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Solo Traveling the Massachusetts North Shore: Salem Day Trip Itinerary

This past November, I took a little solo getaway through the Massachusetts North Shore region, and if you'd like to explore some other beautiful little towns with me, you can catch the links here:

Welcome back, friends. Let's talk about Salem, MA, a town that's known as the Halloween hot spot of New England. This was my second time visiting Salem, and as I mentioned in a prior post, I was last there about six years ago the weekend before Halloween so we could really experience the whole spooky season vibe. It's such a fun place to visit during the month of October, but be forewarned - it's busy. And I mean, BUSY. The streets were packed with people, parking was a nightmare, and it was hard to get tables at restaurants. Especially on weekends. But, there certainly is just something about Salem in October that's unique and quite an experience all on its own.

Despite having had the quintessential experience in the thick of Halloween celebrations, I've always wanted to go back, pretty much any other time of the year, to see Salem in a different light. And I'm laughing as I type this because this trip, I went back the weekend after Halloween - and it was vastly different. Far fewer crowds and plenty of room to walk around. I was there on a Saturday morning/afternoon, and the foot traffic definitely picked up by noontime, but I felt like I had more space to wander and really take it all in. 

Salem is a great little town to explore and wander. It has deep roots in maritimes history, and, of course, the Salem Witch Trials. And much like its neighboring towns (Marblehead is a short 10-min drive away), it has gorgeous tree-lined streets and historic homes at every turn. While the witch vibe is alive and well here (the store fronts won't let you forget it), you still also feel like you're in a picturesque New England town.

I will be honest, I really like Salem - a lot - but it's not my favorite of the North Shore towns, and I think it is because it does have such a strong theme to it. A lot of the shops are all centered around witchery and magic (some of them having a really, kind of, er, cheapened feel to them) and there are times where the town just feels like maybe it's lost some of its authenticity in catering to those who are looking for that kind of experience. It's not necessarily a bad thing, and it can be really fun to immerse yourself in, and just go along for the ride. But, I did want to mention it so it's something you're aware of before your first visit. That said, I still love visiting, and would go back in a heartbeat. 


Salem is an extremely walkable town, and in about 7-8 hours, I pretty much saw all the major sites, and that included spending a couple of hours watching the sunrise at a local park, and a leisurely lunch. You can definitely do it as a day trip. Before I went, I actually made a little itinerary for myself to maximize my time, and listed out everything in order based on the direction I was moving. But once I was there, I realized that pretty much everything is within a half mile from one another at most, so you can definitely wander without a plan, and you won't miss anything. 

Prior to your visit you'll also want to plan ahead for parking, especially if you want to visit in October. The town actually has an entire website dedicated to parking (click here), and I found it super helpful. I chose to park at the South Harbor Garage, and it was great location that was accessible to all the places I wanted to see. Even in November, I didn't see any available street parking while driving around when I first got there (although, I didn't look that hard because I'm more of a convenience over cost person when it comes to parking). 

If you're staying overnight and driving into Salem, try to get a hotel with parking to make it easier on yourself. Otherwise, you'll have to find a parking spot/garage and pay the nightly rate, and then walk to your hotel. There are only a handful of hotels in Salem that offer on-site parking, so be sure to take that into consideration. It's a small, historic town, so you'll be happy you planned ahead once you're there. 

Lastly, as I'm sure you've figured out, October is the town's peak season, so plan for higher hotel prices and get reservations for hotel, restaurants and any tours you want well in advance. When we went years ago in October, we kind of planned it last-minute-ish (I think about 3 months ahead) and pretty much all the hotels were sold out, and the ones that did have rooms available were insanely expensive. We ended up staying in neighboring Marblehead and commuting in. 


Just visiting Salem for the day and want to make the most of your time? I'm going to share my basic itinerary to make it easier for you. For more detailed information on the sites to see, keep reading.

- Drive to Winter Island Park to either watch the sunrise, or see the lighthouse before you start your day in Salem. 
- Drive into Salem and park at the South Harbor Garage once you're ready to explore the town by foot. Or, park at your chosen spot or facility based on your research that you already did based on my helpful tip :)
- Walk on Derby St toward Congress St, and pop into Jaho Coffee and Wine Bar for a warm drink and a breakfast treat on the go (or have a seat on their outdoor sidewalk patio). 
- Once you've got your drink or have refueled yourself with some treats, keep walking down Derby toward Hodges Ct., and in a few minutes, you'll see the Maritimes Historic Site park. Take in views of the Sail Loft building, and walk down to Derby Wharf Lighthouse.

