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July 5, 2025
Lee, Massachusetts

Forever In The Berkshires

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Things To Do

Here are our favorite hiking spots, scenic views, and local eateries!

Ice Glen and Laura's Tower

Ice Glen Trail, Stockbridge, MA 01262

One of our favorite places to take Ralphie when we visit home! Laura's Tower and Ice Glen are both accessible from the same trail head. Highly recommend doing both!

Monument Mountain

Route 7, Stockbridge, MA 01230

Watch bald eagles soar across the Housatonic River Valley from Monument Mountain’s 1,642-foot summit and discover why this ancient landmark has inspired countless generations. Monument Mountain has been sacred to the Mohican people and their ancestors since time immemorial. Tribal members left stone offerings imbued with prayers on the mountain, creating the “monument” for which it’s named. The original monument was destroyed by white residents after the Mohicans were dispossessed and forced from the area, though it was later recreated near the Mohican Monument Trail. The mountain has long inspired works of art and literature, including William Cullen Bryant’s 1815 poem, “Monument Mountain.” Authors Nathaniel Hawthorne and Herman Melville spent a notable afternoon on the mountain and found motivation for future works, including Moby-Dick. Today, more than 20,000 hikers ascend to its summit, Peeskawso Peak, each year.

Tyringham Cobble

20 Jerusalem Road, Tyringham, MA 01264

2-mile loop trail. Moderate hiking, strenuous in places. Hike two miles of trails—including a section of the Appalachian Trail—over the twin knobs of the Cobble for spectacular views of the valley. Keep an eye out for an unusually shaped rock formation known as Rabbit Rock. Hop Brook, a favorite fishing stream of President Grover Cleveland, meanders along the northern edge of the reservation on its way west to the Housatonic River. Along the way, glimpse the wildflowers, blackberries, blueberries, and wild strawberries growing in clearings and open meadows, and carve out time for a picnic in the wildflower-festooned field at the summit.

Ashintully Gardens

27-1 Sodom Road, Tyringham, MA 01264

Nestled within the forested hills of the Tyringham Valley, Ashintully Gardens blends formal and informal gardens and the ruins of a historic mansion in an intimate setting with a multigenerational history.

Naumkeag

5 Prospect Hill Road, Stockbridge, MA 01262

Naumkeag is a public garden and historic home in the heart of the Berkshires, Massachusetts. This 48-acre architectural masterpiece is, at its heart, a family home. In 1884, Joseph Choate, a prominent New York attorney and U.S. Ambassador to Great Britain, and his wife, Caroline, hired the famous architectural firm of McKim, Mead & White to design a summer retreat. The result was a 44-room shingle-style home, where several generations of the Choate family lived until daughter Mabel Choate bequeathed it to The Trustees in 1958.

Berkshire Botanical Garden

5 West Stockbridge Road, Stockbridge, MA 01262

The Berkshire Botanical Garden, is a 24-acre botanical garden in Stockbridge, Massachusetts, United States. Its collections contain over 3,000 species and varieties, with an emphasis on plants that thrive in the Berkshires.

Art Omi

1405 County Route 22, Ghent, NY 12075

We love this place and highly recommend making the 43 minute trip!

Haven

8 Franklin Street, Lenox, MA 01240

Anyone who knows me (Cassie) knows that this is my favorite lunch spot in The Berkshires!

High Lawn Farm

535 Summer Street, Lee, MA 01238

It is an absolute must that you stop by the creamery and visit the cows! There is nothing more beautiful than golden hour here!

The Red Lion Inn

30 Main Street, Stockbridge, MA 01262

Head to Stockbridge and grab a bite and a drink at the Red Lion Inn, sit on the porch or check out the back patio. Don't forget to stop by their gift store and take a stroll over to Sidetracks gift shop (the best little store in The Berkshires!)

For all the days along the way
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