The Berkshire Mountains of MA & CT
The Gilded Age and Norman Rockwell
Sep 15 - Sep 21, 2026Nestled in western Massachusetts and northwestern Connecticut, the Berkshires offers a captivating blend of natural beauty, cultural richness, and outdoor adventures. Charming small towns dot the landscape. Late 19th century “cottages” built during the Gilded Age, the largest collection of Norman Rockwell’s art in the world, and music venues such as Tanglewood are available to explore. There are stunning hiking trails with sweeping views of the mountains. Boasting more than 100 world class cultural attractions, superior outdoor recreation, and a famous farm-to-table food scene, the Berkshires promises an unforgettable experience. We hope you'll join us!
The Berkshire Mountains of MA & CT
Sep 15 - Sep 21, 2026This trip is still in the planning stage. We do this so you can see what will be offered in the coming months/year. Once we have all the activities, hotels, and other details confirmed, and the price finalized, we will replace this information with a completed itinerary, and all of the tabs will function. Get a jump on the crowd by making a no-obligation pre-reservation. Your pre-reservation entitles you to be notified as soon as the full itinerary, with firm dates and pricing, is posted.
Tentative Itinerary
Day 1: Arrive Albany, NY; Welcome Meeting & Dinner
Day 2: Hancock Shaker Village; Group Lunch; Edith Wharton’s Home
Day 3: Berkshire Camino Walk; Norman Rockwell Museum Tour
Day 4: Gilded Age Mansion Tour; Hilltop Orchards
Day 5: White Memorial Conservation Center; Dairy Farm
Day 6: Essex Steam Train and Riverboat; Farewell Dinner
Day 7: Return Home from Hartford, CT
The Berkshire Mountains of MA & CT
Sep 15 - Sep 21, 2026MAKE A PRE-RESERVATION
Here is an easy way, with no obligation whatsoever, to have WTT notify you when this tour is finalized, with all the details including pricing, hotels, firm dates, etc. You can select up to 5 tours per calendar year and can rank your choices.
Our small-group tours often fill up quickly, but your pre-reservation will ensure you are the first to know** when this tour is accepting reservations -and- you will be eligible for the pre-reservation discount.
You are under no obligation once contacted. Just delete the email we send you.
** When a tour is open for reservations, we notify WTT members first, followed by non-members four days later.
You have selected the dates of for your prereservation. Once confirmed, we will add this request to your list of prereservations for the year .