10 Best Places In Boston: Adventures and Affordable Escapes

Boston is a city that seamlessly weaves its historical roots with contemporary dynamism. It’s a place where past, present, and future coexist harmoniously, offering a captivating experience for every visitor. So, whether you’re strolling along the Freedom Trail, savoring culinary delights, or embracing the spirit of sports, Boston promises a journey of discovery that’s as diverse as the city itself.

1. Plum Island

Plum Island is a lovely day trip from Boston in the summer months. The barrier island is just over an hour’s drive on a bad traffic day and gets its name from the wild plum shrubs that grow along its shores. It also earned the title ‘plum’ from the characteristic purple sand that occurs during low tide thanks to pinkish-tinted garnet crystals mixed in with the sand.

As a day trip, it’s one of the most enjoyable places for a beach day, although visitors should remember that there are no on-duty lifeguards. It might not be the best Boston day trip for swimming if you aren’t confident in the water and are visiting with a group of strong swimmers.

Plum Island is only 11 miles long, so you could walk the whole island if you really wanted to. Otherwise, stick to organized hiking trails like the Hellcat Marsh Loop Trail, which cuts through the Parker River National Wildlife Reserve. Plum Island wormed its way onto our list because of its quiet beach vibe and many nature-immersive experiences. It isn’t as busy as the seaside towns, so it is perfect if you just want to beach bum for one of your Boston day trips.

2. Provincetown

Speaking of beach days, Provincetown is one of those busier seaside towns we recommend. When you want a day trip to somewhere busy and entertainment-filled, Provincetown is where to head. The New England town is right at the tip of Cape Cod and is famous for its arts, food, and pilgrim history. In 1620, Provincetown was actually the site of the Mayflower’s landing, commemorated by the Pilgrim Monument today.

However, it’s not all history; its beaches are the cherry on top. Race Point Beach is the most popular spot for sunbathing in Provincetown, so allow time to visit when you head on this day trip from Boston.

Provincetown is friendly, eclectic, and ideal for an impactful addition to our top Boston day trips. You can drive to Provincetown in around 2 hours, passing little coastal towns like Plymouth and Sandwich en route. Alternatively, use public transport to reach the World Trade Center Pier and catch the ferry in approximately a 2-hour total trip. This is an excellent way to sneakily glimpse Boston from the water.

3. Peabody Essex Museum

Art lovers, prepare to be blown away by this one. The Peabody Essex Museum is easily one of the top art galleries you can visit in Boston. And this museum is just a short drive (45 minutes) from central Boston, so it can easily be squeezed into a busy itinerary. If you don’t have a car, you also have public transportation options, with multiple bus lines connecting the two.

The glitzy modern art museum is renowned for its American and Asian art. It has a rather bizarre collection of artifacts and displays. Be prepared for full-room displays and plenty of head-tilting art pieces. A considerable section is dedicated to the Salem witches, a famous story in the museum’s town of over 20 women who were put to death over baseless allegations of witchery.

If you visit the Peabody Essex Museum, you can easily visit the Salem Witch Museum while you are there. Salem is small but mighty, with quite a few high-quality attractions, so don’t hesitate to make your visit to this gallery into a full-day affair. We had to add it to this itinerary because of the witch element to its displays and the glitzy, comprehensive showcasing of such a vast display of quality art. This museum also makes a great rainy-day trip from Boston. Day trips aren’t just for sunny days.

4. Road Trip to Portland, Mainz

Driving to Portland from Boston takes less than a few hours—approximately 2 hours and 1 minute. But instead of rushing up to Portland and back, make a day trip out of the drive and treat it as a single-day road trip. We suggest driving through the beautiful Middlesex Fells Reservation, detouring slightly to stop by Salem and see all the witch history, stopping for lunch at Portsmouth, and then spending a couple of hours soaking up Maine in scenic Portland.

In Portland, you could ride the Maine Narrow Gauge Railroad, visit the Portland Museum of Art, or visit the International Cryptozoology Museum. The last one is enjoyable, with many fictional characters, like Bigfoot and the Loch Ness Monster.

With all these stops on the first part of your journey, allow around 6 hours for the first leg to thoroughly enjoy each stop. Then, your return journey should be about 2 hours unless you stop anywhere pretty for sunset and dinner. The north shore residents are lucky to have such historic towns and beautiful views on their doorstep, so ensure you get a good taste of this incredible stretch.

5. Salem Witch Museum

The Salem Witch Museum is one of the most fascinating day trip ideas from Boston, and even better, it is also one of the most feasible. It is just an hour from Boston by car or a 45-minute direct train ride from North Station. The museum takes you back to 1692, when the Salem Witch Trials were fully underway. Over 200 women stood trial for false claims of witchery, and 19 were convicted and given a death-by-hanging sentence.

