Massachusetts/New York
On the Road: Autumn in the Berkshires and Hudson Valley
Program No. 21402RJ
Treat your senses to an exploration of classic New England as you discover vibrant foliage, picturesque towns, the Norman Rockwell Museum and historic Red Lion Inn in Stockbridge.
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DATES
& starting prices
PRICES
Oct 11 - Oct 18, 2025
Starting at
3,499DATES
& starting prices
PRICES
Oct 11 - Oct 18, 2025
Starting at
4,229Oct 18 - Oct 25, 2025
Starting at
4,059Not seeing the date you're looking for?
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This date is available to book as a private experience for your group!
8 days
7 nights
16 meals
7B 4L 5D
2
Boston Field Trip, Transfer to the Berkshires
Stockbridge, MA
3
Mission House, Norman Rockwell Museum, The Mount
Stockbridge, MA
4
Hancock Shaker Village, Free Time
Stockbridge, MA
5
Hudson Valley, Olana, Huguenot Street
Mid Hudson Valley, NY
6
Val-Kill, FDR Home, Presidential Library, Vanderbilt Mansion
Mid Hudson Valley, NY
7
West Point, Boscobel
Connecticut
8
Transfer to Boston, Program Concludes
Connecticut
At a Glance
Embark on a journey of discovery through the Berkshire Hills and the Hudson River Valley. Meander through the Connecticut River Valley past mountains, meadows and idyllic villages to Stockbridge, one of the oldest settlements in the Berkshires. Experience natural beauty that inspired Melville, Wharton and Rockwell, and examine how the utopian ideals of the Shakers shaped the community. Then, like the early settlers, turn westward along the Hudson River to learn this route’s role in the history of the nation and New York City. Absorb the mood of the river valley that inspired the first regional art movement in America and examine the historic and cultural treasures that line its banks.
Activity Level
Keep the Pace
Walking up to two miles, standing up to two hours at a time on walking explorations and in museums. Getting on and off motor coach.
Best of all, you’ll…
- Visit the Norman Rockwell Museum to see the largest collection of the artist’s original pieces and learn how Rockwell reflected American culture in his work.
- Learn about Shaker settlements and what sets them apart from traditional New England settlements.
- Enjoy expert-led visits to President Franklin Roosevelt’s home, Val-Kill and artist Frederic Church’s home.
Featured Expert
All trip experts
Sheila Moloney
Sheila Moloney, a resident of historic Rhinebeck in the heart of the Hudson Valley, has lived in the area on and off for almost forty years. As a garden designer and garden historian, she has a deep connection to the region’s natural and cultural history. Her interests led her to complete a master’s degree focused on architecture, gardens, and art of the Hudson Valley. Sheila has extensive knowledge and experience of the region’s cultural sites and is passionate about introducing lifelong learners to its wonders.
Please note: This expert may not be available for every date of this program.
Sheila Moloney
View biography
Sheila Moloney, a resident of historic Rhinebeck in the heart of the Hudson Valley, has lived in the area on and off for almost forty years. As a garden designer and garden historian, she has a deep connection to the region’s natural and cultural history. Her interests led her to complete a master’s degree focused on architecture, gardens, and art of the Hudson Valley. Sheila has extensive knowledge and experience of the region’s cultural sites and is passionate about introducing lifelong learners to its wonders.
Suggested Reading List
(5 books)
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
On the Road: Autumn in the Berkshires and Hudson Valley
Program Number: 21402
Berkshire Waterfall Guide: Cool Cascades of the Berkshire & Taconic Mountains
Visit 70 cool cascades in beautiful historic western Massachusetts, led by NYS-licensed hiking guide and outdoors writer Russell Dunn, author of more books on waterfalls than anyone else in the world.
Behind the Scenes with Berkshire Hathaway Billionaire Charlie Munger
Praise for "Damn Right!" From the author of the bestselling "Warren Buffett Speaks...'Charlie Munger, whose reputation is deep and wide, based on an extraordinary record of brilliantly successful business strategies, sees things that others don't. There is a method to his mastery and, through this book, we get a chance to learn about this rare individual' - Michael Eisner, Chairman and CEO, The Walt Disney Company.'Janet Lowe uncovers the iconoclastic genius and subtle charm behind Charlie Munger's curmudgeonly facade in this richly woven portrait of our era's heir to Ben Franklin
The Roosevelts: An Intimate History
A vivid and personal portrait of America’s greatest political family and its enormous impact on our nation
Hudson Valley Ruins: Forgotten Landmarks of an American Landscape
Countless books have been published on the historical sites of the Hudson River Valley. But these books have focused over and over again on the best-known, best-preserved places. Every bit as valuable are dozens of other historical sites that haven’t fared as well. Many of these buildings are listed on the National Register of Historical Places, and a few are even National Historical Landmarks. But in spite of their significance, these structures have been allowed to decay, and in some cases, to disappear altogether.
