Berkshire Highlands of Massachusetts
The Gilded Age and Norman Rockwell
September 14 - September 19, 2026
Berkshire Highlands of Massachusetts
September 14 - September 19, 2026Highlights
- See the grandeur of the Gilded-Age
- Tour the Norman Rockwell Museum
- Sample local cider & cider donuts
- Walk the trails of Pleasant Valley Wildlife Sanctuary
- Visit The Mount - Edith Wharton's Home
- Relax on a porch together and watch the world go by
- Suggestions for things to see and do
- And More... See itinerary for details
Itinerary
Monday, 14 September 2026: Arrive Albany, NY; Welcome Meeting & Dinner (D)
Schedule your arrival no later than 4:00pm and take local transportation to the hotel. The tour begins in the lobby of the hotel at 6:00pm. We will make introductions and then depart for our Welcome Dinner at a nearby restaurant to get better acquainted and discuss our upcoming adventures. Overnight Albany - 1 night
Tuesday, 15 September 2026: Hancock Shaker Village; Hilltop Orchards (B,L,O)
Discover two wonderful Berkshire treasures today. Our day begins with a glimpse into the fascinating world of the Shakers at Hancock Shaker Village. The village is a living history museum showcasing the unique religious and social lifestyle of the Shakers. Explore this beautifully preserved 19th-century community as our guide shares details about their innovative way of life, craftsmanship, and enduring legacy. Wander through historic buildings, gardens and a working farm witnessing the Shakers' remarkable ingenuity and simple living philosophy. After lunch together, we head to Hilltop Orchards. Enjoy an orchard tour before tasting local cider and delicious apple cider donuts! Spend time walking along farm trails and browsing the farm store while taking in the scenic Berkshire countryside. We then settle into our hotel in Stockbridge, a picturesque small Berkshire town. The evening is yours to spend as you wish. Overnight Stockbridge, MA - 3 nights
Wednesday, 16 September 2026: Pleasant Valley Wildlife Sanctuary; The Mount - Edith Wharton’s Home (B,L)
This morning begins with a visit to Pleasant Valley Wildlife Sanctuary. Spanning over 1,000 verdant acres in the Berkshires, Pleasant Valley features diverse trails that meander through woodlands, grasslands, marshes, as well as Lenox Mountain's hillsides, offering a variety of trail options. Your Tour Leader will help the group decide on which path to take. As we explore, it's likely we will encounter signs of the sanctuary's most conspicuous inhabitants—beavers—through their dams, burrows, and lodges. After lunch together, we'll tour Edith Wharton's elegant home and gardens, The Mount, where the famous author lived and wrote. Walking through these rooms offers a glimpse into the life and creative process of America's first woman to win the Pulitzer Prize for Fiction.
Thursday, 17 September 2026: Norman Rockwell Museum Tour; Cooking Class & Dinner (B,D)
This morning begins at the Norman Rockwell Museum to see his delightful depictions of American life. The museum is home to the world's largest collection of Rockwell's original paintings, illustrations, and personal artifacts; spanning his Saturday Evening Post covers to intimate portraits of everyday moments. He lived in Stockbridge for more than 25 years and the town often served as a setting and backdrop to his work. It's a wonderful chance to step into the world that inspired his iconic art. In the afternoon we'll take a scenic drive to a hands-on cooking class where we roll up our sleeves to create and savor a delicious fall soup and it's accompaniments for dinner together.