- Once you've gotten your fill of the Maritimes park, head on over to the House of Seven Gables (book a tour in advance if you want to go inside), and wander the neighborhood to see some really pretty historic homes. 
- Pop into Ye Old Pepper Candy Companie for some sweets to take home with you.
- If you want to visit the Salem Witch Museum, it's on your way to the main town area, so this would be a good time to plan for that.
- Head on over to the Essex Street Pedestrian shopping area to visit some shops.
- Stop into the Lobster Shanty for lunch (it gets popular, and they don't take reservations, so there may be a wait). 
- At the Lobster Shanty, you'll be across the street from the old Town Hall building, which was used in the movie Hocus Pocus.
- Walk over to the Witch Trials Memorial, which is just a few minutes from the Lobster Shanty.
- Head over to the Witch House, and pre-book a tour if you want to go inside. If you want a picture of the exterior, you may also want to be aware of tour times, otherwise your pictures will have a line of people in it (a mistake I made, which is why my photos below are taken at weird angles).
- A few short steps from the Witch House is Allison's house from Hocus Pocus (318 Essex St.), and is set in a really beautiful residential neighborhood that's great for wandering and getting lost.

- Dinner at any of the great restaurants in Salem - take your pick! Josh and I loved Bella Verona when we visited together. 
- Consider a spooky ghost or witch tour after sunset.
- Walk to the Salem Common, which is usually lit up with orange lights during Halloween. 
- If you happen to be near the Witch House at night, it's worth it to walk by to see the windows glowing with a soft light, and the pumpkins lit up in front of the house. You'll see pictures of it all over Instagram, and it's the definition of Halloween in one perfect moment.


So, let's get into the best things to do and see while in Salem - some of which having nothing to do with witches at all (if you can believe it!). 

I had no idea that Salem had two lighthouses. Both are walkable from town, with one being a bit more of a hike than the other. I spent my morning watching the sunrise at the Winter Island Park Lighthouse, and it was stunning. I pretty much had the whole park to myself that morning, and the sun rose right up over the water, and illuminated the little lighthouse perfectly. Winter Island is about a 2-mile walk from the center of the main town area, but it does have a good-sized parking lot if you drive. If you're in Salem just for the day, I'd recommend coming here first before parking in Salem, or as you're leaving the for the day.

Winter Island is a very small little park, but it was so serene and peaceful here. It was one of my favorite things I did, actually. Once you park your car, you'll immediately see the lighthouse to your left, but there some walking paths that'll take you to some benches that overlook the lighthouse, or lead down to the shoreline to walk right up to it. If you chose to get close to it via the shoreline, just know the rocks are very slippery. I wore Bean boots, which have a good amount of grip, and was sliding all over the place. It probably wasn't the safest thing to do while there by myself, but I learned that a little too late.

The second lighthouse in Salem is Derby Wharf Light, and you can easily access it by walking from town. It's located right by the Maritimes History waterfront area, and it's a lovely little walk down a rock wall/gravel foot path. The lighthouse sits at the very end, and it's just a small little one that's absolutely adorable. I got there early morning, about two hours after sunrise, and had the whole thing to myself for about 30 minutes. After that, it seemed to be the place for morning walks with dogs and strollers, and I can see why. 

The Martimes History Waterfront area is right by Derby Wharf Light, and a really pretty little place to visit. My favorite thing here is the old Sail Loft building, which is just so stoically weathered, and perfect. This area is very small, but a nice little reprieve from the town.

Right around the Maritimes History Waterfront are a few sites that are worth scooting over to. The House of Seven Gables is a short 5-min walk from the waterfront park, and was made famous by Nathaniel Hawthorn's book (titled House of Seven Gables). The house was built in the 1660's, and in order to walk the grounds and see inside, you have to pay for a tour. You can see it from the side street, though, and since I traveled during COVID and wanted to stay as far away from people as possible, I just glanced at it quickly from the street to get this view.

Close by is also the Stephen Daniels House, which is the coolest black and red historical home (now converted into a B&B) that's really just fun to see in person. It's located at 1 Daniels St. In fact, that whole neighborhood is really nice for a leisurely walk, and you'll find some really pretty old homes. To read about the history of this house in particular, pop on over here)

Look closely to see the red windowpanes.

This house is on the same street at the House of Seven Gables. You guys know I love my white houses with white walls,
but I loved chasing after all these dark historic homes on this trip.

Much like Marblehead, you'll see homes in every color while wandering the side streets.

Heading into the main town area, you'll stumble across the Essex Street Pedestrian Mall, the Salem Witch Trial Memorial and the old Town Hall next. You will probably recognize the old Town Hall from Hocus Pocus (where they filmed the Halloween party scenes). The rest of this cute little section of town is mostly home to shops and a few restaurants, as well as the Peabody Essex Museum. I personally found the shops in this section to be a little - underwhelming. But, I did love the Wicked Good Books store. It's very small, but the creek of the old wood floors as you walk around and flip through book jackets is such a nice feeling. The folks working the store were so friendly - I won't be able to skip this place whenever I visit (but I also have a thing for book stores, so ... ).

Essex Street Pedestrian Walkway. 

