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Are you traveling to Boston, MA for the weekend and want to also cross the witchy city of Salem off your bucket list? It so happens that these cities are not too far from each other and are fairly easy to combine. This itinerary will make sure you see the very best that Boston and Salem have to offer in just one busy weekend!
This is the type of itinerary where I simply sigh over and over again while writing it because it brings back such lovely travel memories. I adore both of these cities (and New England in general) and love getting back to Massachusetts for more adventures whenever I can. I am truly an all seasons coastal-loving girl.
This itinerary is designed to be doable without a car, although driving between Boston and Salem is still an option. Otherwise, the sites you will see in both of these cities are completely walkable and the subway in Boston is user-friendly.
That being said, let’s get into how you can have an amazing weekend exploring Boston and Salem, Massachusetts!
The Perfect Boston and Salem, MA Weekend Itinerary
Arrive into Massachusetts
If you do not plan to drive into the Boston area, the best way to reach Massachusetts is to fly into Boston Logan International Airport. From there, simply grab a 5-10 minute Uber or Lyft into downtown Boston. Of course, you could also travel onward to base yourself in Salem for the weekend, although it’s much less convenient.
If driving, you have more flexibility to stay in either Salem or Boston, however, there are still pros and cons to consider like traffic and parking. We’ll discuss that more a bit further down.
Day One in Boston, MA
Assuming you arrive the night before (ie. arrive Thursday night and leave Sunday morning), you’ll have two full days for adventure. Here is how to spend your first 24 hours frolicking around Boston, Massachusetts.
If you aren’t staying at a hotel in Boston and need parking, you’ll find plenty in the Boston Common Garage.
8:30am: Grab Donuts & Coffee for Breakfast
Boston is the land of Dunkin Donuts, so why not start your day with a nod to that tradition? Since you can find Dunkin everywhere, try something a bit more local and high quality like the following two options.
Kane’s Donuts in Boston’s financial district offers awesome traditional glazed donuts and is just over a half-mile from Boston Common. Alternatively, for one of the best Boston cream donuts you’ll ever eat, venture a touch further to Bova’s in Boston’s North End.
9:30am: Walk the Freedom Trail
Walking Boston’s iconic three-mile Freedom Trail is an essential and perfectly doable activity over one busy morning. However, expect the tour to run into the afternoon depending on how many stops you make at these sites:
- Old State House & Old South Meeting House (combined ticket): The former is near the site of the March 5, 1770 Boston Massacre that left five colonists dead. The latter held spirited talks and debates as tensions rose against the British crown.
- Faneuil Hall: A meeting hall and marketplace since 1742, which today houses a variety of food stalls.
- Paul Revere House: The home from which Paul Revere departed for his famous ride. Dating back to the 17th century, it’s the oldest building in the downtown Boston.
- Old North Church: 18th century church known for the famous lantern signal “One if by land, two if by sea”.
- USS Constitution: Affectionately known as “Old Ironsides”, this ship was built in Boston in 1797 and served as a naval frigate during the War of 1812. Located in Charlestown, this site is the furthest to walk to, so it could make sense to order an Uber for the way back.
Do this self-guided tour at your own pace by downloading an app or take a guided tour for a 90-minute overview before exploring deeper on your own.
For a comprehensive tour of Boston’s Freedom Trail and beyond, this 3.5-hour tour ensures you don’t miss any of the city’s top sites.
1:00pm: Eat a Lobster Roll
You’ve likely worked up an appetite by now, so it’s time to indulge in my favorite local specialty: a lobster roll. One of my favorite rolls I ate during many Massachusetts adventures was at Luke’s Lobster in downtown Boston. Whereas I am normally a light mayo sans celery kind of girl, at Luke’s I loved the addition of warm butter on their house lobster roll.
2:30pm: Boston Tea Party Ships and Museum
Continue the revolutionary spirit with an immersive and engaging tour at the Boston Tea Party Museum (purchase tickets here). This immersive 1-hour experience transports you to the Boston of 1773. You’ll join a spirited meeting with Samuel Adams, see an original surviving tea chest, and dump your own “tea” into the harbor.
4:00pm: Take a Harbor Cruise
Boston Harbor is not just for tea! Cap off a busy day with a relaxing harbor cruise that allows you to take in views of the coast and skyline. It’s a great opportunity to rest your legs and get some energy back before a fun dinner out.
6:00pm: Dinner in Boston’s Seaport Neighborhood
Boston is loaded with good restaurants and the waterfront Seaport neighborhood (near where you’ve been exploring) is no exception. Legal Sea Foods in a local institution located in this neighborhood, and I’ve also listed a couple of my own favorites:
- Trillium: This laidback brewery has some of the best beer in the region, especially if you like barrel-aged stouts. The compact food menu offers a selection of handhelds and hearty pasta.
