Watch our Online Travel Show about this tour and earn a $100 credit for your next booking with Holiday Vacations.
New England Fall Foliage - WSAW TV
Autumn Landscapes
The Mount, Edith Wharton’s Home
Norman Rockwell Museum
Salem
Courtesy of Destination Salem
Hobo Railroad
Discover the rich history and breathtaking beauty of autumn in historic New England. Our adventures begin in colonial Boston with a guided Freedom Trail tour, a presidential museum visit, and a stop at the famous Faneuil Hall Marketplace. Next, explore the infamous witch trials of Salem before venturing into New Hampshire's White Mountains and along Kancamagus Highway, where the vibrant colors of fall are abundant. Walk through the lives of historical figures and renowned creatives at Hildene, The Mount, and the Norman Rockwell Museum, then experience an authentic Shaker Village. This fantastic journey concludes in New York City with a city tour, Broadway musical, sightseeing cruise, and time at leisure.
Trip overview may vary by departure.
Highlights
Colonial Boston
Join an 18th-century costumed guide for a walk through American history on the Boston Freedom Trail as we view significant sites including the Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, Old South Meeting House, Paul Revere’s Home, and Old North Church. Then, dive into the legacy of one of the most beloved presidents at the John F. Kennedy Presidential Library and Museum. Browse engaging exhibits that detail Kennedy’s life, from his childhood and early political career to his presidency, while getting a glimpse into our country’s past.
New York City
Discover the Big Apple’s most iconic attractions! Glide along the Hudson River on a harbor cruise for breathtaking views of the city skyline, iconic Statue of Liberty, and more.
Hancock Shaker Village
Nestled within the picturesque Berkshire Hills, this beautifully preserved Shaker community transports you back to the 19th century. Enjoy an authentic Shaker lunch, then take a stroll through the charming village and engage with costumed interpreters while viewing historic buildings, peaceful gardens, crafts, tools, furniture, and more. Be sure to stop by the 1826 Round Stone Barn, a truly unique dairy barn that’s considered an agricultural wonder.
Hildene, The Lincoln Family Home
Serving as a living testament to the Lincoln legacy, this gorgeous estate was built by Abraham Lincoln’s son, Robert, at the turn of the 20th century. It’s now a cultural and educational center that offers an immersive opportunity to learn about the Lincoln family history and life in that era. Explore the stately mansion, formal gardens, observatory, restored 1903 railcar, and solar-powered cheesemaking facility.
- Day 1: Fly to MassachusettsUpon arriving in Boston, we check in for a two-night stay.
- Day 2: Boston SightsOur New England exploration begins with a guided tour of the Freedom Trail. View historic sites and learn about the crucial role they played in our colonial history, such as Paul Revere's home and Old North Church, where signal lanterns ignited the American Revolution. Our tour ends at Faneuil Hall with time to grab lunch from iconic Quincy Market. Afterwards, we visit the John F. Kennedy Presidential Library and Museum to browse nostalgic exhibits that celebrate one of our country’s most beloved presidents and the Camelot era. Tonight, we get to know our traveling companions over a delicious Welcome Dinner.
Meals Included: Breakfast, Dinner
- Day 3: SalemThis morning, we visit the home of the infamous 1692 witch trials. A local guide joins us for a city tour to see the Witch Trials Memorial, the Salem Witch Museum, and more. We also enjoy a guided visit to The House of the Seven Gables, a historic home built in 1668 on Salem Harbor. After lunch together, there is time to explore independently and shop. Our travels then continue to North Conway this evening.
Meals Included: Lunch
- Day 4: Kancamagus HighwaySome of New England’s most beloved vistas unfold before us today on the Kancamagus Highway as we travel among the lush foliage and towering White Mountains of New Hampshire. Arriving in Lincoln, we take a charming woodland excursion on the Hobo Railroad and relax in vintage coaches while winding along the picturesque Pemigewasset River. Our afternoon continues with a tour of Fadden’s General Store and Maple Sugarhouse, a family-owned traditional sugar shack dating back to 1896. We then depart for Manchester, Vermont, where our overnight accommodations await. En route, the beautiful scenery of autumn’s vibrant colors, historic bridges, and Quechee Gorge captivate us.