Traitor to His Class: The Privileged Life and Radical Presidency of Franklin Delano Roosevelt
A brilliant evocation of the qualities that made FDR one of the most beloved and greatest of American presidents.
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
Duration
8 days
7 nights
What's Included
16 meals (
7B, 4L, 5D
)
1 expert-led lecture
12 expert-led field trips
An experienced Group Leader
7 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Day
1
Check-in, Registration, Orientation, Welcome Dinner
Location:
Boston, MA
Meals:
D
Stay:
Hilton Boston Logan Airport
Activity Note
4:00 p.m. hotel check in.
Afternoon:
Program Registration. After you check in and have your room assignment, join us at the Road Scholar table to meet the Group Leader and confirm orientation time and place. Please remember to bring the name tag sent to you in the mail to the program. Orientation. The Group Leader will greet everyone with a warm welcome and lead introductions. We will review the up-to-date program schedule discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. Unless specified otherwise, travel and transfers will be via motorcoach, requiring ascending/descending steps. Periods in the daily schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. On the Road programs are journeys that take participants to multiple study sites in a region with a number of overnight stays. Lectures, talks, discussions, field trips, and on-board commentary amplify the program theme. Some journeys involve great distances and may take hours, others are much shorter. Long or short, On the Road journeys are learning experiences that make the most of our time together.
Dinner:
Welcome dinner at the hotel. Plated with tea, coffee, water, and non-alcoholic beverages included
Evening:
At leisure. Continue getting to know your fellow participants, settle in, and get a good night’s rest for the day ahead, including morning check out.
Day
2
Boston Field Trip, Transfer to the Berkshires
Location:
Stockbridge, MA
Meals:
B,L,D
Stay:
Red Lion Inn
Activity Note
Walking up to 1 mile over uneven ground; Driving 130 miles, approximately 2 hours.
Breakfast:
Buffet at the hotel.
Morning:
We will visit the John F. Kennedy Presidential Library and Museum, the nation's official memorial to John F. Kennedy. We will learn about his early life, his experience on the campaign trail, and the legacy of his presidency.
Lunch:
At a local restaurant
Afternoon:
We’ll board our motorcoach and depart for Stockbridge, Massachusetts. The scenic countryside gradually becomes more varied until we reach the Berkshire Hills highland of western Massachusetts. Upon arrival, we will check in at the historic Red Lion Inn on picturesque Main Street in Stockbridge.
Dinner:
At the Red Lion Inn
Evening:
At leisure. You might like to stroll through this quaint New England village, relax in rocking chairs on the inn’s front porch, or enjoy informal activities with new Road Scholar friends.
Day
3
Mission House, Norman Rockwell Museum, The Mount
Location:
Stockbridge, MA
Meals:
B
Stay:
Red Lion Inn
Activity Note
Walking up to 3 miles; walking and standing in museums up to 2 hours at a time.
Breakfast:
At the inn, meal vouchers will be provided.
Morning:
We will walk to one of the Berkshires’ National Historic Monuments known as the Mission House. On Main Street in Stockbridge, this was the home of the first Christian missionary to communicate with the Mohican Native Americans. A docent will lead us through the site, illuminating the intricacies of the historical relationships between the colonial English settlers and the Mohicans, as well as their attempts to work together in this quaint settlement. We will head to the Norman Rockwell Museum. We will get to visit Norman Rockwell's studio, during a private viewing, with docents to help answer questions. We will also have time for a self-exploration of the museum. Experience and examine the deep links between imagery, culture, and history, inspiring considerations of the unique power of the artist as a commentator in his/her time.
Lunch:
On your own to enjoy the local fare.
