Creating an Instagram-Worthy Fall Trip to Southern Vermont This Year!

It’s that time of year again to fall in love with Vermont! We love fall and we love when other people can see our humble and majestic state in its best season!

Time to book your trip, take out your new iPhone and capture the great shots around The Shires of Vermont in Southwestern Vermont. Not too far from New York, Massachusetts or New Hampshire, this is a great long weekend destination to make your friends and family drool over your Instagram feed!

Check out some of these best highlights over the past two seasons. We’ll even give you some hints of the best spots to take photos!

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Let’s start with the basics! Come visit us at the Chamber in Bennington, Vermont to get your start! We know how to do fall in The Shires!


We love our fall apples! And, you should too! Stop by one of our many apple-picking orchards like Mad Tom’s Orchard in East Dorset where you’ll be able to pick up bushels of McIntosh apples! The McIntosh is the most important apple grown in Vermont. This tasty variety accounts for about 50% of Vermont’s apple crop. Each year Vermont growers produce around 1,000,000 bushels (or about 40 million pounds) of apples.

Thanks @sjlauzon for sharing with us!


The fields of Pownal, Vermont are loaded with Monarch butterflies this time of year. It’s always nice to see so many and we love being so green and supportive of all living creatures in this State!

Thanks @burnsy802 for sharing with us!


What’s a visit to Vermont without stopping at one of our many pumpkin patches! As Linus said in It’s the Great Pumpkin, Charlie Brown, “"Each year, the Great Pumpkin rises out of the pumpkin patch that he thinks is the most sincere. He's gotta pick this one. He's got to. I don't see how a pumpkin patch can be more sincere than this one. You can look around and there's not a sign of hypocrisy. Nothing but sincerity as far as the eye can see."

Check out Armstrong’s Farm in Pownal, Vermont


So many ‘noms’ here! Vermont is famous for its apple cider donuts around this time of year. Check them out throughout the region at country stores like The Apple Barn in Bennington, Vermont!


Who doesn’t like a lazy Saturday, wrapped up in a scarf, with a warm beverage in your hand, walking down a Vermont street like this one in Manchester, Vermont! Filter not necessary!


Did you know that the New England Fiber Art Summit is hosted here in The Shires? That’s right, Wing and a Prayer Farm, in Shaftsbury, Vermont, hosted this lovely weekend of workshops for folks interested in learning more about this unique craft. Not to mention - Vermont - red barns - fall - what’s not to love!

Thanks for sharing with us @taprootmag


With rich history and cultural institutions like the Old First Church in Old Bennington, The Shires of Vermont are perfect for a fall excursion! The Old First Church was gathered in 1762, the first Protestant church in Vermont. Famed author and poet, Robert Frost is buried in its cemetery.


And when the weather cools down in The Shires, there’s nothing better than gathering with friends and family around a fire and sharing the day’s stories. Iconic Vermont inns and bed and breakfasts like the Hill Farm Inn in Sunderland are perfect places to end the day… and scroll through your Instagram feed full of new Shires of Vermont pictures!

Explore on!

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