Friday, 18 September 2026: Ventfort Hall Gilded Age Mansion; Afternoon Tea; Farewell Reception (B,R,O)
Spend time exploring Stockbridge this morning at your own pace. Browse local shops or relax on the front porch of our Inn. Your Tour Leader will have suggestions. We'll depart mid morning and step into America's Gilded Age with a visit to Ventfort Hall, a magnificent mansion that showcases the wealth and artistry of the era. Built in the Jacobean Revival style with brick and brownstone trim, this impressive estate was home to Sarah Morgan, sister of financier J.P. Morgan—a striking example of how America's elite lived during one of the country's most opulent periods. We tour the property and enjoy afternoon tea together. Late this afternoon, we return to Albany were we'll gather this evening for a Farewell Reception to recount the memories made on this journey together. Overnight Albany - 1 night
Saturday, 19 September 2026: Return Home from Albany, NY (B)
Sadly, our time together has come to an end. Schedule your departure at your convenience. Transfers are not included but your Tour Leader can assist with organizing travelers into small groups so you can ride-share to the airport if you wish.
Berkshire Highlands of Massachusetts
September 14 - September 19, 2026Pricing
Room Share
$2,849.00Single Room
$3,767.00Non-Members
ADD $50.00Status of this Tour
Trip Full, Accepting Standbys
Tour Pricing Includes
- All meals and activities expressly listed in the itinerary, PLUS...
- All tipping of local guides
- WTT Tour Leader to enhance the individual & group experience
- Arranged room sharing with another solo traveler
- Travel Dollar credits (a benefit of WTT membership) toward future travel with WTT
Not Included In The Price
- Airfare or other transportation to and from the tour
- Airport transfers
- Meals and activities not specified in the itinerary
- Any personal expenses or expenditures
- Any pre- or post- tour arrangements
- Any gratuities for the WTT Tour Leader
- Trip Cancellation / Trip Interruption
Payment Dates -and- Cancellation Terms for This Tour
You have 3 days to cancel and receive a refund. Thereafter, the amount required at time of reservation is non-refundable and the following cancellation penalties will be enforced.
Wednesday, 18 Mar 2026: Last day $250 deposit can be converted to a credit for use on a new reservation; thereafter the deposit is forfeited.
Tuesday, 16 Jun 2026: Balance Due. Cancellation after this date but before Friday, 31 Jul 2026 results in a cancellation penalty of 50% of your Total Tour Cost.
Friday, 31 Jul 2026: Cancellation on or after this date results in a cancellation penalty of 100% of your Total Tour Cost.
Using Parked Credits: If traveler cancels during the 3-day cancel without penalty period, used credits will be re-parked with the original expiration date(s). Thereafter, cancellation will result in forfeiture of the total amount of parked credits used. If applicable, additional cancellation penalties will be assessed based on date of cancellation.
To Cancel: Should you need to cancel after your space on this tour is confirmed, you must use the Cancellation Form. Cancellation penalties are based on the date we receive your cancellation form. No other method of communicating a cancellation will be accepted.
Insurance Reminder
Trip Cancellation / Trip Interruption Insurance is not included in the cost of the tour. It is your responsibility to determine the amount and type of coverage you require to recoup some or all of your travel investment, whether you cancel, are unable to complete the tour, or the tour cannot operate. Section 4.0 of WTT Terms & Conditions explains what will happen to your payments in the unlikely event that your tour cannot operate.
WTT is not licensed to sell travel insurance. You can purchase travel insurance from any provider you choose. To get an idea of rates, please go to NTA Travel Protection Plan (Enter 206063 for the "Tour Operator Location #") or TravelGuard.
Berkshire Highlands of Massachusetts
September 14 - September 19, 2026Flights, Transfers & Lodging
Arrival & Departure Information
Travelers will make their own air arrangements as follows:
Arrival Airport: ALB - Albany, NY (Albany Int'l Airport)
Arrival Date: Monday, September 14. Arrive no later than 4:00pm.
Arrival Transfer: Use local shuttle or taxi service. Details provided in Final Travel Instructions.
Departure Airport: ALB - Albany, NY (Albany Int'l Airport)
Departure Date: Saturday, September 19th. Depart at your convenience.
Departure Transfer: Use local shuttle or taxi service. WTT Tour Leader will assist in coordinating ride sharing.
