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Falling for New England: A Cozy Autumn Itinerary

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by Cassidy Wilson
9 months ago

As someone who grew up in New England, I can assure you the best time to visit states like Connecticut, New York & Massachusetts are in the autumn season. Between the months of September - November, you will get to see stunning foliage views, experience Halloween spookiness, and eat the best apple cider doughnuts. To help you plan your New England itinerary, I’ve listed some of my favorite fall activities in each state.

Photo Credit: Connecticut River Gateway Commission Official Website

CONNECTICUT:

I might be slightly biased since this is where I’m from, but Connecticut truly offers some of the best fall activities. You’ll definitely want to visit Lyman Orchards, one of our most popular apple and pumpkin picking farms. Every year, my family always stop by to get their famous pies and apple cider doughnuts. Exploring Olde Mistick Village is a great family-friendly spot that allows you to stroll through cobblestone streets lined with colonial-style buildings on the water.

The Highland Games Festival takes the excitement up a notch with its lively festivities celebrating Scottish culture and hearty fare. Take a ride on the Essex Steam Train through the scenic Connecticut River Valley, which will truly make you feel like the main character. Lastly, don’t forget to visit Gillette Castle for some of the best panoramic views and a great hike through the foliage. 

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Lyman Orchards Pick Your Own

Typical price per person

$25-50
$$$$
Local Favorite Treat Yourself
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Olde Mistick Village

Typical price per person

$0-25
$$$$
Casual Dining Pet Friendly
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Scotland Connecticut Highland Games

Typical price per person

$0-25
$$$$
Live Music Local Favorite
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Essex Steam Train & Riverboat

Typical price per person

$25-50
$$$$
Scenic Views Local Favorite
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Gillette Castle State Park

Typical price per person

$0-25
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Scenic Views Pet Friendly
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Photo Credit: Country Living Magazine Official Website

NEW YORK: 

This state offers a diverse range of fall activities, as there are some must-visit spots in both the city and upstate. Glide along the Hudson River on a cruise, so you can capture amazing photos of the colorful leaves reflecting on the water. At the Brooklyn Book Festival, immerse yourself in the literary world, engaging with authors at one of the largest (and free) book festivals in New York. 

If you’re visiting the area, you definitely have to take part in the legendary Village Halloween Parade, where the streets of Greenwich Village come alive with hundreds of costumes and characters. Venture to Van Cortlandt Manor, where the Great Jack O’Lantern Blaze casts a spell with thousands of intricately carved pumpkins, illuminating the historic grounds. And, of course, you have to see the Macy’s Parade. This parade is the ultimate Thanksgiving spectacle, with colossal balloons, live performances, and the festive spirit that marks the beginning of the holiday season.

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Hudson River Cruises

Typical price per person

$50-100
$$$$
Scenic Views Local Favorite
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Brooklyn Book Festival

Local Favorite Learn Something New
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The Great Jack O’Lantern Blaze: Hudson Valley

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$0-25
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Local Favorite Family Friendly
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Macy's Thanksgiving Day Parade

Central Location Special Occasion
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Photo Credit: Lonely Planet Official Website

MASSACHUSETTS: 

For my history buffs and Halloween lovers, Massachusetts is by far the coolest place to visit this season. Stop by the House of the Seven Gables, a historic gem in Salem where Nathaniel Hawthorne's tales come to life within its timeworn walls. Become the 4th Sanderson sister on the Hocus Pocus Tour, which navigates through Salem's bewitching past and iconic filming locations. 

For those looking to get outdoors, a trip to Monument Mountain is a great chance to see stunning Berkshires landmarks adorned with foliage views. Bensons Pond is the oldest family farm in the state where you can strap on a pair of boots and step into a cranberry bog. Lastly, make sure to pay tribute to history at the Salem Witch Trials Memorial, a solemn space dedicated to the victims of the infamous witch trials, where stone benches bear the names of those who endured the trials' tragic outcome.

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The House of the Seven Gables

Typical price per person

$0-25
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Local Favorite Family Friendly
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Hocus Pocus Tours

Typical price per person

$0-25
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Central Location Local Favorite
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Monument Mountain Reservation

Typical price per person

$0-25
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Scenic Views Pet Friendly
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Salem Witch Trials Memorial

Typical price per person

$0-25
$$$$
Local Favorite Family Friendly
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Autumn in New England isn't just a season -  it’s the perfect blend of history, nature, and charming communities that welcomes visitors year-round. 

Happy leaf peeping!

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Cassidy Wilson

Hello! I am an aspiring travel blogger and content creator and I want to bring a unique approach to the industry. I want to focus on how travel and service can be used to develop one's personal growth and leadership skills!

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