15 Essential Autumn Activities in New England for a Perfect Fall

Dreaming of Fall Already?

I get it, me too. Once August rolls around, I’m ready to start daydreaming about my New England Pinterest board coming to life for the autumn season. The good news for you is that I actually grew up in New England! This means that I can give you the best advice from a local on how to plan your fall trips in states like Connecticut, New York, and Massachusetts.

Between the months of September and 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.

CONNECTICUT

I might be slightly biased since this is where I’m from, but Connecticut truly offers some of the best fall activities in a calm environment. 

• Lyman Orchards: Whether you’re enjoying a scenic wagon ride, getting lost in a corn maze, or sampling their legendary apple cider donuts, this orchard’s charm is sure to captivate you. Every year, my family stops by to pick up one of their pumpkin pies and to go apple picking!
  
• Olde Mistick Village: This enchanting village is home to over 40 unique shops, galleries, and eateries. To really get in the autumn spirit, stop by Alice’s Haunted Little Bookshop and Cloak and Wand.
  
• Highland Games Festival: Whether you’re diving into a plate of haggis or giving the caber toss a try, the Highland Games offer a day of fun and friendship. You will feel immersed in the spirited culture of Scotland right here in Connecticut.
  
• Essex Steam Train: All aboard! As you chug your way through scenic landscapes, you’ll feel like you’re on your way to Hogwarts.
  
• Gillette Castle: Any Sherlock Holmes fans? This quirky castle, perched on a hill, was once the home of William Gillette, the actor famous for bringing Sherlock Holmes to life. With its whimsical design and enchanting interiors, the castle gives you a peek into Gillette’s imaginative world. The sprawling grounds are perfect for picnics and exploring.

NEW YORK

This state offers a diverse range of fall activities, as there are some must-visit spots in both the city and upstate.

• Hudson River Cruises: For a unique perspective of the Big Apple, a cruise along the Hudson is sure to offer postcard-worthy views. With the stunning Manhattan skyline as your backdrop, every moment on the water will be one of relaxation.
  
• Brooklyn Book Festival: There’s nothing like snuggling up with a book on a cozy autumn day. This festival is the perfect opportunity to buy your next book and attend a variety of events, panel discussions, and book signings.
  
• NYC Village Halloween Parade: Trick or treat anyone? This legendary event transforms the streets of Greenwich Village into a Halloween wonderland and is the perfect place for you to show off your costume this year.
  
• Van Cortlandt Manor: Picture yourself wandering through a dazzling display of over 7,000 intricately carved pumpkins, showcasing everything from classic spooky scenes to incredible works of art. Each year, The Great Jack O’Lantern Blaze is hosted at this manor and is an event attended by thousands around the country.
  
• Macy’s Thanksgiving Day Parade: Since 1924, this iconic parade has captivated millions with its giant balloons, mesmerizing floats, and dazzling performances. Be bold this year and check this experience off your bucket list by viewing the parade in person!

MASSACHUSETTS

For history buffs and Halloween lovers, Massachusetts is by far the best state to visit this season.

• House of the Seven Gables: This iconic mansion, made famous by Nathaniel Hawthorne’s novel, is a living embodiment of Salem’s rich past and literary legacy. You’ll have the chance to explore its charming rooms and secret passageways that inspired the author’s tales of mystery and romance.
  
• Hocus Pocus Tours: It’s finally time to live out your dream of becoming the 4th Sanderson sister! This tour blends spellbinding stories with stunning locations, like Max and Dani’s house, offering a magical mix of film locations and Salem’s unique history. 
  
• Monument Mountain: Grab your hiking boots and play Noah Kahan’s Stick Season for the perfect soundtrack as you explore the reservation. With its breathtaking views of the Berkshires, this spot offers the perfect chance to take stunning foliage photography. 
  
• Bensons Pond: Turn from blogger to bogger at Bensons Pond, where you will have the chance to step into the boots of a cranberry farmer and dive into the fascinating world of cranberry cultivation. Wade through the flooded bog and experience the harvest up close, as you immerse yourself in the hands-on process of this unique seasonal tradition.
  
• Salem Witch Trials Memorial: Step into history’s shadow at the Salem Witch Trials Memorial in Massachusetts. This powerful tribute honors those whose lives were forever altered by the infamous 1692 trials. This serene and reflective space invites you to ponder the tragic events that marked Salem’s past.

So there you have it!

I hope this guide helps you decide which New England state to visit this fall and provides some inspiration to kickstart your travel planning. Whether you’re drawn to scenic landscapes, historical gems, or festive celebrations, there’s a perfect autumn adventure waiting for you!

Since you made it to the end of this blog post, I have a little treat for you! I managed to dig out this picture – blogger Cassie in the making. I guess you could say I was a pro at finding fall activities from day one.

xoxo,
gossip girl (aka Cassie)