When to Book Your Air
Once you have booked your flights (or other transportation arrangements), use the Travel Arrangements Form to send WTT your flight details. Use the same form to update your information should it change.
Airport Transfer Information
When arrival transfers are not included: WTT will provide suggestions to get to the hotel in your Final Travel Instructions about 2-3 weeks before the start of the tour. You'll also be able to see who else is arriving at the same time if you want to coordinate ride-sharing to the hotel.
Don't Worry. We're Expecting You: One of the reasons we ask for your travel arrangements is so we know when you're arriving and can approximate when you should be at the hotel. Your Final Travel Instructions will have instructions on what to do and who to contact if your flight is delayed.
Lodging / Hotels
Albany: Hampton Inn & Suites Downtown
Stockbridge: The Red Lion Inn - Stockbridge. Massachusetts
Albany: Hampton Inn - Wolf Road
Whenever possible, we choose hotels that are near the city center and/or where there are things to do and places to eat within walking distance of the hotel. When the chosen hotel is not within walking distance of much, transportation options, at the traveler's expense, are typically available.
In the unlikely event WTT is unable to provide the hotel accommodation(s) listed, for whatever reason, WTT will substitute similar quality accommodation(s) at no additional cost to the traveler.
Want to Arrive a Day Early?
Worried about possible flight delays? Consider arriving one day before the official tour start date. Many of our travelers choose this optional service. Your pre-tour package includes:
- The room (standard check-in times apply)
- Breakfast the following morning
- Optional activity suggestions prior to tour
$134.00 Roomshare pp $266.00 Single Occupancy
Early Arrival Hotel: This tour uses the same hotel used on the first night of the tour.
Berkshire Highlands of Massachusetts
September 14 - September 19, 2026Destination Information
What do others say about this tour and traveling with WTT?
How Does Room Sharing Work?
On the Reservation Form there are 3 choices regarding room-sharing.
Note: Certain room-types may be unavailable at the time you make your reservation. If a room-type is unavailable the choice will be greyed out.
- Select "Yes, I want to share a room" and WTT will assign you a roommate when Final Travel Instructions are sent.
- You can specify a roommate by entering her name where indicated. If your named roommate is not on the tour, for any reason, WTT will assign you a roommate unless you pay to have your own room, if available.
- Select "No, I do not wish to share a room" if you want to have your own room. Additional costs apply.
- All shared rooms have 2 beds
- All shared rooms are non-smoking
- No special requests about your roommate can be accommodated
- See "Frequently Asked Questions" TAB for more details
How Active is this Tour?
The activities on this tour are rated as follows:
- 85% Easy
- 15% Moderate (hiking trails, walking & standing for extended periods)
As a solo traveler you are responsible for yourself, your possessions, your physical fitness, and all other aspects related to participation in the WTT tour you have chosen. Be sure to read the itinerary closely to better understand the physical requirements necessary for the tour.
WTT tours are not suitable for anyone whose mobility is challenged or compromised. If you struggle with walking, standing or negotiating stairs or if you are in doubt as to your ability to meet the physical activity requirements, you should not sign up for this trip.
What is the Group Size?
You will be introduced to the WTT Tour Leader when you receive your Final Travel Instructions, about 2-3 weeks before the tour begins.
Learn about your fellow travelers after final payment by visiting MyWTT. Room sharing assignments will be listed in the Final Travel Instructions.
What meals are included and how are dietary restrictions accommodated?
Each day of the itinerary lists the included meals for that day (B,L,D,O). When a meal is not included, the WTT Tour Leader will have suggestions for where to eat.
You do not have to dine alone unless it is your personal choice. You'll most likely be dining with new acquaintances you've made, or you can join the Tour Leader.
Dietary Restrictions: Vegetarian and gluten-free dietary restrictions can be accommodated on this tour with limited selections.
What clothing and items should I pack for this trip?