I personally really loved visiting the Salem Witch Trials Memorial. It's not a happy place, by any means, but people here are generally very quiet and respectful of its symbolism, and it's actually quite thought-provoking and allows you some time to reflect on the history of the town in an authentic way. The memorial is very primitive and is home to 20 granite benches that form a U-shaped walkway, and each bench is engraved with the names of the 20 victims of the Salem Witch Trials.

A bit further down from the memorial and pedestrian shopping area is the Witch House, which was home to Jonathan Corwin, a judge at the Salem Witch Trials. They offer tours of the inside of the house (which I have never done), and this house is said to be the only one standing today with direct ties to the trials. If you visit during Halloween season in the evening, I've seen pictures of this house with lit pumpkins in front, which makes for probably best insta-worthy photo moment in town. 

I didn't get a picture during this trip, but I had Josh take one during our last visit. In the center of town is the Bewitched statue, which is kind of - well - a little weird looking, but still fun nonetheless. If you look close at her face, you'll probably cringe a bit. But, since I was named Samantha because my mom's favorite show growing up was Bewitched (and since it's also one of my favorite shows), I had to do it.

Me from six years ago!

One fun thing to do in Salem, which I did during my visit years ago (but not this trip) is visit a psychic. Now, I'm honestly not at all sure if I believe in psychics, or even people with a strong "sense." But, that said, I'm not sure if I don't believe it either. And here's why. Josh and I decided it would be fun to visit a psychic together, so we had a reading at Magika. The gentleman who did our reading said we would buy a lot of land and "something about trees" that he couldn't see clearly (we bought our house, which has 25 acres and a tree farm, a few years later, even though we weren't looking to do so), called out that Josh's dad and I had the same illness (I had a turtleneck on to hide my thyroid scar, but we both had thyroid cancer), that we got married in a town famous for horses (True - Saratoga Springs, but that could have been found online somewhere) and a lot of other small things that were accurate. The land thing totally threw me, which I didn't realize until months after we bought our house. I turned to Josh one day and was like, "Babe, that guy in Salem said this would happen!" and we were both like "That is so weird." So, all that to say, it was really fun and exhilarating, and we enjoyed it. I would probably even do it again sometime. Keep in mind it can be expensive, and like I said, not sure how much is an illusion. But, when in Rome, right? 

One thing we had read prior to booking a reading is that you shouldn't allow the business to take down more than your first name and a phone number (and at Magika, that was all they asked for to secure the appointment). And when you arrive, unless you're dying to know something specific, not say why you're there and just ask them to tell you things they feel or see. So, that's what we did, and we left feeling like it was worth it.


My favorite place to eat in Salem is the Lobster Shanty, which is really popular (lines begin to form outside before opening, so plan accordingly). I had to come back here for lunch after loving it the last time I visited, and the food was just as great. They're famous for their lobster martini (which I have never tried), and all the seafood dishes I've had have been awesome (and, of course, super fresh). The drinks here are also strong, my friends. I ordered a gin cocktail during my recent visit, and it was huge, and pretty much pure alcohol. I definitely had to walk it off for a bit before I felt normal again.

Bella Verona was a tiny little Italian restaurant Josh and I ate at the last time we were here, and it was incredible. But when I say it's tiny, I mean, you can barely walk around once you're inside. But, that kind of adds to the charm of the place. And the food was absolutely killer - I can still almost taste my pasta from 6 years ago. 

I ordered a pizza for delivery to my Marblehead hotel from The Flatbread Company via GrubHub, and it was delicious. And I was shocked that they delivered to the next town over, so if you feel like a night in after exploring, takeout or delivery from here was awesome.

You guys know I love my ice cream, so I walked over to Melt Salem for a scoop before I left for the day. When we were last here, it was called the Salem Screamery, but everything about it was still the same. They have some killer ice cream here with both conventional and seasonal flavors. I was boring and got my usual mint chip, but it was so insanely delicious. It's a bit further outside the main town area, but not too far of a walk (and definitely worth it). 

And that's a wrap on Salem! I had a pretty perfect day here, and I'm so glad I got to experience it after all the Halloween festivities had come to an end. It was actually perfect, too, because a lot of the houses still had their Halloween decorations up, so I kind of got the best of both worlds. 

Next up, on my way back home, I stopped in Newburyport and Plum Island for the morning and afternoon, and I'm excited to share my time there because Plum Island was so stunning. 

* I traveled to this destination during the COVID-19 pandemic and took all necessary and optional precautions. During the limited traveling I have done during the pandemic, I took the responsibility of not only my own health, but also the health of those around me. I planned excursions and activities that were all outdoors, avoided coming within even 12 feet of another person, relied on take-out at restaurants where I could safety eat outside far from others, or back at my room at the inn where everything had been sanitized and aired-out. Safety during this trip was incredibly important to me, and please know that it was always at the forefront of my mind. 

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