Fall Weekend in Boston & Salem, Massachusetts

Location: Boston, Massachusetts (as your home base)
Duration: 4 days, 3 nights
Ideal Season: October for cool weather and peak fall foliage

Fall in New England is the real deal, and there’s no better combo than Boston and Salem. You get the classic charm of a historic city paired with the spooky fun of Salem during Halloween season. This itinerary is built around walking, eating, learning, and seeing the leaves. Even better, you don’t need a car.

Getting Around Without a Car

Boston’s public transit system is excellent. No need to rent a car unless you enjoy paying $40 to $80 a night for hotel parking and dealing with traffic. Trains and commuter rails will get you where you need to go. Within Boston, kids under 12 ride free with an adult. Rides cost about $2.40 and you can tap in with Apple Pay—just wake your phone, tap the screen at the entrance gate, and go. Apple Maps also makes it easy by telling you exactly which train to take, what direction to head in, and how many stops until you get off.

For example, to visit the JFK Library from South Station, take the Red Line southbound toward Braintree or Ashmont and get off at JFK/UMass. From there, a free shuttle gets you to the library entrance.

Day 1: Arrival in Boston

We flew Delta direct from Atlanta to Boston and stayed at the Harborside Inn. The hotel was pricey, but so is everything during peak October season. The location made it totally worth it. It was just steps from the Blue Line for easy airport access and right around the corner from Faneuil Hall and Quincy Market, which means dozens of food options. It’s also within walking distance to the North End, Boston Common, and more. Hotel link here

After checking in, head to Quincy Market and grab dinner from any of the vendors inside. There’s something for everyone.

Day 2: Day Trip to Salem and North End of Boston

Take the commuter rail (Purple T line) from North Station to Salem. On weekends, buy a $10 weekend pass through the T Mobile app, which gets you unlimited commuter rail rides and saves you a few bucks. Alternatively, you can take the ferry, which takes about 50 minutes and costs $48 for adults and $39 for kids.

Most Salem shops don’t open until 10 am, but it’s worth arriving by 8 to enjoy a quiet breakfast and walk around the neighborhoods before the crowds hit. October in Salem is packed. You’ll likely wait in lines to eat, shop, and even use a public bathroom. But if you embrace the chaos, it’s fun.

Salem highlights:

• Witch History Museum
• Old Burying Point Cemetery and Witch Trial Memorial
• House of the Seven Gables
• Winter Island Park and Salem Willows
• Phillips House and Chestnut Street
• Witch Dungeon Museum and Witch House

If you’re a Hocus Pocus fan, there are filming locations scattered throughout town:

• Max & Dani’s House: 4 Ocean Avenue. A bit of a walk from central Salem, so plan accordingly.
• Allison’s House: 318 Essex Street, also known as the Ropes Mansion. The gardens are free and worth a stroll.
• John Bailey High School (now Phillips Elementary) and Salem Commons
• Old Town Hall at 32 Derby Square. There was a live show happening here when we visited called Cry Innocent: The People vs. Bridget Bishop, but it was sold out.

On your way back to Boston, stop in the North End—Boston’s Little Italy. It’s walkable from North Station and has a ton of charm.
Must-dos in the North End:

• Old North Church. For $10 you can tour the church and its crypts. That was a fun little diversion!
• Paul Revere’s House is nearby. We didn’t go in, but admission was only $5.
• Bova’s Bakery. Amazing desserts and open 24 hours.
• Monica’s Sandwich Shop. Huge, delicious sandwiches—easily shareable.

This low-key evening in the North End was perfect after the crowded, high-energy Salem visit.

Day 3: Explore Boston

On your third day, see more of what Boston has to offer. Choose this day or the Salem day based on the weather.

Start with the JFK Presidential Library. Take the Red Line to JFK/UMass and hop on the free UMass shuttle. Entry costs $18 for adults and is free for kids under 12. It was a surprise hit of the trip, especially for my 10-year-old nephew who said it was his favorite stop of the whole trip!

Other worthwhile stops:

• Boston Tea Party Ships and Museum. Expensive but interactive and fun. Probably better if you’re traveling with kids.
• Harvard Square. You can’t get onto campus without a student ID, but the square and surrounding shops are still fun to explore.
• Boston Common. Stunning in the fall with peak leaf color.
• Boston Public Library (Copley Branch). If you love books or beautiful buildings, you’ll want to see the Bates Room and main atrium.
• Granary Burying Ground. We found it by accident but it holds the graves of Paul Revere, victims of the Boston Massacre, and Samuel Adams. Entry is free and someone was handing out free guides at the gate when we went.
• Old State House and Boston Massacre site. Quick photo stop. Look for the medallion marking the site.
• Beacon Hill. One of the prettiest neighborhoods in Boston. Great for a slow walk and photos.
• Hop-on/Hop-off Trolley. We didn’t use one this time, but I did on a past trip. It covers many of these stops, including the Cheers bar and other big-name sights.

Final Thoughts

If you’re looking for a fall trip that checks all the boxes—walkable city, rich history, beautiful leaves, cozy food, and Halloween charm—this is it. Boston and Salem make a great pair. You get the best of both worlds: the steady rhythm and cultural depth of a historic city, plus the lively energy of Salem during its most festive season.

What really makes this trip stand out is how easy it is to get around without a car. Public transportation is clean, fast, and intuitive, and the fact that you can tap in with your phone and get real-time directions makes the whole thing stress-free. It is the kind of trip where you can just show up and explore without needing to over-plan every detail.

If I did it again, I might consider staying a full extra day in Boston just to slow things down and add another museum or walk. I would also aim to get to Salem earlier, or even stay overnight there if you’re set on hitting every spooky stop without rushing. October is an incredible time to go, but it comes with crowds and higher prices. Book early and plan meals ahead if you can.

The magic of this trip is in the mix of moments. Stepping through crunchy leaves in Boston Common, wandering candlelit crypts in old churches, sharing an oversized sandwich from Monica’s, or catching a glimpse of a Hocus Pocus filming spot between lines of tourists. It is full of charm without trying too hard.

So if you’re on the fence, go. Pack good walking shoes, bring a light jacket, and enjoy what New England does best. This trip gave us just the right balance of activity and atmosphere, and I would do it again in a heartbeat.