In general the temperature, rainfall and humidity levels vary based on the time of the year. We suggest you monitor weather apps leading up to the time you depart for the most current information.
For This Trip You Will Need—
You May Also Want—
For This Trip You May Want—
- Shoes that are comfortable for walking
- Refillable water bottle
- Smart-casual wear if you'd like to dress up a bit for dinners
- Lightweight but warm jacket/sweater for the cool mornings and evenings or the unusually brisk day
- Inexpensive rain poncho or travel umbrella, just in case
Good Packing Habits—
- Bring what you need to get a good night's sleep, such as ear plugs, white noise generator, sleeping aids, etc. Unfamiliar noises of all types can disrupt your rest.
- Pack a limited amount of comfortable, casual clothing that layer and coordinate. Your fellow travelers will not mind or even notice – seeing you in the same clothing.
- Bring only two pairs of everyday shoes: one pair of well-broken-in walking shoes, and a second pair that could do double-duty as a walking shoe or a slightly dressy shoe.
- Pare down your beauty regimen to the bare minimum and always pack travel-sized toiletries.
- Pack medication in your carry-on and pack only as much as needed for the duration of your tour plus a few extra days as a precaution.
What are the luggage restrictions for this tour?
We will be using the WTT coach on this tour. The luggage restrictions are driven by the physical space limitations and the requirement that travelers manage their belongings.
- It is best to travel as lightly as possible. Most travelers regret when they have packed too much.
- You may bring one suitcase and a day pack or shoulder bag to keep with you in the coach.
- Maximum suitcase size: 22-24 inches in height. This is the size of bag that fits into the overhead bins of aircraft. Suitcases larger than this will not fit properly in the WTT coach; don't bring them.
- The weight of your bag should not exceed 30 pounds as you will need to lift it into the coach luggage compartment.
- You are responsible for managing your own belongings. We expect you to take your belongings from the coach to your room and to bring it back to the coach and load it on days we change hotels. We do not provide luggage pulls; they are not safe and are inconvenient. The possibility of steps exist at most hotel entrances.
How much money should I bring on this tour?
Only you can determine the optimum amount of cash to take on tour. When budgeting for out-of-pocket expenses, there are several aspects to consider: the number of meals you are responsible for, the amount of money you like to have on-hand for snacks and drinks, and your individual shopping interests and habits. Be sure to keep cash on hand for sharing restaurant tabs, cabs, tips, and smaller purchases. More and more, restaurants are no longer allowing groups to split the bill. Therefore, you might want to have cash-on-hand for meals on your own when dining with others in the group.
What are the tipping guidelines for this tour?
All tips to local guides will be paid on your behalf.
- You are responsible for tipping waitstaff, porters, or other individuals who provide a service to you at the hotel, or other public locations.
- You may want to tip your WTT Tour Leader for an outstanding job. The amount is entirely a personal preference. If you'd like a guideline, consider $8-$10 per day.
Can I transfer my deposit to another tour?
To get off this tour and register for another tour, you must follow these steps - in the order shown:
2) WAIT before submitting your new reservation! You must receive the Cancellation Confirmation email before submitting your new reservation. This can take up to 2 business days. The Cancellation Confirmation email will list the amount of parked credits from this tour that are now available to use on a new reservation.
3) COMPLETE the new Reservation Form and USE the parked credits towards your deposit on the new tour.
Note: If you used Parked Credits to pay the deposit on this tour, these credits cannot be used a second time and are not eligible to be transferred.
What happens if I need to cancel this tour?
Berkshire Highlands of Massachusetts
September 14 - September 19, 2026STANDBY REQUEST FORM
1)There is no obligation to take the tour if you submit a standby request. 2)If an opening occurs, WTT will email you based on the room-type available. 3)WTT membership is not required to go on standby, however we do notify our members ahead of non-members.
Our Promise to You
It doesn’t matter which tour you choose.
You’ll find your people and make memories that last a lifetime.