- Row 34: While I haven’t eaten at the downtown location, I’ve been to the Burlington, MA Row 34 many times. This restaurant manages to offer sophisticated food and drink menus in a casual, jeans-friendly atmosphere. Hint: order the burger with the fried oyster!
Staying out for drinks? Check out some nearby dive bars, like Lucky’s Lounge. Looking for spooky fun? Opt for a haunted trolley tour or ghostly pub crawl.
Also Read: The Perfect 7 Day New England Road Trip Itinerary
Day Two in Salem, MA
Today is all about exploring the Witch City, which is famous for the Salem Witch Trials of 1692 and a little movie called Hocus Pocus. There are several options for getting to Salem from Boston, which I break down in another section below. For now, let’s dig into the good stuff.
Be sure to also check out my other posts about Salem:
9:30am – The Witch Museum or House of Seven Gables
Here’s a dose of honesty: I find the Salem Witch Museum incredibly overrated, so I’ve given an alternative that I adore. That said, I acknowledge that The Witch Museum is possibly the most popular museum in Salem, so I’m leaving the choice in your hands.
- Salem Witch Museum: Has two main exhibit rooms that give a general overview of what happened during the 1692 Salem Witch Trials. Timed-entry tickets must be purchased online on the day of your visit.
- House of the Seven Gables: This 17th century coastal home, which Nathaniel Hawthorne writes about in his namesake novel, was standing during the witch trials. In fact, 1692 testimony accuses the widow Ann Pudeator’s specter of causing the home’s original owner, John Turner, to fall from a cherry tree. Hawthorne’s Salem birth home (he later lived in Concord) is also on the property. Purchase tickets here.
10:30am – Derby Wharf Light Station
There’s more than witches in Salem. In fact, for centuries the city was mostly famous for its maritime history before the commercialization of its witch trials past.
You don’t have to go far to find traces of the seafaring legacy that dominated Salem for so long. Start by taking a pleasant walk along the rocky path jutting into Salem Harbor to the Derby Wharf Light Station. This squat lighthouse dates back to 1871 and only stands at 20 feet tall.
11:00am – Explore the Salem Maritime National Historic Site
Return to land and wander the area around the Salem Maritime National Historic Site. This nine-acre waterfront area encompasses historic wharves and structures that once made Salem a powerful colonial port city until the mid 19th-century.
Unless you visit on a weekend when interpretive rangers are around, most of the structures are not open to enter but instead offer informational signs. That said, you can and should pop into the Waite & Pierce Park Store for a lovely selection of gifts and decor.
12:00pm – Lunch/Coffee Break
After your morning explorations, it’s time for a food break. Here are a couple cute cafes in Salem that are perfect for coffee or lunch (or both!):
- Gulu-Gulu Cafe: Centrally located in the heart of Salem. I enjoyed their oat milk cappuccino and avocado toast.
- Jaho Coffee Roaster & Wine Bar: Charming little spot near the waterfront with an enticing case of baked goods. The smoked salmon bagel was the perfect mid-day fuel I needed.
If you are in the mood for seafood, there is a collection of spots near the harbor, some of which have water views. To watch the boats while enjoying a hot bowl of “chowda”, check out Sea Level Oyster Bar.
12:50pm – Stroll Across Salem Common
After lunch, head towards the center of Salem by crossing Salem Common. This green space has been in use since the 17th century, and was originally where the local militia would perform drills. Look out for food stalls here once Halloween season rolls around.
1:00pm – Witch Trials Walking Tour
Now it’s time to get into why you’re really here: for all things Salem witch trials! Doing a Salem walking tour is the best way to find out just how this 1692 hysteria left 19 people hanged and one man pressed to death. Most were women and all were innocent (of witchcraft at least).
This tour is also great to do after dark if your itinerary allows, as temperatures are more comfortable during summer evenings. The guides also tend to throw in a couple ghost stories, and the darkness makes everything a little spookier.
Travel Savvy Tip
Not in the mood for a walking tour? Visit the Peabody Essex Museum instead to see real artifacts and documents from the Salem witch trials! Prices run steep for this world-class museum at $25 per person (kids are free), but it’s worth it to see the most authentic witch trials exhibits in Salem.
3:00pm – Visit the Witch House
You will probably pass the Witch House during your walking tour, which looks straight out of Godric’s Hollow with its high pitch and angular roof. This home was grand in its day, having belonged to witch trials judge Jonathan Corwin.
For $9 you can enter the residence to find period furnishings and learn about Puritan life and beliefs that led to this society’s suspicious nature. Unsubstantiated rumors even suggest that some witch trials interrogations took place under this roof.
4:00pm – More Salem Sightseeing
If you have dinner reservations in Boston, this is a good time to head back on the train or ferry. Otherwise, stroll around a few more sights in Salem before dinner. Note that the latest ferry out of Salem is at 7:00pm, while the last train departure is around 11pm (check schedule here).
