lasts approximately 3 to 5 hours, depending on how long you linger at each stop and your pace.
Are there any additional costs during the tour?
Yes, any fees for visiting attractions such as the Vermont Antique Mall, Simon Pearce, or the covered bridges are not included. You should budget for personal expenses at these sites.
What do I need to participate?
A smartphone with GPS, the tour app (available on Android and iOS), and headphones are necessary. Also, consider downloading the tour offline to avoid connectivity issues.
Can I start and end the tour at different locations?
No, the tour is designed as a loop starting and ending in Woodstock at the specified addresses.
Is this suitable for families?
Yes, it’s suitable for small groups or families who enjoy independent exploration and scenic drives. The route is flexible, allowing for breaks and sightseeing.
What if my internet connection is poor?
The tour recommends downloading the route in advance because spotty Wi-Fi can cause issues. Once downloaded, you can navigate offline easily.
Is there a guided component?
No, this is a self-guided experience. You follow the GPS route with audio prompts and maps, giving you control over your timing and stops.
Can I cancel or reschedule?
Yes, there’s a free cancellation policy if you cancel at least 24 hours before your scheduled start time.
This self-guided Vermont drive offers a relaxed, authentic way to enjoy the state’s natural beauty and artisanal charm. Whether you’re a history buff, a lover of scenic drives, or simply seeking a peaceful day out, it’s a cost-effective adventure worth considering—just come prepared for spotty Wi-Fi and a flexible mindset.
