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  • ITINspiration
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    • ARGENTINA - BARILOCHE
    • BELIZE - SAN IGNACIO / CAYO / JUNGLE
    • CALIFORNIA - PACIFIC COAST HIGHWAY
    • HAWAII - HONOLULU
    • HAWAII - MAUI
    • ICELAND
    • MASSACHUSETTS - THE BERKSHIRES
    • MEXICO CITY - A PERFECT 36 HOURS IN POLANCO
    • MEXICO CITY - A PERFECT DAY AT THE TEOTIHUACAN PYRAMIDS & CONDESA
    • MEXICO CITY - A PERFECT DAY IN CENTRO HISTORICO & ROMA
    • NEW YORK - BEACON / COLD SPRING
    • NEW YORK - FINGER LAKES
    • NEW YORK - HUDSON
    • NORTH CAROLINA - ASHEVILLE (PERFECT 36 HOURS of FOOD & DRINK)
    • PORTUGAL - PORTO & DUORO VALLEY GUIDE
    • SOUTH AFRICA - INTRO
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Monument Mountain
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Berkshire Mountain Bakery

Berkshires Itinerary - A Perfect Weekend

Seeking Sky August 9, 2021

The Berkshires are not an exact location that you can simply enter into your GPS. They encompass the totality of rural western Massachusetts as New England mingles with the Hudson Valley of New York. They also represent a feeling of escape. A century ago, they were a popular spot for the gilded urbanites of Boston and New York to decamp; a pastoral Newport if you will. Nowadays, the Berkshires offer a different freedom. A chance for those same urban denizens of the northeast corridor to temporarily give up their ersatz connections to constant connectivity and hyperproductivity and seek out a bucolic and verdant holiday to recharge with friends and family and let the mind meander. A fuel for introspection and creativity, the area has been a residence to famed authors Herman Melville and Elizabeth Kolbert, artists such as Norman Rockwell, and even tempting Hollywood glitterati such as composer John Williams and Meryl Streep to buying vacation homes. While peak season in the Berkshires is the summer, we went with some friends in late March as a spring getaway from New York post-vaccination. Read below for our recommendations.

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