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How to Spend Halloween in Salem Massachusetts

EDITOR’S NOTE: This post was updated October 2017.

Halloween in Salem, Massachusetts. You seriously have to experience it once in your life.

I happen to have seven Halloweens in Witch City under my belt, but that’s because I went to college in Salem and lived there after graduation for a year and a half. After all that time, I learned a thing or two about spending Halloween in Salem.

WARNING: Some of these photos are from college. A time when a 3.2-megapixel point-and-shoot camera was within my budget, and I wasn’t aware of blurry shots until the next morning. I’m pretty sure I was still using an actual 35mm camera my freshman year, too. But, these photos show some of the most fun I’ve ever experienced on Halloween, and I hope it inspires you to plan a spooky holiday in Witch City.

how to get to salem mass on halloween

Halloween in Salem Year 1: 2002

I’ve never really been one to spend a lot of money on costumes. As you can see I strapped on a pair of wings and called it a day. Or better yet, a couple of days. My first year living in Salem I didn’t feel the pressure to have a different costume for each party I went to, plus a new one on the actual day of Halloween.


How to get to Salem on Halloween

Do not drive to Salem! It is already a difficult city to get to, tucked away on the coast with no direct exit from nearby highways. All the fun and attractions are located in the oldest part of the city that was established in the early 1600’s, so roads are narrow and parking is limited. Plus, a lot of locals are just trying to live their day-to-day lives amongst the hordes of tourists.

Do yourself, and the locals, a favor and take public transportation to Salem on Halloween instead. The Massachusetts Bay Transit Authority (MBTA) stops at the top of Washington Street, a quick walk away from all the action. From North Station in Boston, take the Outbound Newburyport/Rockport commuter rail (the purple line).

A $10 roundtrip special event ticket can be purchased at North Station on October 31 ONLY. Otherwise, roundtrip fare will cost $15. Click here for details.

Halloween in Salem, Ma

Halloween in Salem Year 2: 2003

I’m pretty sure this was our first house party. The apartment, which I lived in for three years, was a quick 10-minute walk to downtown Salem. Friends were always taking advantage of a free place to stay in Salem for Halloween night.

Halloween in Salem, MA

Halloween in Salem Year 3: 2004

Being a gumball machine is so much fun. You should try it! I only paid for the balloons for this costume, which came to $3. Some other costumes I’ve worn that were basically free include Where’s Wanda (like Where’s Waldo), a bunch of grapes and “gold” (neither one pictured), and a cavewoman (borrowed from a friend).


Tips on choosing a costume for Halloween night

  • You’ll be walking around cobbled streets or standing in crowded bars most of the night, so choose your costume based on comfort and warmth.
  • I do not recommend high heels, no matter how well they pull your ensemble together. This tip is for men just as much as it is for women.
  • Incorporate layers and cold weather gear as much as you can – it can be cold at the end of October!
  • Don’t spend a lot of money on a costume. Lots of costumes can be created with clothes and accessories from around your house or a thrift store. Or borrow costume materials from friends!
  • Make sure you can easily use the bathroom (especially a porta-potty) while in costume!

Halloween in Salem, MA

Halloween in Salem Year 4: 2005

The weather on Halloween in Salem is always a crapshoot. It’s usually quite cold and I’ve even seen snow on October 31, which is fun. It’s also fun to run around the city dressed up as a cavewoman in a one-shoulder cheetah fur dress when it’s abnormally 65F degrees out!


Tips for bad weather on Halloween

Choose your costume wisely (see above) and the weather may not be an issue.

  • If rain is in the forecast, bring an umbrella or get one of those awful clear ponchos. You don’t want to cover up your awesome costume with a raincoat!
  • Find a place to hang out for the night. Many bars charge covers on Halloween night, but it might be worth it to be out of the bad weather.
  • Wear base layers underneath your costume to help you stay warm.

Halloween in Salem, MA

Halloween in Salem Year 5: 2006

I actually don’t have any photos of myself in a costume this year. Strange. Plenty of pictures of going out with friends while they are in costume or hanging out in costume shops, though.


Things to do in Salem during the month of October

There is almost too much to do and see in Salem. Here’s a short list of my favorites.

  • The Derby Street Carnival. It’s located right downtown on Derby Street. Ride the Ferris wheel and eat fried dough and curly fries.
  • Hocus Pocus Filming Locations. There are many! The Ropes Mansion, Salem Common, Philips Elementary School, and Salem Old Town Hall are all easily accessible in downtown Salem.
  • Walk Chestnut Street. This quiet side street is lined with historic mansions that display the wealth of Salem’s early merchants.
  • Visit Pickering Wharf. Home to the Salem Maritime National Historic Site, The Friendship, Derby Wharf Light Station, and the US Custom House, the wharf is a hotbed of history. Plus it’s full of shops, restaurants, and a terrific view of the boat-filled Salem Harbor.

Halloween in Salem, MA

Halloween in Salem Year 6: 2007

This was the year of multiple costumes. I also spent real money (like more than $3) on a packaged costume and multiple accessories for another. It was my last hurrah before moving to California, so I went all out! I also wasn’t a struggling college student anymore and could afford to spend a little extra.

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Halloween in Salem Year 7: 2016

Things have changed a little since my college days. It’s less about drinking and mayhem and more about soaking up the festive buzz in the air.

Last year, I spent my first Halloween in Salem after living in California for five years. My friends and I are now in our 30’s and their families are beginning to grow. I handed candy out to trick-or-treaters from my friend’s stoop for the first time ever.

Tips on spending Halloween in Salem from someone who's done it SEVEN TIMES (and counting). Transportation, costumes, where to eat, and more!

Mercy Tavern, a new restaurant on Derby Street, is a must-visit spot.


Where to eat and drink in Salem

I like to visit friends who still live and work in the area at least once a year, usually in October, but these are my favorite places to eat and drink year round. Give one or two of them a try while you’re in town! Be prepared for crowded spaces, long waits, and menu and take-out policy changes during the month of October.

Coffee

  • Jaho Coffee & Tea at 197 Derby Street
  • Derby Joe at 142 Derby Street
  • Front Street Coffee House at 20 Front Street

Food

  • Howling Wolf Taqueria at 76 Lafayette Street
  • New England Soup Factory at 140 Washington Street
  • Mercy Tavern at 148 Derby Street
  • The Ledger at 125 Washington Street
  • Flying Saucer Pizza at 118 Washington Street

Drinks

  • Witches Brew at 156 Derby Street
  • Sea Level Oyster Bar at 94 Wharf Street 
  • Victoria Station at 86 Wharf Street
  • Far From the Tree Cider at 108 Jackson Street

If you can’t make it this year, start making plans for next October!


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