Top Vermont Sightseeing Tours in 2026

Route 100 is known as Vermont’s Main Street, offering a scenic journey through charming villages, covered bridges, and stunning waterfalls. This self-guided driving tour begins in Wilmington and leads north through picturesque towns such as Stowe and Waitsfield, showcasing the beauty of the Green Mountains. Along the way, enjoy local highlights like the Vermont Country Store, Moss Glen Falls, and the renowned Ben & Jerry’s Factory. Perfect for families, food lovers, and photographers, this tour provides the ultimate Vermont experience at your own pace, with captivating stories of history and culture throughout the drive. - Explore classic Vermont villages and local shops - Visit iconic sites like Moss Glen Falls and covered bridges - Taste local specialties at Ben & Jerry’s and Cold Hollow Cider Mill - Ideal for families, photographers, and those seeking scenic drives

Explore Vermont's Route 100 on a self-guided tour. Embark on a captivating road trip along Vermont's most scenic drive, where brilliant fall foliage and the quintessential charm of New England await. This journey takes you through picturesque towns, idyllic villages, and historic covered bridges. As you travel, explore historic landmarks, visit hidden treasures, and enjoy scenic vistas. Come fall, the route transforms into a vivid tapestry of autumn colors, offering a stunning visual feast that makes this drive truly unforgettable. Purchase one tour per car, not per person. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

Download the GuideAlong self-guided audio tour and you'll discover more on your Vermont Scenic Route 100 Byway drive. Hear fascinating stories, local tips, and directions play automatically based on your location. Explore the charming stops along the way, starting with a taste of Apple Cider and a visit to Ben & Jerry's. Enjoy the artisanal flavors at the Cabot Annex and marvel at the historic Covered Bridges. Discover the President Calvin Coolidge Homestead, the beauty of Smugglers Notch, and the charm of Stowe. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location. Travel at your own pace. Tour offline using GPS, no cell service or WiFi needed. Suggested itineraries for half, full, or multi-day use. Buy once, use forever! No expiry, includes free updates. Like having a tour guide along for the drive. Purchase one tour per vehicle.

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.

From the chilling tales of the Ghosts of the Shanty to the haunted site of Nectar’s to the serial killer HH Holmes, this tour will guide you in the footsteps of Burlington’s haunted history, uncovering the stories that have shaped this city. Go at your own pace, anytime. This is a location aware walking tour and the app plays the stories as you walk. The tour never expires, go as many times as you want.

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 listed here are just the start; this truly is a signature tour, tailored to you and your small group.

Download GuideAlong’s self-guided audio tour bundle to make the most of your Eastern USA road trips. As you drive, hear stories play automatically as you explore scenic drives, national parks, lakeshores, and historic parks. This is the ultimate collection of 14 iconic destinations, including Acadia, Blue Ridge Parkway, Catskills, Florida Keys, Great Smoky Mountains, Lake Superior, Outer Banks, Shenandoah, and Vermont’s Route 100. A memorable adventure awaits on America's iconic roads. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use Buy once, use forever! No expiry, includes free updates Like having a tour guide along for the drive Purchase one bundle per vehicle.

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.

There’s nothing quite like fall in Vermont, and no two foliage days are exactly the same. This private, full-day tour for up to four guests is planned around the best of what Vermont has to offer that day. Foliage changes quickly, weather matters, and some roads are far busier than others during peak season. Depending on the day, we might follow quiet back roads, stop at covered bridges and overlooks, wander through a Vermont village, or visit a farm or local maker. The goal isn’t to check off a list of attractions. It’s to spend the day seeing Vermont at its best, at an easy pace, with time to stop, explore and enjoy it. Visit the Vermont Wayfinders website for more information about tours and availability. **Tour Highlights:** - Scenic back roads and mountain drives - Covered bridges, villages, farms and Vermont landscapes - Stops chosen for the conditions that day - Time to explore and take photos without being rushed - A private itinerary planned for your group

Privately guided 3-4 hour tours give you a bite-sized taste of Vermont’s scenic backroads, charming villages, and local favorites, all in a compact, easygoing experience. Guided by a local, gain insider knowledge of some of the best spots to visit and find even more beautiful routes to explore as you find your way to favorite spots in and around the Connecticut River Valley of Vermont. Various themes for the tour are offered, including 'Bridges and Brews', 'Antiques and Artisans', and 'Ridges and Rivers' and we get started from Woodstock, Ludlow or Springfield Vermont. Be sure to check out the Vermont Wayfinders website for more information on tours and availability! It’s the perfect way to explore if you’re short on time, love a good scenic detour, or just want a more budget-friendly private tour. You’ll still get a local expert as your guide, a perfectly planned route, and plenty of time to soak in the sights—just in a smaller, snackable package.

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!