Your Dream Journey Peeping For Leaves In New England

Andrew Harper Travel Journey Overview


Morris, Connecticut • Lenox, Massachusetts • Warren, Vermont

Duration: 7 Days

Starting at: 4,694 USD Per Person

When autumn arrives, New England is ablaze with color. The leaves start turning colors in the northern regions of New England around mid-to-late September and peaking around mid-October. Quaint towns nestled in rolling hills welcome you to experience their unforgettable charm and natural beauty. This self-guided tour features kayaking, horseback rides, museum tours, and more!

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DAY 1 Arrival in Connecticut

Upon arrival, you will be met at the airport and brought to your waiting luxury transportation and whisked to your hotel. Check into the sumptuous Winvian Farm resort in the Litchfield Hills of Connecticut for a two-night stay.

Stay Overnight Winvian Farm

Winvian Farm

Set amid 113 acres of meadows and woodlands in Litchfield County, this refined 18th-century country house hotel features 19 extraordinary architect-designed cottages.

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DAY 2 Horseback Riding Through the Hills

Start your New England experience on the water! Paddle through the winding bends of the Bantam River in canoes or kayaks, and glide past ornate beaver lodges and blue herons on your way to Bantam Lake. Since no prior experience is required, guests of all ages can escape civilization for a while. Ready for a different view? Saddle up and go horseback riding through hills and valleys on this private riding experience. Choose from either a trail ride or learn a bit of control through an instructor-guided lesson.

Stay Overnight Winvian Farm

Winvian Farm

Set amid 113 acres of meadows and woodlands in Litchfield County, this refined 18th-century country house hotel features 19 extraordinary architect-designed cottages.

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DAY 3 Head to the Berkshires

Next stop—the Berkshires! A rural region in the mountains of western Massachusetts dotted with villages and towns, it is known for outdoor activities, fall foliage viewing, and thriving arts institutions. Your home for the next two nights is the elegant Wheatleigh Hotel in Lenox. Enjoy dinner at your resort.

Stay Overnight Wheatleigh

Wheatleigh

This exquisitely restored 19th-century Italianate palazzo is set amid 22 acres of parkland designed by Frederick Law Olmsted.

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DAY 4 Highlights of Western Massachusetts

Spend a full day exploring the highlights of Western Massachusetts. Then, experience the Gilded Age in person at Ventfort Hall, an imposing Jacobean Revival-style mansion built in 1893 for Sarah Morgan, the sister of J. P. Morgan. One of the approximately seventy-five so-called “Cottages” built in Lenox in the late 19th century when the village became a popular Gilded Age resort, Ventfort Hall is located on spacious grounds in the heart of the village.

No visit to the Berkshires would be complete without a visit to the Norman Rockwell Museum, dedicated to one of the best known and most beloved artists to hail from New England. The Museum houses the world’s largest and most significant collection of Rockwell art and is a world resource for reflection, involvement and discovery inspired by Norman Rockwell. There is a vibrant farm to table restaurant scene in Lenox—be sure to check it out.

Stay Overnight Wheatleigh

Wheatleigh

This exquisitely restored 19th-century Italianate palazzo is set amid 22 acres of parkland designed by Frederick Law Olmsted.

View

DAY 5 MASS MoCA and Arrival in Warren, Vermont

After checking out of your hotel, make your way to Warren, Vermont. En route, visit MASS MoCA (the Massachusetts Museum of Contemporary Art) where you will meet your guide for a private tour of Building 6. MASS MoCA is one of the largest centers for contemporary visual art and performing arts in the United States. Your guide will provide an interactive experience as you view the masterpieces housed in Building 6. Your hour-long tour will be tailored to your interests and provide an overview of the collection.

In the afternoon, arrive at the charming The Pitcher Inn. Use the hotel as a base to see Vermont.

Stay Overnight The Pitcher Inn

The Pitcher Inn

At the heart of the village of Warren sits The Pitcher Inn, encircled by mountains slipping serenely into Vermont's Mad River Valley.

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DAY 6 Tour Charming Vermont

In the morning, kayak, stand-up paddle (available through September) or simply visit beautiful Lake Champlain, the nation’s sixth-largest natural freshwater lake. Make your way across the water and around the Lake Champlain Islands.

Visit the quaint, picturesque towns of Stowe, Woodstock or Weston. Wander arts and crafts fairs, museums and galleries or attend musical and theatrical performances in Stowe, sample maple syrups and cheeses at Sugarbush Farm in Woodstock or visit quintessential country stores in Weston. End the day on a sweet note, enjoying a private tour of the Ben & Jerry’s factory to learn about ice cream manufacturing and of course, sample a few of the cleverly named flavors and local Vermont specials.

Stay Overnight The Pitcher Inn

The Pitcher Inn

At the heart of the village of Warren sits The Pitcher Inn, encircled by mountains slipping serenely into Vermont's Mad River Valley.

View

DAY 7 Departure

Check out of your hotel and be transferred to the airport for your flight home.