Spooky Portsmouth: A Little History, A Little Mystery

Portsmouth can be pretty darn charming. It’s got a welcoming waterfront, more restaurant seats than residents, beautiful old houses, superb shopping, brick sidewalks and more history than you can shake a broomstick at.

And then there’s the spooky side.

Whether you’re a believer, a skeptic who enjoys a good story, or someone who thinks October is an excellent excuse to wander around town after dark, the City of the Open Door (our slogan!) has plenty of ways to get spooky.

After all, the city has been around for more than 400 years. You don’t get that old without gathering a few ghosts, weird stories, and things people still like to talk about.

Take a walk on the spooky side

Downtown Portsmouth was made for wandering, and fall is a pretty great time to do it. The days get shorter, the air gets crisp, and once the sun goes down, those old buildings take on a whole different vibe. (No, you probably can’t go inside them. But you can look curiously at them.)

Local walking tours delve into the stranger, darker and more colorful corners of Portsmouth history, mixing real events with legends that have grown around them. It’s a chance to see familiar streets from a slightly different perspective — and perhaps wonder what was happening here long before today’s restaurants, shops and galleries moved in.

For an even deeper dive into Portsmouth’s past, the Portsmouth Historical Society offers plenty of opportunities to explore the city’s history. Some of it’s spooky. Some of it’s surprising. And some of it is simply a little bit off-beat (which is fun!).

Say hello to the dearly departed

You don’t need a tour guide — or a thermal imaging camera — to conjure up some of Portsmouth’s oldest stories (but the tours do make it better!)

The city’s historic burial grounds are fascinating places to explore during daylight hours. Point of Graves Burial Ground, near the waterfront, is the city’s earliest cemetery, dating to Portsmouth’s colonial era. It features old stones, including The Elisha Briard Stone (1718): with the Latin inscription Memento Mori (“Remember Death”) — a reminder of mortality. You’ll also spy a very interesting turnstile gate that truly sets it apart. And leaves you on the side of it you choose!

There is also the historic North Cemetery—the second oldest in the city— along Maplewood Avenue, where gravestones, family names and centuries-old dates provide a connection to the people who lived (and died) here before us.

Get your Halloween fix at Strawbery Banke

For family-friendly frights, Strawbery Banke Museum gets into the Halloween spirit with Ghosts on the Banke, taking place October 16–17 and 23–24, 2026.

They invite you to “Meet wayward pirates, visit a mysterious fortune-teller, hear ghostly tales, make giant spider webs, dance to haunting music, and play games for prizes”.

While it’s designed for children ages 4-8, they do say guests of every age are welcome.

Go looking for the weird stuff

If your preferred level of spooky is more curious than terrifying, downtown has plenty to keep you entertained.

There are witchy storefronts and emporiums that sell wands and wonderful talismans. Think Harry Potter times 11.

While you might not encounter a ghost, you might, find a very unusual gift for someone who has everything (but not a potion!).

And then: Halloween itself

For Portsmouth at maximum Halloween, there’s one night to circle on the calendar.

October 31.

The Portsmouth Halloween Parade returns Saturday, Oct. 31, 2026, at 7 p.m. Every single year. The community-powered parade begins at Peirce Island and makes its way through downtown, with hundreds of costumed marchers and thousands of people lining the route. Anyone can join — there’s no registration required — so you don’t have to be a professional parade person, a theater kid or goth. You just need a costume and a willingness to march.

And the costumes? They’re often spectacularly creative (and Instagram-worthy if you can get the right streetlighting).

This isn’t a parade where everyone shows up dressed like the same batman, a ghost and a pumpkin. Portsmouth’s Halloween tradition is delightfully unpredictable, with homemade creations, elaborate group costumes, musicians, giant things, tiny things and things that are difficult to explain but very fun to watch.

If marching isn’t your thing, find a spot along the route (Market Square? Daniel Street?) and watch the spectacle roll – or dance – by. There are Thriller Dancers and the crazy creative Monster Troupe (and we hear this is their last year!).

Just remember: Halloween in Portsmouth is a real downtown event, so check the parade information for parking restrictions and street closures before you arrive.

Make a night of it

The best part of spooky Portsmouth is that you don’t have to make Halloween the entire evening.

Start with some history. Take a ghost tour. Wander the old streets. Have dinner and/or a drink downtown. Find a cozy spot for dessert. And, on Halloween itself, join the crowd for the parade. Keep it going as long as you can!