- Browse the shops on Essex Street
- Stroll past stately homes on the brick sidewalks of the McIntire Historic District
- Honor 1692 victims at the Salem Witch Trials Memorial
- Ropes Mansion: This Hocus-Pocus-featured house has limited touring hours on weekends only, but its gardens are always open
- Check out the Bewitched Sculpture – the 7th season of the show was filmed in Salem
6:00pm onward: Dinner in Boston or Salem
Tonight, you have the option to stay in Salem for dinner or head back to Boston. If you are staying in Salem, consider the following:
- Lobster Shanty: (Salem) Has some of the best clam chowder I’ve tried in Massachusetts. You’ll also find lobster rolls and other pub type food at this dive.
- Ledger Restaurant: (Salem) Perfect for classier vibes, this elegant restaurant’s James Beard-nominated chef offers sophisticated takes on 19th century dishes.
- Buttermilk and Bourbon: (Boston) Features awesome southern-inspired small plates, like delicious grilled octopus (when it’s on the menu). Of course, the signature warm honey glazed biscuits are always a must.
Sticking around Salem tonight? Considering heading to All Souls Lounge, Mercy Tavern, or linger at the Lobster Shanty to mingle with locals and have a couple drinks. Otherwise, it’s time to wind down this super fun weekend exploring Boston and Salem and prepare to return home the next day.
Should You Stay in Boston or Salem?
If you are arriving into Boston’s airport, it will be easiest to stay at a hotel in downtown Boston. Otherwise, you will need to lug all your belongings into a train, bus, or rental car to reach Salem, which is another 40 minutes away by car. Note that a rental car will be mostly an inconvenience and extra expense for the purposes of this itinerary.
If you are driving into the area, there’s more flexibility since you won’t need to rely on public transportation. In this case, Salem could be more cost effective to avoid Boston’s steep overnight parking fees.
If you are traveling in October, be aware that traffic gets extremely backed up heading in and out of Salem. It’s best to plan any driving for the early morning or late evening to avoid the worst delays.
Where to Stay in Boston and Salem
Here are the perfect hotels for the best weekend exploring Boston and Salem, MA:
- Hawthorne Hotel (Salem): Great location right in the historic core of Salem and named after their native son Nathaniel Hawthorne. This hotel has free parking – a giant perk in this town! – and is pet friendly.
- Hampton Inn Salem Boston (Salem): Walkable to the Salem waterfront, Essex Street, and gorgeous Chestnut Street. Has free breakfast, an indoor pool for the kiddos, and is also pet friendly.
- Courtyard Boston Downtown/North Station (Boston): This hotel features modern rooms with nice city views and is located literally right off the Freedom Trail and close to the charming North End.
- The Liberty (Boston): Once the historic Charles Street Jail, this luxury pet-friendly stay is located along the Charles River and right on the edge of Beacon Hill – one of Boston’s most beautiful neighborhoods that is especially lovely during fall. Big windows offer gorgeous river and city views
Getting Between Boston and Salem
Boston and Salem are very well-connected by public transportation, with the following being the best options:
- Train: Taking the Newburyport/Rockport Commuter Rail line, Salem Station is located at the northern end of Washington Street. Takes about 30 minutes from Boston to Salem an costs about $16 per person roundtrip. Military personnel (uniformed or with ID) and children 11 and under ride for free.
- Bus: The #450 bus connects Salem to Boston’s Wonderland or Haymarket stops. Roundtrip fare is about $8.50 per person. Military personnel (uniformed or with ID) and children 11 and under ride for free.
- Ferry: A seasonal ferry is available from late May to October 31. Leaving from Boston at 9:30am for the Salem Ferry Terminal on Blaney Street, the trip takes about 50 minutes. The ferry returns to Boston at 7:00pm. Cost is about $27.50 per person, although round trip requires buying two separate tickets ($20.90 per ticket for children). Book ferry tickets here.
If you take the ferry, consider returning by train or bus to save money and have more flexibility.
Book a Salem Ferry, Museum, and Guided Tour Package Here
Getting Around Boston and Salem
This itinerary is designed to be walkable and a rental car is not necessary. Unless you are traveling by car rather than flying to Massachusetts, it is largely impractical to have a car for this trip.
Of course, if your legs get tired you can always enlist the help of an Uber or Lyft to get between sites in Boston. In Salem, the historic area is pretty compact and walking is usually most efficient.
For certain sites along Boston’s Freedom Trail, it can sometimes save time to take the subway system (the T). For example, if you drive from Salem and park at Boston Common, you could take the Green Line three stops to end up in the North End.
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Boston and Salem make the perfect combination for an intriguing weekend in Massachusetts. They are a dream for history buffs, autumn travelers, and coastal lovers alike between the revolutionary history of Boston Harbor and Salem’s witchy legacy. Finally, with top-notch restaurants and seafood joints galore, you’ll never go hungry in either of these iconic New England cities.
