7-Nights New England's Fall Foliage - Classic Group from $4,059

Insight Vacations

OFFER ID 1505935

New England's Fall Foliage
Follow Boston's Freedom Trail, visit a maple syrup farm in Montpelier and admire the bronzing leaves of New England’s trees.

Dining Summary

2 Dinner with Wine (DW)
7 Breakfast (B)
1 Dinner (D)
1 Lunch (L)

Choice Highlights

Choose between two carefully selected activities
Stockbridge: Take a self-guided visit to the Norman Rockwell Museum and grounds, which houses the largest collection of original Rockwell art pieces.
Stockbridge: Enjoy a self-guided tour of Chesterwood, the former summer home and studio of 20th-century sculptor, Daniel Chester French, best known for his work on the Lincoln Memorial in Washington, D.C.

Authentic Dining

Boston: Begin your tour savouring local flavours over dinner at your hotel.
Stowe: Enjoy Austrian-style lagers during your dinner at Von Trap Brewing's bierhall.
Portland: Enjoy an authentic Maine lobster dinner.

Insight Choice

Stockbridge: Take a self-guided visit to the Norman Rockwell Museum and grounds, which houses the largest collection of original Rockwell art pieces.
Stockbridge: Enjoy a self-guided tour of Chesterwood, the former summer home and studio of 20th-century sculptor, Daniel Chester French, best known for his work on the Lincoln Memorial in Washington, D.C.
Stockbridge: Choose a guided tour of Chesterwood, former summer home, studio and gardens of America's foremost 20th century public sculptor. Alternatively, travel west for a visit to the Norman Rockwell Museum.

Make Travel Matter

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

Summary

Lively Welcome Dinner in Boston • Highlight Dinner at the Austrian-style Trapp Family Lodge and Von Trapp Brewery • Celebration Dinner with lobster in Portland.

Top Rated Highlights

Kancamagus Highway: 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 of untouched natural beauty.
Manchester: 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.
Montpelier: Travel to Morse Farm Maple Sugarworks and taste a Vermont tradition 'sugar on snow': maple syrup drizzled over packed snow.
Shelburne: Indulge in a Farm-to-Table lunch and meet chef Tessa Holmes for an in-depth look at regenerative farming and food production.
Boston: Unlock the secrets of the American Revolution on a tour of the historic red-brick Freedom Trail.
Woodstock: Explore the Rockefeller's renowned Billings Farm and Museum, showcasing Vermont's rural history.
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.
Franconia Notch State Park: Take a scenic ride on the Gondola SkyRide (weather permitting).
Kancamagus Highway: Enjoy a picturesque drive along the Kancamagus Scenic Byway.
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.

7 nights from $4,059 per person

Valid for new bookings deposited March 24, 2025 – May 29, 2025 for travel from September 1 – September 30, 2025 (or) on select tours departing in the next 4 months.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply.

Itinerary

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Itinerary Details

Insight Vacations: New England's Fall Foliage

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. Savour dinner accompanied by wine in the company of your fellow travellers.
Accommodations: Hyatt Regency, Boston
Meals: Dinner with Wine

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.
Accommodations: The Gideon Putnam, Saratoga Springs
Meals: Breakfast

Day 3 - The Legends of the Fall and Stowe
Journey through the bronze fall foliage of Vermont. 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.
Accommodations: 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 colours. Visit Lake Champlain Chocolates for chocolate and local ice cream tasting. Like their chocolates, the ice cream Enjoy Vermont’s beautiful scenery ablaze with fall’s golden red colours. Visit Lake Champlain Chocolates for chocolate and local ice cream tasting. Like their chocolates, the ice cream is crafted with only the best local ingredients, including fresh cream, maple syrup and honey. Next, you'll travel to a local sugar house and learn how 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. Return to the enchanting town of Stowe for an afternoon at leisure.
Accommodations: Trapp Family Lodge, Stowe
Meals: Breakfast, Lunch

Day 5 - North Conway and the White Mountains Relaxed Start
Move on to Vermont’s picturesque capital, Montpelier. Journey to New Hampshire’s White Mountains and enter striking Franconia Notch. Take a scenic ride on the Gondola Sky Ride at Loon Mountain Resort (seasonal). 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.
Accommodations: White Mountain Hotel and Resort, 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 metres). 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.
Accommodations: White Mountain Hotel and Resort, 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 travellers.
Accommodations: Westin Portland Harborview, Portland
Meals: Breakfast, Dinner with Wine

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

Featured Destinations

Portland, ME

North Conway

Stowe

Saratoga Springs

Boston

The history and bricklaid beauty of Boston is easy to enjoy. Follow the Freedom Trail past Old North Church, Paul Revere Park, Fanieul Hall, the Commons, Old Ironsides and more landmarks of America's birth. Across the Charles River is Cambridge and Harvard. Venture to Marblehead and Salem to the south, or Lexington and Concord to the north. Back in town, have clam chowder at the warf or great Italian food in North End.

Excursions

Boston: Private North End Italian Food Tasting Walking Tour - 3 Hours

Boston: Private Sunset Boston Harbor Cruise with Cocktails and Hors d'oeuvres - 2 Hours

Boston: Private VIP Boston Yacht Experience With Cocktails & Hors d’oeuvres - 2 Hours

Boston: Boston Private Cycle Boat Charter - 4 Hours

Boston: Discover Boston Private Sightseeing Program - 4 Hours

Boston: Private Historic Boston Pub Crawl - 4 Hours

Boston: Freedom Trail Private Walking Tour - 1.5 Hours

Boston: Private Harvard Campus Tour - 1.5 Hours

Vacation Details

Valid Date Ranges

09/19/2025 - 09/26/2025

from $4,059 per person

09/21/2025 - 09/28/2025

from $4,076 per person *

09/26/2025 - 10/03/2025

from $4,775 per person *

09/27/2025 - 10/04/2025

from $4,825 per person

10/01/2025 - 10/08/2025

from $4,875 per person *

10/03/2025 - 10/10/2025

from $4,775 per person *

10/05/2025 - 10/12/2025

from $4,775 per person *

10/10/2025 - 10/17/2025

from $4,775 per person *

10/12/2025 - 10/19/2025

from $4,775 per person *

10/15/2025 - 10/22/2025

from $4,388 per person *

10/19/2025 - 10/26/2025

from $4,298 per person

10/22/2025 - 10/29/2025

from $4,208 per person

* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.

Prices Start At

from $4,059 per person

Length

7 Nights

Air City

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Vacation Rating

Deluxe

Remarks

Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID

1505935

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