New England's Fall Foliage

(10 reviews)

From:

CAD $6,039 Was CAD $6,711

8 Days

Best Rate: Guarantee

Trip Type: Group Tour

Activity Level: Easy

Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S.

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Price based on per person in Double Room for departure 22 Oct 2025

Experience Overview

Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S. and where much of the country was formed; here, you will traverse part of the red-brick Freedom Trail, where you will see the hall that housed the country’s first-ever town meeting and many more historic sites. Admire the bronzing leaves of Vermont’s lush trees as you travel to Stowe, where the real Von Trapp family of ‘The Sound of Music’ chose to live — and where you will stay. In Montpelier, visit a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ride a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and see as far as Canada. See Maine’s oldest lighthouse in Portland, then celebrate your trip with a decadent fresh lobster dinner.

Highlights

Dining Summary

3 Dinner (D)
7 Breakfast (B)
1 Lunch (L)

Choice Highlights

Choose between two carefully selected activities

Stockbridge: Enjoy the warm, colorful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favorites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.
Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.

Additional Included Highlights

From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.
We carry your bags for you and promptly deliver them to your hotel door.
Our highly-skilled Travel Director will ensure your journey is seamless, serving as your expert guide, consummate organiser, and friend overseas.
Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).

Authentic Dining

Boston: Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.
Stowe: At your dinner, taste the creations of artisan brewers with Austrian-style lagers.
Shelburne: Connect with Vermont’s agricultural heritage at Bread & Butter Farm, where you’ll meet the owners and explore how regenerative practices are restoring the land and honoring local traditions. Stroll the fields with Chef Tessa, a seventh-generation Vermonter, as she shares stories of seasonal living and sustainable sourcing. Then, gather fresh herbs and blooms before enjoying a wholesome Farm-to-Table lunch, thoughtfully prepared by Tessa and her team at Blossom Whole Food Kitchen.
Portland: Enjoy an authentic Maine lobster dinner as you feast on the fresh and local delicacy known for its tender and rich flavor. Raise a glass as you mingle with new friends over this delectable Celebration Dinner.

Insight Choice

Stockbridge: Enjoy the warm, colorful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favorites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.
Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.

Make Travel Matter

North Conway: Learn about regional flora and fauna with a Local Expert during an ecological look at fall in New England. Your experience advances United Nations Sustainable Development Goal 15: Life on Land.

Top Rated Highlights

Boston: Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.
Weston: Step back into history with a visit to the Vermont Country Store where you'll find a nostalgic assortment of products ranging from local cheeses to whiskey pecan pie.
Woodstock: Visit the quintessential Vermont village of Woodstock. Then explore the Rockefeller's renowned Billings Farm and Museum, a captivating working dairy farm which also serves as a museum showcasing Vermont's rural past.
Burlington: Stop by Lake Champlain Chocolates to satisfy your sweet tooth with a taste of their award-winning ice cream. Like their decadent chocolates, their ice cream is crafted with only the best local ingredients — including fresh cream, maple syrup, and honey.
Montpelier: Travel to Morse Farm Maple Sugarworks, where maple syrup is "tapped" from the trees. Taste a Vermont tradition, the unusually named "sugar on snow’" which is maple syrup drizzled over packed snow. This tasty treat is traditionally served with a doughnut and pickle.
Franconia Notch State Park: Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort (weather permitting). On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada.
Kancamagus Highway: Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles (55 kilometers) of untouched natural beauty.
Bretton Woods: More spectacular fall foliage awaits as you journey through Crawford Notch, a scenic pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 meters).
North Conway: Enjoy a scenic hike to Diana's Baths, which features a small series of captivating cascading waterfalls. This historic site is within the White Mountain National Forest and easy paced.

Well-being

Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.
Experience enhanced hygiene protocols to align with the latest guidance following COVID-19. All Travel Directors and Drivers have completed training in enhanced well-being and hygiene protocols.
Hand sanitizer is freely available on board for you to use throughout the day.
We only work with establishments we are confident will consistently adhere to our high well-being standards, which include hotels, restaurants and sight-seeing venues.

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Trip Details

Product Code: 19599

Tour Type: Group Tour

Accommodation: Deluxe

Transport: Private

Guide Language: English

Travel Styles: Family, 55+, Luxury

Tour Operator: Insight Vacations (CA)

Supplier Code: 224.844A

Starts: Boston (MA), United States Of America

Finishes: Boston (MA), United States Of America

Duration: 8 days

Departures: Not Guaranteed

Physical Rating: Easy

Includes

Price

Price per person: (Double Occupancy) CAD $6,039 ($755 /day)

Itinerary

Day 1: Welcome to Boston

Affectionately known as Beantown, this revolutionary city is one of the oldest in the United States. After settling in, perhaps take a stroll to Downtown Crossing or historic Faneuil Hall. For those looking to shop, Quincy Market offers big brands and local products, set indoors and surrounding the columns of a regal 19th-century building. Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.

Accommodation: Hyatt Regency, Boston
Meals: Dinner

Day 2: Beantown to Saratoga Springs

Today you’ll discover some of Boston’s most famous sights as you delve into the city’s transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. See Boston Common, Boston Public Garden, Trinity Church and Copley Square. This afternoon, explore Stockbridge with an Insight Choice. Choose to visit the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art. Alternatively, choose to take a guided tour of Chesterwood, the former summer home and studio of renowned 20th-century sculptor Daniel Chester French, famous for his work on the Lincoln Memorial. Travel on through the rolling hills of the Berkshires and onto your upstate New York hotel, situated within the Saratoga Spa State Park.

