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Sample Trip Itineraries
The Berkshires are known as America's Premier Cultural Resort. From its scenic rolling hills to its historic museums and flower garden adorned gilded mansions, it has become a favorite vacation getaway destination. Excellent shopping can be found at the Lee Prime Outlets as well as at the boutique-type specialty shops offered in abundance throughout the county. Historic museums, art galleries, theatre, famous gilded mansions, abundant outdoor activities like hiking, biking, canoeing, & horseback riding, offer our guests many entertainment and sightseeing opportunities. With famous Tanglewood, Jacobs Pillow and other cultural venues, travellers can be guaranteed a full vacation whether they are visiting for 3 days or 3 weeks....there’s something for every taste in this vacation mecca. Book our Midweek Summer Saver Package and see below for some Trip Planning Ideas...
Family Fun Planner
Day One:
Arrive early afternoon. Take a hike at Pleasant Valley Wildlife Sanctuary with 7 miles of trails that wind through forest, meadows, wetlands and along the slopes of Lenox Mountain filled with Beaver Ponds and other fascinating natural beauty. Check in to your room at The Yankee Inn and relax with a dip in the pool. Dinner at ASTERS Steaks & Raw Bar.
Day Two:
Morning: Complimentary breakfast at The Yankee. Drive to the top of Mount Greylock State Reservation, Massachusetts highes pike and take in breathtaking views of up to 100 miles. Afternoon: Play at Jiminy Peak Mountain Adventure Mountain offering a day of fun with Scenic Chairlift Rides, 3000 ft Apline Slide, Giant Swing, Euro-Bungee Trampoline and much more more situated on a breathtakingly beautiful mountain. Have Lunch at the base of the mountain at Christiansen's Tavern. Evening: Head out to a Pittsfield Dukes baseball game.
Day Three:
Morning: Complimentary breakfast at The Yankee. Visit Hancock Shaker Village. Have lunch in the Florence Gould Cafe or enjoy a picnic on the beautiful grounds. Afternoon: Bring the kids back to the Yankee for a dip, enjoy an early dinner at ASTERS and take in a performance at either Barrington Stage Company or Berkshire Theatre Festival.
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Art, Museum, and History Planner
Day One:
Arrive afternoon and stroll through the streets of historic downtown Stockbridge. Visit The Norman Rockwell Museum. Check into The Yankee Inn. Evening: Dinner at ASTERS Steaks & Raw Bar and attend Emmy Award Winning, side splitting performance News In Revue at Cranwell Resort.
Day Two:
Morning: Complimentary breakfast at The Yankee. Visit The Mount, (the home of novelist Edith Wharton, author of The Age of Innocence, Ethan Frome, and others). Lunch on The Mount's Terrace Cafe. Afternoon: Take a Naumkeag Garden Tour - the summer "cottage" of the Choate family who began summering in Berkshire County in the 1870s. Evening: Have dinner and attend a dance performance at beautiful Jacob's Pillow. (Reservations recommended for dinner at The Pillow Cafe)
Day Three:
Morning: Complimentary breakfast at The Yankee. Shop The Lee Prime Outlets (pick up your complimentary goodie bag with discount coupons at the front desk of The Yankee Inn). Have an early dinner at ASTERS (see the 4 to 6 FIX menu) and attend a musical performance at Tanglewood.
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