New York/Massachusetts
On the Road: Autumn in the Berkshires and Hudson Valley
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.
Rating (5)
Program No. 21402RJ
8 days
Starts at
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8 days
7 nights
17 meals
7 B 5 L 5 D
Getting There
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Check-in, Registration, Orientation, Welcome Dinner
Boston, MA
Embassy Suites Boston Logan

Activity note: Hotel check-in from 3:00 p.m.

Afternoon: Program Registration: After you have your room assignment, come over to the Road Scholar table [location will be posted] to register with the program staff and get your welcome packet containing your name-tag, up-to-date schedule that reflects any last-minute changes, and other important information. If your arrival is delayed, please ask for your packet when you check in.

Dinner: Welcome dinner at the hotel.

Evening: Orientation: The Group Leader will greet everyone with a warm welcome and lead introductions. We will review the up-to-date program schedule and any changes, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer any questions you may have. Unless specified otherwise, travel and transfers will be via motorcoach, requiring ascending/descending steps. Free time is reserved for your personal independent exploration. Please be aware that program activities, schedules, and personnel may need to change due to local circumstances. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. Continue getting to know your fellow participants, settle in, and get a good night’s rest for the full day ahead.

Boston Field Trip, Transfer to the Berkshires
Stockbridge, MA
Red Lion Inn

Activity note: Getting on/off motorcoach; walks of less than 1 mile. Our motorcoach trip today is about 130 miles, approximately 2 hours.

Breakfast: Full buffet at the hotel.

Morning: After checking out of the hotel, we will explore the highlights of Boston and learn about the history and famous stories that make this city so beloved.

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. You may choose to dine at either the Lion’s Den where there is entertainment seven nights a week, or the cozy Widow Bingham’s Tavern. Plated meal vouchers will be available so you may choose what appeals to you most.

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: From the inn we will walk to one of the Berkshires’ National Historic Monuments known as 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 throughout 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. Next, we will go to the Norman Rockwell Museum complex for a Road Scholar exclusive experience. We will go behind the scenes with curators to see and learn about the art and creative process of this influential visual communicator of the American 20th century. As we study original paintings, enjoy a private look at Rockwell’s personal archive from carefully directed photographic references to rarely-seen props, art supplies, and correspondence that will offer fresh insights into the world of this renowned artist. This interactive experience will examine the deep links between imagery, culture, and history, inspiring consideration of the unique power of the artist as a commentator in his/her time. There will also be some time to explore the galleries at leisure.

Lunch: At the museum, we’ll have boxed lunches.

Afternoon: Our next field trip takes us by motorcoach to the town of Lenox and 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. We’ll then return to Stockbridge.

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.

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, prior to public opening hours. 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: In the museum café.

Afternoon: We will have some time for personal independent exploration at Shaker Village before returning to Stockbridge, where the remainder of the afternoon will be free.

Dinner: Plated meal at the inn.

Evening: At leisure. Take some time to prepare for our departure from Stockbridge and transfer to the Hudson Valley in the morning.

Hudson Valley, Olana, Public Art Walk in Poughkeepsie
Mid Hudson Valley, NY
Holiday Inn Express Poughkeepsie

Activity note: Our motorcoach trip today is about 100 miles total with multiple stops; walking up to 2 miles, standing up to 2 hours at field trip sites.

Breakfast: At the inn.

Morning: After checking out of the inn, we will turn westward in the manner 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. Our first stop in the Hudson Valley will be Olana, where a docent will lead us through the Moorish-style home of Frederic Church, a landscape artist of major importance to the artistic movement known as the Hudson River School. The villa offers 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: Following lunch, we'll meet up with a local muralist and art expert, who will instruct us on a walking field trip through Poughkeepsie. We will see several of the public murals, sculptures, architecture, and monuments around town, demonstrating their historic and cultural significance in the development of Poughkeepsie. Being public artworks, some of these pieces will be more iconic representations of city art, while others will be less commonly discovered hidden gems.

Dinner: On your own to enjoy what you like. The Group Leader will be happy to offer suggestions.

Evening: Check-in at the hotel. The remainder of the evening is at leisure.

FDR Home, Presidential Library, Val-Kill, 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; more than 100 steps at Vanderbilt Mansion.

Breakfast: At the hotel.

Morning: Our next field trip is 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: 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 ride 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: At a local restaurant

Evening: At leisure. Prepare for check out and transfer in the morning.

Historic Huguenot, Boscobel
Hampton Inn of Danbury

Activity note: Walking up to 2 miles and standing over the course of visits. Approximately 48 miles by motorcoach.

Breakfast: At the hotel.

Morning: After checking out of the hotel, we will continue to New Paltz, NY, where we will arrive at the Huguenot Street Historic District—a beautiful reflection of the early colonial history of the Hudson Valley. Led by a docent, we will see seven original stone houses dating from 1705, the colonial-era burial ground, and a reconstructed 1705 French church.

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

Evening: At leisure. Say farewells and prepare for departure in the morning.

Transfer to Boston, Program Concludes

Activity note: Our motorcoach trip is about 160 miles, approximately 2.5 hours.

Breakfast: At the hotel.

Morning: We will board our motorcoach for the return trip to Boston, arriving at approximately 11:30 a.m. 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!