New England’s Fall Foliage tours are a quintessential experience, drawing travelers from around the world to witness the vibrant transformation of autumn. These scenic journeys are among the most sought-after trips offered by tour operators each year, and with TripSchool, you'll gain the insider knowledge to truly stand out in the crowd. Learn the best itineraries, uncover hidden gems, and discover expert tips that will make you the go-to Tour Director for Fall!

But we don’t just stop at sightseeing. Over the course of this immersive six-day training, you’ll go beyond the ordinary. Expect to engage with fascinating stories, explore iconic destinations, and dive into authentic local experiences that will leave you inspired—and ready to share your newfound passion and insights with your future guests. This isn’t just a trip; it’s an opportunity to bring the heart of New England’s fall magic to life. 

Plan to arrive in Burlington, VT by 4PM. We will be meeting in the hotel lobby and have a special evening planned! 

Get ready for a thrilling day of adventure through some of New England’s most charming spots! We kick off our journey with a visit to the iconic town of Woodstock, VT—a picturesque gem that captures the very essence of Vermont’s history and charm. Steeped in rich stories and surrounded by stunning landscapes, Woodstock is a quintessential New England town that you won’t want to miss. From there, we’ll stop at the breathtaking Quechee Gorge, a true must-see natural wonder, before continuing our journey to Montpelier, VT—the smallest state capital in the U.S.!

After lunch, we’ll tour the impressive Statehouse, exploring its historic halls and learning about the political heart of Vermont. But the adventure doesn’t stop there! We’ll venture into the scenic Waterbury area, home to local treasures like the legendary Morse Farm and the renowned Cold Hollow Cider Mill, where you’ll get a taste of Vermont’s best. From maple syrup to apple cider and beyond, you’ll experience the true flavors and spirit of the Green Mountain State. It’s a day packed with history, culture, food and local magic—one that you’ll never forget!

We finish near Littleton, NH 

Overnight in Littleton 

Get ready for an unforgettable day of exploration and discovery! This is the most important day on any Foliage itinerary and knowing where to stop, what to say and how to present it is key!

Our adventure begins with a quick but fascinating tour of Littleton, NH, where you’ll hear quirky stories and uncover hidden stops, including a secret museum that few know about and the world’s longest candy counter—yes, you read that right! You’ll be amazed at the sweet surprises this charming town has to offer.

Next, we head to the stunning Franconia Notch, where the beauty of the White Mountains will leave you speechless. Along the way, we’ll make several thrilling stops, each with its own incredible story to tell. Picture this: Franconia State Park’s awe-inspiring vistas, the iconic Old Man in the Mountain (or what remains of it), and the mesmerizing Flume Gorge Visitor Center, where nature’s grandeur takes center stage. 

As we continue, prepare for jaw-dropping views of The Basin —perfect for snapping those picture-perfect memories. The adventure only intensifies as we hit the famed Kancamagus Highway, one of New England’s most scenic drives, where you’ll find the best photo ops at spots like Sabaday Falls, Lower Falls, and the historic Russell-Colbath Homestead. We’ll wrap up with a stop at the Albany Covered Bridge, a postcard-worthy spot that will make you feel like you’ve stepped back in time. Get ready for a day packed with natural wonders, historic landmarks, and hidden stories that will leave you inspired and ready to tackle your next tour here! 

Overnight North Conway 

Today, get ready for an epic adventure that will take you from the towering peaks of New Hampshire to the vibrant shores of Maine! We start with a thrilling ride aboard the legendary Cog Railway as we ascend Mt. Washington—the highest peak in the Northeast. As we climb, you’ll hear captivating stories of the mountain's history, from daring expeditions to the dramatic weather that makes this summit famous. When we reach the top, prepare to be stunned by panoramic views that stretch for miles, offering a perspective few ever get to experience.

After taking in the breathtaking scenery, we’ll head to Portland, ME, where a fascinating city tour awaits. Known for its rich maritime history, Portland’s waterfront and historic sites come alive as we explore the city's coastal charm. The highlight of our visit? A special boat cruise that will take you out onto the water, where you’ll learn all about Portland’s seafaring past and the vital role it played in New England’s history. From soaring cliffs to quaint lighthouses, it’s a day packed with unforgettable experiences and stories you’ll be able to share with your future guests! 

Overnight Portland area

This is a big day! We start with a visit to Kennebunkport, which is on almost every group itinerary and even though it is a small town, it's packed with history and hidden gems. We will teach you the commentary and highlights to make you look like a star. 

We then head to Ogunquit for a beautiful walk along Marginal Way, a coastal walk that is a Wow moment for all  group tours. We will visit Nubble Light House and then make our way to historic (and creepy) Salem, MA! We will show you how to build a self-guided tour for your guests to explore (since only licensed guides can give commentary on-site). 

After checking into the hotel, we will give you an introduction to East Boston,  a neighborhood underutilized by groups. Learn about it's rich history and simple ways to incorporate it into arrival days with groups. Our Farewell Dinner will be at a local East Boston restaurant (One of Alan's faves!)  

Overnight Boston /Logan Airport

Departure day! Or, BONUS tour for those with later flights! Join us at 10AM for a Freedom Trail walking Tour! We will explore the Freedom Trail and go over the basic overall commentary that is expected when leading guests. The tour will finish at the Old North Church in the North End, however, you can continue on to Charlestown on your own or head to the airport for an evening flight. Expected to finish by 3PM, but you can leave whenever you need! 

Bon Voyage!