Top Vermont Historical Tours

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.

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.

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.

Discover the beauty of Lake Champlain aboard Buttercup, where every cruise offers a blend of stunning views and captivating stories about the lake's rich history. Enjoy a leisurely outing on the water, perfect for families, couples, or anyone looking to immerse themselves in the scenic landscapes of Vermont. Choose from regular cruises or arrange a private charter for a more personalized experience. Departing from the Burlington Community Boathouse, this is a great way to relax and take in the sights of one of America’s most beautiful lakes. - Scenic cruises showcasing the stunning landscapes of Lake Champlain - Hear engaging stories about the lake's history and significance - Options for private charters or regular cruises available - Convenient departures from the Burlington Community Boathouse

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.

In Spring and Summer, we offer 5-day guided tours around the state of Vermont. With a maximum of six customers per tour, our Vermont tours are an intimate experience that feels like traveling with a group of friends Note: If flying to Vermont (Burlington International Airport), we ask that you arrive the night before the tour begins. We will pick you up at your hotel in Burlington at 9:00 AM on the first day of the tour.

See quaint villages, striking scenery, and more on this full-day, small-group tour of northern Vermont. Leave the driving and logistics to your guide, and set off via minivan—your first destination is the famed Ben & Jerry’s Factory in Waterbury, where you can enjoy tasty samples. Tour a cider mill before continuing to Smugglers’ Notch State Park, the von Trapp Family Lodge, the village of Stowe, and more.

See the sights of Burlington while having fun with your friends during an active scavenger hunt via your smartphone. Follow the prompts via an app to uncover hidden gems, solve clues, and get to know Burlington better. You can take as much or as little time as you like, as you set the pace. This is an ideal tour for travelers who don’t like traditional guided tours.

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