Hello, Reader.
I know, I know… it's still technically summer. The A/C is still running, the pool floats are still out, and yet here I am, standing in my kitchen, baking sourdough and daydreaming about flannel and pumpkin spice like the basic fall girl I proudly am.
I walked out of work at 7 a.m. the other day and the Indiana humidity hit me like a wall. I just stood there thinking, "I can’t wait for cool, crisp fall mornings." Even though the calendar says we've got plenty more of summer left, my friends have started talking about their kids going back to school in the next couple of weeks and that's usually my sign that things are about to change.
Here's the thing about fall travel: it sneaks up on you.
One minute it's July and you've got all the time in the world. The next, the kids are back in school, everyone's calendar is booked solid with soccer practice and PTA meetings, and suddenly it's October and you're wishing you'd planned that trip when you had the chance.
If a fall getaway is even a little bit on your radar (especially somewhere with the kind of seasonal magic that draws crowds, like Salem, Massachusetts), now is the time to start looking at dates. Popular spots book up fast once the leaves start turning.
Which brings me to the real reason I'm writing today.
Salem wasn’t the original plan. But it became a really cool part of it.
A few years ago, we planned a New England road trip to meet up with my sister and her family, who were flying in from California. We were going to go to Kenny Chesney's closing show in Foxborough (before he started his summer residency at The Sphere in Las Vegas), then explore Boston and Cape Cod.
With five of us, we wanted someplace we could stay together and enjoy every bit of our time on the East Coast. Salem seemed like the smart choice. Close enough to get to the show easily, quieter than the city, and a fraction of the cost. Plus, we’d get to explore the legend that is Salem. Bonus!
We spent two full days in Salem itself and were enchanted by its quirkiness and history.
- We rode a tram through town on day one and got the kind of oral history lesson you can't get from a guidebook.
- We ended up in actual wooden pillories outside the Witch Dungeon Museum, laughing too hard to hold still for the photo.
- We wandered through the New England Pirate Museum and somehow left more invested in 18th-century shipwrecks than we expected to be.
- And we stood at the Giles Corey memorial, a man pressed to death during the witch trials in 1692. Standing there, we felt the weight of a history that this town doesn't shy away from, even while it sells witch hats year-round just two blocks over.
And then there were the quieter moments: walking out to Winter Island as the sun dropped low over the harbor, the lighthouse glowing against a sky doing its best pastel impression.
A candlelit ghost tour that was equal parts spooky and genuinely fun.
And one of our favorite Salem touches: police cars that have a witch on a broomstick on the side. The whole town commits to the bit, and somehow it never feels tacky.
We also learned something we didn't expect: apparently, it’s absolutely acceptable (and expected) to go out in full costume year-round in Salem. We saw multiple witches and warlocks walking around in August. Respect for the dedication. I can only imagine what October looks like.
If Salem's on your radar for this fall, here are some things you should know:
- Give it more than a day trip if you can. Less time will just leave you wanting more.
- Do one of the Salem history tours early to get your bearings.
- Don't skip the museums just because they sound touristy. They absolutely are that, but the history in this town is real and it deserves more than a passing glance.
- And, if you can, walk out to Winter Island in the evening. It's a completely different side of Salem than the one you'll see on Instagram.
I'll be sharing our full Salem guide on the blog soon, plus we'll be building out the rest of this New England road trip guide over the next few weeks: Boston, Cape Cod, Kennebunkport, and a mysterious stone circle in New Hampshire.
So, if fall travel is calling your name, stick around for some great inspiration. 🍂
Now tell me: Is Salem on your fall bucket list, or have you already been? Hit reply and tell me about it. I read every single one of the responses we get and I'd love to hear what drew you there (or what's holding you back).
Until next week... I'll be thinking cool thoughts while weathering the summer heat and humidity.
With love,
P.S. If this email has you dreaming about a fall getaway, here are the travel planning sites we use most often when we're mapping out our own adventures:
🏨 Booking.com or VRBO.com for places to stay.
🧙🏼 Viator for tours, experiences, and local gems.
🏴☠️ Tripadvisor for reviews and even more things to do.