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Explore Vermont’s charming towns, covered bridges, and local artisans on this self-guided drive from Woodstock to Windsor, perfect for a scenic and authentic day trip.
A Scenic Drive Through Vermont’s Artistic Heart: An Honest Look at the Woodstock to Windsor Self-Guided Tour
If you’re craving a relaxed, scenic day that combines Vermont’s iconic covered bridges, small-town charm, and local artisan culture, the “Antiques and Artisans: A Woodstock to Windsor Self-Guided Drive” could be a good fit. Offered by VoiceMap Audio Tours, this self-guided adventure promises the freedom to explore at your own pace, with audio guidance and GPS navigation.
What we love most about this tour are the stunning views—particularly the historic covered bridges—and the opportunity to browse Vermont’s vintage and artistic treasures in a relaxed setting. However, a potential snag is that the route relies heavily on a stable internet connection for downloading the tour content, which can be tricky in some rural areas. If you enjoy discovering hidden gems at your own pace and don’t mind a bit of technical patience, this tour offers a genuine, low-cost way to experience Vermont’s quintessential countryside.
This experience is ideal for those who appreciate self-guided adventures, want to soak in Vermont’s small-town atmosphere, or are looking for a budget-friendly way to discover local craftsmanship without large tour groups. It’s especially suited for travelers with a sense of curiosity and patience for managing on-the-fly navigation.

This tour kicks off in Woodstock, often ranked among the most beautiful small towns in America. The starting point at Pizza Chef sets a casual tone for your day. From there, your journey takes you through some of Vermont’s most picturesque settings.
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Woodstock is a classic Vermont town—imagine a place where the streets are lined with well-preserved 19th-century buildings, and Main Street feels like stepping back in time. The tour’s starting point is conveniently located at the Pizza Chef, setting you up for a day of exploration. While you’re here, you can enjoy a leisurely breakfast or lunch before heading out.
Just a short drive from Woodstock, you’ll pass the Taftsville Covered Bridge, distinguished by its vibrant red color and charming wooden structure. As one of Vermont’s oldest covered bridges, it offers great photo opportunities. Travelers mention that the bridge’s distinctive hue and historic design make it a favorite among visitors.
Next, the route skirts the edges of Quechee Gorge, dubbed “Vermont’s Little Grand Canyon.” While the tour only offers a quick glimpse, the dramatic cliffs and river views are undeniably scenic. If you’re lucky, you might find time to stop and take in the views yourself, although the tour doesn’t cover entrance fees or detailed exploration here.
Vermont Antique Mall and BF Southgate & Company are highlights for those interested in vintage finds and local craftsmanship. The mall is described as a treasure trove of vintage items and curiosities, perfect for browsing or hunting for unique souvenirs. Similarly, Simon Pearce, the renowned glassblowing workshop, showcases Vermont’s artisan talent. Keep in mind, visits to these sites are just passing points, and any expenses are on your tab.
Perhaps the most impressive feature of this drive is crossing the longest covered bridge in the United States, the Cornish-Windsor Bridge. Spanning the Connecticut River, this impressive feat of wooden engineering connects Vermont and New Hampshire. Travelers have mentioned that the views from the bridge are worth the stop, offering a quintessential Vermont photo op.
The route loops back through West Windsor and South Woodstock, ensuring you get a full taste of the scenic countryside. The tour concludes back at Woodstock’s Green, where you can relax and reflect on your day.

The self-guided GPS format allows you to control your pace; you start at the Pizza Chef, follow the provided directions, and explore each stop on your own. The app is available for Android and iOS, with offline access to maps and audio, making it convenient even in areas with spotty service.
However, reviews reveal some technical issues—most notably, the need for reliable Wi-Fi to download the tour content. One traveler noted difficulty completing the tour because of inconsistent internet, which is worth considering if you’re heading into rural Vermont. The support from VoiceMap is available via email or phone, and they seem responsive, but it’s wise to download everything beforehand if possible.
The estimated duration ranges from 3 to 5 hours, flexible depending on how long you linger at each stop. The tour is designed for groups of up to 15, making it more intimate than large guided tours but still manageable for families or small groups.
At just under $20, the price is quite reasonable considering that you’re getting a private, customizable experience without the need for a large tour group or guide. The key is the flexibility—if you love exploring at your own pace and enjoy a scenic drive, the value is good.
While only two reviews are available, they offer some insight. One reviewer was frustrated with connectivity issues but appreciated the route, mentioning the app worked perfectly for the other traveler who loved seeing Vermont’s covered bridges and vintage shops. They say, “Would definitely recommend,” which suggests that, when it works, this tour provides genuine value.
Another comment highlights the beauty of the covered bridges and Vermont’s authentic charm, reinforcing that this route is more about the scenery and local culture than curated attractions.

This self-guided drive is perfect if you’re looking for a relaxed, budget-friendly way to experience Vermont’s postcard-worthy scenery and artisan culture. The ability to set your own pace, combined with the chance to explore charming small towns and architectural marvels like the Cornish-Windsor Covered Bridge, makes it a lovely day trip.
However, it’s best suited for travelers comfortable with managing their own navigation and who don’t mind troubleshooting minor technical issues. If you appreciate authentic scenery, historic covered bridges, and vintage shopping without the hassle of large groups, this tour could be a highlight of your Vermont adventure.
Keep in mind that some stops are more about viewing and browsing than extensive visits, so if you want in-depth experiences or guided commentary, this might not satisfy those needs. Still, if you value flexibility and local charm, this drive delivers a genuine taste of Vermont’s scenic and creative spirit.
“The internet is definitely needed to follow the route. It is extremely spotty in a lot of the places. Was not able to complete the tour because it …”

Is the tour suitable for all ages?
Yes, since it’s a self-guided drive, it’s suitable for families, seniors, or anyone comfortable with driving and exploring at their own pace.
Do I need to have a smartphone to participate?
Yes, you’ll need a smartphone to access the app, GPS navigation, and audio guides. Remember, offline access is available once downloaded.
Are there any additional costs during the tour?
Transportation and the tour itself are included, but any visits to attractions like antique malls, glass workshops, or distilleries will likely have separate costs.
How long does the tour typically take?
Most travelers spend between 3 and 5 hours, depending on how long they linger at each stop and explore.
What if I experience technical problems with the app?
VoiceMap offers support via email and phone. It’s recommended to download the tour content beforehand to avoid connectivity issues.
Can I do this tour with a small group or just as a solo traveler?
Absolutely. It’s designed for groups of up to 15 but works just as well for solo explorers or couples seeking a flexible day out.
In the end, this Vermont self-guided drive offers a pleasant, flexible way to take in some of the state’s most charming sights. It’s not a guided tour with detailed commentary, but it provides enough structure and stunning scenery for a memorable day—especially if you enjoy vintage finds, covered bridges, and scenic drives. Just be prepared for the technical quirks and ensure your device is ready. If that sounds appealing, it’s a lovely way to enjoy Vermont’s quiet, picturesque countryside.