How to live your best life during an October visit to Salem, MA

We all want to be living our best lives, right? Planning an October visit into Salem can be chaotic, so the following are the ways you can enjoy your visit the most, in my opinion.

Before you get there…

Plan ahead. I know I’ve said that before, but I’ll say it again here. Plan as much as you can, ahead of time. Buy or download a map of Salem, get your hands on a few guides, work your way through my Countdown to Salem workbook, follow accounts on social media that deal with travel and tourism in Salem, etc. October is a very busy time in the witch city and those that plan will have an easier go of it.

Book your hotel early. Salem is home to many accommodations, so figure out which ones you’re interested in and book your room as soon as reservations are available. Sign up for newsletters, follow their accounts on social media and keep your eyes open.

Map it out. I suggest at least looking over a map of Salem ahead of time to sort of understand how it is laid out. During my first visit into the witch city I remember walking the same loops over and over again!

Once you’re there…

Now the fun begins.

First, in order to live your best life in the witch city, you’d need to book a hotel room IN Salem. None of that travelling back and forth stuff or moving the car. To make it an easy vacation, stay right in the city.

Wake up bright and early and walk to the Ugly Mug Diner for breakfast. Drink some coffee out of a mismatched mug and relax while you (and the city!) wake up. I personally really like their omelettes.

Next, while you’re waiting for all of the businesses in Salem to come alive for the day, hop onto the Trolley. It takes about an hour and will loop you around to many historic sites and landmarks in the area. While you’re aboard, make note of the ones that stand out to you so you can revisit them once the Trolley ride is done. This is also a good way to get an idea of the layout of Salem and what attractions are close by, etc.

The other attraction I pretty much always suggest (besides the Trolley) is the House of the Seven Gables. I think the tour guides do such a great job and I have learned something new each time I’ve visited. The property is so pretty and I really like their gift shop. Once you’re off the Trolley, I recommend stopping by the Gables for a tour! Once you’re done there, you’re super close to the Wharf. Take a walk down to the Derby Wharf light or stop into the shops along the water.

If you’re a fan of seafood, grab a table at a restaurant where you can see the wharf. Sea Level is always a popular choice and it’s right there. If you’re not a fan of fish (like myself) I’d suggest stopping into Brodie’s for a burger. They have one of my favorites in Salem which is called the Brodie Burger.

Grab some coffee from Jaho and if you’re able to, hop onto the Schooner Fame! I went out on the water with them a few months ago and had such a good time, you guys. Seriously. It was so relaxing and I had a blast, truly.

Once you’re done on the boat, walk up to Jolie Tea Co. for a drink and a scone! I love the whole vibe of the place. If you’d rather a macaron, I’d suggest heading to Caramel French Patisserie for a lemon one. They’re my favorite in Salem!

Now that you’re refueled, I’d suggest wandering the attractions that caught your eye while you were on the Trolley. Take your time and enjoy walking around to Salem’s gorgeous and historic sites. Take in some good people watching, enjoy everyone’s costumes and have fun taking pictures.

When dinner time rolls around I’d say a stop into Rockafellas is in order. Their food is average “American fare”, however it’s the window booths that I am always after. Especially near Halloween, when people are walking around in costume! Relax, have some dinner and a drink and take in the scenes of Essex street.

I think following up dinner at Rockafellas with a drink at The Roof is an awesome way to wind down the night. The Roof is located atop the Hotel Salem and offers a nice view of the city. Hang out, have some chips or snacks if you want something to pick at and enjoy.

Lastly, you wouldn’t be living your best life without cookies from Goodnight Fatty to wrap it up. Serving on the weekends, they can be found slinging the most delicious cookies in Salem.

I hope this helps! My little run down of an awesome day in the witch city is based on my own opinions and preferences of course…feel free to comment below with your picks. Enjoy!! <3