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.
Itinerary
Day 1 - Arrive Boston, MA
Upon arrival in Boston transfer to your hotel (on own) for your 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)
*Please arrive into Boston no later than 12noon.
Day 2 - Boston - Kennebunkport - White Mountains
After breakfast, depart Boston for the picturesque seaside town of Kennebunkport, Maine. Known for its quintessential New England charm and as the longtime summer retreat of the Bush family, Kennebunkport offers a fascinating blend of maritime heritage, coastal beauty, and historic character. We will travel Walkers Point and get a glimpse of the Bush family estate before heading back to the historic district of Kennebunkport for some time on our own to explore this quaint community. Leaving town, we will head to lunch and savor a classic New England experience with a fresh lobster lunch. This afternoon, continue north to the spectacular White Mountains, where dramatic peaks, wooded landscapes, and crisp mountain air set the scene for the evening. Upon arrival, check in to your hotel and enjoy dinner with your fellow travelers. (B,L,D)
Day 3 - White Mountains
Today, discover the dramatic landscapes of New Hampshire’s White Mountains, which span roughly a quarter of the state and are home to Mount Washington, the highest peak in the northeastern United States.
We begin the day by traveling along the scenic Kancamagus Highway, one of New England’s most celebrated byways, before visiting spectacular Flume Gorge. Here we will have time to explore this natural wonder’s winding walkways, towering granite walls, cascading waterfalls, and covered bridges.
After, we will experience an unforgettable journey aboard the historic Mount Washington Cog Railway, the world’s first mountain-climbing cog railway. As you ascend Mount Washington, enjoy sweeping views of rugged peaks, deep valleys, and the surrounding wilderness.
Return to the hotel for an evening at leisure. (B,D)
Day 4 - White Mountains - Stowe, VT - North Adams, MA
Enjoy breakfast before departing for the picturesque village of Stowe, Vermont. Our first stop is the renowned Trapp Family Lodge, founded by the famed von Trapp family of The Sound of Music legacy. After touring the United States as the Trapp Family Singers in the early 1940s, the family chose Stowe as their home, drawn to its striking resemblance to their beloved Austrian landscape.
Take in the lodge’s alpine charm during a guided tour, followed by a delicious lunch on the property.
This afternoon, continue south through scenic New England toward Massachusetts’ beautiful Berkshire region. Time permitting, we will pause to admire the dramatic natural beauty of Quechee Gorge. Upon arrival in North Adams, check in to your hotel before rejoining the group for dinner and an evening at leisure. (B,L,D)
Day 5 - North Adams - Hartford, CT
After breakfast, travel to the Norman Rockwell Museum for an inspiring look at one of America’s most beloved artists. The museum’s exceptional collection includes many of Rockwell’s iconic Saturday Evening Post covers, as well as his powerful Four Freedoms paintings.
Continue south through the scenic Berkshires to Great Barrington, a lively town known for its independent boutiques, galleries, and inviting restaurants. Enjoy lunch on your own, with time to browse and explore at a relaxed pace.
This afternoon, journey through Connecticut’s picturesque Litchfield Hills. Pause in Norfolk to admire the postcard-perfect Norfolk Green, surrounded by beautifully preserved 19th-century architecture and classic New England character.
Arrive in Hartford, check into our hotel, and have dinner on your own. (B)
Day 6 - Hartford - Newport, RI
After breakfast, we’ll visit the Mark Twain House, the magnificent 25-room, 11,500-square-foot Hartford residence built in 1874. It was here that Mark Twain and his family enjoyed what he later described as the happiest and most productive years of his life. Financial difficulties led Sam and Livy Clemens to move their family to Europe in 1891, and they never returned to live in Hartford. Following the tragic death of their daughter Susy in 1896, Livy found it too painful to return to the home, and the Clemens family sold the property in 1903.
Enjoy lunch on your own at Lyman Orchards before continuing to historic Essex in the Connecticut River Valley. There, we’ll board the Essex Steam Train & Riverboat experience. Travel aboard vintage train coaches, then cruise the Connecticut River aboard the Becky Thatcher while taking in the spectacular fall foliage and scenic beauty of the valley. Afterward, we’ll continue to Newport, Rhode Island, and check in for our two-night stay. (B,D)
Day 7 - Martha's Vineyard
Today, set sail for the iconic island of Martha’s Vineyard, one of New England’s most stylish and storied coastal escapes. Upon arrival, we will meet our local guide for a narrated two-hour four-town tour of the island. We will take in sweeping seascapes, pristine beaches, historic villages, and peaceful wildlife preserves as we discover the natural beauty and enduring character of the island.
After the tour, we will enjoy free time to explore at our own pace—admire the historic homes of whaling captains, browse distinctive island shops, or savor lunch at a charming local café in Edgartown and Oak Bluffs. Return to Newport this evening for a relaxing night at leisure. (B)
Day 8 - Newport - Boston, MA
After breakfast, stepback into the opulence of the Gilded Age during a guided tour of Newport. Visit the magnificent Marble House, the Vanderbilt family’s grand estate inspired by the Petit Trianon at Versailles, and discover the extraordinary wealth, ambition, and social history behind this iconic mansion as well as the personality of one of Newport’s most colorful matrons, Ava Vanderbilt.
Enjoy free time to purchase lunch and explore downtown Newport at your leisure. Browse charming boutiques, stroll the historic waterfront, or simply take in the coastal beauty of this storied city.
In the mid-afternoon, bid farewell to Newport and continue to Boston, Massachusetts, where we will settle in for our final evening in beautiful New England. (B,D)
Day 9 - Depart Boston
After breakfast, it’s time say goodbye to your fellow travelers and make your way to the airport for your journey home with colorful memories of New England’s blazing fall foliage and history. (B)
