The Ultimate Guide to Fall in Boston

One day living in Boston and fall had already become my new favorite season. The crisp New England air provided the perfect football weather. And the changing color of the leaves was absolutely mesmerizing. In honor of fall quickly falling upon us (no pun intended), I decided to compile a list of my favorite fall activities—the ultimate guide to fall in Boston!

1. Picking Apples at Honey Pot Hill Orchard


Stow, Massachusetts45 minute drive from Downtown, Boston

Honey Pot Hill Orchard is quintessential New England. Even the drive in will have you excited for fall, exploring the winding roads and colorful forests in the countryside of Stow. Locals will say that it’s too “touristy,” preferring an orchard that sticks purely to apple picking. However, it’s all of Honey Pot’s “extras” that make it #1 on my list.

Upon arrival, I highly recommend investing in the “Farm-Fun-Pack,” available on the weekends beginning in late August. For just $24, you receive:

  • An all-day hayride through the orchard (you’ll appreciate this—the orchard can seem endless)
  • A caramel apple, cider donut, and cider made fresh at the orchard’s general store (the cider was the best I’ve ever had—definitely not the syrupy/sugary mess from the grocery store)
  • Access to the orchard’s maze (you may think this is more of a kiddy activity, but I am embarrassed to say that I have gotten lost in this maze on numerous occasions!)
  • A half peck picking bag (which will usually get you about 10 apples)

When you visit the store for your fall treats, be sure to check out the petting zoo nearby (especially if you’re bringing younger kids). The orchard itself has all different kinds of apples to please even the pickiest of eaters. Not to mention, it provides the perfect fall photo opportunity.

2. Exploring Local Haunts in Salem


Salem, Massachusetts—35 minute drive from Downtown, Boston

The perfect Halloween day trip, Salem honestly deserves its own blog post. But for now, here is a short list of must-see destinations in the notorious Witch City:

  • The Witch Memorial: Located in Witch Village with a fittingly abandoned house adjacent, the Witch Memorial is undeniably Salem’s claim to fame. Though none of the witches are actually buried there (I know, disappointing), Salem has done a wonderful job capturing the history of the infamous Witch Trials through this memorial, with actual quotes from the trials etched in the ground below you. Be sure to check out the local cemetery next door—some tombstones date as far back as the 1600’s.

  • Count Orlok’s Nightmare Gallery: Now located in the heart of Salem, Count Orlok’s Nightmare Gallery provides a truly unique experience. With “nightmare gallery” being an understatement, the gallery is a collection of rare horror movie memorabilia. Very professionally done, the gallery primarily consists of 60+ life-size wax figures of horror movie icons created by Hollywood special effects artists, providing a unique blend of history and terror. The last time I visited, tickets were only $8, though they may have gone up considering their recent move to a larger location.

  • The Witch House: Built in the 1600’s (with the creaky floors to prove it), the Witch House may be the most authentic piece of the Witch Trials left in Salem. From its black exterior to the history behind its owner, the Witch House is the perfect Halloween activity. Judge Corwin lived in the house during the height of witchcraft mania in Salem and served on the court that would ultimately sentence the alleged witches to their deaths. With so much history, there is usually quite a long line for the tour, priced at around $8. But, if you’re a Halloween freak like me, the wait is totally worth it.


  • Ropes Mansion (AKA the Hocus Pocus House): Hocus Pocus. One of my first memories of my favorite holiday, Halloween. If you are a true member of my generation, you have seen the movie hundreds of times. Salem provides the opportunity to delve deeper into those childhood memories by visiting the Ropes Mansion, AKA Allison’s house in Hocus Pocus. With free tours, the line is usually incredibly long, though I highly recommend stopping by, at least to take a picture outside and explore the backyard garden. The house is located within feet of the Witch House, making it a quick and easy stop.


3. An Evening with the Paranormal at Hammond Castle

IMG_1805 (1)

Gloucester, Massachusetts45 minute drive from Downtown, Boston

There is nothing creepier than a 100-year-old mansion with ancient tombstones within the walls. Yet that is exactly what you will find at Hammond Castle, a sprawling estate created by a famous inventor (mad scientist?) for his beautiful wife during the 1920’s. The talk of the town both then and now, the mansion’s architecture and its contents are something out of a horror movie. The original owner was eccentric, to say the least, building pathways to nowhere and installing a weather machine in the indoor courtyard in order to play “tricks” on guests. With that being said, there are moments within the mansion where you can actually appreciate his taste, including the ancient windows brought in from France and the perfectly manicured gardens. However, with the skull of Christopher Columbus’s first mate as a highlight in the Great Room, the mansion is arguably more scary than scenic. Having been featured on Ghost Hunters, the Haunted Tour (taking place in October, priced at $15) is always a Halloween hot spot.

4. Admiring Fall Foliage at the Boston Common


Boston, Massachusetts

Any Bostonian knows, the Boston Common is a treat any time of the year (except maybe during the massive winter snow storms). However, with all of the Common’s trees, the leaves’ transition to fall is truly breathtaking. Even better, the maintenance workers often rake the leaves into big piles—you know where I’m going! I may be 25 but no one is ever too old to play in a big pile of fall leaves, especially at the Common.

That sums up my top four fall activities in Boston! I hope you have the opportunity to check them out within the coming months before things get way too cold for this Texas girl. Comment below to let me know what you think of my recommendations!

Photos edited by: Benchmark Imaging (

5 thoughts on “The Ultimate Guide to Fall in Boston

  1. Tanisha says:

    Hi Haley!!

    First of all, thank you so much for inviting all of us into a piece of your personal life. I think you starting this blog is such a wonderful idea and I very much enjoyed reading your first. I’m a prideful Bostonian so i enjoy reading about other people’s experiences when visiting or moving to this lovely city. I also enjoy reading of the attractions you’ve been to so far because it gives me ideas of some things to do on my days off.

    Congrats on a great first blog and I look forward to reading more from you. 🤗🏈💙


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