Meals Included: Breakfast, Dinner
- Day 5: Hildene, The Lincoln Family HomeOur day kicks off with a fascinating tour of Robert Lincoln’s summer home, a Georgian Revival mansion perched on a hill overlooking the Taconic and Green Mountains. Robert was the only child of Abraham and Mary Todd Lincoln to live to adulthood. While exploring the home and grounds, including the 1903 Pullman Palace Car, Sunbeam, learn how the family legacy and Abraham Lincoln’s values live on today. After an included lunch, we bid farewell to The Lincoln Family Home and head to Bennington Battle Monument. This stone memorial soars over 300 feet tall and was built to commemorate the Battle of Bennington, which historians consider the turning point in the Revolutionary War. Our accommodations for the next two nights are in the heart of The Berkshires - Great Barrington, Massachusetts.
Meals Included: Breakfast, Lunch, Dinner
- Day 6: Historical Homes & Hancock Shaker VillageThis morning, we take a short drive to Lenox and visit The Mount, a country house that belonged to American author Edith Wharton. She is best known as the first woman to win the Pulitzer Fiction Prize in 1921 for her novel, The Age of Innocence. Wharton designed this beautiful home in 1902 and it has been meticulously preserved, now offering many historic exhibits. Next, we see exhibits that showcase the art and legacy of one of America’s most famous illustrators at the Norman Rockwell Museum. Our day concludes at Hancock Shaker Village with immersive experiences that showcase this traditional community. Get a glimpse into the Shaker lifestyle with a delicious lunch and guided tour that features the famous Round Stone Barn, handmade furniture, music, and more. The evening is at your leisure.
Meals Included: Breakfast, Lunch
- Day 7: New York City & Broadway MusicalToday, we trade in nature’s grandeur for the Big Apple’s iconic cityscape. An expert local guide joins us for a driving tour to view Manhattan’s most famous landmarks including Central Park, Lincoln Center for the Performing Arts, Rockefeller Center, and Times Square. After checking in to our centrally located hotel for some leisure time, prepare to be swept away by the bright lights and big personalities at a renowned Broadway musical this evening.
Meals Included: Breakfast
- Day 8: Liberty Midtown Cruise & NYC Your WayOur morning begins with a sightseeing cruise that includes views of Ellis Island, One World Trade Center, the Statue of Liberty, and more. We then celebrate our spectacular adventures and new friendships with a flavorful Farewell Lunch. Afterwards, the rest of the day is yours! Soak up this vibrant city in any way you choose – relax at the hotel, people watch, shop for souvenirs, or easily explore nearby attractions.
Meals Included: Lunch
- Day 9: Fly HomeWe return home today with many incredible memories and photos from our time in the Northeastern United States.
Oct 1-9, 2025
$6,699
per person
$5,499
per person
Jul 18, 2025
What's Included
All Accommodations
- 2 nights at The Royal Sonesta Boston
- 1 night in North Conway, NH
- 1 night at Hampton Inn & Suites Manchester
- 2 nights in Great Barrington, MA
- 2 nights at the Sheraton New York Times Square
Attractions & Highlights
- Boston Freedom Trail guided tour
- Faneuil Hall Marketplace feat. Quincy Market
- John F. Kennedy Presidential Library & Museum
- Salem guided city tour
- The House of the Seven Gables guided tour
- Fadden's General Store and Maple Sugarhouse
- Hobo Railroad
- Kancamagus Highway
- Bennington Battle Monument
- Hildene, The Lincoln Family Home
- Hancock Shaker Village
- Norman Rockwell Museum
- The Mount, Edith Wharton's home
- Broadway musical
- New York City guided tour & time at leisure
- New York City Liberty Midtown Cruise
12 Excellent Meals
- Welcome Dinner in Boston
- Lunch at Hildene, The Lincoln Family Home
- Lunch at Hancock Shaker Village
- Farewell Lunch in New York City
Learn more about what's included with the Holiday Advantage.
Minneapolis - Minneapolis-St Paul International Airport