Salem Outfit Ideas – What to Wear In October

Salem Massachusetts owns Halloween like how the North Pole owns Christmas. And because of that, the whole month of October is one big long Halloween celebration in Salem. So many people plan a visit to Salem in October to be part of the fun, and the magic.

So how do you decide what to wear in October in Salem? We have a few suggested Salem outfit ideas to get you started.

Exploring the Wharf, Cemetery, Willows, Pioneer Village, and Winter Island

Salem has some areas that are “off the path” that are absolutely worth exploring! For this, you will want to make sure you have a jacket, shoes that are easy to walk in, and a super cozy hat. The Winter Island Hat is a super soft pompom hat that will keep you warm whether you’re on the water, or in the woodsy areas. Perfect Salem outfit idea.

Visiting Museums and Shops Downtown

When you’re walking around downtown and popping in and out of shops and museums (definitely check out the Peabody Essex Museum) you will want to have a light jacket, a small bag that you don’t have to think about, and a cozy scarf. The McIntire Scarf is an oversized cowl scarf that is no fuss, and will be the perfect accessory.

Going out for Social Hour

In Salem there are tons of awesome places to grab a drink or bite in the late afternoon / early evening. Many of these options include outdoor options, so you’ll want to be cozy. But since you probably want to travel light, the Anderson Ear Warmer is your perfect companion. It will keep you toasty, but if you find yourself warm inside, you can put it in a small bag for safe keeping. Pair it with a chunky knit and some fall boots, and you’re good to go.

Taking a Cruise Around Salem

Salem is right on the water, and it’s the perfect opportunity to see the area by sea! Escape the crowd of the city and get on a boat! It will be a little chilly, so you’ll want to bundle up! Pair a sweater with some warm pants, and top it off with the Essex Scarf.

Looking for some recommendations from locals? This post is for you!

Local’s Guide to Salem Massachusetts

When you have a business named Salem Style, you often get asked for recommendations by anyone planning a trip to Salem Massachusetts. I have compiled this guide with help from some friends, to give you a few ideas that are recommended by Salem Locals!

Where to Eat –

Howling Wolf 76 Lafayette St, Salem, MA 01970 –

“Great bartenders great margaritas” – Martina

Adriatic 155 Washington St # 1, Salem, MA 01970 –

“Great food, cozy ambiance.” – Patrick

Turners 43 Church St, Salem, MA 01970 –

“They have a cozy atmosphere with a very friendly staff. The seafood is fresh. The food is delicious.” -Allie

Kokeshi  41 Lafayette St, Salem, MA 01970 –

Awesome ramen that is the comfort food you didn’t expect you would be craving, especially on a chilly day.

Red’s 15 Central St, Salem, MA 01970 –

Great spot of breakfast. Don’t be intimidated by the line out the door, it moves quickly and it’s worth it!

Where to Drink –

Notch 283 Derby St, Salem, MA 01970 –

“Great Beer and Atmosphere” – James

Opus 87 Washington St, Salem, MA 01970 –

“Huge variety on their menu and gorgeous ambiance.” – Sarah

“Great bar and vibes and awesome cocktails!! Always consistent.” – Rachel

“Great Bartenders and live music.” – Shay & Chris

Ledger 125 Washington St, Salem, MA 01970 –

“They make the best drinks” – Lindsey

“It’s new and I like the vibes. This is the head chef’s second restaurant – his first one being a huge success.” – Amy

Far From The Tree 108 Jackson St, Salem, MA 01970 –

A few blocks from downtown, Far From The Tree is a great place to grab a drink and hang out. Their menu is always changing, so get a cider flight of 4 ciders to be able to try a variety!

Where to Shop –

Roost 40 Front St, Salem, MA 01970 –

“Great gift selection and I always find something for myself.” – Sarah

HausWitch 144 Washington St, Salem, MA 01970 –

“If you’re into it- the classes/workshops/meditations offered at Hauswitch. The calendar is on their website and there’s almost always a beginner class! The vibes are welcoming and I always leave feeling centered and “witchy”, no matter what the event was.” – Amy

The Cheese Shop 45 Lafayette St, Salem, MA 01970  –

“Friendly staff and delicious selections of meats and cheeses.” – Allie

What to See

Peabody Essex Museum 161 Essex St, Salem, MA 01970 –

“Come down to do historical site seeing” – Taylor

The Trolley 8 Central St, Salem, MA 01970 –

“So many fun stories and you can hop on/hop off all day” – Martina

Salem Food Tour –

“You get a guided walking history tour and get to try the yummy restaurants” – Lindsey

Getting There-

Ferry from Boston 10 Blaney St, Salem, MA 01970  –

“Take the Ferry into Boston instead of the train/car.” – Patrick


You can take the train to avoid overpriced Salem parking. Pro tip – Find another station along the Newburyport/ Rockport line and park there.

Seasonal –

The Christmas Trolley  –

A special trolley tour that helps get you into the holiday spirit.

Essex Street in October

There is nothing like being swept up in the Haunted Happenings action right in the heart of downtown.

Hotel Salem Rooftop Bar 209 Essex St, Salem, MA 01970 –

Opening Summer 2018. We haven’t been here yet, but some of us have seen a sneak peek, and we’re pumped.

Extra Hidden Gems –

Polonus European Deli and Ice Cream 176 Essex St, Salem, MA 01970 –

Perfect spot to grab a bite for lunch or get a sweet treat to snack on!

Derby Joe 142 Derby St, Salem, MA 01970  –

“A small coffee shop down Derby Street with amazing coffee.” – Allie

Caramel 281 Essex St, Salem, MA 01970 –

Get a chocolate croissant or a few macarons and treat yourself!

The Landing Bar  10 Blaney St, Salem, MA 01970 –

Awesome outdoor bar right by the ferry dock with a great vibe.

Enjoy Salem!