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Fall in the Berkshires Travel Guide

Experience the magic of autumn in the Berkshires with our ultimate Fall Travel Guide. Known for its rolling mountains and brilliant foliage, the Berkshires is one of New England’s most iconic destinations for a seasonal getaway. This guide highlights the best things to do, see, and taste during fall—from world-class art museums like MASS MoCA and the Norman Rockwell Museum to charming cafés, award-winning restaurants, and cozy farm-to-table dining. Outdoor lovers will find endless hiking trails with sweeping views, from Monument Mountain to Mount Greylock, while foodies can sip and savor at local wineries, breweries, cideries, and distilleries. Whether you’re planning a weekend escape or a longer road trip, our Berkshires guide covers top attractions, scenic drives, cultural experiences, and hidden gems that make autumn here unforgettable. Discover where to eat, drink, hike, and explore, and start planning your perfect Berkshires fall getaway today.

Guide by Ryan Jones
Made in English
5.0

Local Living Unbound

September 2025

Loved this guide! it was so helpful with planning my fall weekend! Turns out there is SO MUCH to do in the Berkshires that were doing the art itinerary this winter!

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Guide by Ryan Jones
Joined in August 2025

I’m Ryan, the travel advisor and storyteller behind The Wandering Creative. As both a travel blogger and a Fora-certified advisor, I help travelers turn inspiration into actual trips—whether it’s a Disney vacation with the family, a romantic European getaway, or a once-in-a-lifetime adventure.

Through my blog and social platforms, I share detailed guides, insider tips, and curated itineraries designed to make planning easier and more exciting. And when you’re ready to book, I can take care of the heavy lifting—securing exclusive perks at hotels, locking in the best rates, and organizing all the details that make a trip seamless.

My goal is simple: to inspire your next journey and make it stress-free to plan. Whether you’re dreaming of New York City during the holidays, island-hopping in Greece, or finding the perfect all-inclusive resort, I’d love to help you get there.

📩 Ready to start planning? Reach out at Ryan.jones@fora.travel and let’s make your trip happen

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