Afternoon:
We will go to town of Lenox to visit Edith Wharton’s home, The Mount. Designed by Edith herself and built in 1902, the house embodies her interests in the literary arts, interior design and decoration, garden and landscape design, and the art of living outlined in her influential book, “The Decoration of Houses” (1897). We will explore the house and its beautiful formal gardens with a docent. One of America’s greatest writers, Wharton, (1862-1937) is the author of “The Age of Innocence,” “Ethan Frome,” and “The House of Mirth.” She wrote more than 40 books in 40 years, including authoritative works on architecture, gardens, interior design, and travel. Wharton was the first woman awarded the Pulitzer Prize for Fiction and an honorary Doctorate from Yale University.
Dinner:
This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader will be happy to offer suggestions.
Evening:
At leisure.
Day
4
Hancock Shaker Village, Free Time
Location:
Stockbridge, MA
Meals:
B,L,D
Stay:
Red Lion Inn
Activity Note
Walking up to 1 mile; standing up to 1 hour. Driving approximately 26 miles; 1 hour throughout the day.
Breakfast:
At the inn.
Morning:
Upon arrival to Hancock Shaker Village, we will enjoy an immersive walking field trip experience. This 750-acre living-history museum features costumed interpreters, authentic buildings, collections of furniture and artifacts, a working farm with extensive gardens, heritage-breed livestock, and much more. The Shakers sought to create a utopian society based on their precepts of pacifism, celibacy, and communal living. Originally from England, they were called the “Shaking Quakers” — which became Shakers — for expressing their spiritual feelings through singing and dance. The Hancock community was founded in 1783 and reached its peak in the 1840s with more than 300 members. We will explore the 1830 Brick Dwelling, the 1826 Round Stone Barn, and other highlights with a docent. We will also hear an expert presentation explaining how Shaker communities “gathered”, their unique social structure and architecture, and how they differ from traditional New England settlements and villages.
Lunch:
At the museum café.
Afternoon:
We will have time for independent exploration at the Shaker Village before returning to Stockbridge to enjoy a free afternoon.
Dinner:
Plated meal at the inn.
Evening:
At leisure. Get a good night’s rest for the day ahead, including morning check out.
Day
5
Hudson Valley, Olana, Huguenot Street
Location:
Mid Hudson Valley, NY
Meals:
B,L,D
Stay:
Holiday Inn Express Poughkeepsie
Activity Note
Driving 100 miles throughout the day with multiple stops; walking up to 2 miles over uneven and dirt paths, standing up to 2 hours at field trip sites.
Breakfast:
At the inn.
Morning:
We will turn westward, following the footsteps of early settlers and journey along the Hudson River. This route played a major role in the history of our nation and the trade empire that is New York today. We will make a stop at Olana, where we will visit the Moorish-style home of Frederic Church, a landscape artist of major importance to the artistic movement known as the Hudson River School. His grounds offer commanding views of the Hudson Valley that provided inspiration for the work of one of America’s foremost painters.
Lunch:
At a local restaurant.
Afternoon:
We will head to New Paltz, NY and arrive at the Huguenot Street Historic District. This area is representative of the Huguenot settlement from the early 18th century. It includes 30 buildings across 10 acres, offering a glimpse into the past. Led by an expert, we will see the seven original stone houses dating from 1705, the colonial-era burial ground, and a reconstructed 1705 French church.
Dinner:
At a local restaurant, we will have a plated and served meal.
Evening:
At leisure.
Day
6
Val-Kill, FDR Home, Presidential Library, Vanderbilt Mansion
Location:
Mid Hudson Valley, NY
Meals:
B,L
Stay:
Holiday Inn Express Poughkeepsie
Activity Note
Walking up to 2 miles, standing up to 2 hours at a time; climbing more than 100 steps at Vanderbilt Mansion. Driving 1 hour throughout the day; 50 miles.
Breakfast:
At the hotel.
Morning:
Mrs. Roosevelt’s personal retreat, Val-Kill Cottage, is also a National Historic Site and the only one dedicated to a First Lady. We will learn more about her life as we explore the modest cottage and grounds. We'll then head over to the Franklin D. Roosevelt National Historic Site. The home — officially named Springwood but called Hyde Park by the family — is the only site in America where a President was born, had a lifelong connection, and is buried. A Park Service Ranger will lead us through the house. We’ll also walk through the grounds including the Rose Garden where Franklin and Eleanor are buried, and have time for a self-directed exploration of the Franklin D. Roosevelt Presidential Library and Museum, America's first presidential library. It was designed and built under President Roosevelt’s personal supervision and opened to the public in 1941. It is the only presidential library used by a sitting president, as Roosevelt had expected to serve only two terms in office.
Lunch:
We will enjoy boxed lunches at the FDR Museum café.
