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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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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.

What You'll Learn

  • 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
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Gayle Felix
Gayle Felix has been a Road Scholar group leader since 2015. She grew up and raised her family outside of Boston and now resides in Hingham, Massachusetts. With a history/American studies degree from Boston University, she enjoys sharing the history of Boston and surrounding areas. Gayle has led programs in New England; Washington, DC; and other areas in the United States. Gayle enjoys being with her family and friends, biking, kayaking, golfing, and hiking. She especially enjoys traveling and meeting new people.

Please note: This expert may not be available for every date of this program.

Profile Image of Gayle Felix
Gayle Felix View biography
Gayle Felix has been a Road Scholar group leader since 2015. She grew up and raised her family outside of Boston and now resides in Hingham, Massachusetts. With a history/American studies degree from Boston University, she enjoys sharing the history of Boston and surrounding areas. Gayle has led programs in New England; Washington, DC; and other areas in the United States. Gayle enjoys being with her family and friends, biking, kayaking, golfing, and hiking. She especially enjoys traveling and meeting new people.
Profile Image of Mary McGovern
Mary McGovern View biography
Mary McGovern was born in New York and has lived in New England, Florida, and Bavaria. She earned her bachelor's in international business and participated in a trade mission to Japan, which included a family homestay. Mary is a professional group leader in New York City and Washington, DC, and has led field trips on the East Coast and in Germany. In her free time, Mary travels with family and friends to experience new destinations and revisit old favorites.
Profile Image of Sheila Moloney
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.
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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.
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8 days
7 nights
17 meals
7 B 5 L 5 D
Check-in, Registration, Orientation, Welcome Dinner
Boston, MA
Hilton Boston Logan Airport

Activity note: 3:00 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.

Boston Field Trip, Transfer to the Berkshires
Stockbridge, MA
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.

Mission House, Norman Rockwell Museum, The Mount
Stockbridge, MA
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: Boxed lunches at the museum

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.

Hancock Shaker Village, Free Time
Stockbridge, MA
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.

Hudson Valley, Olana, Huguenot Street
Mid Hudson Valley, NY
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.

Val-Kill, FDR Home, Presidential Library, Vanderbilt Mansion
Mid Hudson Valley, NY
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.

West Point, Boscobel
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.

Transfer to Boston, Program Concludes

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 Best wishes for all your journeys!

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