Our pre-planned Vermont road trips do the heavy lifting so you can just hit the gas and enjoy the ride.

A scenic landscape with a small pond reflecting the sky, surrounded by lush green grass, trees with fall foliage in oranges, reds, and yellows, and hay bales scattered across a field. Hills in the background and a clear sky above.

  • Scenic Vermont routes, designed by a local, for those who like to be behind the wheel

  • Turn-by-turn audio directions so you can focus on the views, not your map.

  • Quirky stops, local eats, and surprise gems because road trips should come with a few “whoa, look at that!” moments.

  • Stop, skip, linger—it’s your adventure! Take detours or stick to the plan. No rush, no rules!

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Ready for a scenic journey at your own pace?

Our Self-Guided Vermont Drives are handcrafted (by humans, not AI!). These ready-to-roll, audio-guided adventures lead you through Vermont’s most scenic back roads and downright delightful small towns. You’ll hit some of the best local spots, soak in gorgeous views, and cruise stress-free with turn-by-turn directions and insider tips from a local who actually knows the roads. No getting lost, no tourist traps… just you, the open road, and an amazing drive in Vermont.

  • Audio guided Vermont tours that you download to your phone for GPS-triggered playback. Hands-free guidance and no cell signal required. Learn more about the experience here.

  • Detailed and easy-to-follow audible directions and tips along the way

  • Suggested stops for food, photos, and unique Vermont experiences. Created for you by Vermont Wayfinders - and we love it here!

Timeless Vermont: Antiques and Artisans from Woodstock to Windsor

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

Start & End Location: Woodstock, Vermont

Duration: 3-6 hours, depending on how long you choose to enjoy each stop

Price: $19.99

Some of what you’ll do:

  • Antiquing and browsing of quirky, charming shops

  • Stand in awe at Quechee Gorge, Vermont’s deepest gorge

  • Cruise past rolling hayfields and soak in the postcard-perfect views

  • Watch master glassblowers at Simon Pearce

  • Sip, savor, and cheers while enjoying craft beers and small-batch spirits

  • Wander through an outdoor sculpture park

  • Stroll through Woodstock because… well, it’s Woodstock!

  • And more… because the best road trips always come with surprises!

Best for: Anyone with a love for the open road, a curiosity for history, and a knack for independent adventures. If scenic drives, charming small towns, and discovering hidden gems at your own pace sound like your kind of fun, this one’s for you!

Note: Be sure to download the tour so you can access it offline before starting your tour. It’s also good to take a few minutes to familiarize yourself with the VoiceMap app before starting out. It works great but there is a slight learning curve. See more about VoiceMap here.

Cows grazing in a grassy field in Vermont surrounded by trees with autumn foliage under a clear blue sky.

Woodstock to Windsor: Antiques & Artisans

Discover antiques, artisans, and covered bridges on a scenic Vermont tour

  • This tour begins and ends in Woodstock, Vermont and makes a loop through multiple towns east and south of Woodstock.

  • Embark on a journey through the heart of Vermont with our Woodstock-Windsor Antiques & Artisans Tour! Explore charming antique shops in Quechee, stroll through the inspiring Artisans Way in Windsor, and cross iconic covered bridges like the Cornish-Windsor Bridge, one of the longest wooden covered bridges in the world.

    Enjoy scenic drives through Vermont’s rolling hills, and discover treasures from local artists and craftspeople. Stop to relax at unique spots like the Path of Life Garden, where art and nature combine for a peaceful walk.

    This unforgettable tour blends history, creativity, and natural beauty for a truly authentic Vermont experience.

  • This tour is just over 50 miles and without any stops will take about 90 minutes. But you definitely want to stop along the way! Plan on 6-8 hours, or a full day, to enjoy all this tour has to offer.

    • Taftsville Covered Bridge

    • B.F. Southgate Antiques

    • Quechee Gorge

    • Quechee Gorge Village

    • Simon Pearce - Windsor

    • Harpoon Brewery

    • Silo Distillery

    • Path of Life Garden

    • Windsor, VT

    • Cornish-Windsor Covered Bridge

    • Vermont Horse Country Store

    • South Woodstock VT

    • … and more!

    • Ideally leave Woodstock between 9 and 10am.

    • Consider road conditions and don't take this tour if roads are icy or snowy.

    • During certain times of the year, especially around Fall Foliage, many of the stops on this tour will be quite busy.

  • You'll have plenty of stops along the way to grab a bite to eat or something to drink but bringing along a snack and a bottle of water is always a good idea! There will be lots of options to get out and explore, so have good walking shoes on and dress in layers -- the weather often changes quite a bit over the course of the day.

This tour is hosted on the VoiceMap app; you can preview and purchase it directly using the “Buy Now” link below. Want to know more about VoiceMap? Check out my detailed overview of their platform here.

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