New England Fall Foliage Tour

This Autumn, follow the Freedom Trail in Boston, enjoy fresh lobster in Maine, see the best of fall foliage atop Mount Washington, unwind in the serene beauty of the White Mountains, experience Americana Norman Rockwell style in the Berkshires, cruise the Connecticut River, and island hop to Martha’s Vineyard… this is American Heritage at its very roots.


Day 1 - Arrive Boston, MA

Upon arrival in Boston (please arrive by 2pm), we will transfer to our hotel for our 1-night stay. After some time to freshen-up, we will meet our step-on guide who will take us on an in-depth tour of this incredible city. Follow the Freedom Trail, discover Boston Harbor and spend some time at Quincy market before our welcome dinner at a local restaurant. (D)

Day 2 - Boston - Kennebunkport - White Mountains

After breakfast, we make our way to the famous seaside town of Kennebunkport. As a second home to the Bush family, this small, quaint town has a lot to tell! We meet our local guide who will walk us through everything there is to know about Kennebunkport. After, enjoy fresh Maine lobster for our included lunch before traveling to the White Mountains. Upon arrival, check in to our hotel before dinner this evening. (B,L,D)

Day 3 - White Mountains

The White Mountains cover about a quarter of the state of New Hampshire and are home to the highest peak on the East Coast of the United States – Mt. Washington. Our first stop is the Mt. Washington Cog Railway where we ascend Mt. Washington using the world’s first mountain-climbing cog railway. After, travel the Kancamagus Highway and visit Flume Gorge. Our final stop of the day is for those with a sweet tooth - Faddens General Store. The Faddens have been making maple syrup for nearly 200 years and have been selling the sweet stuff at the Fadden General Store and Maple Sugarhouse since its opening in 1896. We then return to our hotel for an evening at leisure. (B)

Day 4 - White Mountains - Stowe, VT - North Adams, MA

Enjoy breakfast this morning before departing for idyllic Stowe, Vermont and visit the Trapp Family Lodge. In the early 1940s, the von Trapp family toured the United States as the Trapp Family Singers before eventually settling in Stowe, Vermont, reminiscent of their beloved Austria. Here, we have a tour of this gorgeous property and enjoy a delicious lunch. We then make our way into the Berkshire region of Massachusetts and, time permitting, visit the Quechee Gorge and Simon Pearce Glass where we may even get to see the glass blowers in action. Upon arrival in North Adams, we check-in to our hotel and get together for dinner. (B,L,D)

Day 5 - North Adams - Hartford, CT

This morning, we visit the Norman Rockwell Museum. The museum holds the largest and most significant collection of original Rockwell art. Highlights include favorites from Rockwell’s Saturday Evening Post covers and the powerful Four Freedoms paintings. We then make our way to the capitol of Connecticut, Hartford, home to the famous author Mark Twain and visit his homestead. Later, we check-in to our hotel and freshen-up before dinner at a local restaurant. (B,D)

Day 6 - Hartford - Providence, RI

All aboard! After breakfast, we travel Connecticut River valley to historical Essex where we board the Essex Steam Train and Boat. Travel in vintage train coaches and cruise the Connecticut River on the Becky Thatcher while enjoying beautiful scenery of the valley’s fall foliage. Then, we travel to Providence, RI for and check-in for our 2-night stay. (B,D)

Day 7 - Martha's Vineyard

Today, travel to one of the glitziest island enclaves – Martha’s Vineyard. Here you will have free time to view whaling captains’ homes, shop, or enjoy lunch at one of the town’s fine cafés – all just steps away from the famous Chappaquiddick Ferry. After lunch, we are joined by a local guide who will provide a narrative for our 2-hour riding tour around the most picturesque parts of the Vineyard.  Seascapes, beaches, and wildlife preserves highlight the natural beauty of the island. We return to Providence for a night at leisure. (B)

Day 8 - Providence - Boston

Enjoy breakfast before checking-out of our hotel and traveling to Newport. Discover America’s gilded age with our local guide and lay witness to the wealth and power of the Vanderbilts with a visit to the Breakers. After, we travel to Boston for our final night in eloquent New England. (B,D)

Day 9 - Depart Boston

After breakfast and time to bid each other farewell, we make our way to the airport mid-morning for our flight home. (B)

Tour Details

Hotel / Lodging
(or similar)

8-Nights Premier Accommodation




16 Meals: 8 Breakfasts | 2 Lunches | 6 Dinners

Trip Highlights

Fall Foliage Viewing
New England Villages
Local Guides
The Berkshires
Mt. Washington
The Connecticut River
Martha's Vineyard
The Life of Mark Twain
Newport Mansions

Upcoming Departures

Tour DatesAvailabilityDeparture Points Subject to Change 
Tue October 8, 2024 - Wed October 16, 2024
10/8/2024 - 10/16/2024
  • Boston, MA

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