Afternoon:
We will go to the Vanderbilt Mansion National Historic Site, unusual in the sense that it does not pay homage to a particular person or family, but represents the Gilded Age. Anyone familiar with “Downton Abbey” will recognize the similarities to an English country house with the accompanying social stratification. The 54-room mansion, designed in the Beaux Arts style by the country’s leading architectural firm, was built in 1898. The interior includes the finest antiques as well as specially made furnishings. The landscaped grounds feature a formal terraced garden, extensive lawns, carriage roads, and a 3-mile-long riverside hiking trail. Our visit will be narrated by Park Service staff who will lead us through this extraordinary edifice that was used only as a vacation home!
Dinner:
In New Paltz, enjoy dinner on your own.
Evening:
At leisure. Get a good night’s rest for the day ahead, including morning check out.
Day
7
West Point, Boscobel
Location:
Connecticut
Meals:
B,D
Stay:
Hampton Inn of Danbury
Activity Note
Walking up to 2 miles and standing for up to 2 hours over the course of visits; at times ground is unpaved and uneven. Driving 90 miles throughout the day; approximately 2 hours; getting on/off motorcoach. MUST bring a driver's license or passport with you on day of visit to be admitted.
Breakfast:
At the hotel.
Morning:
We will transfer to Highland Falls to meet a local expert at the U.S. Military Academy at West Point. Via motorcoach and our own two legs, we will uncover the history of West Point, its role in the Revolution, and stories of graduates who helped shape the nation.
Lunch:
In Cold Spring. On your own to enjoy the local fare.
Afternoon:
We’ll travel to the Lower Hudson Valley where the grand riverfront mansion of Boscobel sits on a bluff overlooking the Hudson River. Led by a docent, we’ll explore the sumptuous interior’s finest collections of elegant Federal-period furnishings. We’ll learn about its history, how it came to be in its present location, its role in the late 18th and early 19th centuries, and the lives of the Dyckman family.
Dinner:
Farewell dinner In Danbury. Plated meal at a local restaurant.
Evening:
At leisure. Share your favorite memories with your fellow Road Scholars and prepare for departure in the morning.
Day
8
Transfer to Boston, Program Concludes
Location:
Connecticut
Meals:
B
Activity Note
Driving 160 miles, approximately 2.5 hours. We are expected to arrive at Logan airport at approximately 11:30 a.m., so we strongly recommend booking return flights that depart after 2:00 p.m.
Breakfast:
At the hotel.
Morning:
We will board our motorcoach for the return trip to Boston. The coach will make two stops: one at Logan International Airport and the other at the first hotel of the program. This concludes our program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Please join our Facebook page and share photos of your program. Visit us at www.facebook.com/rsadventures. Best wishes for all your journeys!
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MEALS
16 Meals
7 Breakfasts
4 Lunches
5 Dinners
LODGING
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Showing Lodging For:
- Oct 18, 2025 - Oct 25, 2025
- Sep 06, 2025 - Sep 13, 2025 (Boston, MA to Connecticut)
- Sep 13, 2025 - Sep 20, 2025 (Boston, MA to Connecticut)
- Oct 11, 2025 - Oct 18, 2025 (Boston, MA to Connecticut)
- Oct 18, 2025 - Oct 25, 2025 (Boston, MA to Connecticut)
Participant Reviews
Based on 23 Reviews
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This was an AMAZING trip. Our tour guide Gayle Felix was EXCEPTIONAL!!! One of the best tour guides I’ve had on Road Scholar. LOVED this trip! Would HIGHLY recommend doing this trip. THANK YOU!!!
— Review left November 19, 2024
The itinerary for this trip is jam packed with a variety of delightful adventures. It has been fine tuned to offer something(s) for everyone's taste. The beautiful fall foliage everywhere ices the cake!
— Review left October 27, 2024
This well-organized program tours the spectacular countryside of the Massachusetts Berkshires and the Hudson Valley. The tour includes visits to homes and communities, both well-known and lesser known in American history.
— Review left September 22, 2024
On The Road: Autumn in the Berkshires and Hudson Valley was my first Road Scholar trip, but it won’t be my last. Thank you Gayle Felix and Road Scholar for a wonderful experience!
— Review left September 22, 2024
Great trip the views of the Hudson River Valley are incredible! A must see adventure into the past history of America!
— Review left November 9, 2023
On The Road: Autumn In The Berkshires And Hudson Valley is the perfect program if you like historical places and enjoy beautiful scenery! Touring the Kennedy Library, the Norman Rockwell Museum, Edith Wharton's home, the Hancock Shaker Village, and Olana were very interesting. The Franklin Roosevelt Library and home were profound, and touring Eleanor Roosevelt's Val-Kill was a major treat!!! Top that off with a tour of West Point and your trip will be a memorable treasure!!! The history and remarkable graduates of West Point will leave you speechless!
— Review left November 8, 2023
This was the 21st RoadScholar trip my husband and I joined in our 10+ years of retirement. This area of the country has lots to see and do and we were on the go - favorites were being in beautiful Stockbridge and staying at the historic Red Lion Inn, touring the Hancock Shaker Village, the Norman Rockwell Museum and Studio, West Point, FDR home and museum, and Eleanor Roosevelt’s Val-Kill home, The Vanderbuilt Mansion and Boscobel. I would strongly recommend this trip.
— Review left November 1, 2023
Enjoyed this program immensely but not given time to experience the past because I felt rushed!
— Review left October 30, 2023
Road Scholars provided us with an opportunity to see a lot, learn about many interesting people and places, and visit many sites on the east coast we had always wanted to experience. We loved everything we did on this educational trip.
— Review left October 26, 2023
A very enjoyable trip through historic and beautiful countryside. I was much impressed with what I learned about FDR, particularly his leadership during World War II. The trip is not rigorous, but you need to be able climb stairs and lift your legs to ease into a deep tub.
Shelia M. is an accomplished, well-organized group leader.
— Review left October 24, 2023
Road Scholar has done an amazing job with the Berkshires and Hudson Valley program to provide a comprehensive offering of museums, historical homes and presidential libraries, as well as a tour of West Point. The meals and hotels were wonderful, and the interaction with fellow Road Scholars was warm and welcoming. I can’t recommend this program enough—it was outstanding. Time to get on the road with this program and enjoy it for yourself!
— Review left September 26, 2023
Great program with lots of physical activity, as well as mental stimulation.
— Review left September 26, 2023
The highlights of this trip were the visits to the JFK Library,the Norman Rockwell Museum, Edith Wharton's Estate, Frederic Church's home, the FDR Home/Library and Val-Kill, and free time to wander around the town of Stockbridge---great trip for US history buffs.
— Review left November 1, 2022
great trip. well chosen to balance art, history and ambiance of new england
in the fall.
— Review left October 17, 2022
Enjoyable trip. Presidential libraries, Norman Rockwell, West Point were highlights. Beautiful scenery enhanced by changing leaves. Our guide, Sheila, kept us engaged, moving and laughing. Fun group of fellow travelers.
— Review left October 13, 2022
I would highly recommend Road Scholar for content and ease of travel.
— Review left October 11, 2022
A great trip...we hope to return to Road Scholar in the future.
— Review left October 9, 2022
Visiting West Point, presidential libraries and museums as well as staying at the Ted Lion Inn were on my wish list and I got to see and experience them all thanks to this trip. Our group leader, Mary, was excellent in every way.
— Review left October 4, 2022
When I'm traveling I like to see and experience as much as possible and Road Scholar (RS) delivers! We visited mansions (The Mount, Vanderbilt Mansion, FDR home, Boscobel), historic homes (Mission House and Val-Kil), presidential libraries (JFK and FDR), art galleries (Norman Rockwell, Thomas Cole), historic communities (Shaker Village, Norman Rockwell's Stockbridge, Huguenot Street) and a military academy (West Point) as we traveled through lush mountain scenery. Tour guides were excellent communicators and knew their subject well. We had the privilege of staying at Norman Rockwell's historic Red Lion Inn, the inn pictured in Norman Rockwell paintings. There was something for every traveler. I personally enjoyed it all...
— Review left September 28, 2022
It worked. Some don't.
— Review left December 2, 2019
This tour met all my expectations for Fall in New England & Hudson Valley. It was a good combination of touring, education & fun activities, all packed into one week.
— Review left November 1, 2019
I can't imagine a better trip for a first time traveler with Road Scholar. Ahead of time they send you materials to reassure you of each days' events as well as suggestions to help your packing and traveling. What was a big big help to me was that I didn't have to worry about transportation getting to the beginning location and then the return to the airport.
— Review left October 29, 2019
This program is filled with interesting outings that were enjoyable to visit. So much learning took place and the countryside was beautiful.
— Review left October 28, 2019