The ordeal was catastrophic and considered one of the most tragic events in history. You can relive the experience with life-size mannequins and trial scenes at the museum. You can browse through informative exhibits to learn more about the women prosecuted and about attitudes and examples of witchcraft today.

The Salem Witch Museum might not be the first thing that pops into your head when you think of a lovely weekend getaway. However, as a day trip from Boston, it highlights a massively important section of history.

6. Woods Hole

Woods Hole is at the very end of Cape Cod. In fact, it seems closer to the islands than the mainland, despite being on the main peninsula. The tiny village was once a central whaling point, and you can still enjoy a more ethical version of coastal living by walking past the marina and enjoying the waterfront promenade.

There is a lot of science-based entertainment to be had in this village, too; just stop by the Woods Hole Oceanographic Institution Ocean Science Discovery Center. This science museum even has Titanic recovery exhibits. And you can take advantage of the daily tour of Woods Hole that departs from the Woods Hole Historical Museum.

Woods Hole is roughly a two-hour drive from Boston. For us, the main draw is its total science and marine focus. But remember that the driving route down to Woods Hole passes Plymouth or Blue Hills Reservation – depending on your route.

7. North Conway

North Conway is one of the furthest day trips from Boston, taking 2 hours and 50 minutes to reach by car. So why bother? What grip does this little forest town hold on so many visitors? North Conway is a hot spot for hiking, skiing, and waterfalls. The tiny village has more hiking trails and outdoor adventures in a 10-mile radius than most towns combined. Head up to North Conway early in the morning to have a full day enjoying its sublime locale before heading back after dinner. It is a full day, but definitely worthwhile.

Must-visits in North Conway include Diana’s Baths Cascade and Echo Lake State Park. The water attractions here are stunning and a great early morning activity. If it is ski season, you could also spend a full day on the slopes. While catching some beautiful views on a time limit, the Conway Scenic Railroad is your best shot.

The 19th-century steam train whisks you around some of the prettiest scenery in North Conway in traditional dining cars. The outdoor adventure in North Conway is unbeatable, so we had to add it to this guide.

8. The House of the Seven Gables

The House of the Seven Gables may sound familiar to any literature fan. The novel was written by Nathaniel Hawthorne in 1851 and was a major hit. And in Salem (we are starting to think that everything good is in Salem), you can visit the actual house that inspired the novel.

The House of the Seven Gables is now an up-and-running not-for-profit museum dedicated to the author, his life, and his novel. The house itself dates back to 1668 but was restored in 1910, keeping as many period elements and features as possible. Located overlooking the water, it is a beautiful spot full of history and worth visiting.

The House of the Seven Gables is an hour away from Boston by car or an hour by train from North Station. If you catch the train, be prepared for a 25-minute walk to the actual museum from the station.

9. Nantucket

Nantucket is an island more isolated than Martha’s Vineyard and located just a little further offshore. For an adventurous day trip, look no further. The island has a little town center with those cobbled streets that you adore despite yourself. The whole thing has that quaint allure and ruggedness due to its geographical isolation. In short, Nantucket is an island worth day-tripping and a beautiful example of the Cape Cod region.

Nantucket’s main highlights are its waterfront cottages and traditional buildings in the main town. You can also beach hop and jump between lighthouses, reveling in the fewer tourists than you’d find on the mainland or busier islands. It has a return ferry service that perfectly lines up with enough hours on the island to sightsee.

Besides, it is more of a place to experience than to tick off loads of specific things. The ferry is an hour long, and it takes around 2 hours to reach Hyannis Terminal by train from South Station, Boston. Bring a good book and some anti-motion sickness tablets, just in case.

10. New Bedford

New Bedford is one of the top day trips from Boston. With limited time, you can take this trip one of two ways: as an opportunity to learn about maritime history or taste loads of delicious seafood. In an ideal world, we’d suggest staying a full day and ticking off both, but if that isn’t an option, get ready to pick one.

First things first, though, New Bedford is located on the south coast, just outside of Providence and Rhode Island. The city was founded by English Quakers and, since then, has entirely revolved around the fishing industry, which should be easy to tell from all the fishing boats in its harbor.

You can stop by (or jump between) the main wharf area and all the seafood retailers just south of the wharves, off MacArthur’s Drive. There are plenty of high-brow seafood restaurants, like The Black Whale and Merrill’s on the Waterfront.

So you can always book in for a sunset dining experience there, as many tables also come with waterfront views. Otherwise, head to the New Bedford Whaling Museum to keep things educational. This somewhat tragic museum tells the story of the global whaling industry. It provides excellent insight into the toils of these beautiful mammals.

New Bedford is just 1.5 hours from Boston or 3 hours by public transport. It is an easy day trip to organize, whichever way you plan it. And if you drive, then you’ll cut straight through Blue Hills Reservation which is a huge plus.