26034 Painted Hills of New England

Day 1

Day 1: Saturday, September 19
Join us from the available departure location of your choice, meet your friendly on-board host and driver and settle in for a comfortable travel day east with an overnight stay in Indiana.
Relax, enjoy the ride, and get excited for the scenery ahead!

Day 2

Day 2: Sunday, September 20
Another easy travel day with an overnight stop in Batavia, NY as you make your way toward New England.

Day 3

Day 3: Monday, September 21
Your first true taste of New England comes in the postcard village of Stockbridge, where you’ll visit the renowned Norman Rockwell Museum.
Inside this light-filled museum is the world’s largest collection of Rockwell’s original art. You will stand inches away from the paintings you grew up seeing on Saturday Evening Post covers. You’ll see The Four Freedoms up close. You’ll recognize the famous Stockbridge Main Street at Christmas and realize you are standing in the exact town that inspired it.
Lunch is on your own at the museum cafe before continuing to Chicopee for a welcome reception and included dinner.

Day 4

Day 4: Tuesday, September 22
This morning you step inside the working studio of Vaillancourt Folk Art. Here, artists still use antique chocolate molds to create hand-painted chalkware Santas, rabbits, and heirloom ornaments. You will watch the painting process and learn how these pieces become family treasures passed down for generations.
In Portsmouth, one of America’s oldest seaports, you’ll enjoy free time for lunch and shopping before a guided tour through neighborhoods that date to the 1600s. Hear stories of great fires, colonial governors, and the still-active Naval Shipyard across the river in Maine.
By late afternoon you arrive in Ogunquit, a storybook seaside town where you will stay for three nights. The famous Marginal Way walking path hugs the cliffs above the Atlantic and is dotted with benches perfect for watching waves crash against the rocks.
Dinner is on your own tonight in the charming village filled with seafood shacks, cafes, and boutiques.

Day 5

Day 5: Wednesday, September 23
Welcome to the postcard perfect coastal town of Kennebunkport, where sea captains once built their fortunes and weathered shingled homes line quiet harbor streets. You’ll travel past sandy beaches, working marinas, and the dramatic rocky shoreline that defines this stretch of Maine, with views of Walker’s Point, the summer home of the Bush family, where the Kennebunk River meets the Atlantic. Stories of shipbuilding, fishing traditions, and generations of coastal life bring this charming seaside community vividly to life.
Then it’s time to head out on the water for an authentic Maine experience. Climb aboard a real working lobster boat and cruise along the rugged coastline as a lobsterman demonstrates how traps are hauled from the ocean floor. You’ll learn how buoys are marked, how traps are baited, and how lobsters are measured and sorted according to strict Maine conservation laws that protect this time honored industry.
This evening, you’ll pause for photos at the iconic Nubble Lighthouse, one of the most photographed lighthouses in the country. From there, you’re off to enjoy a true Downeast feast. Don your souvenir lobster hat and sit down to an authentic Maine lobster dinner complete with all the traditional fixings.

Day 6

Day 6: Thursday, September 24
In Portland, Maine’s largest seaport, restored brick warehouses line the Old Port waterfront. Here, a Harbor Lights cruise carries you past calendar islands, working fishing boats, and multiple lighthouses. Later, a guided city tour shows you Longfellow’s childhood home and elegant sea captain houses.
You will stand before Portland Head Light, the most photographed lighthouse in America, perched dramatically on the rocks at Fort Williams Park.

Day 7

Day 7: Friday, September 25
Cruise across Lake Winnipesaukee aboard the historic M/S Mount Washington, a graceful replica steamship that has carried passengers across these waters for generations. As you glide between quiet islands and forested shorelines, the surrounding mountains glow with vibrant fall color, creating postcard views in every direction. From the open deck, you’ll feel the crisp mountain air and watch lakeside villages, docks, and sailboats drift past as your captain shares stories of the lake’s history and legends.
Later, step into a different era at Castle in the Clouds, a 1914 mountaintop mansion built as a luxurious retreat overlooking the lake below. From its terraces and windows, sweeping panoramic views stretch for miles across Lake Winnipesaukee and the surrounding peaks dressed in autumn hues. Inside, you’ll explore the beautifully preserved rooms, innovative early 20th century design features, and elegant craftsmanship that made this estate a marvel of its time. Stroll the grounds, take in the mountain scenery, and enjoy the peaceful atmosphere that still surrounds this historic property.
This evening, you travel deeper into the heart of the White Mountains where you’ll settle in for a relaxing two-night stay, surrounded by the very landscapes that make New Hampshire one of the most celebrated fall foliage destinations in the country.

Day 8

Day 8: Saturday, September 26, 2026
Ride the Cannon Mountain Aerial Tramway for panoramic views across four states, where mountain peaks and colorful valleys stretch as far as the eye can see. Travel the legendary Kancamagus Highway, widely called the most scenic drive in America, with stops at waterfalls, gorges, and a classic covered bridge tucked into the forest. This route winds through the heart of the White Mountain National Forest, offering one breathtaking vista after another at every turn.
This evening, dine aboard the beautifully restored Cafe Lafayette Dinner Train for a five-course meal rolling through the forest.

Day 9

Day 9: Sunday, September 27
Visit Billings Farm & Museum in Woodstock to experience a beautifully preserved working dairy farm and living history museum, that showcases Vermont’s rural heritage. Stroll the grounds, see the barns and historic farmhouse, and watch farm life in action before sampling award winning cheeses at Cabot. Then continue to Morse Farm Maple Sugarworks, where eight generations of the same family have perfected the art of producing pure Vermont maple syrup. Learn how sap is collected and boiled down into liquid gold while enjoying a sweet local treat.
Tonight, you’ll settle into Burlington with dinner on your own at lively Church Street Marketplace, a pedestrian filled promenade lined with boutiques, cafes, street performers and inviting local restaurants.

Day 10

Day 10: Monday, September 28
Today you’ll visit the Ben & Jerry’s Factory in Waterbury, where you’ll watch a short “mooovie,” get a bird’s eye view of the production floor, and learn how this iconic Vermont brand creates its famously creative flavors. Of course, no visit would be complete without enjoying a fresh sample of the day in the Flavor Room.
Later, explore Hildene, the beautiful hilltop home of Robert Todd Lincoln. Stroll the manicured gardens, tour the elegant mansion, and take in sweeping views of the surrounding Green Mountains before continuing on to Glen Falls, New York for the evening.

Day 11

Day 11: Tuesday, September 29
Today, explore the remarkable Corning Museum of Glass, where live glassblowing demonstrations bring this ancient art form to life right before your eyes. Wander through expansive galleries filled with dazzling works ranging from delicate historic pieces to bold contemporary glass sculptures, and discover interactive science exhibits that reveal how glass shapes our everyday world.
Before departing, take time to browse the museum shops or relax at the cafe before continuing on to Batavia for the evening.

Day 12

Day 12: Wednesday, September 30
Today will be a relaxing travel day home filled with colorful memories and camera rolls packed with fall scenery.
We’ll overnight in Middlebury, IN this evening.

Day 13

Day 13: Thursday, October 1
Begin the comfortable journey home today with plenty of time to relax, reflect and share favorite moments from touring. As the miles roll by, you’ll carry with you memories of brilliant fall colors, charming coastal towns, mountain vistas, and the warm hospitality of New England.