Berkshire Bounty

Stockbridge, Lenox and The Red Lion Inn

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Get an early taste of autumn during a bountiful escape featuring the best of the Berkshire Mountains, across Lennox and Stockbridge, named Best  Northeastern Town in the USA by USA Today. The area attracts visitors from far and wide with spectacular views, fields, forests, rolling hills and, of course, the splendid Cottages of the American Aristocracy. Spend the night at the highly acclaimed and  prestigious Red Lion Inn, one of the top landmarks in the Berkshires.

Day 1 - For Tea and Country (T, D)
Begin your bountiful beginning to fall with a guided tour at Ventfort Hall, one of the last remaining Gilded Age Cottages, for a glimpse into the lifestyle of the J .P. Morgan family. Next, it’s a unique experience - a Victorian-style afternoon tea in the Hall’s elegant dining room, recently renovated to its original glory. Enjoy finger sandwiches, cookies, cider and of course, hot tea! Meet your local guide to explore Stockbridge and Lenox on a combination walking and driving tour. Stroll Stockbridge’s picturesque Main Street made famous by Norman Rockwell. Drive through the Stockbridge-Lenox countryside witnessing the same vistas that drew the New York Elite during the Gilded Age. Tour Tanglewood, one of the most famous cultural venues in the world. Check into the Red Lion Inn, known as one of the premiere destinations in the Berkshires, dating back to 1773! Relax before joining your fellow travelers for a hearty, three-course dinner at the hotel.

Day 2 - New England Renaissance (B)
This morning begins with another jewel of the Berkshires, the famous Clark Museum . Founded to unveil a private collection held by heirs of the Singer sewing family, the Clark boasts exceptional pieces set against striking architecture. On a guided tour, see the Clark’s many highlights from the Renaissance through the early 20th Century including paintings from Degas, Renoir, Monet, Manet and even a Botticelli!

Visit the quaint village of Williamstown, described by The New York Times as one of the loveliest communities in New England. In the center of town, stroll the charming and eclectic Spring Street, where everything is within easy reach. Explore with plenty of time for lunch and shopping on your own. Finish your Berkshire Bounty at Jaeschke’s Orchard, a third-generation family-owned farm at the base of Mt. Greylock.

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  • $389 Triple
  • $399 Double
  • $499 Single
  • Travel Protection 10%


  • Overnight at Prestigious Red Lion Inn
  • High Tea and Tour at Ventfort Hall
  • Clark Museum Guided Tour
  • Tour of Stockbridge-Lenox, Quaint Williamstown
  • Jaeschke's Orchard
  • 1 Night Hotel, 2 Meals, 1 Afternoon Tea
  • Upper Class Tour Director, Taxes & Gratuities


Monday September 21st, 2020

  • Yonkers 7:30am
  • Mamaroneck 8:30am


Tuesday September 22nd, 2020

  • Mamaroneck 7:15pm
  • Yonkers 8:00pm