Accommodation: The Gideon Putnam, Saratoga Springs
Meals: Breakfast

Day 3: The Legends of the Fall and Stowe

Enjoy Vermont's beautiful scenery ablaze with fall's golden red colors. Visit the Vermont Country Store for a unique shopping experience - you'll step back into history with their nostalgic assortment of products. Followed by a stop in the quintessential Vermont village of Woodstock with its picturesque, covered bridge. Explore the Rockefellers' renowned Billings Farm and Museum, a captivating working dairy and farm life museum. End your day in the northern Vermont town of Stowe, home to the breathtaking alpine setting that attracted the real Von Trapp family of "The Sound of Music." Enjoy Austrian-style lagers over at Von Trapp Brewing Bierhall.

Accommodation: Trapp Family Lodge, Stowe
Meals: Breakfast, Dinner

Day 4: A Taste of Vermont Relaxed Start

Enjoy Vermont’s beautiful scenery ablaze with fall’s golden red colors. Stop by Morse Farm Maple Sugarworks, where maple syrup is 'tapped' from the trees. Taste a Vermont tradition, the unusually named ‘sugar on snow,’ a combination of maple syrup and packed snow. This tasty treat is traditionally served with a doughnut and pickle. Enjoy lunch at Bread & Butter Farm, hosted by Wholesome Foods Kitchen, while you learn about regenerative agriculture and organic farming. Next, travel to Lake Champlain Chocolates for a taste of their award-winning ice cream crafted with local ingredients, before returning to the enchanting town of Stowe for an afternoon at leisure.

Accommodation: Trapp Family Lodge, Stowe
Meals: Breakfast, Lunch

Day 5: North Conway and the White Mountains Relaxed Start

Journey to New Hampshire’s White Mountains and enter striking Franconia Notch. Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort. On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada. Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 55.5 km of untouched natural beauty.

Accommodation: White Mountain, North Conway
Meals: Breakfast

Day 6: Sightseeing in the White Mountains

This morning's MAKE TRAVEL MATTER® Experience with naturalist guide Chris Lewey provides an up-close and personal insight into New England's wildlife and ecology. Then, more spectacular fall foliage awaits as you journey through Crawford Notch, an arresting pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 meters). Your Travel Director will guide you on a scenic hike to Diana's Baths, which features a series of small cascading waterfalls. Return to your hotel where you can enjoy an evening at leisure.

Accommodation: White Mountain, North Conway
Meals: Breakfast

Day 7: The Rugged Maine Coast Relaxed Start

Cross from New Hampshire into Maine this morning as you travel along the jagged coastline. Head to Fort Williams Park which is home to the iconic Portland Head Lighthouse that has been in operation since 1791. Then spend the rest of your afternoon at leisure in Portland. In the evening, enjoy a delicious dinner featuring Maine lobster with your fellow travelers.

Accommodation: Westin Portland Harborview, Portland
Meals: Breakfast, Dinner

Day 8: Back to Boston

Known for its sandy beaches, Kennebunkport is a year-round coastal destination that houses the rich and famous, even serving as the summer retreat of former President George H.W. Bush. Travel along Ocean Drive with more stunning views of the Maine coastline, before driving back to Boston. Guests departing Boston will arrive at Boston Logan International Airport. Those extending their stay will return to the Hyatt Regency Boston hotel.

Meals: Breakfast

Similar Tours

Tour Operator

Insight Vacations (CA)

Part of The Travel Company (TTC) family of brands, Insight Vacations began operations in 1978 and is based in Cypress, CA. Journeys are featured to destinations, such as the U.S. and Canada, Europe, Latin America, North Africa, Asia, the UK and Ireland. The company offers are a variety of tours under the classifications of Regional Journeys, Country Roads, Discovery Journeys, Easy Pace trips, and Special Interest tours. Insight is the ideal name for the tour operator, as the journeys provided by Insight Vacations allow travelers to gain further insight into whatever destination they wish to explore. For example, Discovery Journeys are the ideal choice for first-time visitors to Europe. Itineraries include Dine-at-Home or Farm-to-Table experiences so travelers can learn more about how locals live and dine. Regional Journeys allow trip-goers to see a specific location in Europe that they have always wanted to see – Poland, Switzerland, Italy, etc. The carefully planned trips enable customers to immerse themselves in one specific region or country and to become acquainted with its culture, traditions, and people. For anyone seeking travel off the beaten track, Insight Vacations offers Country Roads – trips that lead travelers off the well-tread tourist trail to explore hidden gems where visitors can savor the local produce with Farm-to-Table dining. Some trips are offered under the Easy Pace travel style – the ideal trip choice for trip-goers who wish to slow their pace during their vacation. During these tours, vacationers stay at least 3 nights at each destination, giving them some additional time to explore a place and enjoy it. Regardless of the travel style, many of the vacations offered by Insight Vacations begin with Relaxed Starts – giving travelers time to sleep in a little, spend more time at breakfast, or explore an area on their own. The tour company prides itself on providing business class tours that features luxury coaches with 40 seats. While most coach touring operators provide vehicles with 53 seats, Insight Vacations has re-configured its motor coaches to hold up to 40 guests. This gives passengers extra leg room while traveling and offers them more space and privacy.

In Business Since 1978

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Reviews

Paul T. - Traveled, October 2024

The holiday was very well organised. Every evening we had an itinerary for the next day. When free time was available, the tour director always had good suggestions for what to do, so you were never “on your own”. The hotels we stayed in were comfortable, clean and quiet. Stunning time of the year to go with gorgeous colours and views. The von Trapp family lodge was superb with marvellous views, food and walks in the grounds. Was an extremely knowledgeable and enthusiastic guide. The only negatives were the food offer at the North Conway hotel which was appalling and not worthy of an Insight tour and the breakfast at the Portland Westin hotel which had limited selection. If Insight could change these two issues it would be a perfect holiday.