When you think perfect small town for a spooky fall trip, you might think Sleepy Hollow or Amityville, but we think Salem, Massachusetts.  Home of the infamous Salem Witch Trials that plagued the tiny town in the late 1600s, today it’s quite possibly the most bizarre blend of quintessential New England charm and over-the-top occult that you could ever hope to find.

My brother and sister-in-law live in Salem, which is considered a suburb of Boston, and their apartment is a beautifully renovated loft in what used to be the Salem Jailhouse, if you can believe it.  Always in the mood for a good skin-tingling story, when they first moved in, I asked if it was haunted.  My brother, ever the cynic, rolled his eyes and told me I was crazy.  

We made a trip to visit them on Halloween last year, and we found the energy of the bustling little town very bizarre, creepy and charming.

Looking for a fun, family-friendly fall trip to take this year? Salem is an awesome option and these are the things that should definitely make your list!  

Salem Witch Trials Memorial

If you’ve spent any amount of time in a high school English class then chances are pretty good that at some point or another you had to read The Crucible by Arthur Miller, a popular play about the witch trials that Salem is so famous for.

It’s one thing to read about the trials, but it’s another to see the location where they happened and the stone walls of the Salem Witch Trials Memorial bearing the names of the 26 people who stood trial for witchcraft and were ultimately convicted and sentenced to death.  

Perhaps not for little kids, it’s a must-see for families with older kids, if for no other reason than to show that those crazy things you read about in English Lit did actually happen.  

The Burying Point

I know it’s a bit weird and morose, but I confess to being a sucker for ancient cemeteries, especially those that have a lot of historical significance to them.  The Burying Point Cemetery (also called Charter Street Cemetery) is located just on the other side of the Salem Witch Trials Memorial and is one of the oldest cemeteries in the United States.  It contains the final resting place of many of the judges and magistrates who oversaw the trials, along with other notable figures from the time.

We totally get it if staring at headstones isn’t your thing.  But if you happen to appreciate the history like I do, the Burying Point is worth a walk-by. And in the fall, with the surrounding oak trees changing color, the cemetery itself is hauntingly beautiful. 

How cute is this little lighthouse?

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Derby Wharf Lightstation

For those looking for a respite from all the mysticism and madness, then the Derby Wharf Light Station is a must.  Located down by the water, a safe distance from all the ghouls and goblins, the small lighthouse is situated at the end of a long spit of rocks and totally walkable.  Perfect for a morning or afternoon stroll, and if you walk all the way out to the end and turn and look back, the autumnal view of Salem is nothing short of postcard perfect.  

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Bewitched After Dark Salem Walking Tours

If you’re looking for an entertaining and educational way to experience Salem, then we say skip the museums and instead do a walking tour of Salem with Bewitched After Dark.  Their interactive walks are a perfect way to learn about the town and also walk off any lingering energy the kids might have after that hot chocolate from Jaho.  Consistently ranked in the top walking tours of Salem, the tours are hosted by locals who have an expansive knowledge not just on the witch trials, but also on Salem’s colonial and maritime history as well (yes, that includes pirates).  Add to that a little bit of folklore and legendary hauntings, and you’ve got yourself the makings of a wicked good time.  

For those that are maybe a little fearful of walking the streets of Salem after dark or have little ones in tow who likely won’t make it past eight (go ahead, blame it on your kids), they have late afternoon walks as well.    

Could you find a better depiction of autumn?
Photo courtesy of Travel Channel

Salem foliage

Okay, so dead leaves might not sound like something you would go out of your way to visit a town for, but trust me when I say that there is no autumn quite like a New England autumn.  There’s something about the smell of the crisp ocean breeze coupled with the rich red, orange, and yellow hues that is pure magic.  With the festive atmosphere and Halloween decor all over the town, it’s quite possibly the most picture-perfect version of fall that we’ve ever seen.

Goodnight Fatty

We never actually got to go to Goodnight Fatty’s because the line was so long it wrapped around the block – that’s how good it is.  But my brother and sister-in-law and their friends all rave about the weekend pop up joint that sells the most amazing cookies and soft-serve ice cream.  And judging by the smell alone, their cookies must be nothing short of heaven.  

Part of their charm is that they’re only open on the weekends, and only in the evening (after 5 on Friday and Saturday, after 2 on Sunday), selling rotating concoctions you can’t get anywhere else, like frosted animal cracker cookies, peanut butter and Reese’s Pieces cookies, and your traditional cookie staples.

Wicked Good Books

We’re book people in my family.  And by that, I mean that I’m a book person and the rest of my family begrudgingly allows me to drag them into every cozy little bookstore we happen to cross in our travels.  

So when we passed Wicked Good Books, as we were walking around town, I was instantly hooked and had to duck inside, to the audible groans of my kids and husband.  But it was one of the more adorable bookstores I’ve ever been in, and I consider myself a connoisseur.  

As the name suggests, the bookstore sells all sorts of dark thrillers and spooky spell books befitting its locale and also boasts a large section dedicated specifically to books about Salem and New England.

Even if you’re not a reader or in the habit of buying physical books (I get it, I’ve got a Kindle too), it’s definitely worth a stop, if for no other reason than to experience the fun and cozy atmosphere. 

Brick on brick on brick!
Photo courtesy of Salem.org

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Walk Around Salem Proper

Part of the charm and mystique of Salem are the many winding alleys and side streets that, around Halloween, can only lead to double, double, toil and trouble.  For the Harry Potter obsessed among us, it reminded my kids of Diagon Alley, though maybe a little bit brighter and more welcoming.  Around Halloween, the quaint cobbled streets are teeming with all manner of ghoulish and masked figures, fortune tellers offering to read your palms, magicians tricking crowds with sleight of hand.  The colonial brick storefronts are bedecked with fake cobwebs, witches’ brooms, and black cats. And the local cafes and coffee shops sell all the festive fall treats – apple cider, candy corn, and pumpkin-spiced everything.

I’m not a big Halloween fan (I’m more of a Christmas and Thanksgiving kind of gal) but even I found myself getting in the spirit in this little town.  The energy is truly infectious and nothing short of magical. 

If you’re needing a good fall trip that the whole family will enjoy, Salem can’t be beat.  Just go prepared for some chills and thrills mixed in with your quaint New England charm.

Morgan is a brand designer and writer who splits her time between managing her creative studio, Atlas + Anchor, and writing about her lifelong love affair with travel. A wanderluster at heart, she’s a big proponent of exploring the roads less traveled because they often lead to amazing views, memorable stories, and the most unassuming but life-changing restaurants. Originally from Ohio, Morgan now lives in the heart of Chicago with her family and is quite possibly the only person within city limits who hates deep dish pizza.

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