Best Boston Day Trips

Historic and Cultural Day Trips

As people continued settling along the New England coast, hundreds of cities and towns developed and became magnets for immigrants from around the globe. Today, not every New Englander can trace their family to the Mayflower—but they can tell you about their first Sox game, where to get the best ice cream, and their lackluster field trip to Plymouth Rock. Speaking of historic sites, experience what makes New England summer special between FIFA World Cup group stage matches in these historic cities.

From World Cup Boston to Historic Salem

For any Boston FIFA fans looking to indulge in a cultural experience vastly different from what’s on offer at Boston Stadium, head north to Salem, Mass, for a walk on the witchy side. Salem’s claim to fame is the 1692 Salem Witch Trials, part of a larger witch-hunting hysteria that swept New England that decade. While historians debate the causes behind the witch allegations, Salem has decided the legends are all true—a decision that makes for an unforgettable visit.

For a fun day that blends the witchy with the wonderful, start with the Salem Witch Trials Memorial located in the heart of town. The memorial grounds your experience in the real events that shook Salem in the 1690s before you indulge in the more fun-filled activities.

The Salem Witch Village captures the small-town New England aesthetic, while the Salem Witch Dungeon museum adds a kitschy touch to the day. Not a believer? Enjoy the spectacular coastal landscape at Fort Pickering, just a couple of miles from downtown.

Explore Southern New England, Providence Style

Providence offers one of the best day trips from Boston because, for the discerning eye and ear, it spotlights an entirely distinct subculture. Providence is the capital of Rhode Island, the smallest state in the US, which makes for a fiercely independent population. Going their own way has sorta been Rhode Island’s thing since Roger Williams fled from Massachusetts in 1636.

Providence is a city best experienced on foot for those who are able, because the city is defined by main thoroughfares buzzing with commercial activity and history. It may not be possible to walk the entire city in a day, but a few blocks on the major streets will give you a chance to sample what this city has in store.

Start off on Providence’s East Side with breakfast at Seven Stars Bakery on Hope Street. Continuing along the East Side down streets like Wickenden will give you a glimpse of colonial-era and early Federal homes while offering a rest at quirky cafes. You can even check out Brown University’s campus and stop for lunch at a student favorite on Thayer Street.

After taking in the historic East Side, you can cut across town using Westminster Street. Westminster showcases the growth of Providence in the 19th and early 20th centuries, including the oldest indoor mall in America, the Arcade. As you cross downtown Providence, you can make your way north and west to Atwell’s Ave—the heart of Federal Hill.

If Boston is synonymous with Irish immigration, then Providence is just as well known for the Italians who settled around Federal Hill. The neighborhood they built is now home to some of the city’s oldest and best-known restaurants. Any spot on Federal Hill will make for a good meal, but we’re partial to the meatballs and French fries at Angelo’s or pizza at Casserta’s. Maybe a visit to Federal Hill will push Italy to the World Cup Boston Quarterfinal match.

Soak Up New England Summer with Coastal Getaways

The FIFA World Cup may have brought you to Boston, but even diehard FIFA fans need a beach day. Even if the beach isn’t your thing, you can still have plenty of fun at one of New England’s premier coastal cities. Want the quintessential New England beach day? Try Cape Cod for a fun day trip from Boston by train or car. Want to stroll along a coastal cityscape? Make the day trip from Boston to Portland.

Cool Off on Cape Cod

As the World Cup Boston action turns up the heat, Boston FIFA fans will need a place to unwind in between matches. If you’re doing Cape Cod as a day trip from Boston, you’ll need to pick a single town or beach to get the most from the trip. The Cape Flyer train will bring you to Hyannis, a worthy spot to spend the day. The Cape Cod Maritime Museum provides a great window into this region’s cultural roots, and nearby beaches offer the perfect place to unwind.

A half-hour drive further out has its own rewards, though, as it brings you to Chatham. Located on the Atlantic side of the Cape, Chatham boasts an impressively charming downtown, and the hydrangeas are likely to be in full bloom right after Norway v. France on June 26th.

Speaking of Norway v. France, if you’re chanting “Allez les Bleus!” on matchday, you may want to make a weekend trip to Cape Cod. With more time on the Cape, you can check out Provincetown and the Dune Shacks Trail. Boston FIFA Fans from France may feel like they’re back on the dunes of Dunkirk or Calais as they walk the 2-mile dune trail.

Pop Up to Picture Perfect Portland

If the England vs. Ghana match has brought you across the Atlantic to Boston, then Portland belongs on your list of day trips from Boston. Whichever team has your heart on matchday, Portland offers rich history, fresh seafood, and picturesque views tied to both countries.

England supporters may feel as if they’re back in Brighton or Dover, given Portland’s maritime tradition and quaint waterfront cityscape. Fans of both teams may appreciate Portland’s Freedom Trail, which recounts Portland’s role on the Underground Railroad and participation in the abolition of slavery in the United States.

Any and all Boston FIFA fans can indulge in the city’s famous lobster rolls and wash them down with a beer from one of the local breweries. Allagash and Shipyard are two Portland-based breweries with a nationwide following, and for good reason. Walk off the calories on your way up to the top of the Portland Observatory Museum, just don’t call it a lighthouse!

Planning a Day Trip From Boston

One of the biggest considerations when it comes to planning the best day trips from Boston is whether to go by car or train. For Boston FIFA fans, they have the distinct option of not having to rent a car to enjoy Boston World Cup action. We think the same goes for fun day trips from Boston too.

New England infrastructure is exposed to everything infrastructure hates: snow, humidity, saltwater, extreme temperature fluctuations, and all four seasons. That means there’s constant road repairs being done, constant improvements, and constant traffic. The only thing that is not constant is the flow of traffic. If you drive, it may not save any time and will likely get you frustrated. Also, for the commuter rail options, you won’t face the price hikes and surges that rideshare companies may create.

Key Transit Information

If you are going to choose trains over cars for day trips, you’ll want to know the prices and schedules. Thankfully, we’ve done the work for you: